Director of Enterprise Sales

FreeWill is seeking an experienced Enterprise Sales Leader to directly manage a team of Enterprise Account Executives focused on closing large, strategic deals with major nonprofit institutions such as hospital systems, national membership associations, Christian denominations and dioceses, higher education systems, and other hub-and-spoke organizations. Enterprise sales at FreeWill involves 3-6 month sales cycles, multiple stakeholders, procurement processes, and complex organizational dynamics. We are looking for someone with strong business acumen and deep experience in SaaS sales, who has personally closed large, complex deals and can support their team in doing the same. This role will develop team capabilities in navigating multi-threaded deals, managing pipeline, and developing executive-level account strategy, while also stepping into the most complex opportunities to help drive deals forward. The Enterprise Sales Leader will work closely with senior sales leadership and cross-functional partners to make data-driven decisions around enterprise strategy, pipeline development, and deal execution, and will ensure strong pipeline coverage, disciplined deal progression, and consistent quota attainment.

Responsibilities will include:

• Develop and manage a team of Enterprise Account Executives to achieve enterprise revenue goals
• Support and coach team members on complex deal strategy, including multi-threading, executive engagement, and procurement navigation
• Ensure each AE maintains a strong pipeline of high-value, strategic opportunities (typically 3–5x quota coverage)
• Manage the overall enterprise pipeline, ensuring clear processes, deal strategy, and consistent progression across long sales cycles
• Actively engage in the most complex and high-impact deals, helping to align stakeholders and move opportunities forward
• Work closely with SDR leadership and Marketing to drive top-of-funnel pipeline for enterprise opportunities
• Partner with RevOps to understand pipeline health, improve forecasting accuracy, and identify opportunities for growth
• Collaborate cross-functionally with Product, Partner Success, and leadership to support deal success and improve positioning
• Serve as a thought partner to senior sales leadership on enterprise strategy, surfacing opportunities and roadblocks

You’re a great fit if you:

• Have 5+ years of experience managing enterprise or strategic sales teams
• Have 7+ years of experience and proven success in full cycle SaaS sales, including closing complex six- and seven-figure deals; experience selling to nonprofits is strongly preferred
• Demonstrate success in coaching and mentoring enterprise account executives and building high performing teams
• Have experience navigating complex procurement processes and multi-stakeholder environments (5+ stakeholders per deal)
• Have experience managing long sales cycles (typically 6–12+ months) and building pipeline for high-value deals
• Are able to take a strategic decision and run with it, developing and executing plans across a complex market segment
• Are able to understand data and make data-driven decisions about pipeline, forecasting, and performance
• Are smart, tenacious, and kind, with a growth mindset

This is a fully remote position, reporting to senior sales leadership.