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Salary: CAD 80,000 - 150,000 / annual
Optionality is a fast-growing Canadian AI company transforming how entrepreneurs prepare for the future, succession, and eventual sale of their businesses. The company's AI-powered platform helps SME owners understand their company's value, identify growth opportunities, explore strategic options, and prepare for their next entrepreneurial chapter. Backed by iNovia Capital and Luge Capital, and part of Google for Startups, Optionality is rapidly expanding its partner network across Canada.
You will lead business development efforts for the Montreal and Eastern Quebec region, reporting directly to the founder and CEO. This is a field-based role requiring deep engagement with the entrepreneurial ecosystem—not a desk job.
Key responsibilities include:
- Converting qualified entrepreneurs entering the platform into customers
- Actively prospecting new SME owners
- Building and managing a robust sales pipeline
- Owning the full sales cycle from initial conversation to signature
- Delivering clear, dynamic product demonstrations
- Actively participating in events, conferences, chambers of commerce, and business networks
- Developing partnerships with chambers of commerce, entrepreneurial associations, accounting firms, professional services, and economic development organizations
- Building relationships with key stakeholders in the SME ecosystem
- Creating speaking, event, collaboration, and referral opportunities
- Building Optionality's brand presence in the Quebec entrepreneurial ecosystem
Average transaction value is $5,000–$10,000 USD, requiring high-volume prospecting and a fast sales pace.
Ideal candidates have experience in chambers of commerce, economic development organizations, business associations, accounting/professional services firms, or companies serving entrepreneurs and SMEs. Background in business development, field sales, partnerships, or membership development is valuable. What matters most is genuine passion for entrepreneurship and the SME ecosystem, a natural ability to build networks, comfort with cold outreach and closing, and a desire to build something from the ground up. Experience in M&A, business transfer, financing, or professional services to SMEs is a plus but not required. You must be comfortable traveling regularly throughout the territory.
