Director of Applied Plan Compliance

About Aboon

Setting up a 401(k) shouldn't be the hardest thing a business ever does. But retirement plan administration is complex, fragmented, and manual, and it slows down both business owners and the advisors who serve them. Aboon was founded to change that.

We're an AI-native third-party administrator (TPA) that makes it easy for advisors to offer 401(k)s and other retirement products by pairing streamlined workflows with dedicated human service. Backed by leading investors including Bain Capital and Edward Jones Ventures, we bring decades of experience building for advisors and the retirement industry. We're looking for exceptional, mission-driven people to build it with us.

About the role

We're looking for a senior plan compliance expert to own compliance testing and the annual Year-in-Review at Aboon. You’ll make sure every plan's testing, contribution calculations, and Year-in-Review results are accurate and timely.

Aboon operates as an AI Native Services (AINS) business, building agents that do plan servicing work with human supervision. You’ll work closely with our Applied AI team, in pods of engineers and SMEs, iterating and evaluating agents. You’ll oversee the agents and automations that drive our plan compliance engine and leverage a suite of internal tools and agents, including Claude/Claude Code. You'll also assess the early versions of our testing engine and compliance calculators and partner with our Plan Administrators on work that isn’t automated yet.

You’ll report to the Head of Applied Plan Services and work closely with Plan Services, Relationship Managers, Documents & Technical Services, and R&D. As an individual contributor, you’ll be tasked with creating a function that needs few people over the long term.

What you'll do

• Own testing, contributions, and Year-in-Review. Own nondiscrimination testing, employer contribution calculations, and reconciliation of deposits against payroll and plan formulas. Own Year-in-Review results and action items for every plan, including corrections that bring plans back into line, such as refunds, true-ups, and amendments.

• Run the compliance season. Oversee every plan's compliance review. Create the processes for exceptions and complete any work we can't automate yet. Coordinate with internal teams to meet clients' needs and deadlines.

• Improve the client experience. Help our internal teams communicate complex data requests and Year-in-Review results to clients in clear, simple terms.

• Define correct. Be the subject matter expert who sets our compliance standards: the requirements and steps each plan must satisfy to complete the annual cycle.

• Evaluate our agents. Working with our Applied AI team, help develop answer keys, review traces, and label datasets that improve the accuracy of our agents.

• Maintain and extend the calculators. Review and expand our compliance calculators. Stay current on new laws, regulations, and best practices so our systems stay correct.

• Prototype automations. Build and test tools yourself and partner with R&D to promote them into our applications.

• Shape the roadmap for your function. Write the pitches for product cycles and recommend build sequences, working within our product roadmap process.

• Define tracking and documentation processes. Establish clear procedures for tracking progress, documenting decisions and handling manual overrides.

• You will not own: complex plan document corrections and EPCRS filings, which sit with Documents & Technical Services; government filings, though plan compliance results feed them

Who you are

• You build things that scale. You think in populations, controls, and pass rates.

• You want to operate AI. Define correct, measure agents against it, and tighten the loop until fewer edge cases need manual work.

• You're the expert people escalate to. You know the rules well enough to spot a wrong answer that looks right.

What you bring

Required

• 8+ years in defined contribution plan administration, with deep knowledge of compliance testing, contribution calculations, and the corrections for each

• Experience designing or running a compliance testing program at scale: procedures, controls, review levels, and quality measurement

• Hands-on fluency with data: spreadsheets as calculators, reconciliation, and reasoning about where a number came from

• Demonstrated interest in applied AI, with examples you can point to of what worked, what didn't, and how you knew

• High agency and comfort with ambiguity as a senior individual contributor in an early-stage company

• Clear communication with engineers, service team members, and clients

Nice to have

• CPC or QPA credential

• Experience building evaluation sets, test harnesses, or QA programs for software or automation

• Python, SQL, or scripting; familiarity with agent frameworks or document-extraction tools

• Familiarity with ftwilliam and major recordkeeper servicing platforms

• Experience at a fintech, wealthtech, or high-growth startup

What we offer

Compensation

The base salary range for this role is $160,000-$200,000, depending on experience, skills, and location. Total compensation also includes an annual bonus and equity.

Benefits

• Comprehensive health, dental, and vision insurance, with additional optional coverage

• 401(k) with company match

• Flexible paid time off and holidays

• 10 weeks paid parental leave

• A fully remote work environment, with all the technology and equipment you need

• Support for professional development and career growth

Location

Remote, though we encourage in-person attendance at 1-2 company retreats per year. This role is open to candidates based in the US. Work authorization required; no visa sponsorship.

Aboon is an Equal Opportunity Employer. We encourage applications from all qualified individuals and do not discriminate based on race, color, religion, sex, sexual orientation, gender identity, national origin, disability, veteran status, or any other protected status.