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Compliance Director, Trust Company and Custody Operations

Vestwell - New York, NY, United States - Hybrid - posted 2026-10-09

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Salary: USD 160,000 - 180,000 / annual

Vestwell is a fintech platform powering the savings economy, enabling over 790,000 businesses and 2.75 million active savers with $57 billion in assets across retirement, education, and healthcare savings products. The company operates a trust company and custodial platform serving financial advisers, employers, third-party administrators, financial institutions, payroll providers, and government agencies. You will lead the regulatory operations function with strategic oversight of the trust company, custodial, and trading operations. Your responsibilities include: • Lead regulatory operations focused on qualified retirement plans (401(k), IRAs, Emergency Savings Accounts) and ensure compliance with ERISA, Internal Revenue Code, DOL, IRS, trust company regulations, and SEC requirements. • Create and implement procedures and internal controls for all trading activities within custodial operations, proactively monitoring teams and systems for regulatory compliance. • Oversee and enhance controls related to trust and custody operations and state savings programs, ensuring alignment with fiduciary standards and regulatory expectations. • Provide regular reporting to internal stakeholders and the Risk Committee on material risks, incidents, and effectiveness of risk mitigation strategies. • Partner with legal, compliance, product, and operations teams 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. • Lead the Legal Team in managing 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, and inquiries. • Oversee 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. The role is based in the New York City office with a hybrid work model, offering flexibility while maintaining access to collaborative offices in Midtown Manhattan, Austin, King of Prussia, and Scottsdale. REQUIREMENTS: Must-Have: • Bachelor's degree in Business, Finance, or related field • Minimum 10+ years of experience in regulatory compliance or operations in 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 ability to influence and collaborate across functions • Exceptional organizational, analytical, and communication skills Preferred: • Advanced degree or professional certification (JD, CPA, CRSP, QKA, CISP) • Experience working with recordkeeping platforms, trust accounting systems, or custodial platforms • Start-up experience

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