Founding GTM Lead for an AI-powered lifestyle coaching company

About

FitMate is the lifestyle layer for weight loss that makes GLP-1 treatment work - and delivers on its own without it. Every member gets a dedicated 1:1 certified coach across both nutrition and strength, made affordable by AI that watches every meal and every workout, so the coach steps in the day someone drifts rather than at the next session.

It's the founder's 2nd startup mixing human and AI to make human services more accessible (first one sold post-Series A).

We're funded and trusted by clients, medical providers and employee benefits platforms.

We're looking for a Founding GTM Lead to own outbound end-to-end, working closely with the founder: build the system, fill the pipeline, book the meetings, and chase every one of them through to a decision.

Everyone who pays for weight loss and isn't getting the results.

Our buyers all have a version of the same problem: they're funding GLP-1 drugs and weight-loss benefits, and the spend is outrunning the outcome, inmcluding:

• Self-insured employers 
• Benefits brokers, consultants and TPAs 
• Employee benefits and lifestyle-spending platforms 
• Direct primary care and risk-bearing provider groups

Build the machine, then run it.

• Build target lists from signals other people miss — Form 5500 filings (who's self-funded, and which TPA they use), job postings disclosing wellness stipends, conference attendee lists, provider and ACO rosters.
• Stand up and own the sending infrastructure: secondary domains, mailbox warmup, SPF / DKIM / DMARC, inbox rotation, suppression lists, deliverability monitoring.
• Write and run multi-channel sequences — email, LinkedIn, and SMS for event and opted-in follow-up — personalized from real account signals, not merge tokens.
• Use AI to research and personalize at a scale that used to take a team: Clay tables, enrichment waterfalls, LLM-written first lines you'd be happy to receive yourself.
• Book qualified meetings, and prepare them properly — we show up knowing what that employer spends and what their plan looks like.
• Work the pipeline so deals keep moving — a planned next touchpoint on every open conversation, re-engagement for anything that's gone quiet, nothing untouched and nothing forgotten.
• Run our conference motion — pre-book meetings off attendee lists, work the floor, follow up within 24 hours while it's warm.
• Optionally, build the marketing plan that keeps leads warm between conversations — a newsletter, LinkedIn posts, the occasional genuinely useful thing — so we're still there when their plan year comes around.

Requirements

You've built the machine before, not just worked it.

• You've done outbound at a startup for 2+ years and built the system yourself, rather than inheriting one someone else ran.
• You know your numbers cold — reply rate, positive-reply rate, meetings booked and held.
• You need to be completely AI-native. If that isn't already how you work, this isn't the job.
• You've run the modern stack hands-on: Clay or equivalent for data and enrichment, Instantly / Smartlead or equivalent for email, a LinkedIn automation tool, and a CRM you kept genuinely clean.
• You own deliverability, not just copy. You can explain why a cold campaign belongs on a separate domain without looking it up.
• You are relentless about follow-through. A booked meeting that no-shows gets rebooked; a stalled deal gets a reason, not a shrug.
• You're comfortable picking up the phone, and doing the manual work that doesn't scale — calling leads, liking and commenting on a prospect's LinkedIn posts one at a time, chasing an intro — when that's what moves a deal forward. AI runs the volume; it doesn't do this part.
• You're early in your career and want a founding seat rather than a rung on a ladder — comfortable with no manager, no support staff and no playbook.
• You write well. Most of this job is words landing in a busy person's inbox.
• You're motivated by our mission in health, behavior change and human support.

Bonus if you have

• Sold into HR, employee benefits, health plans or healthcare — you know what a TPA, a stop-loss carrier and a self-funded plan are.
• Worked a conference-driven pipeline end-to-end.
• Closed deals yourself, not only booked them.
• Built your own automations — Zapier, n8n, scripts — to remove your manual work.

The tools you'll own from day one.

• Data: Clay, Apollo, LinkedIn Sales Navigator, public filings (Form 5500), conference attendee exports.
• Email: Instantly / Smartlead, secondary domains, warmup, SPF / DKIM / DMARC, deliverability monitoring.
• Social: LinkedIn automation — HeyReach, Expandi or your preferred equivalent.
• Messaging: SMS and WhatsApp for event and opted-in follow-up.
• Pipeline: CRM ownership, and reporting the founder actually trusts.
• AI: Claude and LLM-driven research, personalization and call prep — used with judgment, not on autopilot.

Benefits

Competitive base + uncapped commission.

What it's like at FitMate

• We move fast and build things that ship.
• We challenge ideas (not people) and focus on what works.
• Everyone contributes to product ideas — no silos.
• We care about impact, not process for its own sake.
• We're in this to help real people change their lives — and the feedback reminds us why it matters.

See us on Glassdoor for what it's like working here, and on Trustpilot for what our clients think of us.