Enterprise Account Executive - Workplace Scholarships

Remote (U.S.) · ~40% travel · Full-time · Reports to the Executive Director

Most enterprise sales roles ask you to win budget from an existing category. This one asks you to create one.

Workplace Scholarships is building a new employer channel that lets employees fund K-12 scholarships through payroll giving, powered by a new federal tax credit. Employers don't approve a new benefits budget or replace an existing vendor — employees simply redirect federal tax dollars they would owe anyway into scholarships for students in their community. Your job is to educate senior HR, Total Rewards, and CSR leaders, build confidence in a brand-new model, and turn enterprise employers into launch partners before tax season 2027.

This is the ground floor of something large. Workplace Scholarships is the employer channel of a national scholarship organization built for a once-in-a-generation moment — a new federal tax-credit scholarship program that takes effect January 1, 2027, with a Year 1 giving ambition of $500 million nationwide.

You'll be the first enterprise seller focused on this channel. That means building pipelines from scratch, opening doors at Fortune-scale employers, and navigating complex buying groups across HR, Finance, Legal, Payroll, and CSR. Every conversation shapes not only your pipeline, but also the messaging, ideal customer profile, and go-to-market playbook for the entire organization.

This is a role for someone who enjoys building where nothing exists yet. You won't inherit inbound demand or a mature sales process — you'll define it.
What you'll be doing

- Build outbound pipeline with Heads of HR, Total Rewards, Benefits, and CSR at enterprise employers with 10,000+ employees.

- Lead complex, consultative sales cycles across HR, Finance, Legal, Payroll, and executive stakeholders to launch the Workplace Scholarships program.

- Guide employers through payroll deduction, withholding mechanics, ERISA, multi-state eligibility, and implementation — directing tax-specific questions to qualified professional advisors.

- Convert signed employers into successful program launches, with employees enrolling before the 2027 tax season.

- Capture structured market intelligence from buyer conversations to refine the messaging, ideal customer profile, and enterprise go-to-market playbook.
What you will NOT be doing

- Waiting for inbound leads or relying on an established sales playbook.

- Selling another HR platform competing for an existing employer budget.

- Managing employee support, payroll administration, or post-launch account operations.

- Handing opportunities to another team to close.

- Managing a sales organization instead of personally creating and closing enterprise pipelines.
Your mission

Build a converting pipeline of enterprise employers that successfully launch the Workplace Scholarships payroll-giving program — creating a scalable employer channel with enrolled employee donors ahead of tax season 2027.