Founding Account Executive
About The Position
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. What This Actually Is 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. Your Buyers 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.
Requirements
- 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
Responsibilities
- 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
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What This Job Offers
Job Type
Full-time
Career Level
Mid Level
Education Level
No Education Listed
Number of Employees
1-10 employees
