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
Unlike most enterprise sales roles that require you to compete for budget in an existing category, this position requires you to establish an entirely 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 allocate additional benefits budget or transition away from a current vendor. Your role involves educating senior leaders in HR, Total Rewards, and CSR, establishing trust in an entirely novel framework, and securing enterprise employers as launch partners prior to the 2027 tax season.
You will serve as the inaugural enterprise seller dedicated to this channel. This entails generating pipeline from the ground up, gaining access to Fortune-level employers, and steering complex buying groups that span HR, Finance, Legal, Payroll, and CSR. Each engagement will contribute not only to your sales pipeline but also to refining messaging, defining the ideal customer profile, and developing the go-to-market playbook for the broader organization.
This opportunity is designed for someone who thrives in environments where structure does not yet exist. You will not be handed inbound demand or a refined sales process. You will create it. If you have a track record of successfully selling voluntary benefits, workplace giving, or payroll-integrated programs to enterprise employers and are motivated by work with substantial social impact, we would welcome the opportunity to speak with you.
What you will be doing
- Develop outbound pipeline targeting Heads of HR, Total Rewards, Benefits, and CSR at enterprise employers with employee counts exceeding 10,000.
- Manage complex, consultative sales cycles involving HR, Finance, Legal, Payroll, and executive stakeholders to successfully launch the Workplace Scholarships program.
- Support employers in navigating inquiries related to payroll deduction, withholding mechanics, ERISA, multi-state eligibility, and program implementation, while ensuring tax-specific questions are appropriately referred to professional advisors.
- Transition signed employers into live program launches with employee enrollment completed ahead of the 2027 tax season.
- Collect structured market intelligence from buyer interactions to inform messaging refinement, ideal customer profile development, and the enterprise go-to-market playbook.
What you will NOT be doing
- Relying on inbound leads or working from an already established sales playbook.
- Selling yet another HR platform vying for existing employer budget allocation.
- Overseeing employee support, payroll administration, or account operations following launch.
- Transferring opportunities to another team for closure.
- Leading a sales organization rather than directly building and closing enterprise pipeline yourself.
Key responsibilities
Establish a high-conversion pipeline of enterprise employers that successfully deploy the Workplace Scholarships payroll-giving program, thereby creating a scalable employer channel with enrolled employee donors in advance of the 2027 tax season.
Candidate requirements
- A minimum of 7 years in quota-carrying enterprise B2B sales, including no less than 3 years in a senior Enterprise AE or Director-level closing capacity.
- Demonstrated experience selling to HR, Total Rewards, Benefits, or CSR decision-makers at enterprise-level employers.
- Personal ownership of an annual new-business quota of no less than $1.5M (ARR, contract value, premium, or equivalent) with a documented record of quota achievement.
- Direct experience closing complex, multi-stakeholder deals involving employers with 10,000+ employees.
- Background selling employee-elected, payroll-deducted benefits, workplace-giving programs, or comparable enterprise HR solutions.
- Demonstrated capability to build enterprise pipeline from the ground up via outbound prospecting.
- Capacity to explain complex concepts clearly, including payroll deduction and federal tax-credit mechanisms, while appropriately routing tax advice to qualified professionals.
- Legal authorization to work in the United States without the need for sponsorship.
- Availability to work remotely with travel requirements of approximately 40%.
Nice to have
- Background selling voluntary or ancillary benefits including education, financial wellness, pet insurance, legal, or identity protection programs.
- Experience with workplace giving or CSR platforms.
- Pre-existing 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 executing a zero-to-one enterprise GTM motion.
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