Description:

About the role:
In this role, you will be the in-house ERISA expert for Human Interest, applying deep substantive expertise to the ERISA, IRC, and fiduciary obligations inherent in operating a 401(k) recordkeeping platform . The role sits at the intersection of ERISA, technology, and operations. You'll be part of a legal team helping a growth-stage company expand access to retirement plans for small and mid-market employers, making it easier for the businesses that need 401(k) plans to offer them.

You will have two primary internal clients: (1) the teams that work directly with plan sponsors and participants, and (2) the product team responsible for building our features and products. You will bring legal rigor, practical judgment, and the ability to translate applicable regulatory frameworks into actionable guidance. You need to be comfortable applying your expertise in an environment where automated workflows and payroll integrations support the underlying ERISA requirements that govern recordkeeping.

Human Interest's legal team uses AI tools to work efficiently and deliver high-quality legal work. This role will not be a good fit if you are not already familiar with and using AI tools in your daily work.

What you get to do every day
Your work spans two primary internal audiences: the teams that work directly with our customers, and the product team that builds the platform. Across both, you'll apply ERISA fiduciary, qualification, and disclosure expertise to live business questions.

Serve as the Front-Line Legal Advisor to Customer-Facing Teams: Be the go-to ERISA resource for the internal teams that work directly with plan sponsors and participants — providing real-time, practical legal guidance on the ERISA, IRC, and fiduciary questions that surface as customers interact with the platform. This work spans the full customer lifecycle, from new plans coming onto the platform to ongoing administration and customer retention. Day to day, this includes:
Advising on complex plan sponsor or participant questions that internal teams cannot resolve on their own
Working through fact patterns where automation, plan terms, or customer expectations don't align, and determining the right ERISA-defensible course of action
Helping internal teams navigate ERISA-driven constraints when responding to time-sensitive customer matters, including matters requiring EPCRS analysis, anti-cutback considerations under IRC 411(d)(6), or participant disclosure obligations
Advising on when a new or updated fee disclosure is required under ERISA 408(b)(2), 404(a)(5), or related rules, and on the substantive content
Reviewing participant-facing communications, SPDs, SMMs, and plan sponsor disclosures for ERISA compliance, including both the content of individual disclosures and the automated workflows that generate them
Translating technical ERISA conclusions into plain-language guidance that internal teams can confidently deliver to customers

Serve as the ERISA SME for Product: Be the go-to ERISA resource for the product team as they design and build new features. This is on-call SME work — you'll be brought in for discrete ERISA questions as they come up in product development, rather than partnering across the full lifecycle of a feature. This includes:

Translating ERISA and IRC requirements into clear guidance product managers and engineers can build against
Pressure-testing how proposed automation handles edge cases
Flagging when a feature would trigger different 3(16), 3(21), or 3(38) fiduciary duties — and helping the team decide the best path forward
Synthesizing intelligence from customer matters — what they reveal about platform limitations, edge cases, and systemic gaps — and bringing that back to the product team to drive durable product improvements
Across both workstreams, you'll stay current on legislative, regulatory, and judicial developments affecting qualified retirement plans, and advise operations, customer support, and product teams on changes that affect how the platform operates or how the company counsels its customers. You'll also draft and maintain internal policies, procedures, legal guidance, and educational resources that help these teams apply ERISA requirements consistently.

What You Bring To The Role:

ERISA Expert: You bring deep, substantive expertise in ERISA — particularly the fiduciary duty, prohibited transaction, and qualified plan rules that govern 401(k) recordkeeping and fiduciary services. You are recognized as a technical authority on these issues, not a generalist who handles ERISA among other things. Your expertise is the foundation on which everything else in this role depends.
Business-Minded Advisor: You have direct experience providing ERISA advice in operational and product contexts and demonstrate excellent judgment. You bring a strong sense of ownership to complex matters, including time-sensitive plan administration questions that require both technical rigor and practical resolution, and you're skilled at exercising sound judgment in nuanced situations.
AI-Fluent: You actively use modern AI tools in your legal work — for research, drafting, summarization, and analysis — and you bring thoughtful judgment about where AI accelerates the work and where human expertise remains essential. You see AI as a way to do better, faster work, not as a replacement for substantive legal judgment.
Cross-Functional Partner: You work collaboratively and strategically across teams, building cross-functional relationships with product managers, engineers, and operations leaders. You explain complex ERISA issues with clarity in writing and in meetings to a variety of audiences, and your written work — product guidance, decision documents, and legal analyses — holds up to regulator scrutiny.

Qualifications:
Experience:

5–8 years of substantive ERISA experience focused on qualified retirement plans and fiduciary matters (including 401(k), 403(b), and IRA plans)
Of those years, a minimum of two must be at a law firm practicing in this area
Demonstrated experience with qualified plan operational compliance, including EPCRS and the correction principles that apply to qualified retirement plans
Working knowledge of ERISA fiduciary duty and prohibited transaction rules as they apply to plan administration and service provider arrangements
Experience advising non-legal business teams on ERISA issues in real time, including translating technical legal conclusions into actionable guidance
Subject Matter Knowledge: Strong working knowledge of ERISA fiduciary duty and prohibited transaction rules and the IRC qualification rules applicable to 401(k) plans.
Licensure: Admitted to the bar and in good standing, or otherwise authorized to practice law (e.g., registered in-house status) in any state.

Nice to haves:

In-house experience at a recordkeeper, TPA, fintech, or trust company
Direct experience with 3(16), 3(21), or 3(38) fiduciary operations at a recordkeeper or TPA
Experience providing ERISA input on product, operational, or technology decisions — whether at a recordkeeper, TPA, fintech, plan sponsor, or in a law firm advising clients of that type