Director of Retirement Compliance

Human Interest is on a mission to ensure that people in all lines of work have access to retirement benefits. 

More than half of all working Americans are not saving enough for their future. Too often, it’s because they are employed by a company that doesn’t offer a retirement plan. Human Interest is changing that by making it affordable and accessible for small and medium-sized businesses to offer employees a path to financial independence through retirement savings.

We’re a high-growth fintech company changing the retirement industry. We are backed by a number of investors. This includes funding from Marshall Wace and Baillie Gifford, as well as top investors such as BlackRock, TPG (The Rise Fund), SoftBank, Glynn Capital, NewView Capital, USVP, Wing, Uncork, and more.

About the role

The Director of Retirement Compliance is a strategic, high-impact leadership role responsible for ensuring that Human Interest’s platform operates with regulatory precision under ERISA, DOL, and IRS guidelines. This leader will drive continuous innovation across compliance workflows, architecting root-cause feedback loops to resolve plan errors and delinquencies while driving the end-to-end compliance health of our plans at scale.   

Operating at the intersection of regulatory governance, incident management, and product delivery, the Director will oversee high-level customer advocacy escalations in close partnership with Legal, steer feature rollout reviews, and build real-time monitoring infrastructure for SLAs and regulatory deadlines. Reporting directly to the Vice President of Sales Activation & Customer Success, this individual will proactively manage risk and financial exposure, own remediation solutions end-to-end, and actively coach and uplevel frontline compliance managers.

About the team

The Compliance team serves as the guardian of Human Interest’s regulatory integrity and fiduciary excellence. We sit at the nexus of regulatory compliance, customer success, onboarding, operations, and product engineering. Rather than acting as a traditional back-office audit function, our team acts as proactive problem solvers—designing scalable automation, building data pipelines, and establishing closed-loop operational workflows that safeguard plan sponsors and participants. As we continue to democratize access to retirement benefits, we're looking for a visionary leader who can scale our compliance operations through technology while maintaining our commitment to fiduciary excellence.

What you get to do every day

• Lead and direct Human Interest's compliance program ensuring adherence to ERISA, DOL, and IRS regulations across all 401(k) plan operations
• Modernize compliance workflows and build cross-functional feedback loops with Customer Onboarding, Customer Success, and Product to perform root-cause analysis on errors and delinquencies.
• Develop and implement technology-driven compliance frameworks that scale with our growing client base while maintaining regulatory excellence
• Own and drive scalable, technology-enabled initiatives with Product to improve platform-wide plan compliance health. 
• Design and oversee automated compliance monitoring systems to proactively identify and address potential issues
• Build and manage operational dashboards to continuously track team SLAs, operational metrics, and statutory regulatory deadlines.
• Partner cross-functionally with Product, Operations, and Technology teams to review platform feature rollout plans, system copy, and marketing collateral to guarantee strict alignment with ERISA and DOL standards.
• Lead Customer Advocacy and incident management for high-level escalations in close partnership with Legal to resolve plan errors and mitigate exposure.
• Oversee fiduciary governance processes and ensure proper documentation of fiduciary decisions
• Lead compliance technology initiatives including plan document automation, testing workflows, and regulatory reporting systems
• Manage relationships with external auditors, regulatory bodies, and compliance consultants
• Drive continuous improvement of compliance processes through automation and process optimization
• Advise executive leadership on compliance risks and operational failures, proposing and owning strategic remediation solutions end-to-end.as primary point of contact for regulatory inquiries and examinations
• Develop and maintain compliance policies, procedures, and training programs
• Lead crisis management protocols for compliance-related issues requiring immediate attention
• Coach, mentor, and uplevel frontline compliance managers to build operational excellence and scale team leadership.
• Other duties as assigned.

What you bring to the role

• 10+ years of experience in ERISA compliance, with at least 5 years in leadership roles within retirement plan administration
• Current ERISA-related professional certifications (QKA, QPA, RPF, or equivalent)
• Proven track record of leveraging technology to drive compliance efficiency and scalability
• Experience with 401(k) plan administration, including nondiscrimination testing, plan document maintenance, and fiduciary oversight
• Strong ability to develop compliance frameworks and processes that drive measurable results
• Experience implementing compliance technology solutions and automated testing systems
• Exceptional communication skills with ability to translate complex regulatory requirements for diverse stakeholders
• Data-driven approach to compliance management and risk assessment

Nice to have

• Advanced ERISA certifications (CEBS, CPC,)
• Juris Doctor (JD) with an emphasis on ERISA, employee benefits, or administrative law
• Experience within a high-growth fintech, modern TPA, or SaaS retirement platform. 
• Track record of implementing compliance automation in high-growth environments
• Experience scaling compliance functions from startup to enterprise stage
• Background in regulatory technology (RegTech) or compliance software implementation
• Proven ability to influence regulatory strategy based on industry trends and regulatory changes
• Experience managing both remote and in-office compliance teams
• Knowledge of emerging compliance technologies including AI and machine learning applications
• Practical familiarity with workflow automation tools (e.g., Jira, Gemini) and dashboarding software (e.g., Salesforce, Hex). 
• Deep background navigating voluntary correction programs (IRS EPCRS and DOL VFCP/DFVCP).

