Careers

Build the Employment OS with us.

We're a distributed team shipping the tools we wished we had during our own job searches. If you've ever rewritten a resume at 2 AM, you'll fit right in.

Why CareerOS

Careers are the single biggest financial and identity decision most people make — and the tooling around them is stuck in 2011. We're building the operating system for the next decade of hiring: AI that remembers every project you've shipped, applies where you're a genuine fit, and prepares you to win the interview.

We are venture-backed, revenue-positive, and profitable on a per-user basis. Every hire gets meaningful equity and a real voice in what we ship next.

Open roles — Engineering

  • · Founding Design Engineer — Remote · $210–260k + equity
  • · Staff ML Engineer, Career Memory — Remote · $260–320k + equity
  • · Senior Full-Stack Engineer, Auto-Apply — Remote · $200–250k + equity
  • · Infrastructure Engineer, Data Platform — Remote · $210–260k + equity
  • · Applied AI Researcher, Interview Coach — Remote · $240–300k + equity

Open roles — Product, Design & GTM

  • · Product Manager, Auto-Apply — Remote · $200–240k + equity
  • · Product Designer, Resume Studio — Remote · $180–220k + equity
  • · Enterprise AE, Recruiter Cloud — NY / Remote · $180k base + uncapped OTE
  • · Lifecycle Marketing Lead — Remote · $170–210k + equity
  • · Head of Talent — Remote · $200–250k + equity

How we work

Async by default across 11 timezones. Written proposals over meetings. Weekly demo Fridays. Quarterly on-sites in Lisbon, NYC, or Bali.

Every hire ships something to production in their first week. We hire slowly, pay at the top of the market, and expect craft.

Benefits

  • · Fully remote — work from wherever you do your best thinking
  • · Top-of-market cash + meaningful early-stage equity with a 10-year exercise window
  • · $3,000 home-office stipend, $2,400/yr learning budget, $2,000/yr wellness
  • · Full health, dental, and vision across US, EU, UK, and India
  • · Unlimited PTO with a 4-week minimum floor (we track it)
  • · 16 weeks of parental leave, fully paid
  • · Two paid company on-sites per year

Our hiring process

  1. Intro call with the hiring manager (30 min)
  2. Paid take-home or portfolio deep-dive (4–6 hrs)
  3. Working session with your future team (90 min)
  4. Founder conversation + references
  5. Offer within 5 business days of your final interview

Apply

Send a note and your best work to careers@silverspringstaffing.com. Please skip the cover-letter template — tell us what you'd build in your first 90 days instead.