Chief of Staff to the CEO
Chasi Ai
Apply to this job San Francisco on site Until 8/22/2026 First posted May 25, 2026 Last posted May 25, 2026
Job description
About Chasi
Every building, road, warehouse, and farm runs on equipment like tractors, cranes, forklifts, etc. Over 100K dealers and rental companies across North America keep those machines bought, sold, rented, and serviced, but most still operate on phone calls, paper, and decades-old software, with fewer people to do the work every year.
Chasi is building the future of equipment commerce. We help dealers and rental companies sell faster, respond to customers around the clock, and keep machines in the field instead of sitting in a shop or a yard. This is one of the biggest opportunities to bring real-world AI to an industry that software has barely touched. We're based in San Francisco, backed by YCombinator and other top investors, and already working with CAT, John Deere, Bobcat, and other top OEM dealers.
About the role
This is an intense, minimum 2-year role for someone who wants to grow into leadership or eventually start their own company. You'll work directly with me across whatever matters most at Chasi. I'll make sure you have real leverage to get things done, and I want you to push back on me when I'm wrong.
What You’ll Do
You’ll work with me across the highest-priority areas of the company as we scale: go-to-market, pricing and positioning, partnerships, hiring, investor and board work, and the strategic questions that define what we do next. The exact mix will change as the company grows. What won’t change is that you’ll be close to the hardest problems, in the room for important conversations, trusted to act on my behalf when needed, and expected to move things forward with urgency and good judgment. This will be a demanding role, but for the right person, an unusually rewarding one.
Who You Are
No specific years-of-experience requirement, but you’ve done something hard. That could mean private equity, consulting, an early-stage startup, or something you built yourself. What matters more than pedigree is that you’ve operated in high-bar environments, taken ownership, and learned how to figure things out without a playbook.
What matters:
- You’re resourceful and competitive. You move fast and don’t wait to be told what to do.
- You write and think clearly. You can communicate well with customers, candidates, investors, and internal teams.
- You have good judgment and taste - for people, products, and how things should feel.
- You want to build and lead teams over time, and you’re willing to earn that responsibility.
- You’re comfortable being uncomfortable. This role will stretch you, and that’s part of the point.
Other Details
- In-person, San Francisco
- Reports directly to me
- Competitive base + meaningful early-stage equity
- Expect long weeks, travel
About this role
Summary
support executive leadership in strategy, operations, partnerships, and team building in a fast-paced startup environment
Job title
Chief of Staff to the CEO
Experience level
none specified
Industry
software
Location requirements
in-person in san francisco, no remote work
Salary
Not specified
Management role
Yes
Skills & keywords
Required skills
communicationownershipjudgmentresourcefulness
Preferred skills
leadershipstartup experiencehigh-pressure decision making
Specializations
strategyoperationsleadershipstartup
Locations
Structured locations inferred from the posting.
San Francisco, CA, USA
On-site City