Sales Account Executive, Insurance

Division / Department: Sales
Reports to (position): Sales Director, Financial Services
Level / Grade: Individual Contributor
Location: Remote, Canada (Ontario)
Employment Type: Full Time, Exempt
Work Conditions: Remote/Home Office
Travel: Up to 25%
Telecommute: Yes
Minimum Educational Req: Bachelor's degree in Business Administration, Marketing, Finance, Communications, or related field; equivalent combination of education and experience may be considered.
Years of Experience: 5+ years of B2B sales experience selling into RBO organizations, MGA channels, or insurance distribution networks

The Account Executive, Insurance is responsible for driving new business growth and expanding enterprise partnerships within Canada's insurance distribution market. This role focuses on developing relationships and securing strategic partnerships with Recruiting Based Organizations (RBOs), Managing General Agencies (MGAs), and insurance distribution networks to position SeeWhy Learning as the preferred provider of insurance licensing education and compliance training.

This individual will be a hunter-oriented sales professional who excels at identifying decision makers, building executive-level relationships, and creating opportunities that generate measurable adoption and licensing volume. The ideal candidate possesses a strong understanding of the Canadian insurance distribution landscape, including how decisions are made within RBO networks, what motivates field leaders, and how to secure senior-level sponsorship that drives enterprise-wide adoption.

The Account Executive will leverage existing industry relationships, attend networking and industry events, collaborate cross-functionally to support customer success, and maintain a robust pipeline of opportunities while consistently achieving revenue objectives.

• Build and grow a pipeline of Recruiting Based Organization (RBO) networks and Managing General Agency (MGA) accounts across Canada.
• Expand existing SeeWhy Learning relationships while actively identifying and pursuing net-new enterprise partnerships.
• Prospect, qualify, and close strategic agreements that position SeeWhy Learning as the preferred licensing education provider within target organizations.
• Identify, engage, and influence key decision makers including Marketing Directors, Senior Vice Presidents, MGA Principals, and other executive stakeholders.
• Structure partnership agreements that drive measurable learner adoption, enrollment volume, and long-term customer value.
• Develop and execute strategic outreach plans designed to increase market penetration and revenue growth.
• Attend RBO conventions, MGA events, regional meetings, conferences, and industry functions to develop new business relationships.
• Build credibility and trust with senior field leaders and organizational influencers throughout insurance distribution networks.
• Collaborate with product, marketing, and customer success teams to develop onboarding resources, activation strategies, and adoption programs for enterprise partners.
• Gather and communicate market intelligence related to pricing, competitive offerings, partner requirements, and industry trends.
• Maintain accurate pipeline, account activity, forecasting, and contact records within Salesforce or equivalent CRM platforms.
• Deliver weekly, monthly, and quarterly pipeline reports, forecasts, and sales performance updates.
• Consistently achieve or exceed assigned sales quotas and strategic objectives.
• Represent SeeWhy Learning professionally within the Canadian insurance and financial services community.

• Minimum of 5 years of B2B sales experience selling into Recruiting Based Organizations (RBOs), insurance distribution networks, or Managing General Agencies (MGAs).
• Demonstrated understanding of RBO organizational structures, field leader incentives, and enterprise purchasing processes.
• Proven success developing and closing net-new business opportunities.
• Track record of growing existing customer relationships and expanding account revenue.
• Experience working with executive-level decision makers and industry influencers.
• Proficiency using Salesforce or equivalent CRM systems to manage sales activities, pipelines, and account records.
• Ability to develop strategic sales plans and execute independently.
• Strong relationship management skills with the ability to establish credibility quickly.
• Eligible to work within Canada.

• Demonstrated success achieving sales quotas and revenue growth objectives.
• Strong business development, prospecting, and enterprise sales capabilities.
• Excellent relationship-building and networking skills.
• Strong consultative selling and negotiation abilities.
• Exceptional oral, written, and presentation skills.
• Ability to identify and influence multiple stakeholders throughout complex sales cycles.
• Strong organizational, planning, and territory management skills.
• Ability to analyze market opportunities and develop strategic account plans.
• Self-motivated with the ability to work independently and manage competing priorities.
• Strong problem-solving and decision-making capabilities.
• Commission-driven mindset with a history of strong sales performance.

• Proficiency in Microsoft Office Suite (Word, Excel, PowerPoint, Outlook).
• Experience utilizing Salesforce or equivalent CRM platforms.
• Experience with virtual meeting platforms including Microsoft Teams and Zoom.
• Ability to maintain accurate forecasting, pipeline management, and sales reporting.
• Comfortable working with sales technology platforms and business development tools.
• Ability to quickly learn and adapt to new software, systems, and technologies.

• Familiarity with Canadian insurance licensing requirements, including LLQP, A&S, and continuing education requirements.
• Existing relationships within organizations such as WFG, Primerica, Greatway, Experior, IDC WIN, PPI, Hub Financial, or other major Canadian insurance distributors.
• Experience selling EdTech, SaaS, digital learning, compliance, or licensing education solutions.
• Experience working with high-volume insurance distribution channels.
• Bilingual English and French.

The physical demands of this position are representative of those that must be met by an employee to successfully perform essential functions of this job. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.

This position interacts regularly with sales leadership, marketing, customer success, product teams, and executive leadership. External interaction includes prospective and current enterprise partners, RBO leaders, MGA principals, field leaders, insurance professionals, industry associations, and strategic partners throughout Canada.

This position does not supervise the work of others.