Sales Development Representative (Canada)

About Us

FreeWill is an award-winning, social-good startup that has partnered with 2,400+ nonprofits who support our mission while generating $15B 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

As a Sales Development Representative (SDR), you will be staffed on either our outbound team or our inbound team. As an outbound SDR, you will be responsible for generating and qualifying leads to support the sales team in achieving revenue targets. Your primary focus will be on prospecting, lead generation, and initiating contact with potential FreeWill partners. As an inbound SDR you will be responsible for responding quickly to and stewarding marketing leads. You will play a crucial role in the sales process by identifying qualified opportunities and passing them on to the appropriate account executives. The SDR role requires excellent communication skills, a strong work ethic, and the ability to thrive in a fast-paced, target-driven environment.

This role will need to work during general business hours which is typically 9-5pm EST or 7-3pm PST.

FreeWill has set compensation and a non-negotiation policy for fairness reasons (we don't think that an individual's pay should be determined by how comfortable they are negotiating). As a result, we like to be transparent and up front about the compensation. The offer for this role will be a base salary of CAD $61,000 and variable compensation of CAD $15,000 for a potential total OTE of CAD $76,000 . Candidates must have work authorization in Canada to be considered for this position, as we are unable to sponsor visas.

Please note: We are hiring for the SDR role in the US and Canada. Compensation offered for the role may differ based on location and cost of living. We conduct extensive research to ensure compensation is aligned with the experience level of the role, cost of living, and job market. Information shared about compensation in the respective job posting is the compensation being offered for that specific role/location. If you proceed in the interview process and have any questions, you can discuss with the Recruiter.

If you are interested in the role, please apply to our website. Please do not contact Recruiters/employees by email or phone.

Responsibilities

Strategic Prospecting (Outbound): Build your own non-profit prospect lists from an assigned account territory (i.e. universities, animal shelters, environmental based organizations, etc.) based on our ideal customer profiles and initiate contact through phone calls (50+ per day)

High-Velocity Response (Inbound) : Act as the first point of contact for marketing-generated leads and product inquiries, maintaining a strict “Speed-to-Lead” response time to maximize conversion.

Lead Generation & Qualification: Initiate contact with non-profit prospects to educate them on the FreeWill mission, generate high-intent interest, and identify new partnership opportunities

Qualification & Handoff: Qualify leads and schedule discovery meetings for the sales team with interested prospects, ensuring a smooth handover of information

CRM Excellence: Maintain accurate and up-to-date records of all interactions and prospect information in the customer relationship management (CRM) system

Objection Handling: Clearly articulate products and solutions with prospective partners to successfully manage and overcome objections

Collaborative Strategy: Collaborate closely with account executives to align on target accounts and optimize the sales process

Quota Attainment: Meet or exceed assigned targets for lead generation

Qualifications

Ability to work independently and consistently achieve or exceed goals.

Excellent verbal and written communication skills with the ability to engage, persuade, and build rapport with prospects

Strong organizational and time management skills to handle multiple priorities with attention to detail

Some experience with, or strong willingness to learn, sales databases and tools (such as Outreach, Salesforce, and Clay)

Ability to thrive in a fast-paced, dynamic environment and adapt quickly to changing priorities and ever-growing sales team

Collaborative mindset with a willingness to work closely with the sales team members & consistently engage with potential partners

Previous experience in sales, lead generation, or customer-facing roles is advantageous but not mandatory. Those with a passion for sales and a strong desire to learn are also encouraged to apply.

Hiring Process

Recruiter Phone Screen (30 minutes)

Take home assignment (30-45 minutes; on your own time)

Mock Call and Q&A (30 minutes)

Final interviews with 2 FreeWill team members (2 separate 30 minute interviews)

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 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.

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

#LI-DNI

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: Us