Director of Business Development $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 positions require you to capture budget from an established category. This role requires you to establish a new one.
Workplace Scholarships is developing a novel employer channel that allows employees to support K-12 scholarships via payroll giving, leveraging a new federal tax credit. Employers are not required to authorize additional benefits spending or displace a current vendor. Your objective is to inform senior HR, Total Rewards, and CSR executives, establish confidence in an entirely new framework, and convert enterprise employers into launch partners in advance of the 2027 tax season.
You will be the initial enterprise seller dedicated to this channel. That entails creating pipeline from the ground up, accessing Fortune-scale employers, and managing intricate buying committees spanning HR, Finance, Legal, Payroll, and CSR. Each engagement will influence not only your sales pipeline, but also the positioning, ideal customer profile, and commercial strategy for the broader organization.
This position suits someone who thrives in building environments where nothing is yet established. You will not receive inherited inbound interest or a refined sales methodology. You will create it. If you have successfully introduced voluntary benefits, workplace giving, or payroll-integrated solutions to enterprise employers and seek to develop something with substantial social impact, we would like to speak with you.
What you will be doing
- Develop outbound pipeline with Heads of HR, Total Rewards, Benefits, and CSR at enterprise employers with 10,000+ employees.
- Manage complex, consultative sales engagements across HR, Finance, Legal, Payroll, and executive stakeholders to initiate the Workplace Scholarships program.
- Support employers through inquiries regarding payroll deduction, withholding mechanics, ERISA, multi-state eligibility, and program implementation while appropriately referring tax-specific matters to professional advisors.
- Transform signed employers into successful program deployments with employees enrolling prior to the 2027 tax season.
- Collect structured market intelligence from buyer discussions to enhance messaging, the ideal customer profile, and the enterprise go-to-market playbook.
What you will NOT be doing
- Waiting for inbound inquiries or depending on an established sales methodology.
- Selling another HR technology competing for existing employer budget allocations.
- Overseeing employee support, payroll administration, or post-launch account operations.
- Transferring opportunities to another team for closure.
- Leading a sales organization instead of directly generating and closing enterprise pipeline.
Key responsibilities
Establish a converting pipeline of enterprise employers that successfully deploy the Workplace Scholarships payroll-giving program, creating 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, including at least 3 years in a senior Enterprise AE or Director-level closing role.
- Experience selling to 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.
- Demonstrated ability to build enterprise pipeline from zero through outbound prospecting.
- Ability to articulate complex concepts clearly, including payroll deduction and federal tax-credit concepts, while appropriately referring 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 establishing 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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