Founding Account Executive

PeopleJoy helps mission-driven employers — health systems, universities, and public sector organizations — deliver education assistance benefits that reduce turnover and change employees’ financial lives. We’ve been doing this for 10 years. The product works. The market is real. We need someone to go get it.

This is a hunter role. You will own the full sales motion from cold outreach to closed deal. There is no SDR team passing you warm leads. There is no sales ops team running your CRM. 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.

If that sounds exhausting, this isn’t for you. If that sounds like exactly the kind of ownership you’ve been wanting, read on.

You’re selling to CHROs and benefits leaders inside:

•  Regional and national health systems

•  Colleges, universities, and higher education institutions

•  State and local government agencies

These are long-cycle, multi-stakeholder deals. Budget committees, procurement processes, and 9–18-month timelines are the norm. You’ve navigated this before. You know how to keep a deal alive through a budget freeze, an RFP, and three champion changes.

•  Build and manage a qualified pipeline from cold outreach, your personal network, and 6–12 tradeshows per year across the U.S.

•  Qualify, advance, and close deals with ACV of $50K+

•  Manage active opportunities in HubSpot with discipline and precision — this is your source of truth

•  Nurture stalled deals and re-engage dormant prospects across cycles that stretch months

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

•  Use AI tools to prospect, personalize outreach, draft proposals, and move faster than a team of three

•  Pipeline creation and health

•  Deal progression from first touch to closed-won

•  Tradeshow strategy and ROI

•  Win/loss analysis and ICP refinement

•  Revenue — not just activity

•  $3M+ in qualified pipeline with clean attribution

•  3–5 closed-won deals in target verticals (health systems, higher ed, government)

•  A repeatable sales playbook built from your own wins

•  A tradeshow motion that converts — not just generates badges

•  A tight feedback loop with marketing that makes both sides sharper

•  7–10+ years in B2B enterprise sales

•  Sold to CHROs, HR leaders, or benefits buyers in health systems, higher education, or government — this is the hard filter

•  Closed deals with $50K+ ACV and 9+ month sales cycles, repeatedly

•  Built and managed your own book of business — not just worked a handed pipeline

•  Strong in HubSpot or comparable CRM; you run deals there, not in a spreadsheet

•  Actively using AI tools in your sales workflow today — not experimenting with them, using them

•  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 —

•  You need an SDR team to build your pipeline

•  Your last three deals were under $30K ACV or closed in under 6 months

•  You’ve never sold to health systems, higher ed, or government and don’t want to learn fast

•  You measure your own performance by activity metrics, not closed revenue

•  You’re not using AI tools in your work right now