Compliance Director, Trust Company and Custody Operations New York, NY

Compliance Director, Trust Company and Custody Operations

Vestwell is the financial technology company powering the new savings economy. The New York City-based fintech platform redefines how people save for the critical aspects of life across retirement, education, and healthcare savings needs. Today, Vestwell enables over 790,000 businesses and more than 2.75 million active savers, with over $57 billion in assets saved across all 50 United States.

Vestwell offers a range of products, including workplace-delivered retirement plans, employer-offered student loan repayment benefits, and various savings accounts for education, emergencies, and individuals with disabilities.

Vestwell's platform serves a diverse clientele, including financial advisers, employers, third-party administrators, financial institutions, payroll providers, government agencies, and individual savers. To learn more, visit vestwell.com

Who Are We Looking For?

We are seeking an experienced and strategic Compliance Director of Trust Company and Custody Operations to lead and manage regulatory compliance and operational oversight across our trust company, custodial, and trading operations. This individual will play a key role in ensuring compliance with all applicable regulations related to 401(k) plans, ERISA, and trust and custody services. The ideal candidate will bring a deep understanding of regulatory requirements, operational excellence, and a proven track record in managing regulatory operations within financial services or trust company and retirement plan administration.

What Will You Be Doing?

• Lead the regulatory operations function with a focus on qualified retirement plans , particularly 401(k) plans, IRAs, and Emergency Savings Accounts.
• Create and implement procedures and internal controls for all trading activities within our custodial operations and proactively monitor our teams and systems for compliance with applicable laws and regulations.
• Ensure compliance with ERISA , Internal Revenue Code (IRC) , DOL , IRS , trust company regulations, and SEC regulations.
• Oversee and enhance controls related to trust and custody operations, as well as state savings programs , ensuring alignment with fiduciary standards and regulatory expectations.
• Provide regular reporting to internal stakeholders and Risk Committee about material risks, incidents, and the effectiveness of risk mitigation strategies.
• Partner with internal stakeholders (legal, compliance, product, operations) to interpret new and existing regulations and apply them to business practices.
• Monitor regulatory developments and proactively advise senior leadership on potential business impacts and required changes.
• Serve as the lead for the Legal Team to lead the Vestwell Trust Company SOC 1 audit and New Hampshire Banking Department regulatory exam.
• Liaise with external auditors, regulatory agencies, and third-party service providers during examinations, audits, inquiries, or other matters as needed.
• Oversee and support regulatory reporting and filings (e.g., Form 5500, IRS/DOL disclosures).
• Manage a team of regulatory operations professionals, providing leadership, coaching, and performance oversight.
• Drive continuous improvement and automation of regulatory and compliance processes and controls.

Requirements

The Necessities

• Bachelor’s degree in Business, Finance, or a related field required; advanced degree or professional certification (e.g., JD, CPA, CRSP, QKA, CISP) preferred.
• Minimum of 10+ years of experience with a proven track record in regulatory compliance or operations in the retirement, trust, or custodial services industry.
• Deep knowledge of ERISA, 401(k) regulations, trust company laws, custody services, and applicable IRS/DOL regulations.
• Experience managing operational risk, compliance audits, and regulatory examinations.
• Strong leadership and team management skills with the ability to influence and collaborate across functions.
• Exceptional organizational, analytical, and communication skills.
• Experience working with recordkeeping platforms, trust accounting systems, or custodial platforms is a plus.

The Extras

• Start up experience

This role will be based in the New York City office, and will be part of Vestwell's hybrid in-office operation.

The expected base salary range for this position is $160K - $180K base. This position is eligible to participate in the Company Bonus Pool and is eligible to receive new hire equity in the Company. Please note that salary bands are based on NY and other similar metro areas and may differ based on where the role is ultimately hired.

Full-Time Employee Benefits

We’re an innovative, high-growth company with an exciting future ahead. At Vestwell, we prioritize employee wellbeing through comprehensive health benefits, generous time off, and a dedicated Employee Wellbeing Committee. Our hybrid work model offers flexibility while providing access to our collaborative offices in Midtown Manhattan, Austin, King of Prussia, and Scottsdale. And, of course, as a company focused on helping people save for the future, we offer a competitive 401(k) plan.

Interview Process

Our interview process starts the same for every candidate with 1-2 introductory conversations to learn more about your background, interests, and what you're looking for, while also giving you the opportunity to learn more about Vestwell and the team. From there, the process varies by role but typically includes a skills or experience-based assessment, such as a coding interview, portfolio review, or deeper discussion of your relevant experience. Successful candidates then move on to a virtual or in-person interview panel. Before extending an offer, we complete a reference check with a current or former manager and a peer. Throughout the process, we prioritize transparency, clear communication, and minimizing surprises.