Enterprise Sales Director, Workplace Scholarships (Remote) - $400,000/year USD

August 21, 2026

Traditional enterprise sales roles focus on winning a share of existing budgets. This role requires you to establish an entirely new category. Workplace Scholarships is creating a novel employer channel that allows employees to support K-12 scholarships via payroll giving, leveraging a new federal tax credit. Employers face no requirement to allocate new benefits budgets or displace current vendors. Your mission is to educate senior leaders in HR, Total Rewards, and CSR, establish trust in an untested model, and transform enterprise employers into launch partners ahead of the 2027 tax season. As the inaugural enterprise seller for this channel, you'll develop pipeline from the ground up, gain access to Fortune-scale organizations, and guide intricate buying committees spanning HR, Finance, Legal, Payroll, and CSR functions. Each engagement will inform not just your own pipeline, but the broader messaging strategy, customer profile definition, and market approach for the organization. This position suits someone who thrives in building from zero. There is no inherited demand flow or established sales framework. You will create both. If you have a track record selling voluntary benefits, workplace giving platforms, or payroll-integrated solutions to enterprise employers and seek a role with substantial social impact, we want to speak with you. What You Will Be Doing <ul><li>Develop outbound pipelines targeting Heads of HR, Total Rewards, Benefits, and CSR at enterprise organizations employing 10,000 or more people.</li><li>Manage sophisticated, consultative sales processes involving HR, Finance, Legal, Payroll, and executive decision-makers to implement the Workplace Scholarships program.</li><li>Support employers through inquiries regarding payroll deduction, withholding mechanics, ERISA compliance, multi-state eligibility, and program rollout while appropriately routing tax-related questions to professional advisors.</li><li>Transition signed employer agreements into live program launches with employee enrollments completed before the 2027 tax season.</li><li>Document and analyze structured market insights from buyer interactions to improve messaging, refine the ideal customer profile, and optimize the enterprise go-to-market strategy. </li></ul>What You Won’t Be Doing <ul><li>Depending on inbound lead generation or working from a proven sales playbook.</li><li>Selling yet another HR platform that competes for existing employer budget allocation.</li><li>Overseeing employee support functions, payroll administration, or post-launch account management.</li><li>Transferring opportunities to a different team for closing.</li><li>Leading a sales organization rather than personally generating and closing enterprise deals. </li></ul>Enterprise Sales Director Key Responsibilities Create and convert a pipeline of enterprise employers that successfully implement the Workplace Scholarships payroll-giving program, establishing a scalable employer channel with active employee donors enrolled ahead of the 2027 tax season. Basic Requirements <ul><li>At least 7 years of quota-carrying enterprise B2B sales experience, with a minimum of 3 years in a senior Enterprise AE or Director-level closing capacity.</li><li>Demonstrated experience selling to HR, Total Rewards, Benefits, or CSR decision-makers within enterprise employers.</li><li>Personal experience carrying an annual new-business quota of no less than $1.5M (ARR, contract value, premium, or equivalent) with documented quota achievement.</li><li>Track record of personally closing complex, multi-stakeholder transactions with employers employing 10,000 or more people.</li><li>Background selling employee-elected, payroll-deducted benefits, workplace-giving programs, or comparable enterprise HR solutions.</li><li>Demonstrated capability to create enterprise pipeline from zero using outbound prospecting methods.</li><li>Skill in explaining complex concepts clearly, including payroll deduction and federal tax-credit structures, while appropriately referring tax advice to qualified professionals.</li><li>Legal authorization to work in the United States without requiring sponsorship.</li><li>Capacity to work remotely with travel requirements of approximately 40%. </li></ul>Nice-to-have Requirements <ul><li>Background selling voluntary or ancillary benefits including education, financial wellness, pet insurance, legal, or identity protection offerings.</li><li>Experience with workplace giving or CSR platform sales.</li><li>Pre-existing relationships with enterprise HR, Total Rewards, or CSR decision-makers.</li><li>Knowledge of payroll systems, HRIS platforms, and withholding mechanics.</li><li>Experience building a new market category or launching a zero-to-one enterprise go-to-market initiative. </li></ul>About Workplace Scholarships Working with us Crossover is a private recruiter for ESW Capital’s portfolio of global enterprise software companies and AI-first organizations, hiring top talent from around the world. These companies are building the future of software, data, AI, product, education, finance, and operations, without location-based pay or outdated hiring rituals. They’re transparent, metrics-based, and known for their work-life balance. As their recruiter, we use skills-based, science-backed hiring to help them find the top 1% of talent no matter where they live. We’re talking software engineers, AI specialists, product leaders, marketers, analysts, and operators - tech people who excel in autonomous, high-performance, remote-first environments. Roles are fully remote, long-term positions, working with globally distributed teams across the US, Europe, and beyond. This is a full-time role requiring 40 hours per week that you can start immediately. You’ll work as an independent contractor through Crossover, with weekly payments and clear expectations from day one. The pay for this role is $200 USD per hour, which amounts to $400,000 USD per year, based on 40 hours per week over 50 weeks. For full details, visit: www.crossover.com/job-roles Crossover Job Code: LJ-5836-US-SandySpr-EnterpriseSale

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