Senior Account Executive $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 positions, you compete for budget within an established category. In this position, you will establish a new category from the ground up.
Workplace Scholarships is launching a new employer-focused channel that allows employees to contribute to K-12 scholarships via payroll giving, leveraging a new federal tax credit. Employers are not required to allocate new benefits budget or switch existing vendors. Your responsibility is to inform senior leaders in HR, Total Rewards, and CSR, establish trust in an entirely new model, and convert enterprise employers into launch partners in advance of the 2027 tax season.
You will be the first enterprise seller dedicated to this channel. This requires generating pipeline from the beginning, securing access to Fortune-scale employers, and managing complex buying groups spanning HR, Finance, Legal, Payroll, and CSR. Each interaction will inform not only your pipeline development, but also the messaging, ideal customer profile, and go-to-market strategy for the broader organization.
This position is designed for someone who thrives in environments where structures are yet to be built. You will not receive established inbound demand or a proven sales process. You will create it. If you have a track record of selling voluntary benefits, workplace giving, or payroll-integrated programs to enterprise employers and wish to contribute to something with substantial social impact, we would like 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 10,000+ employees.
- Manage complex, consultative sales cycles involving HR, Finance, Legal, Payroll, and executive stakeholders to initiate the Workplace Scholarships program.
- Support employers in addressing questions related to payroll deduction, withholding mechanics, ERISA, multi-state eligibility, and program implementation while appropriately referring tax-specific questions to professional advisors.
- Transition signed employers into active program launches with employee enrollment completed prior to the 2027 tax season.
- Document structured market intelligence from buyer interactions to enhance messaging, the ideal customer profile, and the enterprise go-to-market playbook.
What you will NOT be doing
- Relying on inbound leads or working from an established sales playbook.
- Selling another HR platform in competition for existing employer budget.
- Handling employee support, payroll administration, or post-launch account operations.
- Transferring opportunities to another team for closing.
- Overseeing a sales organization rather than personally generating and closing enterprise pipeline.
Key responsibilities
Establish a high-conversion pipeline of enterprise employers that successfully launch the Workplace Scholarships payroll-giving program, 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.
- 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 documented record of 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 via outbound prospecting.
- Ability to explain 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.
- Pre-existing relationships with enterprise HR, Total Rewards, or CSR leaders.
- Knowledge of payroll systems, HRIS platforms, and withholding mechanics.
- Experience establishing a new market category or launching a zero-to-one enterprise GTM motion.
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