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

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

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

Director of Enterprise Sales

Key skills