Senior Employment Counsel

Senior Employment and Compliance Counsel United States, Remote 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're seeking a Senior Employment Counsel to join Human Interest's Legal team. This is a senior, employment-focused role. You'll serve as the strategic partner and trusted advisor to our People team on the full range of employment matters, and you'll own the company's employment disputes and employment risk end to end. Our workforce is U.S.-based and spans most of the 50 states, so multistate employment compliance is core to the role. It's also a role for a lawyer who digs in beyond employment. We want someone who's genuinely open to learning and taking on adjacent areas of law as the business needs them - from privacy to non-employment litigation to ERISA - rather than routing the unfamiliar elsewhere. Employment is the foundation and the primary focus; the appetite to stretch is what sets the right person apart. This role reports directly to the Assistant General Counsel, Product & Regulatory, and offers a genuine opportunity to grow within a legal team that's scaling alongside the company. What You Get To Do Every Day Employment Counseling, Disputes and Advisory (Primary Focus) Serve as the primary legal advisor to the People team across the full employment lifecycle: hiring, performance management, corrective actions, terminations, reductions in force, accommodations, leaves, compensation, contingent workers, and sensitive employee situations. Own the company's employment disputes. Manage pre-litigation claims, demand letters, administrative charges before the EEOC and state agencies, and settlement negotiations, and direct outside counsel on employment litigation. Oversee and advise on internal employment investigations, including harassment, discrimination, retaliation, whistleblower, and policy-violation matters. Provide proactive counsel on employment law compliance across a multistate workforce, with particular depth advising on non-exempt employee populations, staying ahead of developments in federal, state, and local law and taking the necessary steps to avoid issues before they arise. Advise on employee and HR data privacy and information security, including how personnel data is collected, used, and protected under applicable federal and state law. Draft, review, and negotiate employment-related documents including offer letters, employment agreements, separation and severance agreements, CIIAAs, and equity-related documents. Translate new legal and regulatory developments and 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. Develop and deliver training for the People team, people leaders, and business stakeholders on employment law topics and best practices, policy, and risk mitigation. Beyond Employment (Where You'll Stretch) Dig into adjacent areas of law as the business needs them, learning quickly and taking ownership rather than routing questions elsewhere. Depending on your interests and the team's needs, this can span privacy and information security, non-employment litigation and disputes, regulatory investigations and examinations, ERISA and benefits, commercial contracting, and marketing and advertising review. Support regulatory inquiries and examinations by government agencies, in coordination with outside counsel where appropriate. Advise on privacy and information security matters beyond the employment context, including customer, product, and vendor data, under applicable federal and state law. Support active litigation and disputes, including coordination with outside counsel, document collection and productions, and internal communications. Review and advise on marketing and advertising materials for legal and regulatory compliance. Draft and negotiate commercial agreements and provide general contract support across the business as needed. What You Bring To The Role JD from an accredited law school; active bar admission in at least one U.S. jurisdiction required. 8 to 10+ years of legal experience, with deep, dedicated employment law experience across both counseling and disputes, including demonstrated counseling depth on non-exempt employee populations. At least one prior in-house legal role is strongly preferred; startup or high-growth technology company experience is a strong plus. Demonstrated experience managing employment litigation and pre-litigation matters, including directing outside counsel and driving strategy and resolution. Demonstrated expertise in California employment law. Experience with equity compensation (a meaningful part of our total rewards) and executive compensation. Law firm background is preferred, with a 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. 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. 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 Human Interest