Job Description

The Opportunity:

Our client is seeking a Regional Sales Director to help scale their modern SaaS platform within the Canadian insurance space. With a focus on Eastern Canada, this fully remote role offer the chance to work at the forefront of insurance technology. The successful candidate will bring deep industry knowledge and strong B2B sales experience to help drive adoption of an all-in-one platform tailored for insurers, mutuals, MGAs, and brokerages.

This role is ideal for someone who thrives in a fast-paced environment, values flexibility, and is motivated by the opportunity to transform how the insurance industry operates.

The Employer:

Our client is a rapidly growing technology firm offering a configurable, all-in-one software solution built specifically for the insurance industry. With a strong reputation for innovation and customer focus, they've earned the trust of insurers and brokers across Canada. The company fosters a connected and collaborative culture—despite being fully remote—and is known for valuing initiative, transparency, and team success.

About You:

You're a consultative sales professional with 5+ years of success in B2B software sales—ideally in the insurance or InsurTech space. You bring a deep understanding of insurance workflows and the ability to connect with senior decision-makers. You're motivated by the chance to make a real impact, enjoy autonomy, and thrive in high-growth environments.

Necessary Qualifications Include:

• 5+ years of B2B software sales experience, preferably in InsurTech or related sectors
• Strong understanding of the Canadian insurance market (carriers, mutuals, MGAs, brokers)
• Proven track record of generating and closing new business deals
• Exceptional presentation and communication skills
• Ability to quickly learn and communicate complex software solutions
• Self-starter with a performance-driven, goal-oriented mindset
• Experience in a high-growth SaaS environment is a strong asset

What's in It for You:

• Flexible compensation structure (salary, commission, or blended)
• Extended health, dental, and vision benefits
• Extra time off beyond standard vacation and holidays
• Professional development allowance
• Employee and Family Assistance Program
• Equity participation through Share Appreciation Rights
• Collaborative, remote-first team culture with in-person connection opportunities
• Chance to shape the future of insurance technology across Canada

About Us:

DGA Careers has been proudly serving the Canadian insurance industry for over 30 years, specializing in recruitment for insurers, brokerages, and InsurTech firms nationwide. With offices in Toronto, Vancouver, Montreal, Edmonton, and Calgary, we bring local insight and national reach to every search.

Interested candidates, please contact Kim Ehman at [email protected]