B2B Director Workplace Giving $400,000 USD/year Pay is set based on global value, not the local market.
Most roles = hourly rate x 40 hrs x 50 weeks
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.
What you will 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 questions around payroll deduction, withholding mechanics, ERISA, multi-state eligibility, and program implementation while appropriately directing tax-specific questions to 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.
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 pipeline.
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.
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.
- Experience selling employee-elected, payroll-deducted benefits, workplace-giving programs, or similar enterprise HR offerings.
- 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.
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 GTM motion.
Applying for a role? Here’s what to expect.
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Chat-style screening interview.
Cognitive aptitude test.
Prove real-world job skills.
Interview with the hiring manager.
Pass proctored test.
Accept job offer.
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