UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

WASHINGTON, D.C. 20549

SCHEDULE 14A INFORMATION

Proxy Statement Pursuant to Section 14(a) of the

Securities Exchange Act of 1934

Check the appropriate box:

Staffing 360 Solutions, Inc.

(Name of Registrant as Specified in Its Charter)

N/A

(Name of Person(s) Filing Proxy Statement, if other than the Registrant)

Payment of Filing Fee (Check the appropriate box):

641 Lexington Avenue

27^th
27th Floor

New York, NY 10022

(646) 507-5710

May 7, 2021

Dear Stockholder:

You are invited to attend the Special Meeting of Stockholders (the “Special Meeting”) of Staffing 360 Solutions, Inc. (the “Company”), on June 21, 2021, which will take place on Monday, April 5, 2021be held at www.virtualshareholdermeeting.com/STAF2021SM, at 10:00 a.m., New York time. TheIn light of the ongoing developments related to the novel coronavirus (“COVID-19”), the Company has determined that the Special Meeting will be conducted in a virtual formatmeeting conducted exclusively via live webcast. You or your proxyholder will be able to attend the virtual Special Meeting online, vote, view the list of stockholders¹ entitled to vote at the Special Meeting and submit questions during the Special Meeting by visiting www.virtualshareholdermeeting.com/STAF2021SM. and entering the 16-digit control number included on your proxy card or voting instruction form, as applicable. To receive access to the virtual Special Meeting, registered stockholders and beneficial stockholders (those holding shares through a stock brokerage account or by a bank or other holder of record) will need to follow the instructions applicable to them provided in the accompanying proxy statement. Enclosed with this letter are your Notice of Special Meeting of Stockholders, Proxy Statement and Proxy Voting Card. The Proxy Statement included with this notice discusses the proposals to be considered at the Special Meeting. Please review the voting materials at www.proxyvote.com.

At this Special Meeting, you will be asked to consider and vote upon a proposal to approve an amendment to our amended and restated certificate of incorporation to effect, at the Company’s Amendeddiscretion of our Board of Directors (the “Board”) but prior to our 2021 annual stockholder meeting, a reverse stock split of all of the outstanding shares of our common stock, par value $0.00001 per share (“Common Stock”), at a ratio in the range of 1-for-2 to 1-for-20, such ratio to be determined by the Board (the “Reverse Stock Split”). The Reverse Split proposal was approved by the Board, at a ratio to be determined by the Board in its discretion, and Restated Certificaterequires the vote of Incorporation to increasea majority of the holders of the total number of our authorized common stock from 40,000,000shares outstanding. We are now submitting this proposal to 100,000,000 andvote at the Special Meeting to make a corresponding change toobtain the number of authorized shares of capital stock.requisite votes, so we can proceed with the Reverse Stock Split.

Enclosed with this letter are your Notice of Special Meeting of Stockholders, proxy statement and proxy voting card. The attached proxy statement discussesOur Board has fixed the matterclose of business on May 7, 2021 as the record date for determining the stockholders entitled to be considerednotice of and to vote at the Special Meeting. Meeting and any adjournment and postponements thereof (the “Record Date”).

Accordingly, we urge you to review the accompanying material carefully and to promptly return the enclosed proxy card or voting instruction form.instruction. On the following pages, we provide answers to frequently asked questions about the Special Meeting. The Notice of Special Meeting of Stockholders and proxy statementProxy Statement are also available at www.proxyvote.com.www.proxyvote.com.

In light of public health concerns regarding the coronavirus (“COVID-19”) outbreak, the Special Meeting will be conducted in a virtual format only in order to assist in protecting the health and well-being of our stockholders and employees and to provide access to our stockholders regardless of geographic location. Stockholders will not be able to attend the Special Meeting in person; however, stockholders of record will be able to vote and submit questions electronically prior to the Special Meeting by visiting www.proxyvote.com, and during the Special Meeting by visiting www.virtualshareholdermeeting.com/STAF2021SM. You will also be able to dial-in via telephone to ask questions during the meeting. Specific instructions for accessing the meeting are provided in the Notice of Special Meeting of Stockholders, proxy voting card or voting instruction form you received. If you encounter any difficulties accessing the virtual Special Meeting, please call the technical support number available on the virtual meeting page on the morning of the Special Meeting.

Your vote is very important.Whether or not you expect to attend the virtual Special Meeting, pleaseyou are requested to read the enclosed proxy statementProxy Statement and vote as promptly as possible to ensure your representationsign, date and return the presence of a quorum at the Special Meeting. You may vote online or by phone, or by mail by following the instructions on youraccompanying proxy card or voting instruction form. Voting onlineas soon as possible. I encourage you to vote by telephone, over the Internet, or if you requested to receive printed proxy materials, by phone, writtenmarking, signing, dating and returning your proxy or voting instruction form ensurescard so that your representationshares will be represented and voted at the Special Meeting, regardless of whether or not you plan to attend. If you attend the virtual meeting. If you do attend the virtual Special Meeting, you will, of course, have the right to revoke the proxy and vote your shares during the virtual meeting. online.

If your shares are held in the name of a broker, trust, bank or other nominee, and you receive notice of the Special Meeting through your broker or through another intermediary, please vote or return the materials in accordance with the instructions provided to you by such broker or other intermediary or contact your broker directly in order to obtain a proxy issued to you by your nominee holder to attend the virtual Special Meetingmeeting and vote online. Failure to vote duringdo so may result in your shares not being eligible to be voted by proxy at the meeting.

If you plan to attend the virtual Special Meeting, you will need the 16-digit control number included on your proxy card or on the instructions that accompany your proxy materials. The Special Meeting will begin promptly at 10:00 a.m., New York time. Online check-in will begin at 9:45 a.m., New York time, and you should allow ample time for the online check-in procedures.

On behalf of the Board, of Directors, I urge you to submit your proxy as soon as possible, even if you currently plan to attend the virtual Special Meeting.meeting online.

Thank you for your ongoing support.

NOTICE OF SPECIAL MEETING OF STOCKHOLDERS

Meeting Date: April 5,June 21, 2021

To the Stockholders of Staffing 360 Solutions, Inc.:

Notice is hereby given that the Special Meeting of Stockholders (the “Special Meeting”) of Staffing 360 Solutions, Inc. (the “Company”), will be held on June 21, 2021 at 10:00 a.m., New York time, via a live webcast on April 5,the Internet. Stockholders will be able to virtually attend the Special Meeting online, vote and submit questions during the Special Meeting by visiting www.virtualshareholdermeeting.com/STAF2021SM. During the Special Meeting, stockholders will be asked to approve an amendment to our amended and restated certificate of incorporation to effect, at the discretion of the Board but prior to our 2021 virtually overannual stockholder meeting, a reverse stock split of all of the Internetoutstanding shares of our Common Stock, at a ratio in the range of 1-for-2 to 1-for-20, such ratio to be determined by the Board in its discretion and included in a public announcement (the “www.virtualshareholdermeeting.com/STAF2021SMReverse Stock Split Proposal”), foras more fully described in the following purposes:accompanying proxy statement (the “Proxy Statement”). The Reverse Split Proposal was approved by the Board, at a ratio to be determined by the Board in its discretion, and requires the vote of a majority of the holders of the total number of shares of our common stock, par value $0.00001 per share (“Common Stock”) (including any shares of Common Stock represented by shares of Series F Convertible Preferred Stock, par value $0.00001 (“Series F Preferred Stock”) or shares of Series G Convertible Preferred Stock, par value $0.00001 (“Series G Preferred Stock”), in each case voting on an as-converted basis) outstanding.

Stockholders are referred to the enclosed proxy statement (the “Proxy Statement”) for more detailed information with respect to the matters to be considered at the Special Meeting. After careful consideration, the Board of Directors recommends that youa vote “FOR”FOR the Reverse Stock Split Proposal 1 at the Special Meeting.

In light of public health concerns regarding the coronavirus (“COVID-19”) outbreak, the Special Meeting will be conducted in a virtual format only in order to assist in protecting the health and well-being of our stockholders and employees and to provide access to our stockholders regardless of geographic location. Stockholders will not be able to attend the Special Meeting in person; however, stockholders of record will be able to vote and submit questions electronically prior to the Special Meeting by visiting www.proxyvote.com, and during the Special Meeting by visiting www.virtualshareholdermeeting.com/STAF2021SM. You will also be able to dial-in via telephone to ask questions during the meeting. Specific instructions for accessing the meeting are provided in the accompanying proxy card or voting instruction form you received.

The Board has fixed the close of business on February 24,May 7, 2021 as the record date (the “Record Date”) for determining the stockholders entitled to notice of, and to vote at, the Special Meeting or any adjournments thereof. Only the stockholders of record of our Common Stock, our Series F Preferred Stock and our Series G Preferred Stock are entitled to receive notice of, and to vote at, the Special Meeting or any postponement(s), adjournment(s)adjournments thereof. The date of mailing this Notice of Meeting and Proxy Statement is on or recess(es) thereof. about May 24, 2021.

A complete list of registered stockholders entitled to vote at the Special Meeting will be available for inspection by stockholders online (upon request to us by email at the principal executive offices of the Company during regular business hoursVSMShareholderList@broadridge.com) for the 10 calendar days prior to the Special Meeting. The list will also be availableand during the Special Meeting, for inspection by stockholders. If you are a stockholder as ofand online during the Record Date, you may vote at the meeting.Special Meeting.

You are cordially invited to attend the meeting online. Whether or not you expect to attend the virtual Special Meeting, pleaseyou are requested to read the enclosed Proxy Statement and vote as promptly as possible to ensure your representationsign, date and return the presence of a quorum at the Special Meeting. You may vote online or by phone, or by mail by following the instructions on youraccompanying proxy card or voting instruction form. Voting online or by phone, written proxy, or voting instruction form ensurescard as soon as possible. This will assure your representation and a quorum for the transaction of business at the Special Meeting regardless of whetherMeeting. If you attend the virtual meeting. If you do attend the virtual Special Meeting you will, of course, have the right to revokeonline, the proxy and vote your shares during the virtual meeting. If your shares are heldwill not be used if you so request by revoking it as described in the nameProxy Statement.

Hard copies of a broker, trust, bank or other nominee, and you receive notice ofthe Company’s Proxy Statement to security holders in connection with the Special Meeting through your broker or through another intermediary, please vote or return the materials in accordance with the instructions provided to you by such broker or other intermediary or contact your broker directly in order to obtain a proxy issued to you by your nominee holder to attend the virtual Special Meeting and to vote during the meeting.

If you plan to attend the virtual Special Meeting, you will need the 16-digit control number included on your proxy card or on the instructions that accompany your proxy materials. The Special Meeting will begin promptly at 10:00 a.m., New York time. Online check-in will begin at 9:45 a.m., New York time, and you should allow ample time for the online check-in procedures.

