Chief of Staff

Bluejay; San Francisco (CA); On-site; USD 100,000 - 250,000; Full time

Benefits offered by this job

Early-stage equity

Close collaboration with founders

Job summary

Bluejay, based in San Francisco, is seeking a Chief of Staff to support the founders in driving the company forward. This role will focus on high-leverage projects across multiple areas including operations, hiring, and fundraising.

The ideal candidate will possess extreme ownership and be comfortable with ambiguity, executing projects that require quick decision making and strong organization skills. Compensation includes a competitive salary and equity opportunities.

Qualifications

• Proven experience in a startup environment or as a founder.
• Ability to build systems and processes from scratch.
• Strong communication skills for interacting across functions.

Responsibilities

• Take work off founders' plates and execute key projects.
• Develop and track goals, metrics, and company rhythms.
• Connect product, engineering, and go-to-market efforts.

Skills

Extreme ownership

Sharp thinker and clear writer

Comfort with ambiguity

Job description

Bluejay is building the simulation, evaluation, and observability layer for voice + text AI agents. We work with Fortune 500s, multinational corporations, and high-growth startups to ensure their AI agents actually perform as intended in production. We raised a $4M seed backed by Floodgate, Peak XV, and YC — and we've been doubling every 3 months since inception.

Now we're looking for a cracked Chief of Staff to be the founder’s force multiplier and help run the company. We don't want someone to "manage calendars." We want someone who takes whatever’s most important and least owned, and makes it happen — then builds the system so it never falls through the cracks again.

What You’ll Actually Be Doing

The honest answer: whatever moves the company forward most, that no one else owns yet. In practice that clusters into a few areas.

Force‑Multiply the founders

• Take work off the founders plate and run it to done — fundraising prep, hiring, ops, GTM, whatever’s hot
• Turn half‑formed ideas into plans, owners, and deadlines
• Be the person who closes loops so nothing slips
• Execute on special projects that advance the company

Run the Operating Cadence

• Own goals, metrics, and the rhythm the company runs on (standups, reviews, planning)
• Prep board and investor materials, and keep the numbers honest
• Bring structure to chaos without smothering speed

Own High‑Leverage Projects End to End

• Run special projects across GTM, product ops, hiring, finance, and partnerships
• Go deep on whatever needs deciding — research it, model it, write the memo, make the call
• Build the systems and processes that let the company scale past you

Be the Glue

• Connect product, engineering, and GTM so nothing gets lost between functions
• Spot the problems no one is looking at yet and get ahead of them
• Represent the founders when they can’t be in the room

You Will Be

• Deciding
• Executing
• Building systems
• Closing loops
• In the trenches with founders

Who You Are

We’re looking for a hustler with extreme ownership — someone who runs through walls and brings order to chaos. Titles matter less than range and judgment.

Must‑Haves

• Extreme ownership. You see a problem, you take it, you finish it. No "that’s not my job."
• Sharp thinker and clear writer. You can research something messy, form a view, and write the one‑pager that drives a decision.
• Range. You can swing from a financial model to a hiring plan to a customer fire to a board deck in the same day.
• Comfort with ambiguity. You’re given outcomes, not instructions, and you’re fine with that.
• You can hold a credible conversation about our world — AI agents, evals, observability — well enough to be useful across the company.

Core Traits

• Highly AI‑native in how you work
• Scrappy and resourceful
• Gets excited bringing structure to chaos
• Thinks in outcomes, not activity
• Comfortable being wrong quickly and adjusting

Desirable Quirks

• Physically cringes at a dropped ball or an open loop
• Keeps a running list of everything and actually closes it out
• Gets irrationally excited about a clean system or process
• Has strong opinions about what the team should and shouldn’t be spending time on
• Thinks the job is part operator, part strategist, part firefighter

Experiences That Pique Our Interest

• Former founder, early‑startup operator, or first‑few‑employees somewhere
• Background in consulting, banking, ops, or another high‑ownership, high‑output environment
• Worked closely with a founder or executive before
• Built systems or processes from scratch at an early‑stage company
• Career‑pivot candidates welcome if you can show relentless ownership and range

What This Is Not

• Not an executive‑assistant or scheduling role
• Not a single‑function job
• Not a late‑stage, highly specialized position
• Not for someone who needs rigid structure or a clear mandate handed to them

Logistics

• Full‑time, in‑office
• You’ll work extremely closely with the founders, especially the founders — this is the closest seat to the founders in the company

This is for someone who wants to help run the company and grow with it.

Compensation

• Base: ~$100K–$250K, calibrated to experience
• Meaningful early‑stage equity

If you want the closest seat to the founders at the company building the infrastructure powering AI agents at the largest companies in the world… Let’s talk.