Careers at Workplace Scholarships
Workplace Scholarships is a new national nonprofit built around a simple idea: employees should be able to fund K-12 scholarships for kids who need them — through their employer, at zero net cost to themselves or their company. We're launching a payroll-giving channel that lets large employers offer this as a benefit, powered entirely by a new federal tax credit rather than a line item in anyone's budget. We're part of a growing nationwide network of scholarship-granting organizations (SGOs) committed to expanding school-choice options for students across the country, backed by a major philanthropic commitment to transform K-12 education. Because our founders cover startup costs directly, every dollar donated through Workplace Scholarships goes to scholarships — not administrative overhead. At the center of our model is the Education Freedom Tax Credit (EFTC), a federal tax credit representing a $100 billion-a-year opportunity that's still largely unknown to employers. We're positioning Workplace Scholarships as the trusted expert helping HR, Total Rewards, and CSR leaders bring this benefit to their workforce — backed by an AI-first operating model and exclusive access to Alpha's education technology platform. We work with partners across the political spectrum — including Yes Every Kid, Stand Together, and Democrats for Education Reform — because expanding access to education shouldn't be a partisan issue. At public launch, we'll be announcing our founding employer partners alongside our nonprofit coalition. Workplace Scholarships is led by Executive Director Joshua Dwyer, the architect of Illinois' school-choice legislation and founder of Empower Illinois, the state's first scholarship-granting organization.
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B2B Director Workplace Giving
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B2B Director Workplace Giving @ Workplace Scholarships
Key responsibilities
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.
Description
Most enterprise sales roles ask you to win budget from an existing category. This one asks you to create a new category.
Workplace Scholarships is building a new employer channel that enables employees to fund K-12 scholarships through payroll giving using a new federal tax credit. Employers don't need to approve a new benefits budget or replace an existing vendor. Your job is to educate senior HR, Total Rewards, and CSR leaders, build confidence in a completely new model, and turn enterprise employers into launch partners before tax season 2027.
You'll be the first enterprise seller focused on this channel. That means building pipeline from scratch, opening doors at Fortune-scale employers, and navigating complex buying groups across HR, Finance, Legal, Payroll, and CSR. Every conversation helps shape 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. If you've successfully sold voluntary benefits, workplace giving, or payroll-integrated programs into enterprise employers and want to build something with meaningful social impact, we'd like to meet you.
Candidate 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 quota attainment.
- Personally closed complex, multi-stakeholder deals with employers of 10,000+ employees.
- Personally sold one of the following into HR, Total Rewards, Benefits, or CSR decision-makers at enterprise employers (10,000+ employees): voluntary / employee-elected benefits (education, pet, legal/identity, financial wellness), workplace-giving or CSR platforms, or HCM/PEO/benefits-administration solutions — able to name the specific product, the buyer's title, and the quota carried.
- Proven ability to build enterprise pipeline from zero through outbound prospecting.
- Ability to communicate complex concepts simply, including payroll deduction and federal tax-credit concepts, 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.
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