Hard copies of this Notice of Special Meeting, Proxy Statement and additional proxy materials are being mailed to stockholders of record as of the close of business on May 7, 2021, beginning on or about March 1,May 24, 2021. The Company’s Proxy Statement to security holders is also available at www.proxyvote.com.www.proxyvote.com.

If you have any questions about accessing materials or voting, please call 1-800-690-6903.

YOUR VOTE AND PARTICIPATION IN THE COMPANY’S AFFAIRS ARE IMPORTANT.

If your shares are registered in your name,, even if you plan to attend the Special Meeting or any postponement or adjournment or recess of the Special Meeting in person,online, we request that you vote by telephone, over the Internet, or that you complete, sign and mail your proxy card to ensure that your shares will be represented at the Special Meeting.

If your shares are held in the name of a broker, trust, bank or other nominee,, and you receive notice of the Special Meeting through your broker or through another intermediary, please vote or complete and return the materials in accordance with the instructions provided to you by such broker or other intermediary or contact your broker directly in order to obtain a proxy issued to you by your nominee holder to attend the Special Meeting and vote your shares at or prior to the virtual Special Meeting.online. Failure to do so may result in your shares not being eligible to be voted by proxy at the Special Meeting.

By order of our Board,

PROXY STATEMENT

SPECIAL MEETING OF STOCKHOLDERS

TO BE HELD ON APRIL 5,JUNE 21, 2021

This proxy statement (the “Proxy Statement”) is furnished to you by the Board of Directors (the “Board”) of Staffing 360 Solutions, Inc. in connection with the solicitation of proxies for use at our Special Meetingthe special meeting of Stockholdersstockholders (the “Special Meeting”) to be held virtuallyvia a live webcast on the Internet at www.virtualshareholdermeeting.com/www.virtualshareholdermeetin.com/STAF2021SM,, on April 5,June 21, 2021 at 10:00 a.m., New York time, for the purposes set forth in the accompanying Notice of Special Meeting of Stockholders (the “Notice”), and at any postponement(s), adjournment(s) or recess(es) thereof.

This Hard copies of this Proxy Statement, along with athe Notice of the Special Meeting and either a proxy card or a voting instruction form,card, are being mailed to our stockholders of record as of the close of business on May 7, 2021, beginning on or about March 1,May 24, 2021.

Unless the context otherwise requires, in this Proxy Statement, we use the terms “Staffing,” “we,” “our,” “us” and the “Company” to refer to Staffing 360 Solutions, Inc. and its subsidiaries on a consolidated basis, and we usesubsidiaries. In addition, unless the terms “stockholder(s)” and “holder(s) of record”context otherwise requires, references to refer“stockholders” are to the holders of shares of our common stock, par value $0.00001 per share entitled to vote at the Special Meeting.(“Common Stock”), our Series F Convertible Preferred Stock, par value $0.00001 per share (“Series F Preferred Stock”), and our Series G Convertible Preferred Stock, par value $0.00001 per share (“Series G Preferred Stock”).

QUESTIONS AND ANSWERS ABOUT THE SPECIAL MEETING

What am I voting on?

At the Special Meeting, you will be asked to approve the proposal to authorize the Board, in its discretion but prior to our 2021 annual stockholder meeting, to amend our amended and restated certificate of incorporation to effect a reverse stock split of all of the outstanding shares of our Common Stock, at a ratio in the range of 1-for-2 to 1-for-20, such ratio to be determined by the Board and included in a public announcement (the “Reverse Stock Split Proposal”).

Why is the Company electing to effect a reverse stock split?

Our Board has unanimously adopted a resolution declaring advisable, and recommending to our stockholders for their approval, an amendment to our amended and restated certificate of incorporation (the “Reverse Stock Split Amendment”) authorizing a reverse stock split of the outstanding shares of our Common Stock at a ratio in the range of 1-for-2 to 1-for-20, such ratio to be determined by the Board and included in a public announcement (the “Reverse Stock Split”), and granting the Board the discretion to file a certificate of amendment to our amended and restated certificate of incorporation with the Secretary of State of the State of Delaware effecting the Reverse Stock Split prior to our 2021 annual stockholder meeting or to abandon the Reverse Stock Split altogether. The form of the proposed Reverse Stock Split Amendment is attached to this proxy statement as Annex A. The Reverse Stock Split Amendment will effect the Reverse Stock Split by reducing the number of outstanding shares of Common Stock as compared to the number of outstanding shares immediately prior to the effectiveness of the Reverse Stock Split, but will not increase the par value of Common Stock, and will not change the number of authorized shares of our capital stock. Stockholders are urged to carefully read Annex A. If implemented, the number of shares of our Common Stock owned by each of our stockholders will be reduced by the same proportion as the reduction in the total number of shares of our Common Stock outstanding, so that the percentage of our outstanding Common Stock owned by each of our stockholders will remain approximately the same, except to the extent that the Reverse Stock Split could result in some or all of our stockholders receiving one share of Common Stock in lieu of a fractional share.

Who is entitled to vote at the Special Meeting, and how many votes do they have?

Stockholders of record, including holders of our Common Stock, par value $0.00001 per share, holders of our Series F Preferred Stock and holders of our Series G Preferred Stock, at the close of business on May 7, 2021 (the “Record Date”) may vote at the Special Meeting. Pursuant to the rights of our stockholders contained in our charter documents, each share of our Common Stock is entitled to one vote on all matters listed in this proxy statement; each holder of Series F Preferred Stock is entitled to the number of votes equal to the number of whole shares of Common Stock into which the shares of Series F Preferred Stock held by such holder are then convertible at the deemed conversion price of $0.725 (subject to certain ownership limitations) with respect to any and all matters presented to the common stockholders for their action or consideration; and each holder of Series G Preferred Stock is entitled to the number of votes equal to the number of whole shares of Common Stock into which the shares of Series G Preferred Stock held by such holder are then convertible with respect to any and all matters presented to the common stockholders for their action or consideration. There are 39,166,528 shares of Common Stock, 4,697.6328 shares of Series F Preferred Stock, and 6,172 and 1,493 shares of Series G Preferred Stock and Series G-1 Preferred Stock, respectively, outstanding on the Record Date. A complete list of registered stockholders entitled to vote at the Special Meeting will be available for inspection by stockholders online (upon request to us by email at VSMShareholderList@broadridge.com) for the 10 calendar days prior to and during the Special Meeting, and online during the Special Meeting.

What is a proxy?

A proxy is anothera person that you legally designateappoint to vote on your stock. Ifbehalf. By using the methods discussed above, you designate someonewill be appointing Brendan Flood, Khalid Anwar and Nick Koutsivitis as our proxy agent(s) as your proxy. The proxy inagent will vote on your behalf, and will have the authority to appoint a written document, that document is also called a “proxy” or a “proxy card.”substitute to act as proxy. If you are a “street name” holder, you must obtain aunable to attend the Special Meeting, please vote by proxy from your broker or nominee in order to voteso that your shares in person at the Special Meeting.

may be voted.

What is a proxy statement?

A proxy statement is a document that regulations of the SEC require that we give to you when we ask you to sign a proxy card to vote your stock at the Special Meeting.

What am I voting on?

At the Special Meeting, you will be asked to approve an amendment to the Company’s Amended and Restated Certificate of Incorporation to increase the number of authorized shares of common stock from 40,000,000 to 100,000,000 and to make a corresponding change to the number of authorized shares of capital stock (Proposal 1 – the “Proposal to Increase Authorized Shares”).

Who is entitled to vote at the Special Meeting, and how many votes do they have?

Holders of record of our common stock at the close of business on February 24, 2021 (the “Record Date”) are entitled to notice of and may vote at the Special Meeting. The Record Date is established by the Board as required by Delaware law. Pursuant to the rights of our stockholders contained in our organizational documents, each share of our common stock is entitled to one vote on all matters to be considered at the Special Meeting. A complete list of stockholders entitled to vote at the Special Meeting will be available for inspection at the principal executive offices of the Company during regular business hours for the 10 calendar days prior to the Special Meeting, and such list will also be available for inspection during the Special Meeting. As of the Record Date, we had 39,166,528 shares of common stock outstanding.

None of our outstanding shares of preferred stock, including our Series E Convertible Preferred Stock (the “Base Series E Preferred Stock”) and Series E-1 Convertible Preferred Stock (the “Series E-1 Preferred Stock”), have voting rights with respect to any of the matters to be considered at the Special Meeting. As of the Record Date, we had 6,172 and 1,409 shares of Base Series E Preferred Stock and Series E-1 Preferred Stock outstanding, respectively.

Unless the context otherwise requires, in this proxy statement, we use the terms “stockholder(s)” and “holder(s) of record” to refer to holders of shares of our common stock.

What is the difference between a stockholder of record and a “street name” holder?

If your shares of common stock are registered directly in your name with Vstock or, with respect to the Series F Preferred Stock or Series G Preferred Stock, Continental Stock Transfer & Trust Company, our stock transfer agent,agents, you are considered the stockholder of record with respect to those shares of our common stock.shares. The Notice has been sent directly to you by the Company.us.

If your shares of common stock are held in a stock brokerage account or by a bank or other nominee, youthe nominee is considered the record holder of those shares. You are considered the beneficial owner of these shares, of common stock, and your shares of common stock are held in “street name.” Your broker, bankA notice or nominee is considered, with respectProxy Statement and voting instruction card have been forwarded to those shares of common stock, the stockholder of record.you by your nominee. As the beneficial owner, you have the right to direct your nominee regardingconcerning how to vote your shares.

How do I vote my shares if I am a stockholder of record?

If you are a stockholder of record, you may vote overby using the Internet,voting instructions they included in the mailing or by telephone, by mail or during the Special Meeting. Please be aware that if you votefollowing their instructions for voting by telephone or over the Internet, you may incur costs such as telephone and Internet access charges for which you will be responsible.

By completing and submitting the proxy card or by submitting your instructions via the Internet or by telephone, you will direct the designated persons (known as “proxies”) to vote your shares of common stock at the Special Meeting in accordance with your instructions. The Board of Directors has appointed Brendan Flood or, in his absence, Nick Koutsivitis, to serve as the proxies for the Special Meeting. Submitting a proxy will not affect your right to virtually attend the Special Meeting and change your vote online during the Special Meeting.

How do I vote my shares if I hold my shares in “street name”?

If you hold your shares in “street name,” your broker, bank or other nominee should provide you with a voting instruction form along with the proxy materials. By completing the voting instruction form, you may direct your nominee how to vote your shares.

