Director of Enterprise Sales
FreeWill
full-time
Posted on:
Location Type: Remote
Location: Alabama • Colorado • United States
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Salary
💰 $161,000 per year
Job Level
About the role
- 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
Requirements
- 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
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
- 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
Applicant Tracking System Keywords
Tip: use these terms in your resume and cover letter to boost ATS matches.
Hard Skills & Tools
SaaS salespipeline managementdeal strategyforecastingprocurement navigationsales cycle managementdata analysiscoachingmentoringstrategic decision making
Soft Skills
people managementteam buildingcommunicationcollaborationproblem solvinggrowth mindsettenacitykindnessexecutive engagementstakeholder alignment