FreeHire

Bluejay

Founding SDR

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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 SDR who wants to build the pipeline engine behind the Bluejay rocketship.

What You'll Actually Be Doing

You'll be designing, testing, and iterating on the systems that create pipeline and put qualified meetings on the calendar.

Outbound & Pipeline

  • Architect and run multi-channel outbound (email, LinkedIn, calls, events, enterprise segmentation)
  • Treat outbound like a product: test → measure → refine
  • Write cold outreach that AI engineers and founders actually reply to — you're selling to the people building the agents, not generic IT buyers
  • Work conferences, dinners, and in-person events alongside founders

Discovery & Qualification

  • Research target accounts and figure out who's deploying agents and where they're hurting
  • Run sharp discovery conversations to qualify fit and intent
  • Set up and cleanly hand off meetings to the founder
  • Turn what you hear on calls into signal the whole team can use

GTM Engineering & Systems

  • Build lead lists using enrichment, automation, and AI-native tools
  • Create semi-automated workflows that increase pipeline velocity
  • Constantly experiment with tools, sequences, and growth mechanics
  • Obsess over what's working, what's not, and why

You Will Be

  • Prospecting
  • Qualifying
  • Iterating
  • On-site at events with customers
  • In the trenches with founders

Who You Are

We're looking for a hustler ready to swing big. Minimum bar: at least 1 year of experience doing outbound.

Must-Haves

  • You can hold a credible conversation about our world — what simulation and evals are, why observability matters, what happens when an AI agent drifts or fails in production. You don't need to be an engineer, but you need to know our customers' world cold.
  • Sharp written voice. We sell to technical buyers, and marketing-speak gets ignored. Your DMs need to read like an engineer wrote them.
  • Hustle and outcome bias. We measure meetings booked and pipeline created, not activity counts.
  • Comfort with ambiguity — you're helping write the playbook, not executing someone else's.

Core Traits

  • Highly AI-native in how you work
  • Scrappy and resourceful
  • Gets excited building systems from zero
  • Thinks in experiments, not opinions
  • Comfortable being wrong quickly

Desirable Quirks

  • Physically cringes at a messy pipeline
  • Has strong opinions about what makes a cold email land
  • Loves clean, organized CRM systems
  • Gets irrationally excited about automation
  • Thinks outbound is part art, part math

Experiences That Pique Our Interest

  • Prior SDR experience selling dev tools or AI infra
  • Familiarity with AI agent eval, observability, or LLM tooling
  • You've cold-called or DM'd technical buyers before and have the scars to show it
  • Worked at an early-stage startup, or built outbound sequences from scratch
  • Career-pivot candidates welcome if you can show you've taught yourself the space

Titles matter less than impact.

Logistics

  • Full-time, in-office (111 Ellis Street, San Francisco)
  • You'll work extremely closely with the founders (especially the CEO)
  • Hiring in the next ~2 months, but we'll move fast for someone exceptional

Compensation

  • Base: $60k-$80k
  • OTE: $120k OTE
  • Meaningful early-stage equity

If you want to build the pipeline engine behind the infrastructure powering AI agents at the largest companies in the world…

Let's talk.