In addition, you may vote your shares by telephone or via the Internet, by following the instructions provided by your broker, bank or other nominee and using the control number appearing on your voter instruction form or in the email you received from your banker, broker or other nominee if you have previously opted for electronic delivery of proxy materials. Alternatively, if you want to vote your shares during the virtual Special Meeting, you must contact your nominee directly in order to obtain a proxy issued to you by your nominee holder. Note that a broker letter that identifies you as a stockholder is not the same as a nominee-issued proxy. If you fail to obtain a nominee-issued proxy prior to the Special Meeting, you will not be able to vote your nominee-held shares during the Special Meeting.

Can I vote my shares at the Special Meeting?

Yes. If you are a stockholder of record, you may vote your shares at the Special Meeting by submitting your vote electronically during the Special Meeting.

If you hold your shares in “street name,” you may vote your shares during the Special Meeting only if you obtain a proxy issued by your bank, broker or other nominee giving you the right to vote the shares.

Even if you currently plan to attend the virtual Special Meeting, we recommend that you also return your proxy or voting instructions as described above so that your votes will be counted if you later decide not to attend the Special Meeting or are unable to attend.

What should I do if I receive more than one set of voting materials?

You may receive more than one set of one of the proxy materials (consisting of this Proxy Statement, the accompanying Notice and the proxy card or voting instruction form). For example, if you hold your shares in more than one brokerage account, you will receive a separate voting instruction form for each brokerage account in which you hold shares. Similarly, if you are a stockholder of record and also hold shares in a brokerage account, you will receive a copy of the proxy materials, including a proxy card, for shares held in your name and a voting instruction form for shares held in “street name.” Please complete, sign, date and return each proxy card and voting instruction form that you receive to ensure that all of your shares are voted.

How do I change my vote?

If you are a stockholder of record, you may revoke your proxy at any time before your shares are voted at the Special Meeting by:

If you are a “street name” holder, your broker, bank or other nominee should provide instructions explaining how you may change or revoke your voting instructions. Logging in for virtual attendance at the Special Meeting alone will not revoke your proxy.

What constitutes a quorum?

The presence in person or by proxy of the holders of record of a majority of the shares of common stock entitled to vote at a meeting of stockholders constitutes a quorum for purposes of the Special Meeting. A quorum is necessary in order to conduct the Special Meeting. If you choose to have your shares represented by proxy at the Special Meeting, you will be considered part of the quorum. Both abstentions and broker non-votes are counted as present for the purpose of determining the presence of a quorum. See “What is a broker non-vote?”

If a quorum is not present at the Special Meeting, the stockholders present in person or by proxy may adjourn the meeting to a later date. If an adjournment is for more than 30 days, or if after the adjournment a new record date is fixed for the adjourned meeting, we will provide notice of the adjourned meeting to each stockholder of record entitled to vote at the meeting.

What is a broker non-vote?

Broker non-votes occur when shares are held indirectly through a broker, bank or other intermediary on behalf of a beneficial owner (referred to as held in “street name”) and the broker submits a proxy but does not vote for a matter because the broker has not received voting instructions from the beneficial owner and (i) the broker does not have discretionary voting authority on the matter or (ii) the broker chooses not to vote on a matter for which it has discretionary voting authority. Under the rules of the New York Stock Exchange (the “NYSE”) that govern how brokers may vote shares for which they have not received voting instructions from the beneficial owner, brokers are permitted to exercise discretionary voting authority only on “routine” matters when voting instructions have not been timely received from a beneficial owner. The Reverse Stock Split Proposal 1 is considered a “routine matter.” Therefore, if you do not provide voting instructions to your broker regarding such proposal,the Reverse Stock Split Proposal, your broker will be permitted to exercise discretionary voting authority to vote your shares on such proposal.the Reverse Stock Split Proposal.

AssumingIf I am a quorumbeneficial owner of shares, can my brokerage firm vote my shares?

If you are a beneficial owner and do not vote via the Internet or telephone or by returning a signed voting instruction card to your broker, your shares may be voted only with respect to so-called “routine” matters where your broker has discretionary voting authority over your shares. Under the rules of the NYSE, the Reverse Stock Split Proposal is presentconsidered a “routine” matter. Accordingly, brokers will have such discretionary authority to vote on the Reverse Stock Split Proposal and may vote “FOR” the Reverse Stock Split Proposal.

We encourage you to provide instructions to your brokerage firm via the Internet or telephone or by returning your signed voting instruction card. This ensures that your shares will be voted at the Special Meeting what vote is required to approve Proposal 1 and what are my voting choices with respect to the proposal?proposal described in this Proxy Statement.

How do I vote?

You may vote over the Internet, by telephone, by mail or online at the Special Meeting. Please be aware that if you vote by telephone or over the Internet, you may incur costs such as telephone and Internet access charges for which you will be responsible.

Vote by Internet. You can vote via the Internet at www.proxyvote.com. You will need to use the control number appearing on your proxy card to vote via the Internet. You can use the Internet to transmit your voting instructions up until 11:59 p.m. Eastern Time on June 20, 2021, which is the day before the meeting date. Internet voting is available 24 hours a day. If you vote via the Internet, you do not need to vote by telephone or return a proxy card.

Proposal 1 - ProposalVote by Telephone. You can vote by telephone by calling the toll-free telephone number 1-800-690-6903. You will need to Increase Authorized Shares. The affirmativeuse the control number appearing on your proxy card to vote of holders ofby telephone. You may transmit your voting instructions from any touch-tone telephone up until 11:59 p.m. Eastern Time on June 20, 2021, which is the day before the meeting date. Telephone voting is available 24 hours a majorityday. If you vote by telephone, you do not need to vote over the Internet or return a proxy card.

Vote by Mail. If you received a printed proxy card, you can vote by marking, dating and signing it, and returning it in the postage-paid envelope provided to Vote Processing, c/o Broadridge, 51 Mercedes Way, Edgewood, NY 11717. Please promptly mail your proxy card or voting instruction card to ensure that it is received prior to the closing of the sharespolls at the Special Meeting.

Vote Online at the Meeting. To vote online during the Special Meeting, you must be logged in and registered to virtually attend the Special Meeting and cast your vote before the announcement of the Company’s common stock outstandingclose of voting during the Special Meeting. You are entitled to virtually attend the Special Meeting only if you were a stockholder of the Company as of the close of business on the Record Date or hold a valid proxy for the Special Meeting. If your shares are registered directly in your name, you are considered the stockholder of record and you have the right to vote virtually at the Special Meeting. If your shares are held in the name of your broker or other nominee, you are considered the beneficial owner of shares held in street name. As a beneficial owner, if you wish to vote at the Special Meeting, you will need to bring to the Special Meeting a legal proxy from your broker or other nominee authorizing you to vote those shares.

If you are not a stockholder of record but hold shares through a broker, bank, trustee or nominee (i.e., in street name), you should provide proof of beneficial ownership as of the Record Date is required(such as your most recent account statement prior to approve Proposal 1.the Record Date), a copy of the voting instruction card provided by your broker, bank, trustee or nominee, or similar evidence of ownership.

If you vote by any of the methods discussed above, you will be designating Brendan Flood, Khalid Anwar or Nick Koutsivitis, as your proxy, and they will vote your shares on your behalf as you indicate.

Submitting a proxy will not affect your right to attend the Special Meeting and vote virtually.

If your shares are held in the name of a bank, broker or other nominee, you will receive separate voting instructions from your bank, broker or other nominee describing how to vote your shares. The availability of Internet voting will depend on the voting process of your bank, broker or other nominee. Please check with your bank, broker or other nominee and follow the voting instructions it provides.

How will my proxy vote my shares?

For Proposal 1,If you mayare a stockholder of record, your proxy will vote according to your instructions. If you choose to vote “FOR,” “AGAINST” or “ABSTAIN.”by mail and complete and return the enclosed proxy card but do not indicate your vote, your proxy will vote

Because the

We do not intend to bring any other matter for a vote is based on the total number of shares outstanding rather than the votes cast at the Special Meeting, your failureand we do not know of anyone else who intends to do so. Your proxies are authorized to vote or marking “ABSTAIN” on your behalf, however, using their best judgment, on any other business that properly comes before the Special Meeting.

If your shares are held in the name of a bank, broker or other nominee, you will receive separate voting instructions from your bank, broker or other nominee describing how to vote your shares. The availability of Internet voting will depend on the voting process of your bank, broker or other nominee. Please check with your bank, broker or other nominee and follow the voting instructions your bank, broker or other nominee provides.

As described above, under the rules of the NYSE, the Reverse Stock Split Proposal is considered to be a “routine” matter. Accordingly, brokers will have such discretionary authority to vote on the Reverse Stock Split Proposal and may vote “FOR” the Reverse Stock Split Proposal.

How do I change my vote?

If you are a stockholder of record, you may revoke your proxy with respect toat any time before your shares are voted at the Proposal 1 has the same effect as a vote against this proposal.Special Meeting by:

How are abstentions and broker non-votes treated for purposes of the Special Meeting?

Abstentions are included in the determination of the number of shares of common stockCommon Stock present at the Special Meeting for determining a quorum at the meeting. An abstention is not an “affirmative vote,” but an abstaining stockholder is considered “entitled to vote” at the Special Meeting. Accordingly, an abstention will have the effect of a vote against the Proposal to Increase Authorized Shares.Reverse Stock Split Proposal.

Broker non-votes will be included in the determination of the number of shares of common stockCommon Stock present at the Special Meeting for determining a quorum at the meeting. Broker non-votes, to the extent applicable, will have the effect of a vote against the Proposal to Increase Authorized Shares.Reverse Stock Split Proposal. Because your broker will have discretionary voting authority with respect to the Reverse Stock Split Proposal, to Increase Authorized Shares, a broker non-vote would only arise in the event that your broker does not receive your voting instructions and chooses not to exercise its discretionary voting authority with respect to such matter. We understand that certain brokers have

If your shares are held in the name of a policybank, broker or other nominee, you should check with your bank, broker or other nominee and follow the voting instructions provided. Attendance at the Special Meeting alone will not to exercise discretionary voting authority. Therefore, we encourage you to instructrevoke your broker how to vote your shares.proxy.

Who counts the votes?

All votes will be tabulated by Nick Koutsivitis, the inspector of election appointed for the Special Meeting.

What constitutes a quorum?

The holders of a majority of the Company’s eligible votes as of the record date, either present or represented by proxy, constitute a quorum. A quorum is necessary in order to conduct the Special Meeting. If you choose to have your shares represented by proxy at the Special Meeting, you will be considered part of the quorum. Both abstentions and broker non-votes are counted as present for the purpose of determining the presence of a quorum. Regardless of whether a quorum is present at the Special Meeting, the chairman of the Board or the person presiding as chairman of the Special Meeting may adjourn the Special Meeting to a later date, without notice other than announcement at the Special Meeting. If an adjournment is for more than 30 days, or if after the adjournment a new record date is fixed for the adjourned meeting, we will provide notice of the adjourned meeting to each stockholder of record entitled to vote at the meeting.

