Enterprise Account Executive — Founding Sales Team

PeopleJoy

8d•$120,000 - $130,000•Remote

About The Position

This is a founding sales seat for a company that has spent ten years building a successful product serving nonprofit health systems, universities, and government agencies. The company helps employees navigate student loan debt and access education benefits. While the product is proven and clients renew, there isn't a pre-established sales motion at scale. The role involves taking the existing, CEO-led sales strategies, proving what works, discarding what doesn't, and building a repeatable sales process. The buyer is typically a CHRO or Chief People Officer in large nonprofit health systems, universities, or government agencies who value trust and relationships. This is a hunter role responsible for the full sales motion from cold outreach to closing deals, with support from the CEO, Head of Customer Success and Operations, VP of Engineering, and a sales advisor. The opportunity is for individuals experienced in selling mission-driven benefits to CHROs and who are excited by the challenge of building a sales motion from the ground up.

Requirements

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.
Experience navigating long sales cycles, multi-stakeholder deals, budget committees, procurement processes, and 9–12-month timelines.
Patience, discipline, and resilience.

Nice To Haves

Experience selling to CHROs and Total Rewards leaders inside regional and national health systems, and local government agencies.
Experience selling a mission-driven benefit.

Responsibilities

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
Own the full sales motion from cold outreach to closed deal
Build your own pipeline, run your own process, and close your own deals