FirstWork Verified
HR Tech
Chief Of Staff
New York, New York, United StatesOnsiteFull TimeChief / Executive$80,000–$125,000 /yrPosted 2 months agoHidden Gem · YC Startup
Role summary
Firstwork is seeking a Chief of Staff to the CEO to drive strategic initiatives and operational improvements within their AI operating system for frontline labor. This role focuses on building new commercial channels, evolving pricing and packaging, optimizing sales and operational systems, and leading cross-functional projects. The ideal candidate will have 4-8 years of experience, a background in structured environments like consulting or banking, and operating experience in early-stage companies. Success will be measured by the launch of new revenue streams, sharper pricing, faster enterprise initiatives, and improved internal execution, allowing the CEO to focus on external leverage.
**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.
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.
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