Sr. Director, People Operations

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.

Helping companies reimagine how companies take care of their people.

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.

• Founder Story - Jaclyn Chen

• Benepass Raises $40M Series B

• Benepass | Candidate Resource Page

• Benepass Listed on Inc. Magazine's Best Workplaces of 2023

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.

• 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.

• 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,…