What vote is required to approve each proposal?

The affirmative vote of holders of a majority of the shares of our Common Stock (including shares of Series F Preferred Stock and Series G Preferred Stock, voting on an as-converted basis) outstanding as of the Record Date is required to approve the Reverse Stock Split Proposal. The principal terms of the amendment to the amended and restated certificate of incorporation have been approved by the Board. Because the vote is based on the total number of shares outstanding rather than the votes cast at the Special Meeting, your failure to vote or marking “ABSTAIN” on your proxy or ballot with respect to the Reverse Stock Split Proposal has the same effect as a vote against this proposal. We expect that the directors and executive officers will vote all their shares in favor of the Reverse Stock Split Proposal.

What are the consequences if the Reverse Stock Split Proposal is not approved by stockholders?

If stockholders fail to approve the Reverse Stock Split Proposal our Board would not have the authority to effect the Reverse Stock Split to, among other things, facilitate the continued listing of our Common Stock on Nasdaq by increasing the per share trading price of our Common Stock to help ensure a share price high enough to satisfy the $1.00 per share minimum bid price requirement. Any inability of our Board to effect the Reverse Stock Split could expose us to delisting from Nasdaq. In addition, our financing alternatives will be limited by the lack of any available unissued and unreserved authorized shares of Common Stock, and stockholder value may be harmed by this limitation. Moreover, our future success depends upon our ability to attract, retain and motivate highly-skilled employees, and if this proposal is not approved by our stockholders, the lack of any available unissued and unreserved authorized shares of Common Stock to provide future equity incentive opportunities could adversely impact our ability to achieve these goals.

Will the Company change its name as a result of the Reverse Stock Split?

No. The Company will retain the name “Staffing 360 Solutions, Inc.” and will remain incorporated under the laws of the State of Delaware.

Will the Reverse Stock Split change the business of Staffing?

No. The Reverse Stock Split will not change the current business of the Company. Following the Reverse Stock Split, we will continue to operate in the staffing sector.

Will Staffing have the same directors and executive officers that the Company currently has following the Reverse Stock Split?

Yes. The executive officers and members of the Board will not change as a result of the Reverse Stock Split.

Who is soliciting proxies, how are they being solicited, and who pays the cost?

Proxies are being solicited by the Board of Directors on behalf of the Company. In addition, we have engaged Morrow Sodali LLC (“Morrow”), the proxy solicitation firm hired by the Company, at an approximate cost of $7,500, to solicit proxies on behalf of our Board. Morrow may solicit the return of proxies, either by mail, telephone, telecopy, e-mail or through personal contact. The fees of Morrow as well as the reimbursement of expenses of Morrow will be borne by us. Our officers, directors, and employees may also solicit proxies personally or in writing, by telephone, e-mail, or otherwise. These officers and employees will not receive additional compensation but will be reimbursed for out-of-pocket expenses. Brokerage houses and other custodians, nominees, and fiduciaries, in connection with shares of the common stockCommon Stock registered in their names, will be asked to forward solicitation material to the beneficial owners of shares of common stock.Common Stock. We will reimburse brokerage houses and other custodians, nominees, and fiduciaries for their reasonable out-of-pocket expenses for forwarding solicitation materials and collecting voting instructions.

Do I have any dissenters’ or appraisal rights or cumulative voting rights with respect to any of the matters to be voted on at the Special Meeting?

No. None of our stockholders have any dissenters’ or appraisal rights or cumulative voting rights with respect to the matter to be voted on at the Special Meeting.

Where can I find the voting results of the Special Meeting?

The Company expects to publish the voting results of the Special Meeting in a Current Report on Form 8-K, which it expects to file with the SEC within four business days following the date of the Special Meeting.

Who can help answer my questions?

The information provided above in this “Question and Answer” format is for your convenience only and is merely a summary of the information contained in this proxy statement.Proxy Statement. We urge you to carefully read this entire Proxy Statement, including the documents we refer to in this proxy statement.Proxy Statement. If you have any questions, or need additional material, please feel free to contact Giselle Trent,the firm assisting us in the solicitation of proxies, Morrow Sodali, if you have any questions or need assistance in voting your shares. Banks and brokers may call Morrow Sodali at 646-507-5710.203-658-9400. Shareholders may call Morrow Sodali toll-free at 1-800-662-5200 or may send an email to STAF.info@investor.morrowsodali.com.

How many shares of Common Stock and Preferred Stock are outstanding?

As of May 7, 2021, there are 39,166,528 shares of Common Stock, 4,697.6328 shares of Series F Preferred Stock (representing 7,829,388 shares of Common Stock on an as-converted basis for purposes of voting on the Reverse Stock Split Proposal), and 7,665 shares of Series G Preferred Stock (including shares of both Series G Convertible Preferred Stock and Series G-1 Convertible Preferred Stock, and representing 7,665,000 shares of Common Stock on a fully-converted basis for purposes of voting on the Reverse Stock Split Proposal) outstanding.

PROPOSAL 1 –- APPROVAL OF AN AMENDMENT TO THE COMPANY’S AMENDED AND RESTATED CERTIFICATE OF INCORPORATION TO INCREASE THE NUMBER OF AUTHORIZED SHARES OF COMMONREVERSE STOCK SPLIT PROPOSAL

Our Board of Directors has approved, subject to stockholder approval, an amendment to our Amended and Restated Certificate of Incorporation to increaseReasons for the number of authorized shares of common stock, par value $0.00001, from 40,000,000 to 100,000,000 and to make a corresponding change to the number of authorized shares of capital stock. The form of the proposed Certificate ofReverse Stock Split Amendment effecting the amendment is attached to this Proxy Statement as Appendix A (the “Amendment”).

We currently haveMaintain Nasdaq Listing

On the date of the mailing of this proxy statement, our Common Stock was listed on the Nasdaq Capital Market (“Nasdaq”) under the symbol “STAF.” The continued listing requirements of Nasdaq, among other things, require that our Common Stock must maintain a totalclosing bid price in excess of 60,000,000$1.00 per share. On April 27, 2021, we received a letter from Nasdaq noting the Company’s failure to maintain a minimum bid price of $1 per share for 30 consecutive trading days. Nasdaq rules provide an initial 180-day period within which the Company may regain compliance by achieving ten consecutive trading days with a closing bid of $1. If the Company is not able to regain compliance during the initial 180 day period, Nasdaq will grant an additional 180 day period, provided the Company meets the applicable market value of publicly held shares requirement for continued listing, meets all other applicable standards for initial listing other than bid price, and notifies Nasdaq of capitalits intent to cure the deficiency and its willingness to effect a reverse stock authorized undersplit should it become necessary. However, if it appears to Nasdaq that the Company will be unable to regain compliance after the additional 180 day cure period, or if the Company is not otherwise eligible for the additional 180 day cure period, Nasdaq will provide notice that our Amended and Restated CertificateCommon Stock will be subject to delisting. If our Common Stock is delisted from Nasdaq, the Board believes that the trading market for our Common Stock could become significantly less liquid, which could reduce the trading price of Incorporation, consisting of 40,000,000 shares of common stock and 20,000,000 shares of preferred stock. Our Board is asking our stockholders to approve an amendment that will increase the number of authorized shares of common stock from 40,000,000 to 100,000,000Common Stock and increase the numbertransaction costs of authorizedtrading in shares of all classes of stock from 60,000,000 to 120,000,000. Theour Common Stock.

If the Reverse Stock Split Amendment is effected, it would cause a decrease in the total number of shares of authorized preferred stock would remain unchanged.

Backgroundour Common Stock outstanding and Purposeincrease the market price of our Common Stock. The Board intends to effect the Proposal

Our Board has determinedReverse Stock Split only if it believes that it would bea decrease in the Company’s best interests andnumber of shares outstanding is in the best interests of the Company and our stockholders and is likely to increaseimprove the number of authorized shares of common stock in order to provide the Company with the flexibility to pursue all finance and corporate opportunities involving our common stock, which may include private or public offeringstrading price of our equity securities, withoutCommon Stock and improve the needlikelihood that we will be allowed to obtain additional stockholder approvals. Each additional authorized sharemaintain our listing on Nasdaq. Accordingly, our Board approved the Reverse Stock Split as being in the best interests of common stock would have the same rights and privileges as each share of currently authorized common stock.Company.

Additional Authorized and Unissued Shares of Common Stock

On February 12, 2021, we closed a public offering (the “February 2021 Offering”) of 20,851,199 shares of our common stockCommon Stock at an offering price of price of $0.90 per share, as well as pre-funded warrants to purchase 1,004,081 shares of common stockCommon Stock to certain purchasers at a purchase price of $0.8999 per pre-funded warrant (equal to the price per share at which shares of common stockCommon Stock were sold to the public in the February 2021 Offering, minus the exercise price of $0.0001 for each pre-funded warrant). While the Board believes that the February 2021 Offering provided the Company with much needed equity financing, the offeringFebruary 2021 Offering required us to utilize all of the remaining authorized shares of common stockCommon Stock that were unreserved and available for issuance.

The Board believes that unless we obtain stockholder approval to amend our Amended and Restated Certificate of Incorporation to increaseeffect the number of authorized shares of common stock,Reverse Stock Split Amendment, we will be severely limited by the inability to issue additional shares of Common Stock in connection with future capital raising transactions or strategic transactions. This may cause a delay in our future capital raising or other strategic transactions and may have a material adverse effect on our business and financial condition. Accordingly, our Board approved the Reverse Stock Split as being in the best interests of the Company.

As of February 24,May 7, 2021, 39,166,528 shares of common stockCommon Stock were outstanding, with the remaining 833,472 shares of authorized common stockCommon Stock reserved for issuance. As of February 24,May 7, 2021, we had reserved, pursuant to various equity award plans, 162,100 shares of common stock,Common Stock, of which 76,500 were reserved for options granted and outstanding and 85,600 were reserved for future grants to our employees and Board of Directors.Board. In addition, as of that date, we had outstanding warrants to purchase up to 671,372 shares of common stock.Common Stock.

In addition to the above, as the February 24,of May 7, 2021, 8,490,5087,829,388 shares of common stockCommon Stock were issuable upon the conversion of the Base Series EF Preferred Stock (which may only be converted upon the Company amending its Certificate of Incorporation to effect a reverse stock split within a range of 2-into-1 to up to 20-into-1 to be determined by the Board, which must be in a ratio sufficient to provide for the full conversion of the Series F Preferred Stock, the full exercise of the Jackson Warrants and the satisfaction of the minimum bid requirements of the Nasdaq Capital Market (the “Reverse Stock Split Condition”)), and 8,570,507 shares of Common Stock were issuable upon the conversion of the Series E-1G Preferred Stock and the exercise of warrants (the “Jackson Warrants”) owned by Jackson Investment Group, LLC (“Jackson”). As further described below under “Jackson Waiver,” Jackson temporarily waived its right to convert or exercise such securities in order to facilitate the February 2021 Offering.

