Enterprise Account Executive — Founding Sales Team [Remote]

Read This First

This is a founding sales seat. We've spent ten years building something that works. Near-100% client retention. A profitable business serving nonprofit health systems, universities, and government agencies that are trying to do right by their employees. We help people navigate student loan debt and access education benefits that actually change their financial lives. The mission is real and our clients feel it.

We don't have Series A money or a flashy growth story. What we have is a proven product, paying clients who renew, and a market that is vastly underpenetrated. There is no ceiling — but there is also no proven sales motion waiting for you. We have scripts and playbooks battle-tested from ten years of CEO-led sales, ready to be proven at scale, and a Head of Customer Success and Operations who owns the infrastructure behind you. Your job is to take what exists, prove what works, discard what doesn't, and build the repeatable motion that scales beyond one person.

The buyer is a CHRO or Chief People Officer at a large nonprofit health system, a university, or a government agency. They care deeply about their people. They move slowly. They buy on trust and relationships, not on a slick deck. If you have sold to them before — navigated the long silence, survived the procurement committee, closed through the budget cycle — you know exactly how hard this is and why it is worth it. If you haven't, this is not the seat to learn it in.

Here's the part that matters just as much: you won't be doing it alone. We have a Head of Customer Success and Operations who owns the client infrastructure behind you, a VP of Engineering who ships, a sales advisor who has been in this market and will help keep you on track, and a CEO who has been in the room with these buyers for a decade and will open doors alongside you. We are builders who support each other. You will own your number but you will never be without people in your corner.

This is a rare opportunity — especially if you have sold a mission-driven benefit to a CHRO and know what it takes to build a sales motion from the ground up. If that excites you, keep reading. If it worries you, this isn't the seat.

About PeopleJoy

PeopleJoy helps mission-driven employers — health systems, and public sector organizations — deliver education assistance benefits that reduce turnover and change employees' financial lives.

What This Actually Is

This is a hunter role. You will own the full sales motion from cold outreach to closed deal. You will build your own pipeline, run your own process, and close your own deals — with best-in-class AI tools at your disposal and the CEO in your corner.

Your Buyers

You're selling to CHROs and Total Rewards leaders inside:

• Regional and national health systems

• Local government agencies

These are long-cycle, multi-stakeholder deals. Budget committees, procurement processes, and 9–12-month timelines are the norm.

What You'll Do

• Build and manage a qualified pipeline from cold outreach, existing leads, and attending 2–4 tradeshows per year across the U.S.

• Nurture stalled deals and re-engage dormant prospects 

• Work directly with the CEO to set revenue targets and sharpen the ICP and sales playbook

• Use AI tools to prospect and personalize outreach

What You'll Own

• Pipeline creation and health

• Deal progression from first touch to closed-won

What Success Looks Like

• $600K in ARR per year once fully ramped

• A repeatable sales playbook refined from your own wins

The Ideal Background

• 2–4+ years in B2B enterprise sales

• Demonstrated experience selling to HR leaders at large enterprise organizations — nonprofit health systems, higher education, or government strongly preferred.

How We Win (Our Core Values)

• We serve mission-driven institutions. Do Right by Others —

• We test, learn, and optimize. Improve Every Time —

• Directness, transparency, and ownership. Be All-In & Honest —

• Sales and marketing operate as one team. Win Together —

• Enterprise sales aren't instant. You're patient, disciplined, and resilient.  Grit —

Logistics, comp & benefits

• Location: Virtual
• Travel: ~2-6 times per year for events
• Compensation: Base + Variable
• Benefits: Competitive compensation, medical, dental, and vision coverage, Apple laptop, PTO, and Stock Options