Director of Enterprise Sales, FreeWill
$230k
OTE
$161k
BASE
+ Company stock options
More information about location
Tech to make charitable donations easier for donors
Be an early applicant
Tech to make charitable donations easier for donors
201-500 employees
Be an early applicant
$230k
OTE
$161k
BASE
+ Company stock options
More information about location
201-500 employees
Company mission
To help people do the most good for the people and causes they love.
Role
Who you are
- 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
- 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
- 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
What the job involves
- 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
- 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
- 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
- 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
- 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
Application 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)
Our take
Estate planning has long been seen as a complex, intimidating, and costly process, resulting in a significant number of adults in the US, approximately 70%, not having a will. FreeWill, however, aims to change this perception by offering a user-friendly tool that enables anyone to create these crucial documents.
By leveraging FreeWill, individuals can take control of their end-of-life planning and ensure that their assets are distributed according to their wishes. The platform guides users through the necessary steps, helping them name beneficiaries, designate asset distribution, and appoint executors to manage their estates. The company also sets itself apart with its Crypto for Charity platform. By including options on digital currencies, FreeWill makes it easier for Crypto and NFT users to make tax-advantaged donations as well.
FreeWill's no-cost estate planning tools are made possible through the support of non-profit organizations, allowing individuals to create their wills and leave a gift for a cause they care about. By integrating charitable giving into the estate planning process, FreeWill encourages individuals to consider philanthropy as part of their end-of-life plans. With over $13.8B+ committed to non-profit organizations to date, the company's dedication to supporting charitable causes and the significant impact individuals can make through their estate planning choices is truly evident.
Kirsty
Company Specialist at Welcome to the Jungle
Insights
-12% employee growth in 12 months
Company
Funding (1 round)
Mar 2022
$30m
SERIES B
Total funding: $30m
Company benefits
- Competitive pay and stock options
- Medical, dental, and vision coverage
- Unlimited PTO
- Flexible work hours
- Paid parental leave
- (Virtual) Team Events
- Professional development
- Monthly co-working reimbursement
Leadership
Jennifer Xia Spradling
(Co-Founder & Co-CEO)Graduated from Stanford University with a Masters in Business Administration. Previously worked as an Advisor at Paribus, a Private Equity Associate at Bain Capital and as a Business Analyst at McKinsey & Company.
Patrick Schmitt
(Co-Founder & Co-CEO)Graduated from Stanford University with a Masters in Business Administration. Previously the VP of Marketing at Farmingo and the Head of Innovation at Change.org.
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