Rainmaker Systems (VCTL) 10-K 2008 FY Annual report

Exhibit 31.1

CERTIFICATION

I, Michael Silton, certify that:

1. I have reviewed this annual report on Form 10-K of Rainmaker Systems, Inc. (“Rainmaker”);

2. Based on my knowledge, this report does not contain any untrue statement of a material fact or omit to state a material fact necessary to make the statements made, in light of the circumstances under which such statements were made, not misleading with respect to the period covered by this report;

3. Based on my knowledge, the financial statements, and other financial information included in this report, fairly present in all material respects the financial condition, results of operations and cash flows of Rainmaker as of, and for, the periods presented in this report;

4. Rainmaker’s other certifying officer and I are responsible for establishing and maintaining disclosure controls, internal controls and procedures (as defined in Exchange Act Rules 13a-15(e) and 15d-15(e)) and internal control over financial reporting (as defined in Exchange Act Rules 13a-15(f) and 15d-15(f)) for Rainmaker and have:

a. designed such controls and procedures or caused such disclosure controls and procedures to be designed under our supervision, to ensure that material information relating to Rainmaker, including its consolidated subsidiaries, is made known to us by others within those entities, particularly during the period in which this report is being prepared;

b. designed such internal control over financial reporting, or caused such internal control over financial reporting to be designed under our supervision, to provide reasonable assurance regarding the reliability of financial reporting and the preparation of financial statements for external purposes in accordance with generally accepted accounting principles;

c. evaluated the effectiveness of Rainmaker’s disclosure controls and procedures and presented in this report our conclusions about the effectiveness of the disclosure controls and procedures, as of the end of the period covered by this report based on such evaluation; and

d. disclosed in this report any change in Rainmaker’s internal control over financial reporting that occurred during Rainmaker’s fourth fiscal quarter that has materially affected, or is reasonably likely to materially affect, the registrant’s internal control over financial reporting;

5. Rainmaker’s other certifying officer and I have disclosed, based on our most recent evaluation of internal control over financial reporting, to Rainmaker’s auditors and the audit committee of Rainmaker’s board of directors (or persons performing the equivalent function):

a. all significant deficiencies and material weaknesses in the design or operation of internal controls over financial reporting which are reasonably likely to adversely affect Rainmaker’s ability to record, process, summarize and report financial information, and

b. any fraud, whether or not material, that involves management or other employees who have a significant role in Rainmaker’s internal controls over financial reporting.

Date: March 31, 2009

/s/    MICHAEL SILTON        

Michael Silton

President, Chief Executive Officer and Director

(Principal Executive Officer)