Thus, as of the Record Date, we had zero shares of authorized common stock remaining that were unissued and unreserved for issuance.

Jackson Waiver

On February 5, 2021, we received a waiver from Jackson (the “Jackson Waiver”) in connection with the February 2021 Offering. As part of the Jackson Waiver, Jackson agreed that it would not convert any shares of the Base Series E Preferred Stock or Series E-1 Preferred Stock into shares of our common stockCommon Stock or exercise any warrants to purchase sharesJackson Warrants until April 6, 2021, in order to allow us to utilize the authorized shares of common stockCommon Stock otherwise reserved for such issuances in the February 2021 Offering. Jackson iswas the sole holder of our outstanding shares of Base Series E Preferred Stock and Series E-1 Preferred Stock.Stock, and is the sole holder of our outstanding shares of Series G Preferred Stock, issued in exchange for the Series E Preferred Stock pursuant to the Exchange (as defined herein). This agreement was subsequently extended, most recently by the letter agreement between the Company and Jackson, dated May 6, 2021, pursuant to which Jackson extended the waiver to June 30, 2021.

As of February 24,May 7, 2021, without giving effect to such agreement not to exercise or convert, 1,413,000and giving effect to the recent exchange between the Company and Jackson of its shares of common stockBase Series E Preferred Stock and Series E-1 Preferred Stock for the same number of Series G Convertible Preferred Stock and Series G-1 Convertible Preferred Stock respectively, consummated on May 6, 2021 (the “Exchange”), 1,493,000 shares of Common Stock were issuable upon conversion of the 1,4131,493 shares of Series E-1G-1 Preferred Stock outstanding, 6,172,000 shares of common stockCommon Stock were issuable after October 31, 2022 upon conversion of the 6,172 shares of Base Series EG Convertible Preferred Stock outstanding, and 905,508 shares of common stockCommon Stock were issuable upon the conversion of the warrants owned by Jackson.Jackson Warrants.

Under the terms of the Jackson Waiver, we agreed to take all actions necessary to cause a meeting of stockholders to be held as soon as is reasonably possible and to present at such meeting a proposal to increase the number of authorized shares of common stockCommon Stock to at least a total of 100,000,000 shares, and to use our reasonable best efforts to solicit votes of our stockholders in favor of such proposal. Pursuant to such agreement, on March 1, 2021 we filed a proxy statement with a proposal to effect the foregoing, with a special meeting date set for April 5, 2021, later adjourned to April 20, 2021. The proposal to increase the number of authorized shares of Common Stock to at least a total of 100,000,000 shares was not successful.

Base Series EF Convertible Preferred Stock

As of May 7, 2021, the Series F Preferred Stock is convertible into an aggregate of approximately 7,829,388 shares of Common Stock at a conversion price of $0.60 per share, subject to certain ownership limitations, upon the occurrence of the Reverse Stock Split Condition. Under the terms of the securities purchase agreement entered into in connection with the sale of the Series F Preferred Stock, we are required to hold a special meeting of shareholders by June 22, 2021 for the purpose of obtaining stockholder approval of the Reverse Stock Split Amendment.

The Series F Preferred Stock is only entitled to dividends in the event dividends are paid on our Common Stock and will not have any preferences over our Common Stock, including liquidation rights.

Subject to certain beneficial ownership limitations, the Series F Preferred Stock shall vote on an “as converted” basis on all matters submitted to the holders of Common Stock for approval; provided, however, that solely for purposes of determining the number of votes that the Series F Preferred Stock is entitled to, the “Conversion Price” of the Series F Preferred Stock shall be deemed $0.725.

Series G Convertible Preferred Stock and Series E-1G-1 Convertible Preferred Stock

The Base Series EG Preferred Stock ranks senior to each of the Company’s Common Stock, Series A Convertible Preferred Stock, Series B Convertible Preferred Stock and Series E-1C Convertible Preferred Stock, rank senior to common stock and any other classes and series or classes of preferred stock of the Company now or afterhereafter authorized, issued or outstanding, which by their terms expressly provide that they are junior to the Series G Preferred Stock or which do not specify their rank (which includes the Series F Preferred Stock). Each share of Series G Preferred Stock is initially convertible into 1,000 shares of Common Stock at any time from and after, (i) with respect to the Series G Convertible Preferred Stock, the earlier of October 31, 2022 or the occurrence of a Preferred Default (as defined in the Certificate of Designation of Series G Preferred Stock (the “Certificate of Designation”)) and, (ii) with respect to the Series G-l Convertible Preferred Stock, October 31, 2020. A holder of Series G Preferred Stock is not required to pay any additional consideration in exchange for conversion of the Series G Preferred Stock into the Company’s Common Stock.

The Series G Convertible Preferred Stock carries monthly dividend rights and rights on liquidation, winding up and dissolution. Holders of Base(a) cash dividends accruing (i) at an annual rate per share equal to 12% from the date of issuance (plus any accrued dividends with respect to the Series E Convertible Preferred Stock are entitled to receiveunpaid as of the date of the Exchange) and (ii) 17% after the occurrence of a Preferred Default, and (b) a dividend payable in shares of Series E-1G-1 Convertible Preferred Stock. The shares of Series G-1 Convertible Preferred Stock which will accrue at a rate of 5% per year ofhave all the liquidation value ofsame terms, preferences and characteristics as the outstanding Base Series EG Convertible Preferred Stock while(including, without limitation, the Baseright to receive cash dividends), except Series E Preferred Stock remains outstanding.

Shares of Series E-1G-1 Convertible Preferred Stock are convertible into our common stockmandatorily redeemable by the Company within thirty (30) days after written demand received from any holder at any time after the earlier of the occurrence of a conversion ratePreferred Default or September 30, 2022, for a cash payment equal to the liquidation valueLiquidation Value (as defined in the Certificate of each share of Series E-1 Preferred Stock divided by $1.00 per share. Each share of Series E-1 Preferred Stock has a liquidation value of $1,000 per share.

Shares of Base Series E Preferred Stock will also be convertible into shares of our common stock after October 31, 2022. The conversion rate for Base Series E Preferred Stock is equal to the liquidation value of each shares of Base Series E Preferred Stock divided by $1.00 per share. Each share of Base Series E Preferred Stock has a liquidation value of $1,000 per share.Designation) plus any accrued and unpaid dividends thereon.

As of February 24,May 7, 2021, 6,172,000 shares and 1,413,0001,493,000 shares of common stockCommon Stock were issuable upon the potential conversion of Base Series EG Convertible Preferred Stock and Series E-1G-1 Convertible Preferred Stock, respectively.

Holders of Base The Series E Preferred Stock are entitled to monthly cash dividends at a per annum rate of 12%. At our option, up to 50% of the cash dividend on the Base Series E Preferred Stock may be paid in kind by adding such 50% portion to the outstanding liquidation value of the Base Series E Preferred Stock (the “PIK Dividend Payment”), with this option ending on October 25, 2021. If the PIK Dividend Payment is elected, a holder of Base Series E Preferred Stock is entitled to additional fee to be paid in shares of our common stock an amount equal to $10 divided by the average closing price, as reported by Nasdaq of such shares of common stock over the 5 trading days prior to the applicable monthly interest payment date. If such average market price is less than $0.50, or is otherwise undeterminable because such shares are no longer publicly traded or the closing price is no longer reported by Nasdaq, then the average closing price for these purposes shall be deemed to be $0.50, and if such average closing price is greater than $3.50 then the average closing price for these purposes shall be deemed to be $3.50.

Except as provided by law or by the other provisions of the Certificate of Incorporation and as provided below, holders of Base Series E Preferred Stock and Series E-1G Preferred Stock shall have no rightvote on an “as converted” basis on all matters submitted to vote such shares on any matter presented to our stockholdersthe holders of Common Stock for their action or consideration.approval.

Potential Consequences if the Reverse Stock Split Proposal 1 is Not Approved

If this proposalthe Reverse Stock Split Proposal is not approved by our stockholders, our Board will not have the authority to effect the Reverse Stock Split Amendment to, among other things, facilitate the continued listing of our Common Stock on Nasdaq by increasing the per share trading price of our Common Stock to help ensure a share price high enough to satisfy the $1.00 per share minimum bid price requirement. Any inability of our Board to effect the Reverse Stock Split could expose us to delisting from Nasdaq. In addition, our financing alternatives will be limited by the lack of any available unissued and unreserved authorized shares of common stock,Common Stock, and stockholder value may be harmed by this limitation. In addition,Moreover, our future success depends upon our ability to attract, retain and motivate highly-skilled employees, and if this proposal is not approved by our stockholders, the lack of any available unissued and unreserved authorized shares of common stockCommon Stock to provide future equity incentive opportunities could adversely impact our ability to achieve these goals. In short, if our stockholders do not approve this proposal, we may not be able to maintain our Nasdaq listing, access the capital markets, complete corporate collaborations, partnerships or other strategic transactions, attract, retain and motivate employees, and pursue other business opportunities integral to our growth and success.

Additionally, in the event we may fail to secure the requisite stockholder approval for the increase inReverse Stock Split Proposal or to effect the number of authorized shares of common stock,Reverse Stock Split Amendment by June 30, 2021, it will result in an event of defaulta “Preferred Default” under our Second Amended and Restated Note Purchase Agreement, dated as of October 26, 2020 (the “Amended Note Purchase Agreement”), the Series E Certificate of Designation, and the amended and restated warrant agreement, dated as of April 25, 2018, as amended, with Jackson. As of February 24, 2021, $19,154,364 of principal is outstanding under the Amended Note Purchase Agreement. If not cured or waived, such event of default couldwhich would result in usthe higher interest rate of 17% being required to repay these borrowings before their due date or require us to redeem outstanding shares of Series E Preferred Stock,triggered, which would have a materialan adverse effect on our business, financial condition and results of operations.

Additionally, the Series E Certificate of Designation only permits us to pay a quarterly cash dividend of one cent per share of issued and outstanding common stock;stock, provided, that such cash dividend does not exceed $100,000 in the aggregate per fiscal quarter. We may not pay such dividends if any events of default existPreferred Default exists under our debt agreements or the Series E Certificate of Designation.

Management has historically been able to obtain from Jackson waivers of any non-compliance and management expects to continue to be able to obtain necessary waivers in the event of future non-compliance; however, there can be no assurance that we will be able to obtain such waivers. Furthermore, Jackson may require fees and expenses to be paid or other changes to terms in connection with waivers or amendments. If we are forced to refinance these borrowings on less favorable terms, our results of operations and financial condition could be adversely affected by increased costs and rates.

