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Clipboard Health
On-demand healthcare staffing marketplace · Series C · YC W17
Founded
2016 · San Francisco
Stage
Series C (~$80M raised)
Team
1,000+ (fully remote)
Comp Range
$80K – $160K USD
Two-sided marketplace connecting healthcare professionals with facilities for on-demand shift work. Professionals pick up shifts via the app; facilities get vetted, reliable workers on short notice.
Millions
Shifts filled annually
Mission
"Lift as many people up the socioeconomic ladder as possible" — let professionals turn extra time and ambition into career growth and financial opportunity.
Verticals
- Long-Term Care / Skilled Nursing — original and largest vertical
- Dental — expansion market
- Home Health — expansion market
- Full-time product — permanent placement beyond per-diem shifts
Investors
Y Combinator (W17), Sequoia Capital, DNX Ventures, Initialized Capital
| Name | Role | Notes |
|---|
| Bo Lu | Co-founder & CEO | Ex-McKinsey. Prolific writer on the company Substack. Strong opinions on hiring, first-principles culture. |
| Wei Deng | Co-founder & COO | Handles operations side. |
| Jesse F. | Head of People | Authored the People team blog post. Defines the team as "defect hunters." |
Not traditional HR. They call themselves the "designated group of defect hunters for the internal corporate team." The team runs things down, implements solutions, and makes judgment calls.
What people should say about the team: "They enforce high standards across the org." "They are my go-to resource to think through tough people problems." "They are some of the most strategic thinkers in the org."
Four Pillars
| Pillar | What It Means |
|---|
| Make it make sense | Relentless curiosity. Don't accept answers from people just because they're experts — push until it makes sense or you've found a flaw in thinking. |
| Touch reality | Don't rely on secondhand opinions. Review support tickets, listen to sales calls, audit feedback directly. Form your own view from primary sources. |
| Think from first principles | Don't default to "how it's always been done." Start with the ideal, work backwards to the best solution — even if it means scrapping everything. |
| Drive towards the unknown | Seek out uncomfortable, scary work. Be first into the fire. Share learnings openly so others can avoid the same mistakes. |
Writing Is Thinking
Deeply embedded, not performative. Memos over meetings. Decisions documented in writing. The hiring process is writing-heavy by design — if you can't write clearly, you can't think clearly.
Who Thrives Here
- High autonomy, high accountability — senior people expected to operate independently
- Speed and intensity — they move fast, expect high output, and are upfront that it's not for everyone
- First-principles reasoning over industry convention
- Results-oriented — compensation tied to output, not tenure or credentials
- Comfortable with chaos — priorities shift, you adapt
The Ideal Candidate (from JD)
- Not from traditional HR — they've found the best people don't carry preconceptions about what HR "should" be
- "Put me in coach" — game for anything, chases the most important problems
- Knows their limits — self-aware enough to seek help when a wrong call would have serious consequences
- Thrives on feedback — seeks challenge from peers and managers, implements immediately
High-impact IC role within the People team. No direct path to people management. Significant opportunities for skill development and expanded influence.
What You'd Do
- Partner with leaders on key personnel decisions — from designing hiring automations to conducting exit conversations to coaching managers on leave decisions
- Quarterly departmental audits — deep dives into each team, partnering with leaders to create strategic, impactful changes
- Own org-wide initiatives — new system implementations, rebuilding onboarding/offboarding, running point across teams
- Notice and solve problems — see what's broken, connect dots, take ownership of fixing it
Logistics
| Detail | Info |
|---|
| Location | Remote (Canada) — must work Pacific or Mountain hours |
| Compensation | $80K – $160K USD |
| Type | Full-time, IC |
| Visa | No sponsorship |
Positives
- Smart colleagues, high autonomy, real impact
- Writing culture praised by people who value clear thinking
- Genuinely remote with flexibility
- Profitable and stable — no layoff anxiety
- Mission feels tangible (healthcare workers getting better pay and flexibility)
Watch For
- Intensity is real — long hours, high expectations. "Work-life balance" is not the brand.
- Culture is polarizing by design — passionate advocates and vocal detractors
- Startup chaos — rapid changes in priorities and processes even though they're profitable
Role is a departure from PM. This is People/Ops, not product management. Worth considering: is this a lateral move that plays to your strengths (ops instinct, problem-solving, building systems) or a detour from your PM trajectory? The "not traditional HR" framing works in your favor — they explicitly don't want HR people.
Strong Fit Signals
- Writing-first culture maps directly to your communication strengths
- First-principles, "touch reality" philosophy mirrors your product approach
- They want problem chasers, not policy writers — your ops/product hybrid background fits
- Profitable Series C = stability without big-company bureaucracy
- Remote Canada, Pacific hours = logistically perfect
Open Questions
- Wide comp band ($80K–$160K) — where would you land? Important to clarify early.
- How does this People Ops role translate back to PM if you want to return?
- Intensity signals — what does "high output" mean in practice for this team?