About the Role:

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.

About the Team:

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

Our cash compensation amount for this role is $156,170/yr to $192,610/yr in Denver & most major metro locations, and $183,830/yr to $226,724/yr for San Francisco & New York. Final offer amounts are determined by multiple factors including candidate location, experience and expertise and may vary from the amounts listed above.

About the Role:

We're looking for a Legal AI Engineer for a fixed engagement to build foundational legal team AI infrastructure. You'll design and stand up these systems, document them thoroughly, and hand them off to the team in a state where they can be maintained and iterated on internally.

You'll provide services to a legal team that is already building its own AI tooling and infrastructure through Claude. Your engagement will be with the Senior Manager of Legal Contracting Operations & AI Systems. Your project will be to add the technical depth that turns promising experiments into robust, shared systems, and to deliver a coherent stack of tools and workflows.

During this engagement, you'll design workflows that are fast, measurable, and safe based on specifications from legal, legal ops, and cross-functional stakeholders. You'll leave behind documented systems and run books so the team can maintain and evolve what you've built. This engagement is equal parts legal infrastructure + applied AI, ideal for a hybrid legal/technical practitioner who can translate legal work into scalable systems and then make those systems real.

Here’s what you’ll do day-to-day during this engagement:

• Connect the AI Stack
  • Take the skills, workflows, and dashboards that individual team members have already built in Claude and package them into shared, maintainable assets the whole team can use.
  • Wire together current AI tooling — build MCP integrations so data flows where it's needed without manual handoffs; engage with Gusto's AIT team on connections where native integrations don't exist.
  • Further operationalize AI tools and integrations as agreed upon.
• Build a Legal Repository
  • Stand up a structured, queryable knowledge layer fed by the team's existing research, positions, precedents, and playbooks — one that can be searched by any team member, can be invoked by automated workflows, and continuously ingests new information as the team works in the tool.
• Implement AI Workflows
  • Working from priorities set by legal ops and attorneys, implement AI-assisted workflows for the team's highest-volume use cases — likely including contract first-pass review, matter intake and routing,  litigation operations to enable intake, routing and response drafting for subpoenas, demand letters and notices and prompt libraries for recurring legal tasks.
• Document and Hand Off
  • Deliver a maintenance runbook for every system built and train designated team members on administration, so nothing requires the contractor to maintain it after the engagement ends. Establish adoption baselines so the team can measure progress and know what to iterate on next.

Here’s what we're looking for:

• Hands-on experience building and shipping AI-assisted workflows — not evaluating tools or writing specs, but actually standing systems up. Be ready to walk through something you built from prompt to production.
• Direct, working proficiency with Claude or comparable LLMs: prompt engineering, agentic workflows, and iterating on outputs until they're reliable. This is the core technical skill for everything we're building.
• Integration experience — you've wired tools together using APIs, MCPs, or similar patterns, and you know what breaks and why. Coordinating with engineering or IT teams to scope and execute those connections is second nature to you.
• Comfort operating in ambiguity. You can take a business problem and context from attorneys or legal ops — not a technical spec — and turn it into a working system. You know how to ask the right questions, fill in gaps with judgment, and move forward.
• Comfort working within internal technology governance processes. You know how to communicate with an IT or AI team on tool approvals, data access, and security reviews — and you don't try to go around them. You build within the guardrails, and you help the team understand why those guardrails matter.
• Bonus: Experience working alongside attorneys: you understand contracting workflows, matter intake, research cycles, and how legal teams make decisions.

Compensation will be $150/hr, approximately 20 hours per week, commensurate with experience and expertise. This is a 3-month engagement.