Enterprise Sales Director $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
In most enterprise sales roles, you compete for budget within an established category. In this one, you establish the category itself.
Workplace Scholarships is launching a new employer-driven channel that allows employees to contribute to K-12 scholarships via payroll giving, leveraging a new federal tax credit. No employer budget approval or vendor displacement is required. Your mission is to educate executive-level HR, Total Rewards, and CSR decision-makers, instill confidence in an entirely new approach, and secure enterprise employers as launch partners ahead of the 2027 tax season.
You will be the inaugural enterprise seller for this channel. This means generating pipeline from the ground up, gaining access to Fortune-class employers, and coordinating with multifaceted buying committees spanning HR, Finance, Legal, Payroll, and CSR. Each engagement informs not only your own pipeline but also the organization's messaging, customer profile definition, and go-to-market strategy.
This role suits someone who thrives in environments where structure is yet to be built. There is no inherited demand or established sales framework. You will create it. If you have a proven track record selling voluntary benefits, workplace giving programs, or payroll-integrated solutions to enterprise employers and seek to contribute to a mission with social significance, we want to speak with you.
What you will be doing
- Develop outbound sales pipeline targeting Heads of HR, Total Rewards, Benefits, and CSR at enterprise organizations with 10,000+ employees.
- Manage complex, consultative sales engagements involving HR, Finance, Legal, Payroll, and executive leadership to secure adoption of the Workplace Scholarships program.
- Support employers through inquiries related to payroll deduction mechanics, withholding procedures, ERISA considerations, multi-state eligibility, and implementation logistics, while routing tax-specific questions to appropriate professional advisors.
- Drive signed agreements to full program activation with employee enrollment completed prior to the 2027 tax season.
- Collect and synthesize actionable market intelligence from buyer interactions to improve messaging, refine the ideal customer profile, and advance the enterprise go-to-market strategy.
What you will NOT be doing
- Depending on inbound lead flow or following a pre-built sales process.
- Competing for budget with another HR technology platform.
- Overseeing employee support functions, payroll processing, or ongoing account operations after launch.
- Transferring sales opportunities to another team for closure.
- Leading a sales team rather than directly building and closing enterprise deals yourself.
Key responsibilities
Establish a high-converting pipeline of enterprise employers that successfully implement the Workplace Scholarships payroll-giving program, enabling a scalable employer channel with active 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 role responsible for closing deals.
- Track record selling to HR, Total Rewards, Benefits, or CSR executives within enterprise organizations.
- Direct ownership of an annual new-business quota of at least $1.5M (ARR, contract value, premium, or equivalent), with documented quota achievement.
- Proven success closing complex, multi-stakeholder deals at employers with 10,000+ employees.
- Background selling employee-elected, payroll-deducted benefits, workplace-giving platforms, or comparable enterprise HR solutions.
- Demonstrated capability to generate enterprise pipeline from the ground up using outbound prospecting strategies.
- Skill in simplifying complex subject matter, including payroll deduction and federal tax-credit concepts, while appropriately referring tax-related advice to qualified professionals.
- Legal authorization to work in the United States without sponsorship.
- Willingness to work remotely with approximately 40% travel required.
Nice to have
- Background selling voluntary or ancillary benefits, including education programs, financial wellness, pet insurance, legal services, or identity protection.
- Prior experience with workplace giving platforms or CSR solutions.
- Established network of enterprise HR, Total Rewards, or CSR decision-makers.
- Working knowledge of payroll systems, HRIS platforms, and payroll withholding processes.
- Experience building a new market category or executing a zero-to-one enterprise go-to-market strategy.
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