Founding Account Executive

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.

Now we're looking for a cracked, founding AE to report directly to the CEO and build Bluejay's revenue engine from the ground up-from first outbound message to signed contract.

Why this role exists

We have real early traction, but founder-led sales has a ceiling. We need someone who can turn that traction into a repeatable, scalable commercial motion.

This is not a role where you inherit a mature playbook or a fat pipeline. You'll be the first dedicated seller at Bluejay, working directly with the founder to define how we sell, who we sell to, and what the commercial motion looks like as we scale.

What You'll Own

Close, Full-Cycle

• Build and own pipeline from scratch-you can self-source, not just work what's handed to you
• Run deals end to end: discovery, demo, technical validation, POC, negotiation, close
• Sell to AI engineers, founders, and enterprise buyers deploying agents in production
• Translate technical product value into real business urgency

Build the Motion

• Turn the founder-led sale into a documented, repeatable playbook
• Define sales stages, qualification criteria, and deal-progression standards
• Build CRM infrastructure and real forecasting discipline
• Partner with our founding SDR as pipeline scales, but never depend on it

Own the Hard Parts of Enterprise

• Navigate the full commercial gauntlet: security reviews, procurement, and legal redlines
• Shape competitive and POC strategy, including evaluation frameworks that show off where Bluejay wins
• Close with clear success criteria and set the foundation for expansion and retention

You Will Be

• Closing
• Self-sourcing pipeline
• Building systems
• On-site with customers
• In the trenches with founders

This is a founding-level ownership role, not a seat where leads get handed to you. You're building how Bluejay sells.

Who You Are

We're looking for a builder-seller who has created pipeline from zero and carries a number like it's personal.

Must-Haves

• You've run full-cycle deals and self-sourced your own pipeline-and you can prove it.
• You can hold a credible conversation about our world-simulation, evals, observability, what happens when an AI agent fails in production. You translate technical value into business urgency without losing the technical buyer.
• You're comfortable owning commercial complexity: security reviews, procurement, and legal redlines don't scare you.
• You think in systems, not just deals. You're building a motion, not closing in a vacuum.
• Highly autonomous, adaptable, and coachable, with real comfort in a no-playbook environment.

Core Traits

• Highly AI-native in how you work
• Scrappy and resourceful
• Gets excited building process from zero
• Works well across engineering, product, and design
• Comfortable being wrong quickly

Desirable Quirks

• Physically cringes at a stalled deal or a sloppy pipeline
• Has strong opinions about what actually moves a buyer
• Loves a clean, honest CRM and tight forecasting
• Reads the room better than the script
• Thinks selling is part discovery, part teaching, part timing

Experience That Matters

• 3-5 years of full-cycle closing experience
• Time in an early-stage or no-playbook environment
• Demonstrated ability to self-source pipeline
• Comfort selling technical or infrastructure products to technical buyers
• Experience navigating enterprise procurement and security review

Strong Signals

• You've sold AI infrastructure, dev tools, observability, or trust/compliance platforms
• You've sold to both technical buyers and business stakeholders
• You've shaped competitive POC criteria and won nuanced enterprise deals
• Former founder, or early/founding seller somewhere before

What This Is Not

• Not a "work the leads handed to you" role
• Not a single-stage or SDR seat
• Not a late-stage, highly specialized position
• Not for someone who needs rigid structure

This is for someone who wants to define how Bluejay sells.

Logistics

• Full-time, in-office
• You'll report to and work extremely closely with the CEO

Compensation

• Base + uncapped commission, calibrated to experience (placeholder - confirm before posting)
• Meaningful early-stage equity
• A path to sales leadership as we grow

If you want to own closing and build the sales engine behind the infrastructure powering AI agents at the largest companies in the world…

Let's talk.

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 target account and ask you to build your approach to it. You might map the account and buying committee, write the discovery you'd lead with, lay out how you'd run the deal from first touch to signed contract, design a POC and the evaluation criteria you'd use to win it, or show how you'd self-source pipeline into a segment. Keep it to a few focused hours-we care less about polish and more about how you think, qualify, and build a motion. It's paid, and we'll send a clear, bounded prompt so you're not guessing at scope.

Round 3 - Take-Home Review + Live Mock (30 minutes) We'll walk through your take-home together-why you'd run the deal the way you would-then run a live mock: a discovery call or a tough objection, with us playing the buyer. We want to see how you get to real pain, translate technical value into urgency, and handle pushback on your feet.

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 a deal you're proud of, talk through a loss and what you learned, debate how we should sell, or get a feel for how you'd work across engineering and product. 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.