Most Loved Workplace® Certified JobDirector of Enterprise Sales
Most Loved Workplace® Certified JobAbout the Role
At FreeWill, a Most Loved Workplace® certified employer in the Internet/E-Commerce space.
We are looking for an experienced enterprise sales leader to directly manage a team of Enterprise Account Executives focused on closing large, strategic deals. 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.
Want to learn more about what it's like to work at FreeWill? View our full profile.
Requirements
- 5+ years of experience managing enterprise or strategic sales teams
- Experience managing long sales cycles (typically 6–12+ months) and building pipeline for high-value deals
Benefits
- Full time employees at FreeWill are eligible for benefits
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Why This Is a Most Loved Workplace® Certified Job
Systemic Collaboration
Our employees have a positive vision for the future because every day they show up to work and build things that help nonprofits raise money. They can directly see the impacts of their work shifting money into high-impact organizations.
Positive Vision for the Future
FreeWill values of kindness, courage, focus and joy are aligned with our employees because they want to show up every day to do work that matters toward a clear goal, be treated well by colleagues, and celebrate wins, big and small.
Alignment of Values
They are very transparent with the team and act on feedback they receive. For example, when they heard from employees that there wasn’t enough clarity on our strategy, they started providing a bi-weekly update in our all-team meeting to make sure that employee’s had that focus.
Respect
We do a monthly Ask Me Anything with our co-CEOs where employees anonymously submit questions, ideas and feedback and the co-CEOs spend an hour responding to them live. We do regular pulse surveys and an annual engagement survey to create additional anonymous ways for people to raise concerns and share ideas and feedback.
Killer Outcomes
Employees at FreeWill collaborate by working together to build, design, and roll out products that help nonprofits raise money. We have brainstorm sessions, collaborative decision “gate” meetings, and use Slack to be in regular communication about projects.
Frequently Asked Questions About Working at FreeWill
Common questions candidates ask about this role and FreeWill's workplace
Apply for Director of Enterprise Sales
Submit your application directly to the FreeWill team. Let them know why you'd be a great addition to their loved place to work.

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