FreeWill

Sales

• 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 that 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

Director of Enterprise Sales

• Develop and manage 6-8 account executives to hit sales goals
• Leverage the sales tech stack (Salesforce, Gong, 6 Sense, ZoomInfo, Chilipiper, Looker), to have a holistic view of the team and individual performance; surface who is thriving and who is struggling, develop plans to support staff and address challenges, and identify opportunities for individual coaching and training
• Ensure that company quotas are met by holding regular one on one check-ins with sales team to set objectives and monitor progress
• Manage the overall pipeline for your team, making sure that processes, checkpoints and systems are set up and that the team is using these effectively
• Work closely with the revenue operations team to understand the overall pipeline, gain insights into sales opportunities, and work with team leaders to adjust plans for the team
• Serve as a thought partner to the Director of Sales on strategic decisions, thinking critically and surfacing opportunities and roadblocks

Director of Enterprise Sales

Sales Manager