Rights of Additional Authorized SharesEffective Time

If and when issued, the additional common stockReverse Stock Split proposal is approved by our stockholders, the Board will have the discretion to implement the Reverse Stock Split or to not effect the Reverse Stock Split at all. The Board currently intends to effect the Reverse Stock Split. If the trading price of our Common Stock increases without effecting the Reverse Stock Split, the Reverse Stock Split may not be authorized by adoptionnecessary. Following the Reverse Stock Split, if implemented, there can be no assurance that the market price of our Common Stock will rise in proportion to the reduction in the number of outstanding shares resulting from the Reverse Stock Split or that the market price of the Amendment would have rightspost-split Common Stock can be maintained above $1.00. There also can be no assurance that our Common Stock will not be delisted from Nasdaq for other reasons.

If our stockholders approve the Reverse Stock Split proposal at the special meeting, the Reverse Stock Split will be effected, if at all, only upon a determination by the Board that the Reverse Stock Split is in the best interests of the Company and privileges identicalits stockholders at that time. No further action on the part of the stockholders will be required to either effect or abandon the Reverse Stock Split. If our Board does not implement the Reverse Stock Split prior to our currently outstanding common stock. Those rights do not include preemptive rights with respect2021 annual stockholder meeting, the authority granted in this proposal to implement the future issuance of any additional shares of common.

Potential Adverse Effects of Increase in Authorized CommonReverse Stock

Future issuances of common stock or securities convertible into common stock could have a dilutive effect on our earnings per share, book value per share, Split will terminate and the voting power and ownership interest of current stockholders. Stockholders shouldReverse Stock Split Amendment will be aware that because we currently have almost no authorized but unissued shares of common stock remaining, the holder of our Base Series E Preferred Stock and Series E-1 Preferred Stock is currently prevented from converting shares of Base Series E Preferred Stock and Series E-1 Preferred Stock into our common stock. As discussed above, as of February 24, 2021, 6,172,000 shares and 1,413,000 shares of common stock were issuable upon the potential conversion of Base Series E Preferred Stock and Series E-1 Preferred Stock, respectively. As a result, future conversions of the Base Series E Preferred Stock and Series E-1 Preferred Stock would likely cause substantial dilution to existing stockholders.

Anti-Takeover Effectsabandoned.

The increased proportionmarket price of unissued authorizedour Common Stock is dependent upon our performance and other factors, some of which are unrelated to the number of shares compared to issued shares could, under certain circumstances, haveoutstanding. If the Reverse Stock Split is effected and the market price of our Common Stock declines, the percentage decline as an anti-takeover effect (for example, by permitting issuances thatabsolute number and as a percentage of our overall market capitalization may be greater than would dilute the stock ownership of a person seeking to effect a changeoccur in the compositionabsence of the Reverse Stock Split. Furthermore, the reduced number of shares that will be outstanding after the Reverse Stock Split could significantly reduce the trading volume and otherwise adversely affect the liquidity of our Board or contemplating a tender offer or other transaction for our combination with another company). However,Common Stock.

We have not proposed the Amendment is not being proposedReverse Stock Split in response to any effort of which we are aware to accumulate our shares of our common stockCommon Stock or obtain control of ourthe Company, nor is it part of a plan by management to recommend a series of similar amendmentsactions to our Board andor our stockholders.

Notwithstanding the decrease in the number of outstanding shares of Common Stock following the Reverse Stock Split, our Board does not intend for this transaction to be the first step in a “going private transaction” within the meaning of Rule 13e-3 of the Securities Exchange Act of 1934 (the “Exchange Act”).

Timing of Proposed AmendmentAnti-Takeover Effects

If Proposal 1 is approved byIn addition, we have not proposed the stockholders, as soon as practicable after the Special Meeting, we will file the AmendmentReverse Stock Split, with the office of the Secretary of State of Delaware to implement theits corresponding increase in the authorized and unissued number of shares of common stockCommon Stock, with the intention of using the additional shares for anti-takeover purposes, although we could theoretically use the additional shares to make more difficult or to discourage an attempt to acquire control of the Company.

We do not believe that our officers or directors have interests in this proposal that are different from or greater than those of any other of our stockholders.

Effects of the Reverse Stock Split on Common Stock

Pursuant to the Reverse Stock Split, each holder of our Common Stock outstanding immediately prior to the effectiveness of the Reverse Stock Split (“Old Common Stock”) will become the holder of fewer shares of our Common Stock (“New Common Stock”) after consummation of the Reverse Stock Split.

Although the Reverse Stock Split will not, by itself, impact our assets or prospects, the Reverse Stock Split could result in a decrease in the aggregate market value of our Common Stock. The Board believes that this risk is outweighed by the benefits of continued listing of our Common Stock on the Nasdaq exchange.

If effected, the Reverse Stock Split will result in some stockholders owning “odd-lots” of less than 100 shares of Common Stock. Brokerage commissions and corresponding changeother costs of transactions in odd-lots are generally higher than the costs of transactions in “round-lots” of even multiples of 100 shares.

Based on 39,166,528 shares of our Common Stock outstanding as of the date hereof, the following table reflects the approximate number of shares of our Common Stock that would be outstanding as a result of the Reverse Stock Split under certain possible exchange ratios.

The Reverse Stock Split will affect all stockholders equally and will not affect any stockholder’s proportionate equity interest in the Company, except for those stockholders who receive an additional share of our Common Stock in lieu of a fractional share. None of the rights currently accruing to holders of our Common Stock will be affected by the Reverse Stock Split. Following the Reverse Stock Split, each share of New Common Stock will entitle the holder thereof to one vote per share and will otherwise be identical to Old Common Stock. The Reverse Stock Split also will have no effect on the number of authorized shares of our Common Stock. The shares of New Common Stock will be fully paid and non-assessable.

The par value per share of the Common Stock will remain unchanged at $0.00001 per share after the Reverse Stock Split. As a result, on the effective date of the Reverse Stock Split, if any, the stated capital stock. Upon approvalon our balance sheet attributable to the Common Stock will be reduced proportionately based on the Reverse Stock Split ratio, from its present amount, and the additional paid-in capital account will be credited with the amount by which the stated capital is reduced. After the Reverse Stock Split, net income or loss per share and other per share amounts will be increased because there will be fewer shares of our Common Stock outstanding. In future financial statements, net income or loss per share and other per share amounts for periods ending before the Reverse Stock Split would be recast to give retroactive effect to the Reverse Stock Split. As described below under “Effects of the Reverse Stock Split on Outstanding Equity Awards and Warrants to Purchase Common Stock,” the per share exercise price of outstanding option awards and warrants would increase proportionately, and the number of shares of our Common Stock issuable upon the exercise of outstanding options and warrants, or that relate to other equity awards (e.g., restricted stock awards) would decrease proportionately, in each case based on the Reverse Stock Split ratio selected by the Board. The Company does not anticipate that any other accounting consequences would arise as a result of the Reverse Stock Split.

We are currently authorized to issue a maximum of 40,000,000 shares of our Common Stock. As of the Record Date, there were 39,166,528 shares of our Common Stock issued and outstanding. Although the number of authorized shares of our Common Stock will not change as a result of the Reverse Stock Split, the number of shares of our Common Stock issued and outstanding will be reduced in proportion to the ratio selected by the Board. Thus, the Reverse Stock Split will effectively increase the number of authorized and unissued shares of our Common Stock available for future issuance by the amount of the reduction effected by the Reverse Stock Split. Conversely, with respect to the number of shares reserved for issuance under, for example, our 2020 Omnibus Incentive Plan (the “2020 Plan”), our Board will proportionately reduce such reserve in accordance with the terms of the 2020 Plan. As of the Record Date, there were 750,000 shares of Common Stock reserved for issuance under the 2020 Plan, of which 718,997 remained available for future awards, and following the Reverse Stock Split, if any, such reserve will be reduced to between 37,500 - 375,000 shares of Common Stock, of which between approximately 35,950 - 359,499 shares will be available for future awards.

Following the Reverse Stock Split, the Board will have the authority, subject to applicable securities laws, to issue all authorized and unissued shares without further stockholder approval, upon such terms and conditions as the Board deems appropriate. We do not currently have any plans, proposals or understandings to issue the additional shares that would be available if the Reverse Stock Split is approved and effected, but some of the additional shares underlie warrants or shares of convertible preferred stock, which could be exercised or converted after the Reverse Stock Split Amendment is effected.

Effects of the Reverse Stock Split on Outstanding Equity Awards and Warrants to Purchase Common Stock

If the Reverse Stock Split is effected, all outstanding options entitling their holders to purchase shares of our Common Stock, as well as any other equity awards granted pursuant to the 2020 Plan (e.g., restricted stock awards) or pursuant to the 2014 Equity Incentive Plan (the “2014 Plan”), the 2015 Omnibus Incentive Plan (the “2015 Plan”), or the 2016 Omnibus Incentive Plan (the “2016 Plan”, and together with the 2014 Plan, the 2015 Plan, and the 2020 Plan referred to herein as, the “Incentive Plans”), will be proportionately reduced, in accordance with the terms of the applicable Incentive Plan, in the same ratio as the reduction in the number of shares of outstanding Common Stock, except that any fractional shares resulting from such reduction will be rounded down to the nearest whole share to comply with the requirements of Code Sections 409A and 424. Correspondingly, the per share exercise price of any such options will be increased in direct proportion to the Reverse Stock Split ratio (rounded up to the nearest whole cent), so that the aggregate dollar amount payable for the purchase of the shares subject to the options will remain materially unchanged. For example, assuming that we effect the Reverse Stock Split at a ratio of 1-for-5, and that an optionee holds options to purchase 1,033 shares of our Common Stock at an exercise price of $1.00 per share, upon the effectiveness of the Reverse Stock Split at such ratio, the number of shares of the Common Stock subject to that option would be reduced to 206 (rounded down from 206.6 to account for fractional shares) and the exercise price would be proportionately increased to $5.00 per share.

As of May 7, 2021, there are 1,576,879 warrants to purchase Common Stock outstanding, representing 1,576,879 shares of Common Stock at a weighted average exercise price of $0.99 per share. If the Reverse Stock Split is effected, the outstanding warrants will automatically be reduced in the same ratio as the reduction in the number of shares of outstanding Common Stock. Correspondingly, the per share exercise price of such warrants will be increased in direct proportion to the Reverse Stock Split ratio, so that the aggregate dollar amount payable for the purchase of the shares subject to the warrants will remain unchanged.

