What the role involves
Chief of Staff to the CEO
Firstwork is building the AI operating system for frontline labor
The companies that staff hospitals, power cities, run warehouses, and move freight still hire and onboard workers through systems built decades ago - fragmented, manual, slow
We replace that with AI agents that compress time-to-hire by up to 80% and turn compliance into real-time infrastructure.
We work with complex enterprise operators across the US and EMEA. Backed by Y Combinator, Gradient (Google’s AI fund), and leading AI investors, with offices in New York and globally.
Frontline labor powers more than half the economy. When hiring stalls, capacity collapses. We’re rebuilding that layer properly.
The Role
This is force multiplication for the CEO.
Not coordination. Not slide-making. Not “strategy support.” You ship.
You will
- Build and launch new commercial channels (including PE partnerships)
- Own pricing and packaging evolution
- Tighten sales, billing, and operational systems
- Drive cross-functional initiatives that don’t have obvious owners
- Turn ambiguity into measurable outcomes
- You operate across product, GTM, marketing, and strategy.
- If something is stuck, you unstick it.
- If something is unclear, you clarify it.
- If something matters, you own it.
- What Success Looks Like (6-12 Months)
- New revenue channels are live and producing results
- Pricing is sharper and commercially defensible
- Enterprise initiatives move faster and with less noise
- Internal execution is tighter and more predictable
- CEO time shifts toward external leverage, not internal coordination
- Who Wins Here
You likely have
- 4-8 years of experience
- Time in structured environments (consulting, banking, investing)
- Real operating exposure in early-stage companies (bonus points if in workforce operations, HR, or similar categories)
- Strong analytical horsepower
- Exceptional written clarity
- Comfort with pace and imperfect information
- A bias toward action over process
- You prefer ownership over commentary.
- You care about rebuilding the real economy; logistics, infrastructure, healthcare - not just digital funnels.
- You want proximity to real decisions and real consequences.
About FirstWork
Firstwork is a next-generation HR platform designed specifically for companies with dynamic workforce needs. Our mission is to streamline and automate key HR processes to help businesses operate more efficiently and effectively. What We Do (for now): (1) Smart Onboarding 📋: Our platform simplifies the onboarding process by automating the collection and verification of credentials, such as right-to-work documents, insurance forms and driver’s licenses. This reduces administrative burden and accelerates the time-to-productivity for new hires. (2) AI-Assisted Activation 🤖: Leveraging AI, we enhance communication and messaging for new hires, ensuring they receive timely and relevant information. This helps in better engagement and faster integration into their roles. (3) Perpetual Compliance ✅: Our system uses AI and OCR technology to continuously monitor and ensure compliance with various regulatory requirements. This includes tracking expirations of critical documents, updating records, and generating compliance reports, thus reducing the risk of penalties and legal issues.
Full FirstWork profile