Director of Enterprise Sales at Freewill

FULL-TIME • EXCELLENT BENEFITS • WORK FROM ANYWHERE IN THE US (EXCEPT AL, CO, OR LA) ABOUT THE ROLE Our sales team is growing quickly as we expand into larger, more complex nonprofit partnerships. We are looking for an experienced enterprise sales leader to directly manage a team of Enterprise Account Executives focused on closing large, strategic deals. This team is responsible for pursuing partnerships with major nonprofit institutions such as large hospital systems, national membership associations, Christian denominations and dioceses, higher education systems, and other hub-and-spoke organizations where a central office deploys solutions across many distributed entities. 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. Many of our AEs bring strong nonprofit experience and relationship-building skills, and need support in navigating multi-threaded deals, managing pipeline, and developing executive-level account strategy. We are looking for someone who can develop these capabilities across the team while also stepping into the most complex opportunities to help drive deals forward. This role works closely with senior sales leadership and cross-functional partners to make data-driven decisions around enterprise strategy, pipeline development, and deal execution. Additionally, this role will work closely with each direct report to ensure strong pipeline coverage, disciplined deal progression, and consistent quota attainment. This is an incredible opportunity to help define and scale FreeWill’s enterprise sales motion at a high-impact, mission-driven company. This is a fully remote position, reporting to senior sales leadership. FreeWill has set compensation and a non-negotiation policy for fairness reasons (we don't think that an individual's pay should be determined by how comfortable they are negotiating). As a result, we like to be transparent and up front about the compensation. The offer for this role will be $161,000 base salary and $69,000 variable compensation based on OTE of $230,000. RESPONSIBILITIES - 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 MANAGER EXPECTATIONS This is a people management role, meaning you'll have one or more FreeWillians reporting to you in a management capacity. We believe that when staff own their work and are invested in the outcomes, we get better results. A manager’s role is to ensure that their team members have the skills, support, autonomy, guidance, mentorship and relationships to succeed in their work and develop professionally. As a manager you’ll have the following responsibilities: - Achieve enterprise revenue targets and pipeline goals - Inspire and motivate your team to operate at a high level in complex sales environments -  Make key decisions that impact your direct reports, their deals, and overall team strategy - Trust and advocate for your staff while maintaining a high bar for performance - Create a thoughtful, caring, and high-performance team environment - Develop and invest in team member growth, particularly in enterprise selling skills - Integrate DEI considerations into the team’s work - Create a safe working environment - Facilitate relationship building among your team and cross departmentally - Ensure strong communication with your team HOW YOU’LL DO THIS: - Weekly 1-1 check-ins with your team focused on deal strategy, pipeline health, and skill development - Supporting clear goal setting and action plans for both near-term deal execution and long-term pipeline creation - Writing and discussing 360’s and formal annual reviews - Skip level meetings (for managers of managers, if applicable) - Hands-on involvement in key deals, including deal reviews and executive alignment - Making important decisions on the following (in conjunction with Recruitment, HR, and your manager, where needed): hiring, performance management (annual reviews, 360s, development plans, PIPs, and disciplinary action), termination and offboarding, budgetary spending, and delegating work REQUIRED SKILLS AND EXPERIENCE - People management: 5+ years of experience managing enterprise or strategic sales teams - Great sales experience: 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 - Demonstrated success in coaching and mentoring enterprise account executives and building high performing teams - Experience navigating complex procurement processes and multi-stakeholder environments (5+ stakeholders per deal) - Experience managing long sales cycles (typically 6–12+ months) and building pipeline for high-value deals - Ability to take a strategic decision and run with it, developing and executing plans across a complex market segment -  Ability to understand data and make data-driven decisions about pipeline, forecasting, and performance - Smart, tenacious, and kind, with a growth mindset HIRING PROCESS - Recruiter Phone Screen (30 minutes) - Hiring Manager Interview (30 minutes) - Take Home Assignment (1 hour; on your own time) - Final interviews with 2-4 FreeWill team members (2-4 separate 30 minute interviews) - Offer (contingent on positive references) Please note that steps in the hiring process can and may change and the Recruiter will be your point of contact in sharing about any updates in terms of the process. If you are selected to move forward in this process, the Recruiter will share more details about the hiring process and interviewers. However, this is a good estimate of what you can expect. For most roles, our hiring processes take an average of 4-6 weeks. BENEFITS In addition to the immense personal and professional satisfaction you’ll gain from helping to raise $1T for high impact nonprofits in a kind and joyful work environment, full time employees at FreeWill are eligible for the following benefits: - Work from home  - Flexible Paid Time Off policy. We trust staff to manage their own schedules and take the time off you need to be your best, as long as your work is on track. We recommend staff take a minimum of three weeks annually - Flexible hours - Competitive salary - Commuter benefits - Company stock options - 401k - Medical/Dental/Vision (some single coverage medical plans are 100% employer paid, subsidized rates for spousal, parent-child, and family coverage) - Short-term and long-term disability insurance - Life and AD&D insurance - Free One Medical membership - Paid parental leave for all parents PERKS - Regular (virtual) team events - $250 monthly co-working budget which can be used for local co-working spaces and your home wifi bill - $300 annual budget to outfit your home office or cover utility bills - $1,000 referral bonuses for growing our FreeWill community - $1,000 annual professional development budget FreeWill is an equal opportunity employer and we value diversity. We are committed to finding talent that is not determined on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, disability status, or any other characteristic protected by law. We are a remote-first company that’s able to hire in 47 states and D.C. Unfortunately, we are unable to hire in Colorado, Alabama, or Louisiana at this time. We also can’t sponsor working visas, so all applicants will need to have work authorization in the US. Don’t check off every box in the requirements listed above? Please apply anyway! Studies have shown that marginalized communities - such as women, LGBTQ+ and people of color - are less likely to apply to jobs unless they meet every single qualification. FreeWill is dedicated to building an inclusive, diverse, equitable, and accessible workplace that fosters a sense of belonging – so if you’re excited about this role but your past experience doesn’t align perfectly with every qualification in the job description, we encourage you to still consider submitting an application. You may be just the right candidate for this role or another one of our openings! AI POLICY We are excited to engage with candidates who can demonstrate their experience and skills through their own words and work, not through AI-generated content. We want to understand your genuine interest in the company and your unique perspectives, not simply AI-driven responses. We ask that you refrain from use of AI-generated content during the hiring process which includes phone screens, video interviews, tech screens, or other assessment stages except as otherwise indicated to you by the Recruiter. For example: Using ChatGPT to generate scripted answers to application questions or during phone screens and video interviews is strongly discouraged and will result in not moving forward in the hiring process. However, the use of an AI design tool to enhance the design of a presentation deck is permitted. The Recruiter will be able to provide additional guidance during the hiring process if needed. If hired at FreeWill, we do encourage the use of AI in your role to build upon or enhance your skill set.