Lead, People Operations
Company shown to members 🔒 · Remote · US only
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First recorded by Psst: 23 October 2026. Your first 3 jobs are free to apply to (the first right away, 2 more with your email). After that, the company and the apply link are for Psst members, from $4.99 for 7 days.
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The 20-second read
- Experience
- Senior
- Where you can live
- US only
- Skills and tools
- payroll, hris, compliance
- Job type
- Full-time
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Job details
- Where you can work
- United States
- Employment type
- Full-time
- Advertised pay
- $120K–160K/yr
- Experience
- Senior
- Employer publication date
- 22 October 2026
- First recorded by Psst
- 23 October 2026
- Last checked at the source
- 10 November 2026
About the job
THE JOB
In the next two years, we aim to help over 250,000 Americans get access to life-changing benefits. Behind that impact is a remarkable group of people — attorneys, engineers, client advocates, marketers, product managers, and more. The company People team makes that work possible — we build the systems, policies and operations that enable us to do our best work.
We’re hiring a People Operations Lead to run the backbone of our People function: benefits, systems, payroll and multi-state compliance through our PEO, people policy, and our performance and merit cycles. You’ll be the day-to-day owner of how this work gets done — managing our vendors, keeping us compliant as we grow, running our cycles cleanly, and improving the employee experience at every touchpoint. You’ll also play a central role in the bigger decisions ahead of us — when and how we leave our PEO, how we replace our HRIS, how our policies and benefits should evolve — bringing the analysis and recommendations that shape them.
You’ll report to Amy Yu [link for members] our Head of People, and join a small, high-ownership team that cares deeply about our mission and about having real impact. The ideal candidate has run core People Operations programs at a tech-driven company and is ready to take on a broader scope somewhere the work really matters. We’ve helped hundreds of thousands of people get the benefits they deserve, and the people doing that work are who you’d be building for.
WHO YOU ARE
- 5+ years in People Operations at a venture-backed tech company, with hands-on ownership of at least a few of: benefits, HRIS, payroll, compliance, performance cycles, and policies
- You’re equally comfortable running a benefits analysis as you are having a tough leave conversation, and handle both with tact and clarity
- You’ve administered an HRIS end-to-end and managed People vendors and partners; you’ve driven a system implementation or migration and know what makes one go well
- You’ve automated and improved HR processes to be more efficient, accurate and seamless for both HR and business users
- You operate with low ego but high ownership, and are comfortable both doing the work and figuring out how it can be improved
SALARY AND BENEFITS
The role is a rare opportunity to join a fast-growing Series C startup that doubles as a B-corp social enterprise. Our team is still small enough for you to have an outsized impact on how we operate and how our people experience unfolds.
We offer competitive pay — including equity — and generous benefits
- Medical and dental insurance with 100% of employee and family premiums covered
- 15 vacation days & ~20 paid holidays each year (including two weeks at end-of-year)
- Free membership to OneMedical
- $600/year internet stipend
- $1,000 reimbursable stipend for education and training outside of work
- Up to $1,200/year student loan repayment assistance
- 401(k) and optional HSA/FSA
- Humble, thoughtful, smart, fun colleagues
We anticipate the base salary band for this role will be between $120,000 to $160,000 in addition to equity and benefits. The salary at offer will be determined by a number of factors such as candidate’s experience, knowledge, skills and abilities, as well as internal equity among our team.
LOCATION
This job is fully remote and we’re committed to empowering everyone with flexibility. Work remotely, and travel to LA (on the company dime) as needed to be with your colleagues – usually quarterly, plus offsites. We care a lot about building a great culture and we think some interactions need to happen in person, so we put a lot of thought into retreats, offsites, and other ways to gather.
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