Chief of Staff

Prox builds AI technical support for complex physical products (think power tools, powersports equipment, agriculture, heavy machinery -- anything that requires an installation guide or complex manuals).

Backed by Y Combinator, Bloomberg Beta, Paul Graham, SV Angel, Burst Capital and many more.

Intro to the role

We run the company out of a git-based knowledge graph. Every customer meeting note. Every investor and vendor conversation. Our writing style, our voice, ICP, our positioning. Product ideas, platform new features and roadmap decisions. Marketing campaigns, LinkedIn content, outreach sequences, conference pipeline.

Structured, linked, versioned, with an agent layer on top that reads, writes, syncs, briefs, and completes tasks. This is what we build for our customers: take everything a company knows about its products -- manuals, specs, forum threads, support history -- and make it queryable by an AI that never forgets and never sleeps. We do the exact same thing for ourselves.

Work culture and location

This is an in-person San Francisco role.

We operate at a 996-style founding-team cadence: roughly 9am-9pm, six days a week, in office. There will be intense conference weeks, customer travel, late-night prep, weekend work, and periods where the company needs full founder-level intensity from you.

This is not a balanced corporate operations role. It is for someone who actively wants to be inside the machine while we try to turn Prox into a generational company. If that schedule sounds incompatible with your life right now, this is not the right role.

The person we're looking for has a specific character flaw:

They cannot do the same thing twice without immediately wanting to eliminate the second time it happens. Not from laziness, but because repetition feels like a design failure.

They think like a hacker. Every system has a seam, and if you find it, you can usually make 10x the impact with a fraction of the effort. They don't ask permission to automate. They notice the pattern and close it.

But they have taste. Output that looks like AI slop bothers them. Be it an email, customer proposal, blog post, or event announcement. The aesthetic of the work matters a lot as we're entering the brand age.

Your job is to be the judgment layer on top of everything the agents can't decide -- and to keep extending the system so the list of things agents can't decide gets shorter.

What you'll juggle

⊹ Communication ops -- drafting, editing, and sending on behalf of the founders. Investor updates, customer threads, recruiting replies, vendor back-and-forth. High volume, high taste bar.

⊹ GTM and BD ops -- pipeline, outreach, follow-ups, proposals

⊹ Executive assistance -- scheduling, travel, logistics, occasional personal tasks

⊹ Content and marketing ops -- LinkedIn, campaigns, contractor coordination

⊹ Video content -- capturing, coordinating, and helping shape what gets made

⊹ Knowledge graph maintenance -- keeping the company ontology clean, current, and growing

⊹ Agent development -- extending the system so fewer things need manual handling

Skills required:

⊹ Obsessively detail-oriented and caring

⊹ Able to work in person in San Francisco on a 996-style cadence

⊹ Comfortable in a terminal -- git, basic unix commands, CLI tools + Claude Code

⊹ Comfortable with APIs -- you don't need to be an engineer, but you need to know how systems talk to each other

⊹ Fast learner -- productive in a new system within days

⊹ Strong writer -- natural voice, clean formatting, can quickly catch AI slop, drafts that don't need editing

⊹ Taste -- cares about quality and aesthetic of work

⊹ Systems thinker -- sees a recurring task as a design failure, not a to-do item

Bonus: prompt engineering experience

Comp:

⊹ $135K + 0.35% equity

⊹ $11,250 signing bonus · full health, dental, vision · daily meals

⊹ In-person SF, 996-style cadence

Process:

Application → founder call → take-home challenge → paid work trial → offer