Enterprise Account Executive – Workplace Scholarships

Texas Sports Academy

Enterprise Account Executive creating Workplace Scholarships’ employer payroll-giving channel. Building and closing Fortune-scale employer partnerships before the 2027 tax season.

Posted 8/22/2026full-timeRemote • 🇺🇸 United StatesSeniorLeadWebsite

Core Competencies

Role fit

Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates extensive experience in enterprise B2B sales, particularly in HR, Total Rewards, and Benefits sectors, with a proven track record of building and closing complex sales pipelines. Capable of effectively communicating intricate payroll and tax concepts while guiding employers through program implementation.

Highest-signal resume keywords

7+ Years Of Quota-Carrying Enterprise B2B Sales ExperienceExperience Selling Into HR, Total Rewards, Benefits, Or CSR Decision-MakersProven Ability To Build Enterprise Pipelines From ZeroExperience Selling Employee-Elected, Payroll-Deducted BenefitsAbility To Communicate Complex Concepts Simply

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Complex Multi-Stakeholder Deal ClosingOutbound ProspectingPayroll Deduction MechanicsFederal Tax-Credit MechanicsMarket Intelligence Capture

Soft Skills

Consultative SalesCommunication Skills

Tools & Technologies

Payroll SystemsHRIS Platforms

Industry Keywords

Workplace Scholarships ProgramEnterprise EmployersVoluntary BenefitsAncillary BenefitsWorkplace-Giving ProgramsCSR Platforms

About the role

Key responsibilities & impact

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 messaging, the ideal customer profile, and the enterprise go-to-market playbook
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
Personally create and close enterprise pipelines rather than manage a sales organization

Requirements

What you’ll need

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 have: Experience selling voluntary or ancillary benefits such as education, financial wellness, pet insurance, legal, or identity-protection programs
Nice to have: Experience selling workplace-giving or CSR platforms
Nice to have: Existing relationships with enterprise HR, Total Rewards, or CSR leaders
Nice to have: Familiarity with payroll systems, HRIS platforms, and withholding mechanics
Nice to have: Experience creating a new market category or launching a zero-to-one enterprise go-to-market motion

Benefits

Comp & perks

Remote, U.S.-based, with approximately 40% travel
Start date: as soon as possible