Outbound Experimentation Lead Creative Prospecting

Retell AI Outbound Sales Development Representative

Retell AI is a Y Combinator-backed voice AI platform that powers AI phone agents for enterprise call centers. We're at ~$36M ARR with a team of ~20. Our customers replace legacy IVR systems and human agents with conversational AI that actually sounds human.

We sell to call centers with 100+ agents. Our buyers are VP of Operations, CX leaders, and contact center directors at companies like insurance carriers, healthcare orgs, financial services firms, and BPOs.

The Role

We don't need another SDR who sends 500 emails a week. We need someone who treats outbound like a lab.

You'll own the full experimentation cycle for creative prospecting designing new outreach plays, running them, measuring results, and scaling what works. You report directly to the CEO.

This is not a "set up sequences in Outreach and optimize subject lines" role. Here's a sample of experiments on our roadmap:

• IVR teardowns : Call a prospect's 1-800 number, record the experience, build a side-by-side with what Retell sounds like, and send it to their VP of CX
• Permissionless pilots : Build a working demo of a prospect's use case before they ask for one, and send it cold
• Physical gifting : Send cookies, handwritten notes, or a relevant book with a sticky note to decision-makers who won't respond to digital
• LinkedIn voice messages : Record personalized 60-second voice notes to prospects
• Community infiltration : Find where call center ops people hang out (Slack groups, Reddit, CX forums) and become a trusted voice before ever pitching
• Champion-building from below : Reach agent supervisors who feel the pain daily, arm them with materials to push the conversation up
• VidYard walkthroughs : Record a personalized video showing the prospect's exact use case on the Retell platform, including how the AI voice sounds on a real call
• Warm path engineering : Map mutual connections, YC network ties, and board-level relationships to broker warm intros
• Signal-based triggers : Monitor job postings, tech stack changes, funding rounds, and earnings call language to time outreach perfectly
• MS Teams / Slack Connect messages : Find and reach people on platforms they actually check

You'll also own the tracking infrastructure what experiment ran, to whom, what happened, and what we learned. We want a system, not a spreadsheet of hunches.

What We're Looking For

Must-haves:

• You've done outbound before and know what "normal" looks like so you can go beyond it
• You think in experiments: hypothesis ? test ? measure ? iterate
• You can write. Your emails, notes, and scripts need to sound like a human who did their homework, not a template
• You're resourceful and scrappy you'll figure out how to get handwritten notes sent, how to find someone's direct line, how to get into a niche Slack group
• You can self-manage. We'll set goals together but you run your own calendar

Strong signals:

• You've used tools like Clay, Apollo, LinkedIn Sales Nav, Sendoso, Vidyard, BuiltWith, or similar but more importantly, you've stitched tools together into workflows that actually produced pipeline
• You've worked at a startup where outbound was the primary growth lever
• You've sold or prospected into call centers, BPOs, or enterprise CX teams
• You've done something creative in outbound that actually worked and can tell us the story

Not looking for:

• Someone who only knows email sequences and cold calling
• Someone who needs a playbook handed to them
• Someone uncomfortable with ambiguity or running plays that might not work

How This Works

• Start as a contract (30-40 hrs/week). If it's working, we convert to full-time.
• You'll work directly with the CEO and our outbound SDR.
• First 2 weeks: audit our current outbound, pick 3 experiments, and run them.
• We evaluate based on experiments launched, quality of execution, and pipeline generated.

To Apply

Skip the generic cover letter. Instead, tell us:

1. One creative outbound play you've run that actually generated meetings or pipeline. What was it, why did it work, and what did you learn?
2. Look at retellai.com. If you were prospecting a call center with 200 agents, what's one experiment you'd run to get a meeting with their VP of Operations?