Account Executive - SMB (Canada)

FreeWill (HearstLab); United States; Remote; USD 90,000 - 130,000; Full time

Benefits offered by this job

Health, dental, vision insurance

Work from home

Flexible PTO

Flexible hours

Paid parental leave

Professional development reimbursement

Work from home reimbursement

Co-working stipend

Referral bonuses

Claude AI account

Job summary

FreeWill is recruiting a Grassroots Account Executive to drive revenue by building strategic nonprofit relationships and generating net-new opportunities within an assigned territory. You will prospect, conduct discovery, demo the platform, and negotiate contracts to close deals.

You should have 2+ years of AE experience in a startup SaaS environment, with a track record in product demos, negotiations, and self-managed prospecting. Nonprofit sales experience is a plus.

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 product demos.
• Experience handling negotiations and contract signing.
• Ability to manage own prospecting and drive opportunities.

Responsibilities

• Prospect and schedule new meetings with potential nonprofit clients.
• Conduct discovery with new prospects to understand needs.
• Demonstrate platform solutions and thought leadership to advance sales.
• Negotiate terms and pricing; prepare proposals and contracts.
• Develop strategic plans to drive sales within territory and close deals.

Skills

Prospecting

Negotiation

Product demos

Data-driven decisions

Startup environment

Nonprofit sales

Job description

FreeWill is seeking an SMB Account Executive (internally known as a Grassroots Account Executive) to help fuel our mission to provide the FreeWill platform to nonprofits and raise $1T. The Account Executive is responsible for revenue generation through strategic relationships with nonprofits, identifying net-new opportunities within an assigned territory of accounts.

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
• Executing a sales process through discovery, solution, pricing, negotiation, and close
• Participating in brainstorming, team meetings, and client meetings, researching and assisting with program development for new prospects
• Collaborating with Sales Development Reps to prospect for new business
• Illustrating the value of products and services to create growth opportunities; compiling and analyzing data to identify trends
• Becoming an expert in the FreeWill platform and the broader nonprofit fundraising landscape
• Staying current with changes and developments in the nonprofit industry, gathering competitive information, and sharing with internal teams
• Managing complex contract negotiations and working with legal counsel as required
• Meeting quarterly sales objectives
• Acting with FreeWill’s values of focus, joy, kindness, and courage

You’re a great fit if you:

• Have 2+ years of successful Account Executive experience in a startup SaaS company with multiple products
• Have experience selling to nonprofits (a plus)
• Have experience leading your own product demos
• Have experience handling negotiations and contract signing
• Have experience managing your own prospecting
• Are able to make strategic decisions and run with them
• Are able to understand data and make data-driven decisions
• Are smart, tenacious, and kind, with a growth mindset
• Are comfortable moving quickly in a fast-paced and/or start-up environment
• Can demonstrate actual performance against past quotas
• Are able to learn different customer profiles/personas through team collaboration and self-started learning

Total Compensation

• Competitive salary

Additional benefits include:

• Health, dental, vision, critical illness, disability, and life insurance
• Work from home
• Flexible Paid Time Off policy (minimum time required based on compliance with local laws and public holidays in Canada)
• Flexible hours
• Paid parental leave for all parents
• Professional development reimbursement of CAD$800 annually
• Work from Home reimbursement of CAD$300 annually
• CAD$250 per month co-working reimbursement (for local co-working spaces and home wifi)
• CAD $1,000 referral bonuses
• 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 and one 45-minute interview)
• Offer (contingent on positive references)

AI Policy

Candidates are expected to demonstrate their experience and skills through their own words and work, not through AI-generated content, except as otherwise indicated by the Recruiter. FreeWill may use AI-assisted tools for interview transcription, evaluation, or fraud detection, with human oversight and decision making maintained throughout the hiring process.

EEOC & Diversity Statement

FreeWill is an equal opportunity employer and values diversity. We are committed to building an inclusive, diverse, equitable, and accessible workplace that fosters a sense of belonging. If you’re excited about this role but your past experience doesn’t align perfectly with every qualification, we encourage you to apply.