Account Executive - Eastern Canada

Account Executive - Eastern Canada

We Know Training Inc. (WKT) ·  Remote (Greater Toronto Area, Ontario)  · Full-Time

Every insurer, managing general agent and dealer firm in Canada has the same standing problem. They need to get people licensed, keep them current, and prove it to a regulator. We have been solving that problem since 2002, and we are looking for someone who already knows that world from the inside to own it for us.

Compensation

Base salary of $100,000 to $110,000 per year.

Quarterly commission on your own net new revenue, rising as you go. Two percent on your first $500,000 in the calendar year, two and a half percent from $500,000 to $600,000, and three percent on everything above that.

It is paid on your individual results, whether or not the company hits its overall targets. On target earnings at quota are $110,000 to $120,000.

Commission is paid quarterly, once payment has been collected. Expansion, renegotiation and competitive bid wins all count as net new, and multi-year agreements are commissioned across the full original term.

The Role 

You own the financial services and insurance vertical for We Know Training nationally, and every vertical across Eastern Canada. This is a hunting role. You build your target list, run your own discovery, demonstrate the platform, and close.

Your buyers sit at head office. They are the compliance leads, learning teams and distribution executives responsible for getting hundreds of advisors licensed and keeping them current. You are selling to the firms, not to their clients, and you do not need to be licensed yourself.

The anchor is Business Career College, a recognized name in licensing and continuing education. It covers the Life Licence Qualification Program (LLQP), Canadian Investment Regulatory Organization (CIRO) courses, and exam preparation for the Certified Financial Planner and Qualified Associate Financial Planner designations. You will also sell across our wider catalogue, including Danatec, Fleet Safety International, CannSell, Relo and Canadian Academy of Guard Training, to the training managers and learning leaders responsible for keeping regulated workforces compliant.

           What Makes This Role Different

• You are not starting from scratch. This seat has been built out ahead of you. On day one you inherit a live client base with account history documented, a written go to market playbook, defined buyer personas for each credential with the triggers behind them, a research and outreach toolkit the sales team built, and a confirmed event calendar covering the associations that actually matter. You will not spend your first quarter working out who to call.
• Your network is the job, not a nice to have. We are hiring for the doors you can open. If you already know who runs training and compliance at the carriers, managing general agents and dealer firms, you will be productive in weeks rather than months, and you will be given the room to work that way.
• Work that matters. You are helping organizations across Canada improve safety, compliance and performance, through brands the people in those industries already recognize and trust.
• Real growth. We are a growing Canadian company, expanding across industries, and this vertical is a priority. Build it well and it becomes yours to grow.
• A team worth joining. Accountable, Curious, Driven, Nimble and Relationship focused is not a poster on the wall. It is how we work.
  
  What You Will Do
  

• Own the vertical nationally. Build and work a named target list of insurers, managing general agents, dealer firms, brokerages, advisor networks and wealth teams, prioritized by potential rather than current spend.
• Own Eastern Canada. Sell our full catalogue to large employers in regulated industries across Ontario and the East.
• Hunt new business. Run structured discovery to understand each buyer’s compliance and workforce pain, demonstrate the platform against that pain, and close.
• Lead consultative demonstrations. Virtual and in person, building trust through education rather than pressure.
• Grow strategic accounts. Own expansion and new scope conversations. Standard renewals sit with our Delivery team, so your focus stays on new revenue.
• Represent us in market. Industry events, association conferences and trade shows across the year.
• Run a disciplined pipeline. Every lead, touchpoint and deal stage accurate and current in FreshSales.
  

          What You’ll Bring

• Financial services or insurance, from the inside. Either you have sold into insurers, managing general agents, dealer firms or advisor networks, or you have worked in one, in compliance, learning and development, advisor development or distribution. Either way, you can name the people who own training decisions and pick up the phone to them. This is what sets the right candidate apart.
• A track record of winning new business. Three to five years in consultative outbound sales or new business development, with a history of hitting target and managing deals in the $25,000 to $35,000 range and above.
• Fluency in licensing and continuing education. You can hold a conversation about licensing programs, regulator requirements, continuing education credits and provincial councils without needing any of it explained. You do not need to have sold training before. You do need to know why a firm cares.
• Confident communication. Credible with senior decision makers and training managers, in writing and in the room.
• Comfort with technology. You work easily in a customer record system, ideally FreshSales, and use tools like Claude and ChatGPT for research, personalized outreach and call preparation.
• Discipline with records. Meticulous pipeline hygiene and deal documentation.
• French. An asset, not a requirement.
  

          What Success Looks Like

• $500,000 in net new revenue annually, ramped across your first two quarters
• Roughly seven sales meetings a week with target accounts, and two new opportunities added
• Enough qualified pipeline to comfortably cover the quarterly target
• Your market knows you, and your network has become warm entry points and active deals
• Clients treat you as a compliance and training advisor rather than a vendor
• You bring market feedback back that sharpens how we position, bundle and sell
  

          What We Offer

• Base salary plus quarterly individual commission, with no company performance gate
• Health and dental benefits, and a corporate Registered Retirement Savings Plan
• Remote work from the Greater Toronto Area, with travel to clients and industry events
• Onboarding that includes time in our Edmonton office with the wider revenue team
• Professional development as we expand across industries
  

About We Know Training

We Know Training has been building learning solutions for regulated industries since 2002. We are a growing Canadian company that unleashes confidence by improving competence, on a mission to revolutionize training through expertly crafted, industry leading programs. We empower organizations across Canada to meet compliance standards and elevate workforce performance.

Equal Opportunity Statement

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. Any information provided by you for accommodations will be kept confidential and won’t be used in the selection process.

Please note that if you are selected for this role, a criminal record check will be mandatory.

This posting is for a real, currently available vacancy.

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