Director of B2B Sales

If you're currently selling group health benefits, PEO services, HR tech, or B2B SaaS to small businesses — and you're tired of being one of forty reps in a regional org — this is the seat that fixes that.

About Members Health Co

We are a doctor-led, membership-based primary care and wellness practice based in Nashville. We don't run a volume practice. We don't sell fear. We don't medicalize normal life. Our members stay because we actually know them — and because we get them care that moves the needle on their long-term health.

We've quietly become Nashville's most credible alternative to traditional employer health benefits for small and mid-sized businesses. Companies of 4 to 40 employees — music industry management firms, boutique law and accounting practices, creative agencies, hospitality groups, tech startups, real estate brokerages — choose MHC because real primary care, real relationships, and real outcomes are something their team can actually use.

The story sells itself once it's in the right room. We're hiring the person whose job it is to get it in the right room, over and over again.

The role

You will own B2B sales end-to-end — prospecting, outreach, qualification, discovery, proposals, negotiation, and close. You will report directly to the CEO. You will build the playbook. You will hit a real number. And you will own the function that becomes a team under you as we scale.

This is not a sales rep seat. It is a founding sales leader seat — with the autonomy, accountability, and upside that come with it.

Who we're looking for

You've spent the last 3–10 years selling B2B into small and mid-sized businesses. Most likely you're currently selling group health insurance, PEO services, HR tech (Gusto, Justworks, TriNet, Rippling, Insperity), payroll, benefits administration, or B2B SaaS into the SMB space. You know the buyer. You know how to find them, qualify them, run a discovery, build a proposal, and close.

And you're ready for more. You want to spread your wings. You want to own the function. You want to walk into an executive's office, talk to them like a peer, and walk out with a signed deal — not file it through three layers of approval first.

If that's you, we should talk.

What you'll do

•     Own B2B sales end-to-end — prospecting, outreach, qualification, discovery, proposals, negotiation, and close.

•     Build the pipeline from scratch — outbound, industry partnerships, broker relationships, member referrals, events, and networking.

•     Run executive conversations with founders, CEOs, COOs, and HR leads at 4–40 employee businesses across Nashville.

•     Educate the buyer — most of our deals require teaching the buyer that this category exists. You'll be the one doing that teaching.

•     Build the playbook — the discovery questions, objection handling, proposal templates, and close sequence that the team you eventually build will run.

•     Partner with marketing to develop the B2B brand engine — collateral, LinkedIn presence, case studies, and proof points.

•     Hit your number. Year one is about establishing what's repeatable. Year two is scale. Year three is hiring and leading the team.

What you'll bring

•     5–10 years selling B2B into small and mid-sized businesses. Health benefits, group insurance, PEO, HR tech, payroll, benefits administration, or SMB SaaS — all qualifying.

•     A documented track record of consistently hitting and exceeding quota.

•     Comfort and confidence in front of executive buyers — owners, founders, CFOs, CEOs.

•     Ability to teach a buyer something new and convert that education into a contract.

•     A point of view on benefits, healthcare, and what's broken about the status quo. Opinions welcome.

•     Independence. Self-starter is not a buzzword for this role — it is the role.

•     A sense of urgency that matches our pace. We move fast.

•     Bonus: existing relationships with Nashville-area businesses, brokers, or industry verticals (music, hospitality, real estate, creative, tech, healthcare-adjacent).

What we offer

Compensation. Competitive base salary plus heavily commission-based variable compensation, fully uncapped. Significant accelerators on over-quota performance, plus a renewal residual that compounds your earnings as the book grows. Specifics shared during the interview process — and they're competitive.

Autonomy. Real autonomy. You report to the CEO. There is no manager between you and the seat. You own the function.

A product worth selling. Doctor-led, premium, locally beloved, obsessively cared for. You won't be selling something you don't believe in — you'll be selling something members rave about.

A path. As you build the function, the title and scope grow with you. VP of Sales, VP of Employer Partnerships, or Chief Revenue Officer — earnable, not promised, and visible from day one.

Benefits. Health, dental, and vision insurance. Generous PTO and parental leave. Reasonable expense reimbursement, equipment, and sales tooling provided.

A Members Health membership of your own. The same product our members pay for, included for you and your immediate family. You'll be a member of the practice you're selling — which is the point.