Effects of the Reverse Stock Split on Preferred Stock

As of May 7, 2021, there are 4,697.6328 shares of Series F Preferred Stock, representing 7,829,388 shares of Common Stock, and 7,665 shares of Series G Preferred Stock (including shares of both Series G Convertible Preferred Stock and Series G-1 Convertible Preferred Stock) representing 7,665,000 shares of Common Stock. If the Reverse Stock Split is effected, each of our outstanding series of convertible preferred stock have adjustment provisions such that the number of shares of Common Stock issuable upon conversion of such preferred stock shall be decreased in proportion to such decrease in the aggregate number of shares of Common Stock outstanding.

Shares of Common Stock Issued and Outstanding

With the exception of the number of shares issued and outstanding, the rights and preferences of the shares of our Common Stock prior and subsequent to the Reverse Stock Split will remain the same. After the effectiveness of theReverse Stock Split, we do not anticipate that our financial condition, the percentage ownership of management, the number of our stockholders, or any aspect of our business would materially change as a result of the Reverse Stock Split.

Our Common Stock is currently registered under Section 12(b) of the Exchange Act, and as a result, we are subject to the periodic reporting and other requirements of the Exchange Act. If effected, the proposed Reverse Stock Split will not affect the registration of our Common Stock under the Exchange Act or our periodic or other reporting requirements thereunder.

Increase of Shares of Common Stock Available for Future Issuance

As a result of the Reverse Stock Split, there will be a reduction in the number of shares of our Common Stock issued and outstanding, and an associated increase in the number of authorized shares that would be unissued and available for future issuance after the Reverse Stock Split. Such shares could be used for any proper corporate purpose approved by the Board including, among other purposes, future financing transactions.

Holders of our Common Stock have no preemptive or other subscription rights.

Effectiveness of the Reverse Stock Split

The Reverse Stock Split, if approved by our stockholders, will become effective upon the filing with the Secretary of State of the State of Delaware of a certificate of amendment to our amended and restated certificate of incorporation in substantially the form of the Reverse Stock Split Amendment attached to this proxy statement as Annex A. The exact timing of the filing of the Reverse Stock Split Amendment will becomebe determined by the Board based upon its evaluation of when such action will be most advantageous to the Company and our stockholders. The Board reserves the right, notwithstanding stockholder approval and without further action by our stockholders, to elect not to proceed with the Reverse Stock Split if, at any time prior to filing such Reverse Stock Split Amendment, the Board, in its sole discretion, determines that it is no longer in the best interests of the Company and our stockholders. The Board currently intends to effect the Reverse Stock Split. If our Board does not implement the Reverse Stock Split prior to our 2021 annual stockholder meeting, the authority granted in this proposal to implement the Reverse Stock Split will terminate and the Reverse Stock Split Amendment to effect the Reverse Stock Split will be abandoned.

Effect on Registered and Beneficial Stockholders

Upon the Reverse Stock Split, the Company intends to treat stockholders holding shares of our Common Stock in “street name” (that is, held through a bank, broker or other nominee) in the same manner as stockholders of record whose shares of Common Stock are registered in their names. Banks, brokers or other nominees will be instructed to effect the Reverse Stock Split for their beneficial holders holding shares of our Common Stock in “street name”; however, these banks, brokers or other nominees may apply their own specific procedures for processing the Reverse Stock Split. If you hold your shares of our Common Stock with a bank, broker or other nominee, and have any questions in this regard, the Company encourages you to contact your nominee.

Effect on “Book-Entry” Stockholders of Record

The Company’s stockholders of record may hold some or all of their shares electronically in book-entry form. These stockholders will not have stock certificates evidencing their ownership of our Common Stock. They are, however, provided with a statement reflecting the number of shares of Common Stock registered in their accounts.

If you hold registered shares of Old Common Stock in a book-entry form, you do not need to take any action to receive your shares of New Common Stock in registered book-entry form, if applicable. A transaction statement will automatically be sent to your address of record as soon as practicable after the effective time of the Reverse Stock Split indicating the number of shares of New Common Stock you hold.

Effect on Registered Certificated Shares

Some stockholders of record hold their shares of our Common Stock in certificate form or a combination of certificate and book-entry form. If any of your shares of our Common Stock are held in certificate form, you will receive a transmittal letter from the Company’s transfer agent as soon as practicable after the effective time of the Reverse Stock Split, if any. The transmittal letter will be accompanied by instructions specifying how to exchange your certificate representing the Old Common Stock for a statement of holding or a certificate of New Common Stock.

STOCKHOLDERS SHOULD NOT DESTROY ANY SHARE CERTIFICATE(S) AND SHOULD NOT SUBMIT ANY CERTIFICATE(S) UNTIL REQUESTED TO DO SO.

Fractional Shares

Fractional shares will not be issued in connection with the Reverse Stock Split. Each stockholder who would otherwise hold a fractional share as a result of the Reverse Stock Split will receive one share of Common Stock in lieu of such fractional share.

Appraisal Rights

Under the Delaware General Corporation Law, our stockholders are not entitled to appraisal or dissenter’s rights with respect to the Reverse Stock Split, and we will not independently provide our stockholders with any such rights.

Regulatory Approvals

The Reverse Stock Split will not be consummated, if at all, until after approval of the Company’s stockholders is obtained. The Company is not obligated to obtain any governmental approvals or comply with any state or federal regulations prior to consummating the Reverse Stock Split other than the filing of the Reverse Stock Split Amendment with the Secretary of State of the State of Delaware.

Certain Federal Income Tax Consequences

The following is a discussion of certain material U.S. federal income tax consequences of the Reverse Stock Split to U.S. holders (as defined below). This discussion is included for general information purposes only and does not purport to address all aspects of U.S. federal income tax law that may be relevant to U.S. holders in light of their particular circumstances. This discussion is based on the date it is filed.Internal Revenue Code of 1986, as amended (the “Code”), and current Treasury regulations, administrative rulings and court decisions, all of which are subject to change, possibly on a retroactive basis, and any such change could affect the continuing validity of this discussion.

STOCKHOLDERS ARE URGED TO CONSULT THEIR TAX ADVISORS AS TO THE PARTICULAR FEDERAL, STATE, LOCAL, OR FOREIGN TAX CONSEQUENCES TO THEM OF THE REVERSE STOCK SPLIT.

This discussion does not address tax consequences to stockholders that are subject to special tax rules, such as banks, insurance companies, regulated investment companies, personal holding companies, U.S. holders whose functional currency is not the U.S. dollar, partnerships (or other flow-through entities for U.S. federal income purposes and their partners or members), persons who acquired their shares or equity awards in connection with employment or other performance of services (who will not incur a taxable event in connection with the reverse stock split), broker-dealers, foreign entities, nonresident alien individuals and tax-exempt entities. This summary also assumes that the Old Common Stock shares were, and the New Common stock shares will be, held as a “capital asset,” as defined in Section 1221 of the Code.

As used herein, the term “U.S. holder” means a holder that is, for U.S. federal income tax purposes:

Other than with respect to any stockholder that receives a full share for a fractional share (which will not apply to outstanding equity awards granted under the Incentive Plans), a stockholder generally will not recognize a gain or loss by reason of such stockholder’s receipt of shares of New Common Stock pursuant to the Reverse Stock Split solely in exchange for shares of Old Common Stock held by such stockholder immediately prior to the Reverse Stock Split. A stockholder’s aggregate tax basis in the shares of New Common Stock received pursuant to the Reverse Stock Split (including any fractional shares) will equal the stockholder’s aggregate basis in the Old Common Stock exchanged therefore and will be allocated among the shares of New Common Stock received in the Reverse Stock Split on a pro-rata basis. Stockholders who have used the specific identification method to identify their basis in the shares of Old Common Stock held immediately prior to the Reverse Stock Split should consult their own tax advisers to determine their basis in the shares of New Common Stock received in exchange therefor in the Reverse Stock Split. A stockholder’s holding period in the shares of New Common Stock received pursuant to the Reverse Stock Split will include the stockholder’s holding period in the shares of Old Common Stock surrendered in exchange therefore, provided the shares of Old Common Stock surrendered are held as capital assets at the time of the Reverse Stock Split.

No gain or loss will be recognized by us as a result of the Reverse Stock Split.

Required Vote

The approval of the proposal to effect the increase in the authorized sharesReverse Stock Split will require the affirmative vote of the holders of a majority of the shares of the Company’s outstanding common stock.Common Stock. Because the vote is based on the total number of shares outstanding rather than the votes cast at the Special Meeting, your failure to vote on the Reverse Stock Split Proposal 1 has the same effect as a vote against the proposal.Reverse Stock Split.

With respect to any other matter that properly comes before the meeting, the proxy holders will vote as recommended by the Board or, if no recommendation is given, in their own discretion.

If you sign and return your proxy card but do not specify how you want to vote your shares, the persons named as proxy holders on the proxy card will vote in accordance with the recommendations of the Board.

Recommendation

THE BOARD UNANIMOUSLY RECOMMENDS THAT THE STOCKHOLDERS

VOTE “FOR” APPROVAL OF PROPOSAL 1.THE REVERSE STOCK SPLIT.

SECURITY OWNERSHIP OF CERTAIN BENEFICIAL OWNERS AND MANAGEMENT

The following table sets forth certain information with respect to the beneficial ownership of our common stockCommon Stock as of the Record DateMay 7, 2021 for: (i) each of our directors; (ii) each of our named executive officers; (iii) all of our directors and executive officers as a group; and (iv) all persons, to our knowledge, that are the beneficial owners of more than 5%five percent (5%) of the outstanding shares of our common stock.Common Stock. Beneficial ownership is determined in accordance with the rules of the SEC, and includes voting or investment power with respect to the securities.

Except as indicated in footnotes to this table, we believe each person named in this table has sole voting and investment power with respect to the shares of commoncapital stock set forth opposite such person’s name. Percentage ownership is based on 39,166,528 shares of common stockCommon Stock outstanding on the Record Date.

* less than 1%

(1) Shares of common stock beneficially owned and the respective percentages of beneficial ownership of common stock assume the exercise of all options and other securities convertible into common stock beneficially owned by such person or entity currently exercisable or exercisable within 60 days of the Record Date, except as otherwise noted. Shares issuable pursuant to the exercise of stock options and other securities convertible into common stock exercisable within 60 days are deemed outstanding and held by the holder of such options or other securities for computing the percentage of outstanding common stock beneficially owned by such person, but are not deemed outstanding for computing the percentage of outstanding common stock beneficially owned by any other person.

(2) Includes 695,512 shares of common stock owned and 19,200 options that are currently exercisable or may be exercised by Mr. Flood within 60 days of February 24, 2021

(3) Mr. Anwar owns 10,000 shares of common stock.

(4) Includes 5,550 shares of common stock held personally by Mr. Villard and 37,800 shares held through Byzantine Productions, Inc., for which Mr. Villard is deemed the beneficial owner with sole voting and dispositive power over the securities held by the entity, and Mr. Villard holds options to purchase 1,000 shares.

