Down the rabbit hole we go.
Chief of Staff | San Francisco (On-site, Full Time) | US$120,000 to US$160,000 + Equity (0.30% to 0.60%)
Big Wave Digital is partnering with one of our premier AI technology clients in San Francisco, a YC and Google-backed startup building self-improving software for some of the fastest-growing consumer apps in the world.
Think AI that does not just sit politely in the corner writing summaries.
This is AI that generates, tests, learns, improves product experiences, lifts revenue, optimises onboarding, experiments with paywalls, and helps consumer apps convert and retain more users at serious scale.
Very Alice in Wonderland, except the rabbit hole leads to revenue growth, operational chaos, enterprise customers, and a CEO who needs a brilliant right hand.
The company is tiny, elite, and moving absurdly fast.
- 8 people
- Mostly engineers
- 75% ex-founders
- All three co-founders have ML degrees
- $6M raised from world-class AI investors
- Revenue doubling monthly
- Series A trajectory
The kind of place where “that’s not my job” gets politely shown the trapdoor.
The Role
This is a Chief of Staff role for someone who wants to be inside the engine room of a high-growth AI startup.
You will work directly with the CEO across whatever matters most that week, that day, or that hour.
One day you might be helping onboard enterprise customers. The next, building internal processes so the company does not melt under its own growth. Then jumping into hiring, growth projects, fundraising prep, customer support, events, automation, product feedback, or whatever weird and wonderful problem just appeared on the table marked “Drink Me.”
This is not a calendar-management Chief of Staff role. This is not a polished corporate strategy role where you build slides and wait three weeks for sign-off.
This is operator mode.
- Messy problem? You turn it into a plan.
- Customer issue? You jump in.
- Growth project? You ship it.
- Process broken? You fix it.
- Team drowning? You build the raft.
- CEO moving at 200 miles per hour? You become the person who makes the madness useful.
Who You Are
You probably have 1 to 4 years of experience in a high-intensity environment: startup, consulting, banking, operations, elite sport, military, or somewhere that taught you pace, discipline, judgement, and follow-through.
You are organised without being rigid.
You can take a chaotic pile of context, customer noise, half-finished thoughts, Slack threads, product feedback, and vague strategic urgency, then somehow turn it into a clean plan that actually gets done.
You are a seriously strong communicator. Clear, calm, likeable, direct, and good in tricky conversations.
You are low ego. Properly low ego. You are happy owning strategic projects, but also happy jumping on bugs, late-night support, messy customer questions, or annoying operational details if that is what moves the needle.
You use AI tools daily, not as a party trick, but to produce faster, sharper, better work.
You like intensity. You want to be close to the founders. You want ownership. You want the kind of role where the answer to “what will I own?” is “quite possibly half the company’s operating system by month three.”
Nice to Have
- Early-stage startup experience
- Consulting, banking, operations, founder, sport, or military background
- Strong academic signal
- AI-native working style
- Evidence you have built, launched, shipped, organised, or rescued things under pressure
- A slightly unhinged ability to stay calm when the flamingo mallets come out
The Deal
- Location: San Francisco
- Work style: In-person
- Salary: US$120,000 to US$160,000
- Equity: 0.30% to 0.60%
- Experience: 1 to 4 years
- Visa sponsorship: Not available
- Benefits: all meals in office, gym membership, quarterly off-sites, real ownership, and the chance to build around frontier AI models before the rest of the world gets them
Who This Is NOT For
- This is not for someone looking for a calm 9 to 5.
- This is not for someone who wants a pure strategy role with no execution.
- This is not for someone who needs a large team, perfect structure, or a clearly defined lane.
- This is not for someone who says “I’ll circle back next week” when the answer needs to be figured out tonight.
This is for the person who sees chaos and thinks:
Lovely. Game on.
To Apply
Send your CV or LinkedIn profile to Big Wave Digital.
Bonus points if you can show us something you have built, launched, fixed, scaled, improved, or dragged across the finish line when everyone else was still discussing the roadmap.
Curiouser and curiouser.
