Director of ERISA 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 co