Account Executive - SMB (Canada)

About Us

FreeWill is an award-winning, social-good startup that has partnered with 2,400+ nonprofits who support our mission while generating $14B in gift commitments for nonprofits since we were founded in 2017. We’ve been featured in the New York Times, Forbes, Oprah’s magazine, and our co-CEOs have even been named to Town & Country’s “Top 50 Philanthropists” list.

All of this is because we’ve figured out how to make some powerful (but complicated!) ways to donate much easier and more accessible. Our products make things easier for the donors who want to change the world and for nonprofits doing heroic work around the planet. We partner with nonprofits of all sizes to diversify fundraising across individual and institutional giving, from legacy gifts and tax-smart donations to foundation, corporate, and government grants.

In the last 9 years, we’ve grown from 5 people to 200+ (all smart, tenacious, and kind), and continue to grow. We’d love to have you be a part of this adventure. We were named a "Most Loved Workplace" by both Newsweek and Best Practice Institute and the 2025 Most Loved Workplaces® for Diversity by the Best Practice Institute. In 2026, we were named as one of Forbes' Best Startup Employers .

Curious about company culture and management at FreeWill? Check out the 2025 Best Manager Ever podcast featuring Anthony Sottile, FreeWill's VP of Partner Success on either Spotify or Apple .

Full-time • Excellent Benefits • Work from Anywhere in Canada

About the Role

FreeWill is seeking an SMB Account Executive (internally known as a Grassroots Account Executive) to be a leading force that fuels our mission to provide the FreeWill platform to nonprofits to raise $1T.

The Account Executive position is responsible for revenue generation through strategic relationships with nonprofits. You will identify net-new opportunities within an assigned territory of accounts. We are a customer-centric sales team where your daily responsibilities will include:

Prospecting and booking new meetings

Conducting discovery with new prospects

Communicating via phone, email, and teleconference

Demonstrating thought leadership and platform solutions to advance sales

Negotiating contract terms and customer pricing during the sale

Preparing proposals, presentations, and contracts resulting in closed-won deals

Developing strategic plans to drive sales within your territory

We are looking for proven experience with prospecting that results in 3-5 new meetings per week. Experience with managing $500K pipeline at all times and closing $100K ARR quarterly while navigating a buying process where C-Suite decisions are the norm. Candidates should be able to demonstrate actual performance against past quotas. We expect the responsibilities to sometimes shift, and aim to hire an individual who is comfortable moving quickly in a fast-paced and/or start-up environment. The right candidate will be an energetic person with passion and innate drive to excel at any task. We are also looking for someone who is able to learn different customer profiles/personas through team collaboration and self-started learning.

Responsibilities

Execute a sales process through discovery, solution, pricing, negotiation, and close

Participate in brainstorming, team meetings and client meetings, researching and assisting with program development for new prospects

Collaborate with Sales Development Reps to prospect for new business

Illustrate the value of products and services to create growth opportunities; compile and analyze data to identify trends

Become an expert in the FreeWill platform and the broader nonprofit fundraising landscape

Stay current with changes and developments in the nonprofit industry. This includes gathering competitive information on products and services, and sharing this information with the product development, marketing, customer service, and executive teams

Manage complex contract negotiations and work with legal counsel as required

Meet quarterly sales objectives

Act with FreeWill’s values of focus, joy, kindness, and courage

Qualifications

2+ years of successful Account Executive experience in a startup SaaS company with multiple products

Experience selling to nonprofits is a plus

Experience leading your own product demos

Experience handling negotiations and contract signing

Experience managing your own prospecting

Ability to make a strategic decision and run with it

Ability to understand data and make data-driven decisions

Smart, tenacious, and kind, with a growth mindset

Benefits

In addition to the immense personal and professional satisfaction you’ll gain from helping to raise $1T for high impact nonprofits in a kind and joyful work environment, full time employees at FreeWill are eligible for the following benefits:

Health, dental, vision, critical illness, disability, life insurance through Sun Life

Work from home

Flexible Paid Time Off policy. Minimum time required based on compliance with local laws and public holidays in Canada

Flexible hours

Competitive salary

Paid parental leave for all parents

Perks

Professional development reimbursement of CAD$800 annually

Work from Home reimbursement of CAD$300 annually to outfit your home office or cover utility bills

CAD$250 per month co-working reimbursement which can be used for local co-working spaces and your home wifi bill

CAD $1,000 referral bonuses for growing our FreeWill community

Claude (AI Assistant) company/team account

Hiring Process

Recruiter Phone Screen (30 minutes)

Hiring Manager Interview (30 minutes)

Mock Discovery Call (30 minutes)

Final Interviews (Two total- one 30 minute interview and one 45 minute interview)

Offer (contingent on positive references)

Please note that steps in the hiring process can and may change and the Recruiter will be your point of contact in sharing about any updates in terms of the process. If you are selected to move forward in this process, the Recruiter will share more details about the hiring process and interviewers. However, this is a good estimate of what you can expect. For most roles, our hiring processes take an average of 4 weeks.

AI Policy

We are excited to engage with candidates who can demonstrate their experience and skills through their own words and work, not through AI-generated content. We want to understand your genuine interest in the company and your unique perspectives, not simply AI-driven responses. We ask that you refrain from use of AI-generated content during the hiring process which includes phone screens, video interviews, tech screens, or other assessment stages except as otherwise indicated to you by the Recruiter.

For example: Using ChatGPT to generate scripted answers to application questions or during phone screens and video interviews is strongly discouraged and will result in not moving forward in the hiring process. However, the use of an AI design tool to enhance the design of a presentation deck is permitted.

The Recruiter will be able to provide additional guidance during the hiring process if needed. If hired at FreeWill, we do encourage the use of AI in your role to build upon or enhance your skill set.

AI use by FreeWill: Our hiring process may include the use of AI- assisted tools for interview transcription, evaluation, or fraud detection. Human oversight and decision making is maintained throughout the hiring process and for all final hiring decisions. This processing is conducted in compliance with applicable Data Protection, AI Governance, and Labor Laws.

EEOC & Diversity Statement

FreeWill is an equal opportunity employer and we value diversity. We are committed to finding talent that is not determined on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, disability status, or any other characteristic protected by law.

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