Founding GTM Lead for an AI-powered lifestyle coaching

Fitmate Coach•Palo Alto, CA

21h

About The Position

FitMate is seeking a Founding GTM Lead to own outbound sales end-to-end. This role involves building the sales system, filling the pipeline, booking meetings, and managing the sales process through to a decision. The ideal candidate will work closely with the founder to target self-insured employers, benefits brokers, consultants, TPAs, employee benefits platforms, direct primary care groups, and risk-bearing provider groups who are experiencing challenges with the effectiveness of their weight loss spending. The position requires a hands-on approach to building and running the sales machine, leveraging AI for research and personalization, and managing the entire sales pipeline.

Requirements

Minimum of 2 years of outbound sales experience at a startup, with a proven track record of building the sales system from scratch.
Proficiency in using AI tools for work.
Hands-on experience with modern sales tools including data enrichment (e.g., Clay, Apollo), email automation (e.g., Instantly, Smartlead), LinkedIn automation, and CRM management.
Strong understanding of email deliverability, including domain strategy and authentication protocols.
Relentless follow-through and a proactive approach to managing deals and rebooking no-show meetings.
Willingness to perform manual, non-scalable tasks when necessary to advance a deal.
Comfortable working independently in a founding role with no established playbook or management structure.
Excellent written communication skills.
Motivated by the company's mission in health, behavior change, and human support.

Nice To Haves

Experience selling into HR, employee benefits, health plans, or healthcare sectors.
Familiarity with terms like TPA, stop-loss carrier, and self-funded plan.
Experience managing a conference-driven pipeline.
Proven ability to close deals, not just book meetings.
Experience building custom automations using tools like Zapier or n8n.

Responsibilities

Build target lists using unique signals such as Form 5500 filings, job postings, conference attendee lists, and provider rosters.
Establish and manage the sending infrastructure, including secondary domains, mailbox warmup, SPF/DKIM/DMARC, inbox rotation, and deliverability monitoring.
Develop and execute multi-channel outreach sequences (email, LinkedIn, SMS) with personalized messaging based on account signals.
Utilize AI tools for research and personalization at scale, including data enrichment and AI-generated first lines.
Book and properly prepare qualified meetings, ensuring a deep understanding of the prospect's spending and plan.
Actively manage the sales pipeline, ensuring every open conversation has a planned next step and re-engaging stalled deals.
Manage the conference strategy, including pre-booking meetings, working the event floor, and prompt follow-up.
Optionally, develop a marketing plan (newsletter, LinkedIn posts) to maintain lead engagement.