Director of Employer Partnerships $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
Unlike typical enterprise sales roles where you compete for budget within an established category, this position requires you to define and build an entirely new one.
Workplace Scholarships is establishing a novel employer channel that allows employees to contribute to K-12 scholarships via payroll giving, leveraging a new federal tax credit. Employers are not asked to allocate new benefits budget or displace an existing provider. Your responsibility is to educate senior leaders in HR, Total Rewards, and CSR, establish trust in an unprecedented model, and transform enterprise employers into launch partners ahead of the 2027 tax season.
As the inaugural enterprise seller dedicated to this channel, you will construct pipeline from the ground up, access Fortune-scale employers, and manage intricate buying groups spanning HR, Finance, Legal, Payroll, and CSR. Each engagement will not only advance your pipeline but also inform messaging, ideal customer profiling, and the broader go-to-market strategy for the organization.
This position suits someone who thrives in environments where infrastructure does not yet exist. There is no inherited inbound demand or mature sales methodology to lean on. You will create it. If you have a track record selling voluntary benefits, workplace giving, or payroll-integrated programs to enterprise employers and seek to contribute to something with significant social impact, we invite your application.
What you will be doing
- Develop outbound pipeline targeting Heads of HR, Total Rewards, Benefits, and CSR at enterprise employers with 10,000+ employees.
- Manage complex, consultative sales cycles involving HR, Finance, Legal, Payroll, and executive stakeholders to launch the Workplace Scholarships program.
- Support employers through inquiries regarding payroll deduction, withholding mechanics, ERISA, multi-state eligibility, and program rollout, while appropriately referring tax-specific questions to professional advisors.
- Drive signed employers through to successful program launches with employee enrollment completed prior to the 2027 tax season.
- Collect and document structured market intelligence from buyer interactions to refine messaging, ideal customer profiles, and the enterprise go-to-market playbook.
What you will NOT be doing
- Relying on inbound leads or working from an established sales playbook.
- Competing for existing employer budget by selling another HR platform.
- Overseeing employee support, payroll administration, or post-launch account operations.
- Passing opportunities to another team for closing.
- Leading a sales organization rather than personally building and closing enterprise pipeline.
Key responsibilities
Establish a converting pipeline of enterprise employers that successfully launch the Workplace Scholarships payroll-giving program, thereby building a scalable employer channel with enrolled employee donors in advance of the 2027 tax season.
Candidate requirements
- 7+ years of quota-carrying enterprise B2B sales experience, with at least 3 years in a senior Enterprise AE or Director-level closing role.
- Track record 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 documented quota attainment.
- Personally closed complex, multi-stakeholder deals involving employers of 10,000+ employees.
- Experience selling employee-elected, payroll-deducted benefits, workplace-giving programs, or comparable enterprise HR offerings.
- Demonstrated ability to build enterprise pipeline from zero using outbound prospecting.
- Capability to explain complex concepts clearly, including payroll deduction and federal tax-credit concepts, while directing tax advice appropriately 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 including education, financial wellness, pet insurance, legal, or identity protection programs.
- Track record selling workplace giving or CSR platforms.
- Established relationships with enterprise HR, Total Rewards, or CSR leaders.
- Knowledge of payroll systems, HRIS platforms, and withholding mechanics.
- Experience building 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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