Every insurer, managing general agent and dealer firm in Canada has the same standing challenge: get people licensed, keep them current, and prove it to a regulator.

We’ve been solving that problem since 2002. Now we’re looking for someone who already knows this world from the inside to own it for us.

THE ROLE

You’ll own the financial services and insurance vertical for We Know Training nationally, while also selling across our full portfolio in Eastern Canada.

This is a hunting role. You’ll build your target list, run discovery, demonstrate our solutions and close new business.

Your buyers sit at head office: compliance leaders, learning teams and distribution executives responsible for getting hundreds of advisors licensed and keeping them current.

You’re selling to the firms, not their clients, and you do not need to be licensed yourself.

Our anchor in financial services is Business Career College (BCC), a recognized name in licensing and continuing education, including:

- Life Licence Qualification Program (LLQP)
- Canadian Investment Regulatory Organization (CIRO) courses
- CFP and QAFP exam preparation
- Custom Continuing education

You’ll also sell across the wider We Know Training portfolio, including Danatec, Fleet Safety International, CannSell, Relo and Canadian Academy of Guard Training.

WHAT MAKES THIS ROLE DIFFERENT

- You’re not starting from scratch.
- This role has been built out ahead of you. On day one, you’ll inherit a live client base with documented account history, a written go-to-market playbook, defined buyer personas, a research and outreach toolkit, and an established industry event calendar.
- You won’t spend your first quarter figuring out who to call.
- Your network matters. We’re looking for someone who already understands the financial services and insurance ecosystem. If you know the people responsible for training, compliance and advisor development at carriers, MGAs and dealer firms, you can be productive quickly.
- Work that matters. You’ll help organizations across Canada improve compliance, safety and workforce performance through brands already recognized in their industries.
- Real growth. We’re a growing Canadian company, and this vertical is a priority. Build it well and you’ll have significant room to grow with it.
- ccountable. Curious. Driven. Nimble. Relationship-focused.



These aren’t words on a poster — they’re how we work.

WHAT YOU’LL DO

- Own the financial services and insurance vertical nationally, targeting insurers, MGAs, dealer firms, brokerages, advisor networks and wealth teams.
- Own Eastern Canada for our broader portfolio, selling to large employers in regulated industries.
- Hunt new business through thoughtful, targeted prospecting.
- Run structured discovery to uncover compliance, licensing and workforce challenges.
- Lead consultative demonstrations, virtually and in person.
- Grow strategic accounts through expansion and new-scope opportunities. Standard renewals are managed by our Delivery team so you can stay focused on growth.
- Represent We Know Training at industry events, association conferences and trade shows.
- Maintain a disciplined, accurate pipeline in Freshsales.
- Partner with our Western Canada Account Executives on shared prospecting, demonstrations and go-to-market strategy.

WHAT YOU’LL BRING

- Financial services or insurance experience from the inside.
- You’ve either sold into insurers, MGAs, dealer firms or advisor networks, or you’ve worked within one in compliance, learning and development, advisor development or distribution.
- Either way, you understand who owns training decisions and how these organizations operate. This is what will set the right candidate apart.
- A track record of winning new business.
- Ideally, you bring 3–5 years of consultative outbound sales or business development experience, with a history of hitting targets
- Knowledge of licensing and continuing education.
- You can comfortably discuss licensing programs, regulatory requirements, continuing education credits and provincial councils. You don’t need to have sold training before, but you need to understand why firms care about it.

Confident communication.

- You’re credible with senior decision-makers and training leaders, both in writing and in the room.
- Comfort with technology.




- You work comfortably in a CRM (we use Freshsales) and use tools such as ChatGPT or Claude for research, personalized outreach and call preparation.
- Robust record discipline.
- You keep your pipeline, account notes and deal documentation accurate and current.
- French is an asset, but not required.

WHAT SUCCESS LOOKS LIKE

- $500,000 in annual net new revenue, ramped across your first two quarters
- Approximately seven target-account sales meetings per week
- Approximately two new qualified opportunities added each week
- Healthy qualified pipeline coverage against quarterly targets
- Your existing network becomes warm introductions, conversations and active opportunities
- Clients see you as a trusted training and compliance resource, not simply a vendor
- You bring market intelligence back to the team that improves how we position, bundle and sell

WHAT WE OFFER

- $100,000–$110,000 base salary plus commission
- Quarterly individual commission with no company-performance gate
- Health and dental advantages
- Corporate RRSP
- Remote work from the Greater Toronto Area
- Travel to clients and industry events
- Professional development and growth opportunities as we expand

ABOUT WE KNOW TRAINING

We Know Training has been building learning solutions for regulated industries since 2002. We’re a growing Canadian company that unleashes confidence by improving competence. Our mission is to revolutionize training through expertly crafted, industry-leading programs that help organizations meet compliance requirements and elevate workforce performance.

We Know Training is an equal opportunity employer and values a diverse workforce. We encourage applications from all qualified individuals without regard to ethnicity, religion, gender identity, sexual orientation, age or disability.

Accommodations for disability-related needs are available upon request throughout the recruitment and selection process. Information provided for accommodation purposes will be kept confidential and will not be used in the selection process.

If selected for this role, a criminal record check will be required.

This posting is for a real, currently available vacancy.

Artificial intelligence may be used to screen, assess or select applicants during our recruitment process.

📌 Enterprise Account Executive: Financial Services (Canada)
🏢 We Know Training]
📍 Canada