Rival Job Board
Vice President of Sales
remote
Montreal, Quebec, Canada .
full-time . June 3, 2026
Montreal, Quebec, Canada .
full-time . June 3, 2026
Description
About Rival
Rival Insurance Technology is a Canadian insurtech company modernizing how brokers run their business. With nearly 30 years in the industry and a fully remote team across Canada, we are at an inflection point -- new product family, growing broker network, and a leadership team that moves fast.
The Role
This is a builder role. You will own the full revenue and marketing function -- developing strategy, leading a growing team, and driving measurable results. You report directly to the CEO and operate at the intersection of sales execution, team leadership, and market presence.
What You Will Own
Revenue & Growth
• Develop and implement sales strategies to achieve revenue targets
• Identify new business opportunities, potential clients, and broker channel partnerships
• Build and maintain strong relationships with key customers, brokers, and stakeholders
• Represent Rival at industry events and conferences
Team Leadership
• Lead, mentor, and develop the sales team to drive performance against defined targets
• Set sales targets and KPIs, and hold the team accountable to outcomes
• Design and manage commission structures aligned with industry practices
• Hire, coach, and scale the team as the business grows
Operations & Collaboration
• Streamline sales processes and drive operational efficiency
• Collaborate with the leadership team on product and service requirements
• Shape and execute marketing strategy in partnership with internal stakeholders
What You Bring
• 8+ years in insurance or insurtech, with 3+ years in a sales leadership role
• Demonstrated track record building and scaling a B2B sales team
• Proven ability to design commission structures and sales performance frameworks
• French/English bilingualism with strong Quebec market understanding
• Familiarity with the AMF-regulated market and Quebec broker associations (strong asset)
• Hunter mindset for net new business, with the discipline to build repeatable process
• Comfortable in a fast-moving, remote-first, tech-forward environment
Why Rival
Rival is at an inflection point. We have a proven platform, a modernization roadmap, and ambitious plans for the broker market across Canada. The company is small enough that your decisions have visible impact -- and large enough to present real commercial challenges.
We are remote-first, Canada-based, and run by a leadership team that trusts its people to make real decisions.
Our Commitment
We are committed to fostering an accessible and inclusive workplace. If you require accommodation during the recruitment process, let us know—we’ll work with you to meet your needs. We appreciate all applications; however, only those selected for interviews will be contacted.