The posting
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.
Requirements
- 7+ years of quota-carrying enterprise B2B sales experience, including at least 3 years in a senior Enterprise AE or Director-level closing role.
- Experience selling into HR, Total Rewards, Benefits, CSR, or Payroll decision-makers at enterprise employers.
- Personally carried an annual new-business quota of at least $1.5M (ARR, contract value, premium, or equivalent), with a measurable record of attainment.
- Personally closed complex, multi-stakeholder deals with employers of 10,000+ employees.
- Experience selling corporate social responsibility platforms, payroll systems, employee-elected payroll-deducted benefits, workplace-giving programs, or similar enterprise HR offerings.
- Proven ability to build enterprise pipelines from zero through outbound prospecting.
- Ability to communicate complex concepts simply — including payroll deduction and federal tax-credit mechanics — while appropriately directing tax advice to qualified professionals.
- Able to quickly learn complex concepts and communicate them clearly and credibly over time.
- Legally authorized to work in the United States without sponsorship.
- Able to travel approximately 40%.
Nice to have
- Experience selling voluntary or ancillary benefits such as education, financial wellness, pet insurance, legal, or identity-protection programs.
- Experience selling workplace-giving or CSR platforms.
- Existing relationships with enterprise HR, Total Rewards, or CSR leaders.
- Familiarity with payroll systems, HRIS platforms, and withholding mechanics.
- Experience creating a new market category or launching a zero-to-one enterprise go-to-market motion.
- Able to confidently present to large groups and host webinars with enterprise audiences.
