Retell AI
Outbound Experimentation Lead — Creative Prospecting
New
70000 –120000 USD / yearUSALeadRemoteoutreachlinkedin
Lead and own the experimentation cycle for creative prospecting and outbound outreach strategies to improve sales results.
Responsibilities
- 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.
Requirements
- 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
Other
- 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.
- 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
- 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
- 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.
- Skip the generic cover letter. Instead, tell us:
- 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?
- 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?