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 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. #J-18808-Ljbffr Bluejay