Sr. Director, People Operations at Benepass

ABOUT US At Benepass we're making benefits easy. We believe people are the most important asset to any company. Traditional one-size-fits-all benefits packages no longer cut it in today's hybrid and remote-first environment. With Benepass, companies can tailor their benefits to the unique needs of their workforce. Through our easy-to-use and highly customizable fintech platform, People teams can implement, administer, and track the benefits that meet employees where they are. Employers design their benefits and perks plan by setting a contribution amount and eligible spend categories. Every employee has their own individual definition of wellness and needs different things to help them be their most productive, fulfilled self. OUR MISSION Helping companies reimagine how companies take care of their people. OUR INVESTORS We are backed by leading investors, including Portage Ventures, Threshold Ventures, Gradient Ventures, Workday Ventures, and Clocktower Technology Ventures. To date, the company has raised $35 million of equity capital. ARTICLES - Founder Story - Jaclyn Chen [Upgrade to PRO to see link] - Benepass Raises $40M Series B [Upgrade to PRO to see link] CANDIDATE RESOURCES - Benepass | Candidate Resource Page [Upgrade to PRO to see link] - Benepass Listed on Inc. Magazine's Best Workplaces of 2023 [Upgrade to PRO to see link] THE ROLE We’re looking for a Senior Director of People Operations to establish and lead the People function at Benepass as we scale past 100 employees. As our first senior HR hire, this role will be both strategic and hands-on, owning everything from core HR operations, policies and compliance to, performance management, total rewards, benefits, manager development, and organizational design. This leader will build scalable people programs and infrastructure, partner with leadership on workforce planning and culture, and help Benepass grow thoughtfully while maintaining a strong employee experience This role will establish the systems, programs, and processes that create a best-in-class employee experience and enable Benepass to scale effectively. A major focus will be developing the right people infrastructure — implementing and optimizing our HR tech stack, benefits administration, and compensation frameworks — while ensuring compliance and operational excellence. You’ll partner closely with company leadership to shape the future of our organization and people strategy. WHAT YOU’LL DO - Build and lead the People function across HR operations, employee experience, and strategic people initiatives. - Design and implement HR infrastructure, including payroll, HRIS, and benefits administration systems that can scale with company growth. - Lead compensation and benefits strategy, partnering with Finance and leadership to evolve salary frameworks (including evaluating geo-based ranges) and optimize total rewards. - Oversee all aspects of the employee lifecycle, including onboarding, performance management, development, and offboarding. - Act as a trusted advisor to executives and people managers on organizational design, leadership development, and employee relations. - Negotiate and manage benefit programs with external brokers and partners to ensure competitive, compliant, and cost-effective offerings. - Develop and maintain people data infrastructure to enable accurate reporting, analytics, and compliance across jurisdictions. - Drive cultural initiatives that enhance engagement, belonging, and manager effectiveness. - Lead annual review cycles for performance, compensation, and goal-setting, ensuring alignment with company strategy. - Plan for scale, laying the groundwork for future programs in manager enablement, learning and development, and workforce planning. WHAT YOU BRING - Proven experience building and scaling People functions from the ground up, including people operations, manager enablement, and core employee programs that support growth and performance. - Strong track record designing and evolving talent processes such as performance management, feedback and development frameworks, succession planning, and leadership development. - Experience partnering with executive leaders on organizational design, workforce planning, and change management in rapidly scaling environments. - Solid understanding of compensation philosophy and strategy, including market benchmarking and geo-based frameworks, with the ability to balance competitiveness, equity, and sustainability. - Experience evaluating, implementing, and optimizing People systems and infrastructure (e.g., HRIS, payroll, people analytics), with a focus on scalability and employee experience. - Working knowledge of employment law and compliance across multiple U.S. states, with the judgment to apply best practices pragmatically rather than bureaucratically. - Excellent communication, influence, and stakeholder management skills, with the ability to coach leaders, navigate sensitive situations, and build trust across the organization. - A thoughtful, empathetic, and data-minded approach — able to advocate for employees while driving outcomes that support Benepass’ goals. COMPENSATION Base salary of $180,000 to $210,000 + equity. RANGE(S) IS SUBJECT TO CHANGE. BENEPASS TAKES A NUMBER OF FACTORS INTO ACCOUNT WHEN DETERMINING INDIVIDUAL STARTING PAY, INCLUDING MARKET COMPARABLES, INTERVIEW PERFORMANCE, PEER COMPENSATION, AND YEARS OF EXPERIENCE. #LI-DNI RANGE(S) IS SUBJECT TO CHANGE. BENEPASS TAKES A NUMBER OF FACTORS INTO ACCOUNT WHEN DETERMINING INDIVIDUAL STARTING PAY, INCLUDING MARKET COMPARABLES, INTERVIEW PERFORMANCE, PEER COMPENSATION, AND YEARS OF EXPERIENCE. WHAT WE OFFER - 95% coverage of medical, dental, and vision - Fantastic benefits (of course 😃), including: - $250 WFH setup (one time) - $500/year Learning & Development Benefit - $150/month cell phone + internet - $100/month Wellness - $100/month Co-working and Commuter Benefit - We offer several team onsites a year - Flexible PTO At Benepass, we are working towards reimaging how companies take care of their people. We are committed to creating an inclusive environment for all our employees and are seeking to build a team that reflects the diversity of the people we hope to serve with our revolutionary products. Benepass is proud to be an equal-opportunity employer.