Compliance Lead, Broker-Dealer & Investment Adviser

Compliance Lead, Broker-Dealer & Investment Adviser

Denver, CO; San Francisco, CA; New York, NY

At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff payroll, health insurance, 401(k)s, and HR so owners can focus on their craft and their customers. With teams in Denver, San Francisco, and New York, we support more than 500,000 small businesses nationwide and are building a workplace that reflects the people we serve.

All full-time employees receive competitive base pay, benefits, and equity (RSUs) because everyone who helps build Gusto should share in its success. Offer amounts are determined by role, level, and location. Learn more about our Total Rewards philosophy.

AI is a fundamental part of how work gets done at Gusto. We expect all team members to actively engage with AI tools relevant to their role and grow their fluency as the technology evolves. AI experience requirements vary by role and will be assessed during the interview process.

The Compliance Lead, Broker-Dealer & Investment Adviser is a senior member of the Gusto Retirement Compliance Team, reporting directly to the Head of Compliance. This role is the operational backbone of the compliance program, owning the compliance programs of the Registered Investment Advisor (RIA) and Broker-Dealer (BD) entities, including their AI governance frameworks, and serving as a trusted senior member of the RIA/BD Compliance team.

In this role, you would own the supervisory architecture (including the governance of AI tools used across the compliance program), drive exam readiness, and ensure the program is running effectively, documented thoroughly, and defensible under SEC and FINRA scrutiny. This is not a policy-only role, and it is not a passive-user-of-technology role. It requires someone who can move fluidly between strategic oversight and hands-on execution, who understands what it means to carry a compliance program in a regulated financial services environment, and who can serve as a supervisory principal over AI, ensuring tools are deployed lawfully, outputs are validated, and the program evolves alongside regulatory expectations.

Gusto operates RIA and BD affiliated entities, serving customers across the retirement savings landscape. Our Compliance Team is a lean, high-impact function responsible for maintaining robust, defensible compliance programs across both regulatory regimes, built to scale alongside the business. That includes staying ahead of how AI is reshaping compliance operations: the team actively governs and oversees AI tools used across the program, identifies where AI can responsibly expand team capacity, and ensures that any AI use meets the supervisory standards required by SEC and FINRA. We are building a compliance program that is both modern and defensible.

Here's what you'll do day-to-day:

• Own and mature the end-to-end compliance program across both the BD and RIA, ensuring the frameworks, controls, and infrastructure, including AI governance, keep pace with Gusto's growth
• Serve as the primary compliance lead on all FINRA and SEC regulatory matters, including filings, examinations, supervisory control testing, and evolving regulatory guidance on AI use in compliance programs
• Lead and develop the relationship with compliance consulting firm(s), directing their work across both entities and ensuring coverage is aligned with Gusto's risk posture
• Build and maintain policies and procedures across both entities, covering advertising, Reg SP, complaints, books and records, BCP, Code of Ethics/Conduct, trade errors and more
• Own incident management and escalation, including compliance violations, whistleblowing, and heightened supervision, and report trends to the Head of Compliance
• Partner cross-functionally with Legal, Product, Finance, Marketing, Sales, and FinCrime to embed compliance into how Gusto builds and sells
• Supervise AI tools used across the compliance program, including ongoing review and testing, ensuring outputs are validated by qualified licensed humans, identifying opportunities to expand team capacity, and flagging functions where AI use is not permitted
• Lead training programs and annual compliance meetings for both BD and RIA, and own the advertising and communications review process
• Assess whether resources, controls, and coverage are sufficient as Gusto scales into new markets and upmarket customer segments
• Oversee all firm filings, employee registrations and licensing across the BD and RIA, including U4/U5, fingerprints, background checks, CRD, Form CRS, Form BD, ADV, and more
• Lead suitability, rebalancing, and custody review and testing for the RIA, including coordination of the annual Surprise Custody Exam

Here's what we're looking for:

• 7+ years of compliance experience at a FINRA-registered broker-dealer and SEC-registered investment adviser, with deep working knowledge of FINRA Rules, the SEC Rules (including the Marketing Rule, Reg S-P and Reg S-ID), GLBA, and Bank Secrecy Act
• Proven track record owning regulatory filings (Form BD, ADV, U4/U5, CRS), leading exam preparation and response, and running supervisory control testing and advertising review across both RIA and BD entities
• Familiarity with compliance technology (e.g., ComplySci, Global Relay), books and records obligations under Rules 17a-4 and 204-2, and AI governance frameworks in a regulated environment
• Strong written communication skills with the ability to draft, own, and defend compliance documentation under regulatory scrutiny and comfortable managing multiple programs in a lean, high-accountability team
• Active SIE, Series 7, and Series 24 licenses
• Experience at a fintech-integrated RIA/BD, comfortable working at the intersection of technology, product, compliance, and AI governance
• Experience with outsourced compliance models (e.g., third-party consulting firms)
• Prior experience managing compliance staff