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Account Executive - SMB (Canada)

FreeWill - Remote - Remote - posted 2026-09-08

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FreeWill is a social-good SaaS startup that has partnered with 2,400+ nonprofits and generated $14B in gift commitments since 2017. The company makes sophisticated donation methods (legacy gifts, tax-smart donations, grants) accessible to donors and nonprofits. With 200+ employees and recent recognition as a Most Loved Workplace and Forbes Best Startup Employer, FreeWill is scaling rapidly. As an SMB Account Executive (Grassroots Account Executive), you will drive revenue generation through strategic relationships with nonprofit organizations. You'll own an assigned territory and be responsible for identifying and closing net-new opportunities. Your daily responsibilities include prospecting and booking 3-5 new meetings per week, conducting discovery calls, demonstrating the FreeWill platform, negotiating contracts, and preparing proposals. You'll manage a $500K+ pipeline and close approximately $100K ARR quarterly, navigating complex buying processes where C-suite decisions are typical. You'll execute the full sales cycle from discovery through close, collaborate with Sales Development Reps on prospecting, and become an expert in both the FreeWill platform and the nonprofit fundraising landscape. You'll stay current with industry trends, gather competitive intelligence, and share insights with product, marketing, and executive teams. The role requires managing complex negotiations, meeting quarterly sales objectives, and embodying FreeWill's values of focus, joy, kindness, and courage. The ideal candidate has 2+ years of successful Account Executive experience in a startup SaaS environment with multiple products. Experience selling to nonprofits is a plus. You should have a track record of leading product demos, handling negotiations, and managing your own prospecting pipeline. You're data-driven, strategic, smart, tenacious, kind, and thrive in fast-paced startup environments.

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