Chief of Staff

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

This is a founding-level ownership role, not an executive-assistant seat. You're helping run the company, and the role grows into whatever you make of it.

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

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

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

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.

Interview Process

Round 1 — Intro Call (15 minutes) You'll talk directly with the CEO. Tell us why you think you'll succeed at Bluejay, ask us why you should join, and get a feel for the role, the company, and how we work.

Round 2 — Take-Home Exercise (a few hours, on your own time) We'll give you a real Bluejay problem—a strategic call, an operating challenge, or a messy decision the company is actually facing—and ask you to work it through. You might write a one-page recommendation, build a simple model, prioritize where we should spend the next quarter, or design a process to fix something broken. Keep it to a few focused hours—we care less about polish and more about how you think, prioritize, and write under ambiguity. It's paid, and we'll send a clear, bounded prompt so you're not guessing at scope.

Round 3 — Take-Home Review + Live Jam (30 minutes) We'll walk through your take-home together—why you made the calls you made, where you'd push further, and how you respond when we push back. Then we'll jam live on a different problem: maybe untangle a real operating bottleneck, react to a curveball, or rework your recommendation on the spot. We want to see how you think out loud and handle ambiguity in real time.

Round 4 — Team Meetup (30 minutes) Meet the team and see whether Bluejay feels like the right place for you—and whether you feel like the right addition to the team. We might dig into something you've owned before, talk through a hard call you've made, debate where the company should focus, or just get a feel for how you'd work alongside everyone. The goal is a meaningful conversation and a real sense of what it would be like to work together.

Final Step — References and Offer If there's a strong mutual fit, we'll speak with a few references and move quickly to an offer.