What are the responsibilities and job description for the Chief of Staff — AI Startup (YC W26) position at Benchstack Ai?
A YC-backed (W26) AI startup that just raised a $5M seed round — with backing tied to the investors behind OpenAI, plus names like Max Altman and Jerry Ting (Head of AI at Workday). They're bringing AI to the $1T equipment industry and already have real revenue from enterprise customers you'd instantly recognise (think the biggest names in heavy equipment). Founders previously led AI deployments at Tesla, Cummins, and Boeing.
You'd join as one of the first five hires, working directly with the CEO, in the room for every major decision — with a clear path into a leadership seat (Head of CS, Pre-Sales, or beyond) as they scale
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What you'll
- Work shoulder-to-shoulder with the CEO across the highest-priority parts of the busine
- Own pre-sales and post-sales: customer calls, events, building enterprise relationship
- Drive strategic projects — OEM and partnership deals
- Build and run customer onboarding
- Experiment across GTM channels (outbound, ads, events, BDR
- Represent the company in customer dinners and investor meetings
What they're looking
- 2–6 years' experience
- Tier-1.5 consulting (Strategy&, Oliver Wyman, Kearney, LEK, Monitor) or MBB / PE /IB
- STEM undergrad (engineering, maths, physics, CS)
- Startup experience — you've worked at or built something early-stage
- High agency: figure things out without a playbook, move fast
- Polished enough to hold a room, from SMB owners to enterprise CEOs
Logistics
- On-site SF, 5 days/week (relocation welcome)
- US work auth required (TN and OPT fine; no H-1B/O-1 sponsors
- Final stage: paid 3-day in-person work trial (travel covered)
Salary : $140,000 - $170,000