Head of Regulatory Affairs & Examinations-Hybrid NY/SF

Summary

Job Description Job Description

Confidential Search Solutions (CSS) is conducting a confidential search for a Head of Regulatory Affairs & Examinations on behalf of a payroll, benefits, and financial services organization. This role is suited to an experienced regulatory professional who can take ownership of examinations and regulator relationships while strengthening supervisory processes across a growing business.

The organization is particularly interested in candidates who have directly managed money transmission examinations for a fintech company. Experience with financial services licensing and regulatory inquiries or examinations at banks and other financial institutions, particularly those subject to FINRA or SEC oversight, is also valuable.

You will coordinate engagement with state financial regulators, FINRA, and the SEC; manage examinations from initial requests through the closure of findings; and work with Legal, Risk, Product, Engineering, and business leaders on regulatory commitments. You will report to the Head of Financial Services & Corporate Compliance.

What You'll Do

• Serve as a primary contact for supervisory matters involving state financial regulators, FINRA, and the SEC.
• Manage examinations from start to finish, including scope review, evidence collection, examiner requests, responses, and remediation.
• Lead responses to regulatory inquiries and information requests, ensuring submissions are accurate, consistent, and well documented.
• Track examination findings, matters requiring attention, owners, deadlines, and evidence of closure.
• Maintain examination readiness, regulatory calendars, evidence retention practices, and clear records of positions taken with regulators.
• Partner with the licensing function on money transmitter licenses, NMLS status, renewals, and post-approval conditions.
• Explain regulatory expectations to Product, Engineering, Risk, and business teams and help them address supervisory concerns.
• Improve processes for managing examinations and regulatory commitments across multiple jurisdictions.

What You Bring

• At least 10 years of experience in regulatory affairs, compliance, or examination management at a regulated financial institution or fintech, or comparable experience with a financial regulator.
• Direct ownership of regulatory examinations, including examiner engagement, evidence production, responses to findings, and remediation.
• Experience engaging state money transmission regulators and a working knowledge of FINRA and SEC supervision.
• Strong understanding of money transmission obligations and the ability to manage regulatory work across multiple jurisdictions.
• Clear, precise writing and documentation habits, with the ability to verify facts and preserve important qualifications in regulatory responses.
• Sound judgment under scrutiny and the ability to keep commitments on track in a fast-moving product environment.
• Experience building or improving a regulatory affairs or examinations program.

Preferred, but Not Required

• Direct experience managing money transmission examinations for a fintech company.
• Experience with financial services licensing and managing regulatory inquiries or examinations at banks and other financial institutions, particularly those regulated by FINRA or the SEC.
• A Juris Doctor (JD) degree.
• Familiarity with multistate examination frameworks and money transmission modernization efforts.
• Experience with payroll, payments, embedded finance, or related financial products.
• CRCM, CAMS, or a comparable professional certification.

Location: Hybrid, based in San Francisco, Denver, or New York
Compensation: Based on experience

This position begins as a full-time contract assignment with the potential to convert to a permanent role. CSS welcomes candidates who enjoy hands-on examination management, thoughtful regulator engagement, and close collaboration with teams developing financial products

Company Description

About us: Confidential Search Solutions ("CSS") is a full-service equal opportunity employment consulting and legal staffing firm. Headquartered in San Antonio and is one of the premiere executive searches and recruiting firms nationwide. We specialize in helping high performance companies and law firms identify, recruit, and train top talent for their growing organizations. We offer direct hire, contract, and temporary staffing services. For more information about us, visit our website at

Company Description About us: Confidential Search Solutions ("CSS") is a full-service equal opportunity employment consulting and legal staffing firm. Headquartered in San Antonio and is one of the premiere executive searches and recruiting firms nationwide. We specialize in helping high performance companies and law firms identify, recruit, and train top talent for their growing organizations. We offer direct hire, contract, and temporary staffing services. For more information about us, visit our website at

Job Description

Job Description Job Description

Confidential Search Solutions (CSS) is conducting a confidential search for a Head of Regulatory Affairs & Examinations on behalf of a payroll, benefits, and financial services organization. This role is suited to an experienced regulatory professional who can take ownership of examinations and regulator relationships while strengthening supervisory processes across a growing business.

The organization is particularly interested in candidates who have directly managed money transmission examinations for a fintech company. Experience with financial services licensing and regulatory inquiries or examinations at banks and other financial institutions, particularly those subject to FINRA or SEC oversight, is also valuable.

You will coordinate engagement with state financial regulators, FINRA, and the SEC; manage examinations from initial requests through the closure of findings; and work with Legal, Risk, Product, Engineering, and business leaders on regulatory commitments. You will report to the Head of Financial Services & Corporate Compliance.

What You'll Do

• Serve as a primary contact for supervisory matters involving state financial regulators, FINRA, and the SEC.
• Manage examinations from start to finish, including scope review, evidence collection, examiner requests, responses, and remediation.
• Lead responses to regulatory inquiries and information requests, ensuring submissions are accurate, consistent, and well documented.
• Track examination findings, matters requiring attention, owners, deadlines, and evidence of closure.
• Maintain examination readiness, regulatory calendars, evidence retention practices, and clear records of positions taken with regulators.
• Partner with the licensing function on money transmitter licenses, NMLS status, renewals, and post-approval conditions.
• Explain regulatory expectations to Product, Engineering, Risk, and business teams and help them address supervisory concerns.
• Improve processes for managing examinations and regulatory commitments across multiple jurisdictions.

What You Bring

• At least 10 years of experience in regulatory affairs, compliance, or examination management at a regulated financial institution or fintech, or comparable experience with a financial regulator.
• Direct ownership of regulatory examinations, including examiner engagement, evidence production, responses to findings, and remediation.
• Experience engaging state money transmission regulators and a working knowledge of FINRA and SEC supervision.
• Strong understanding of money transmission obligations and the ability to manage regulatory work across multiple jurisdictions.
• Clear, precise writing and documentation habits, with the ability to verify facts and preserve important qualifications in regulatory responses.
• Sound judgment under scrutiny and the ability to keep commitments on track in a fast-moving product environment.
• Experience building or improving a regulatory affairs or examinations program.

Preferred, but Not Required

• Direct experience managing money transmission examinations for a fintech company.
• Experience with financial services licensing and managing regulatory inquiries or examinations at banks and other financial institutions, particularly those regulated by FINRA or the SEC.
• A Juris Doctor (JD) degree.
• Familiarity with multistate examination frameworks and money transmission modernization efforts.
• Experience with payroll, payments, embedded finance, or related financial products.
• CRCM, CAMS, or a comparable professional certification.

Location: Hybrid, based in San Francisco, Denver, or New York
Compensation: Based on experience

This position begins as a full-time contract assignment with the potential to convert to a permanent role. CSS welcomes candidates who enjoy hands-on examination management, thoughtful regulator engagement, and close collaboration with teams developing financial products

Company Description

About us: Confidential Search Solutions ("CSS") is a full-service equal opportunity employment consulting and legal staffing firm. Headquartered in San Antonio and is one of the premiere executive searches and recruiting firms nationwide. We specialize in helping high performance companies and law firms identify, recruit, and train top talent for their growing organizations. We offer direct hire, contract, and temporary staffing services. For more information about us, visit our website at

Company Description About us: Confidential Search Solutions ("CSS") is a full-service equal opportunity employment consulting and legal staffing firm. Headquartered in San Antonio and is one of the premiere executive searches and recruiting firms nationwide. We specialize in helping high performance companies and law firms identify, recruit, and train top talent for their growing organizations. We offer direct hire, contract, and temporary staffing services. For more information about us, visit our website at