Account Executive - SMB (Canada)

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.

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 4-6 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.

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.

We are a remote-first company with employees in the US, Brazil, Canada, and Pakistan. In the US, we are able to hire in 47 states and D.C. Unfortunately, we are unable to hire in Colorado, Alabama, or Louisiana at this time. We also can’t sponsor working visas, so all applicants will need to have work authorization in their respective country.

Don’t check off every box in the requirements listed above? Please apply anyway! Studies have shown that marginalized communities - such as women, LGBTQ+ and people of color - are less likely to apply to jobs unless they meet every single qualification. FreeWill is dedicated to building an inclusive, diverse, equitable, and accessible workplace that fosters a sense of belonging – so if you’re excited about this role but your past experience doesn’t align perfectly with every qualification in the job description, we encourage you to still consider submitting an application. You may be just the right candidate for this role or another one of our openings!