Why you will love working at Human Interest

Human Interest is tackling one of our country's biggest challenges - closing the retirement gap. You'll be instrumental in architecting and scaling solutions that bring financial security to employees at small and medium-sized businesses nationwide. We’ve made significant progress, but there is still growth ahead, offering you a unique opportunity to solve complex problems, drive innovation, and advance your career alongside a dedicated, mission-driven team. We value hard work and recognize that our team's contributions are key to our continued success.

Join Human Interest and make a lasting impact by shaping the future of retirement.

Our operating principles define how we work together as a team. They reflect Human Interest’s unique view on what’s important and what’s right. Documenting this core aspect of our culture helps employees make good decisions on their own. It also helps candidates considering career opportunities critically evaluate whether they will thrive at Human Interest. 

• Customer obsession: We're all about creating amazing experiences for our customers. We put their needs first and go the extra mile to make them smile.
• Long-Term Orientation: We're not just playing for today; we're building a legacy. We think big, plan strategically, and invest in our future.
• Autonomous and Accountable Teams: We trust our team members to take ownership and make smart decisions. We empower you to be your best self!
• An Escalating Bar for Talent and Performance: We're constantly raising the bar and challenging ourselves to be better. We believe in growth and continuous improvement.
• Fundamental Optimism: We see the glass as half full (and then we fill it up with more amazing ideas!). We believe in the power of positivity and the potential for greatness.

Compensation - At Human Interest, there are a number of factors that are used to determine the appropriate pay range for each position. We take into account the cost of labor for each position in various markets across the U.S. The base salary for this position spans $150,000 - $180,000and represents the minimum in our lowest geographic region to a maximumin our highest geographic region. The salary we offer to a new employee within this range is based on their location within the U.S., their relevant job-related skills, and experience. At Human Interest, base salary is one component of the overall total rewards package. Depending on the position, additional compensation components such as bonuses, commissions, and equity may be offered. All of our employees are offered a robust suite of physical, financial, and mental wellness benefits. In compliance with applicable laws, we do not inquire about salary history, or about criminal history prior to a conditional offer of employment.

Benefits - 

• A great 401(k) plan: Our own! Our 401(k) includes a dollar-for-dollar employer match up to 4% of compensation (immediately vested) and $0 plan fees
• Top-of-the-line health plans, as well as dental and vision insurance
• Competitive time off and parental leave
• Addition Wealth:  Unlimited access to digital tools, financial professionals, and a knowledge center to help you understand your equity and support your financial wellness
• Lyra: Enhanced Mental Health Support for Employees and dependents  
• Carrot: Fertility healthcare and family forming benefits
• Candidly:  Student loan resource to help you and your family plan, borrow, and repay student debt
• Monthly work-from-home stipend; quarterly lifestyle stipend
• Engaging team-building experiences, ranging from virtual social events to team offsites, promoting collaboration and camaraderie.

We’re a great place to work (but don’t take our word for it) 

Here’s a list of our awards and accolades:

• Certified as a Great Place To Work® (2023-2025)
• Fortune Best Place to Work in the Bay Area (2024)
• Best Places to Work by Built In (2023-2024)
• America’s Best Startup Employers by Forbes (2020-2022, 2024) 
• A Top Company by Y Combinator (2020-2023)
• Inc. Fastest Growing Companies (2021)

Human Interest is an equal opportunity employer. All applicants will receive consideration for employment without regard to race, color, religion, sex, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, veteran or military status, pregnancy, or any other characteristics protected under federal, state, or local laws. Employment with Human Interest is at-will, meaning either you or the company may terminate employment at any time, with or without cause or notice, except as otherwise provided by law or written agreement.

We are committed to making every stage of our application process fully accessible to all individuals. If you need a reasonable accommodation at any point in the process, please let us know at [email protected].

Protect yourself against fraud and identity theft. Apply to our open positions directly via our careers page on Greenhouse. Human Interest will never ask applicants for their financial or banking information as part of our application process. All legitimate communication will come from a @humaninterest.com email address. If you have questions, please reach out to us directly at [email protected]

Please note Human Interest does not accept unsolicited resumes from any source other than directly from candidates. We will not consider resumes from vendors, including and without limitation search firms, staffing agencies, fee-based referral services, and recruiting agencies. 

Pursuant to the San Francisco Fair Chance Ordinance, we will consider employment-qualified applicants with arrest and conviction records. We comply with CCPAguidelines.

See more: https://humaninterest.com/disclosures