Employment and Compliance Counsel

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

We are seeking an Employment & Compliance Counsel to join our Legal team. This is a dual-mandate role: approximately half of your time will be dedicated to serving as a strategic partner and trusted advisor to our People Team on all aspects of employment law, and the remainder will consist of broad generalist legal work supporting a fast-moving, regulated fintech business.
This role reports directly to the Assistant General Counsel – Regulatory Compliance & Litigation, and offers a genuine opportunity to grow within a legal team that is scaling alongside the company.

AI Fluency & Adoption

Human Interest’s Legal team is committed to working at the frontier of how in-house legal work gets done. We are not looking for someone who is curious about AI — we are looking for someone who has already made AI a core part of how they practice law.

• You have developed genuine fluency with AI tools and use them daily — not as a novelty, but as a core part of how you research, draft, analyze, and think through legal problems.
• You build workflows and, where applicable, agents that multiply your effectiveness and reduce manual, repetitive work — and you bring that same instinct to the team around you.
• You actively seek out new AI capabilities as they emerge, evaluate them critically, and apply them thoughtfully to legal work — with an eye toward both quality and risk.
• You can articulate both the power and the limitations of AI in legal contexts, and you help others on the team develop their own fluency over time.

What you get to do every day

Employment Counseling & Advisory (~50%)

• Serve as the primary legal advisor to the People Team on the full range of employment matters, including hiring, performance management, terminations, reductions in force, and sensitive employee situations.
• Provide proactive counsel on employment law compliance — with particular depth advising on non-exempt employee populations — staying ahead of developments in federal, state, and local law and positioning the company to avoid issues before they arise.
• Support and advise on internal employment investigations.
• Draft, review, and negotiate employment-related documents including offer letters, employment agreements, separation and severance agreements, PIIAs, and equity-related communications.
• Translate new legal and regulatory requirements into clear, practical guidance for the People Team and business stakeholders.
• Partner with the People Team to develop and maintain employment policies, handbooks, and compliance procedures.

Generalist Legal Support (~50%)

• Support regulatory investigations and examinations by government agencies, in coordination with outside counsel where appropriate.
• Advise on privacy and information security matters under applicable federal and state law.
• Support active litigation and disputes, including coordination with outside counsel, document collection, and internal communications.
• Provide legal support to the Customer Success and Operations teams on client-facing matters, escalated issues, and contractual questions.
• Review and advise on marketing and advertising materials for legal and regulatory compliance.
• Draft and negotiate commercial agreements and provide general contract support as needed across the business.

What you bring to the role

• JD from an accredited law school; active bar admission in at least one U.S. jurisdiction required.
• 8–10+ years of legal experience, with meaningful, dedicated employment law experience — including demonstrated counseling depth on non-exempt employee populations.
• At least one prior in-house legal role is required; startup or high-growth technology company experience is a strong plus.
• Law firm background is preferred, with demonstrated ability to translate analytical rigor into practical, business-ready guidance.
• Comfort advising and building relationships with non-legal stakeholders, including the People team, senior executives, and business leaders across functions.
• Ability to work autonomously, manage competing priorities, and make sound judgment calls in an ambiguous, fast-paced environment.
• Exceptional written and verbal communication skills.

Who you are

Beyond credentials and experience, we are looking for a specific kind of person:

• You are naturally curious — you read widely, ask good questions, and are genuinely energized by learning things you don’t already know.
• Your foundation is U.S. employment law, and you know it well — but you don’t stop there. You have a demonstrated interest in and aptitude for adjacent areas of law, and you are comfortable engaging with unfamiliar legal questions rather than routing them elsewhere.
• You are a team player in the truest sense — you pitch in wherever you’re needed, you help your teammates without being asked, and you don’t let ‘that’s not my job’ be a reason not to help.
• You are deeply process- and documentation-oriented. You understand that high-quality legal work requires diligence, consistency, and rigor — and you apply those qualities even when no one is checking.
• You take pride in your work product, sweat the details that matter, and know how to distinguish signal from noise.

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