Enterprise Account Executive - Workplace Scholarships

Texas Sports Academy Main

3d•Remote

About The Position

This role is for an Enterprise Account Executive focused on building a new employer channel for Workplace Scholarships. The program allows employees to fund K-12 scholarships through payroll giving, utilizing a new federal tax credit. Employers do not need to approve new benefits budgets or replace existing vendors, as employees redirect federal tax dollars they would owe anyway into scholarships. The primary responsibility is to educate senior HR, Total Rewards, and CSR leaders, build confidence in this novel model, and secure enterprise employers as launch partners before the 2027 tax season. This is a ground-floor opportunity within a national scholarship organization, capitalizing on a once-in-a-generation federal tax-credit scholarship program starting January 1, 2027, with a significant Year 1 giving ambition. As the first enterprise seller for this channel, the role involves building pipelines from scratch, engaging Fortune-scale employers, and navigating complex buying groups across HR, Finance, Legal, Payroll, and CSR. Every interaction will shape the organization's messaging, ideal customer profile, and go-to-market strategy. The ideal candidate enjoys building in uncharted territory, defining processes rather than inheriting them, and has experience selling voluntary benefits, workplace giving, or payroll-integrated programs to enterprise employers, with a desire to create meaningful social impact.

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, or CSR 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 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.
Legally authorized to work in the United States without sponsorship.
Able to work remotely with approximately 40% travel.

Nice To Haves

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.

Responsibilities

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.