Startups · AI

Lead AI Systems Engineer

Benepass · U.S Remote · Remote

← All jobs
About Benepass

Backed by Y Combinator.

About the role

This role is deeply technical, highly strategic, and critical to Benepass’s velocity. You will own the AI systems roadmap and architect a shared internal AI platform that starts with the engineering SDLC, and is explicitly designed to scale into automation and agentic systems across the company (Operations, Product, Design, Support, and other internal workflows).

What they're looking for

  • Staff-level (or equivalent platform/cross-functional) impact shipping systems others depend on
  • Strong programming fundamentals (Python and/or TypeScript/JavaScript preferred)
  • Experience building internal platforms, developer tools, or automation integrated into CI/CD
  • Hands-on with modern AI systems: coding agents, LLM APIs, orchestration, and production operability
  • Experience enabling quality through automation (E2E/integration testing, intelligent quality gates)
  • Solid systems instincts: APIs, permissions, observability, reliability
More about this role

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 Centana Growth Partners, Portage Ventures, Threshold Ventures, Gradient Ventures, Workday Ventures, and Clocktower Technology Ventures. To date, the company has raised approximately $75 million in equity capital.

Founder Story - Jaclyn Chen

Benepass Raises $40M Series B

Benepass | Candidate Resource Page

Benepass Listed on Inc. Magazine's Best Workplaces...

Read the full posting on Benepass's site ↗

Engineering

Build your edge while you search

Free tools for founders and investors, plus VC Unfiltered, our take on startups, venture and the people who build them.