(5) Mr. Grout owns 43,934 shares of common stock and holds options to purchase 1,000 shares of stock.

(6) Includes 4,200 shares of common stock held personally by Mr. Florio and 40,299 shares of common stock and options to purchase 1,000 shares of common stock held in the name of Citrin Cooperman for which Mr. Florio is deemed the beneficial owner with sole voting and dispositive power over the securities held by the firm.

(7) Ms. Barker owns 76,800 shares of common stock.

(8) Includes 2,068,696 shares of common stock owned, 905,508 shares of common stock issuable upon the exercise of warrants with an exercise price of $1.00, 6,172,000 shares of common stock issuable upon conversion of 6,172 shares of Base Series E Preferred Stock (convertible after October 31, 2022), and 1,413,000 shares of common stock issuable upon conversion of 1,413 shares of Series E-1 Preferred Stock. Does not give effect to the Limited Waiver and Agreement Jackson and we executed on February 5,May 7, 2021.

(9) As reported in a Schedule 13G filed on February 19, 2021 by Heights Capital Management, Inc. giving information on share holdings as of that date. Heights Capital Management, Inc. is the investment manager to CVI Investments, Inc. and as such may exercise voting and dispositive power over these shares.

SUBMISSIONREQUIREMENTS FOR ADVANCE NOTIFICATION OF FUTURENOMINATIONS
AND STOCKHOLDER PROPOSALS

Pursuant to Rule 14a-8 under the Exchange Act, a stockholder proposal submitted for inclusion in our proxy statement for the 2021 annual meeting must be received no later than April 16, 2021. However, pursuant to such rule, if the 2021 annual meetingAnnual Meeting is held on a date that is before August 30, 2021 or after October 29, 2021, then a stockholder proposal submitted for inclusion in our proxy statement for the 2021 annual meetingAnnual Meeting must be received by us a reasonable time before we begin to print and mail our proxy statement for the 2021 annual meeting.Annual Meeting. Stockholder proposals should be addressed to the CorporationCompany at 641 Lexington Avenue, Suite 2701, New York NY 10022.

Proposals submitted outside Rule 14a-8 of the Exchange Act must comply with our bylaws. To be timely in connection with our next annual meeting, a stockholder proposal concerning director nominations or other business must be received by the Company at its principal executive offices between June 1, 2021 and July 1, 2021; provided, however, if and only if the 2021 annual meetingAnnual Meeting is not scheduled to be held before August 30, 2021 or after December 8, 2021, such stockholder’s notice must be delivered not earlier than 120 days prior to the date of the 2021 annual meeting and not later than the later of (A) the tenth day following the date of the public announcement of the date of the 2021 annual meetingAnnual Meeting or (B) the date which is 90 days prior to the date of the 2021 annual meeting.Annual Meeting. Recommendations from stockholders which are received after the applicable deadline likely will not be considered timely for consideration by our Nominating and Corporate Governance Committee for next year’s annual meeting.

HOUSEHOLDING OF PROXY MATERIALS

If you and other residents at your mailing address own shares in street name, your broker or bank may have sent you a notice that your household will receive only one copy of proxy materials for each company in which you hold shares through that broker or bank. This practice of sending only one copy of proxy materials is known as householding. If you did not respond that you did not want to participate in householding, you were deemed to have consented to the process. If the foregoing procedures apply to you, your broker has sent one copy of our Proxy Statement and related proxy materials to your address. If you want to receive separate copies of the proxy materials in the future, or you are receiving multiple copies and would like to receive only one copy per household, you should contact your stockbroker, bank or other nominee record holder, or you may contact us at the address or telephone number below. In any event, if you did not receive an individual copy of this Proxy Statement, we will send a copy to you if you address your written request to, or call, the corporate Secretary of Staffing 360 Solutions, Inc., 641 Lexington Avenue, 27^th Floor, New York NY 10022, telephone number 646-507-5710.

OTHER MATTERS

The Board does not intend to bring any other matters before the Special Meeting and has no reason to believe any other matters will be presented. If other matters properly do come before the Special Meeting, however, it is the intention of the persons named as proxy agents in the enclosed proxy card to vote on such matters as recommended by the Board, or if no recommendation is given, in their own discretion.

REGARDLESS OF WHETHERIf you and other residents at your mailing address own shares in street name, your broker or bank may have sent you a notice that your household will receive only one copy of proxy materials for each company in which you hold shares through that broker or bank. This practice of sending only one copy of proxy materials is known as householding. If you did not respond that you did not want to participate in householding, you were deemed to have consented to the process. If the foregoing procedures apply to you, your broker has sent one copy of our Proxy Statement to your address. If you want to receive separate copies of the proxy materials in the future, or you are receiving multiple copies and would like to receive only one copy per household, you should contact your stockbroker, bank or other nominee record holder, or you may contact us at the address or telephone number below. In any event, if you did not receive an individual copy of this Proxy Statement, we will send a copy to you if you address your written request to, or call, the corporate Secretary of Staffing 360 Solutions, Inc., 641 Lexington Avenue, 27th Floor, New York NY 10022, telephone number 646-507-5716.

Copies of the documents referred to above that appear on our website are also available upon request by any stockholder addressed to our corporate Secretary, Staffing 360 Solutions, Inc., 641 Lexington Avenue, 27th Floor, New York NY 10022.

WHERE YOU PLAN TO PARTICIPATE IN THE VIRTUAL MEETING, PLEASE READ THIS PROXY STATEMENT AND THEN VOTE, ELECTRONICALLY BY INTERNET OR BY TELEPHONE, OR BY POSTAL MAIL, AS PROMPTLY AS POSSIBLE. VOTING PROMPTLY WILL ENSURE THAT YOUR SHARES ARE REPRESENTED AT THE VIRTUAL MEETING.CAN FIND ADDITIONAL INFORMATION

We are subject to the informational requirements of the Exchange Act and, therefore, we file annual, quarterly and current reports, proxy statements and other information with the SEC. Our SEC filings are available to the public on the SEC’s website at www.sec.gov. The SEC’s website contains reports, proxy and information statements and other information regarding issuers, such as us, that file electronically with the SEC. You may also read and copy any document we file with the SEC at the SEC’s Public Reference Room at 100 F Street, N.E., Room 1580, Washington, D.C. 20549. You may also obtain copies of these documents at prescribed rates by writing to the SEC. Please call the SEC at 1-800-SEC-0330 for further information on the operation of its Public Reference Room.

Annexes

(see following pages for each Annex referenced in the Proxy Statement)

AppendixAnnex A

Form of Proposed Amendment
to

the
Amended and Restated Certificate of Incorporation
of

Staffing 360 Solutions, Inc.

The Fourth Article ofIf the Amended and Restated Certificate of IncorporationReverse Stock Split Proposal is herebyapproved, the amended and restated certificate of incorporation of Staffing 360 Solutions, Inc. will be amended to add the following as paragraph (e) of Article FOURTH in its entirety as follows:the form below:

FOURTH. Capital“(e). Upon the effectiveness of the filing of this Certificate of Amendment (the “Effective Time”) each share of the Corporation’s common stock, $0.00001 par value per share (the “Old Common Stock”), either issued or outstanding or held by the Corporation as treasury stock, immediately prior to the Effective Time, will be automatically reclassified as (without any further act) into a smaller number of shares such that each two (2) to twenty (20) shares of Old Common Stock issued and outstanding or held by the Company as treasury stock immediately prior to the Effective Time is reclassified into one share of Common Stock, $0.00001 par value per share, of the Corporation (the “New Common Stock”), the exact ratio within such range to be determined by the board of directors of the Corporation prior to the Effective Time and publicly announced by the Corporation (the “Reverse Stock Split”). The totalBoard of Directors shall make provision for the issuance of that number of fractions of New Common Stock such that any fractional share of a holder otherwise resulting from the Reverse Stock Split shall be rounded up to the next whole number of shares of New Common Stock. Any stock certificate that, immediately prior to the Effective Time, represented shares of the Old Common Stock will, from and after the Effective Time, automatically and without the necessity of presenting the same for exchange, represent the number of shares of the New Common Stock into which the Corporationsuch shares of Old Common Stock shall have authoritybeen reclassified plus the fraction, if any, of a share of New Common Stock issued as aforesaid.

STAFFING 360 SOLUTIONS, INC.

THIS PROXY IS BEING SOLICITED ON BEHALF OF THE BOARD

The undersigned stockholder hereby appoint(s) Brendan Flood, Khalid Anwar or Nick Koutsivitis, or any of them, as proxies, each with the power to issueappoint his substitute, and hereby authorizes them to represent and to vote, as designated on this ballot, upon the following items more fully described in the notice of proxy statement for the Special Meeting (receipt of which is 120,000,000 shares, consisting of: (x) 100,000,000hereby acknowledged), all of the shares of common stock par value $0.00001 per shareof Staffing 360 Solutions, Inc. (the “Common Stock”“Company”), and (y) 20,000,000 that the stockholders are entitled to vote (including any shares of preferred stock, par value $0.00001 per share (the “Series F Preferred Stock”), issuable and/or Series G Preferred Stock, voting on an as-converted basis) at the Special Meeting of the Stockholders to be held at 10:00 a.m. Eastern Time on June 21, 2021, via live webcast at www.virtualshareholdermeeting.com/STAF2021SM, and at any adjournments thereof. The undersigned hereby revokes any proxy or proxies previously given to represent or vote such shares and hereby ratifies and confirms all actions that said proxy, his substitutes, or any of them, may lawfully take in one or more series as hereinafter provided.accordance with the terms hereof.

 The Board of Directors unanimously recommends a vote FOR proposal 1.

THIS PROXY, WHEN PROPERLY EXECUTED, WILL BE VOTED IN THE MANNER DIRECTED HEREIN.

IF NO SUCH DIRECTION IS MADE, THIS PROXY WILL BE VOTED “FOR” PROPOSAL 1.

In their discretion, the Proxies (or any of them) are authorized to vote as they deem advisable on such other matters as may properly come before the Special Meeting of Stockholders or any adjournment(s) or postponement(s) thereof.

Please mark, sign, date and return this Proxy promptly using the accompanying postage pre-paid envelope.

THIS PROXY IS SOLICITED ON BEHALF OF THE BOARD OF STAFFING 360 SOLUTIONS, INC.

Please sign exactly as the name appears on your stock certificate. When shares of capital stock are held by joint tenants, both should sign. When signing as attorney, executor, administrator, trustee, guardian, or corporate officer, please include full title as such. If the shares of capital stock are owned by a corporation, sign in the full corporate name by an authorized officer. If the shares of capital stock are owned by a partnership, sign in the name of the partnership by an authorized officer.

PLEASE MARK, DATE, SIGN AND RETURN THIS PROXY PROMPTLY

IN THE ENCLOSED ENVELOPE