Learning Executive Jobs in Kitchener, ON (NOW HIRING)

As a B2B Sales Executive, Commercial Lines Insurance, you will sell commercial property and casualty insurance and risk management services to small and medium-sized business owners and C-suite decision makers across the GTA and surrounding areas of Ontario.

You will sell primarily to business owners, CFOs, and senior operations leaders at companies in construction, manufacturing, technology, food and beverage, life sciences, not-for-profit, and transportation and logistics.

This is a pure hunter role: 100% new business development in Year 1, with approximately 75% of leads self-generated through networking, cold outreach, referrals, and self-built target lists. The sales territory is open across the GTA and surrounding areas, with no overnight travel required.

This is an expansion hire reporting to the Sales Manager, with the VP Commercial Sales as the broader leader of the team.

This posting is for our industry-experienced track: candidates with prior commercial lines or personal lines insurance sales experience, RIBO licensed before start.

COMPENSATION & BENEFITS

• $70,000 to $90,000+ scaling with experience level (draw against commissions, guaranteed for 2 years to help you build your book of business), plus bonuses
• Year 1 Total Compensation at Target: $70,000 to $90,000 for candidates with 2 to 4 years of commercial lines or 2+ years of personal lines experience (RIBO licensed)
• Year 1 Total Compensation at Target: $90,000 to $120,000 for seasoned producers with 5+ years of commercial experience (RIBO licensed)
• Long-term earnings: $120,000+ to unlimited as the book of business grows, no cap

Benefits and perks (applies to this role):

• Commission paid monthly, no commission cap
• Personal performance bonus paid annually, not capped
• President's Club Trip Awards and additional performance-based incentives
• Health benefits, partially company-paid
• Profit sharing (company-wide bonus)
• Further education reimbursement
• Employee recognition and gift programs
• Company social events
• Deferred Compensation program for long-term wealth planning
• Salespeople manage their own time off against performance standards

THE COMPANY & CULTURE

Our client was founded in approximately 1983 and is a family-owned, privately held full-service commercial insurance brokerage with 42+ years in business. Headquartered in Hamilton, Ontario, they provide commercial property and casualty insurance and risk management services to business clients across Ontario.

They serve small-to-medium businesses (typically 20 to 100 employees) across construction and development, manufacturing, technology, food and beverage, life sciences and pharma, not-for-profit, transportation and logistics, electrical contracting, and landscaping. They are an established and mature company, actively growing at 10 to 15% revenue per year, with a total headcount of 125.

Our client has been recognized as one of Canada's Top Small and Medium Employers. The culture is participatory, supportive, and engaging. Employees describe a welcoming, collaborative environment with strong learning and career growth opportunities. Average employee tenure is 5 to 10 years and company-wide turnover is under 10%. Leadership style on the sales team is servant leadership, with a newly added Sales Manager creating additional bandwidth for onboarding and coaching new producers.

OFFICE LOCATION & SALES TERRITORY

• Head office: Hamilton, Ontario, Canada
• Sales territory: open. GTA and surrounding areas, including Hamilton, Burlington, Oakville, Mississauga, Toronto, and Ontario more broadly
• Hours: 40 hours per week, Monday to Friday. Occasional evening or weekend client calls as required
• Overnight travel: none required
• Dress code: business casual for client-facing activities
• Valid driver's licence and personal vehicle are required

Work arrangement for this profile:

• Training period: office-based, 5 days per week, for approximately 1 to 3 months depending on depth of commercial insurance experience
• Post-training: work from home, with visits to the office as required. Specific cadence agreed with the VP Commercial Sales.

EXPERIENCE, BACKGROUND & EDUCATION REQUIREMENTS

• 2 to 4 years of commercial lines insurance sales experience; 5+ years considered at a higher base salary
• Minimum of 2 years of personal lines insurance sales experience also considered for this profile
• RIBO licence required before start date for training purposes. Prep resources and online exam booking are available through our client. Candidates at the carrier level holding an OTL licence are acceptable depending on depth of commercial experience.
• Experience with major Canadian commercial carriers (for example, Intact, Aviva) is an asset
• Proven B2B outside sales track record. Must be a hunter with a demonstrable new business development history.
• Post-secondary education or equivalent professional experience
• Basic proficiency in Microsoft Excel, PowerPoint, and Word. CRM experience an asset.
• Valid driver's licence and personal vehicle required

TECHNICAL SKILLS

• Microsoft Word: basic
• Microsoft Excel: basic
• Microsoft PowerPoint: basic
• CRM software: basic (asset; our client uses a proprietary CRM)

THE PRODUCT / SERVICE / SOLUTION

• Commercial property and casualty insurance
• Risk management advisory services
• Claims advocacy and support
• Specialist practice-area solutions across construction, manufacturing, technology, food and beverage, life sciences, not-for-profit, transportation, and related sectors

PROSPECTIVE CUSTOMERS, INDUSTRY FOCUS, DECISION MAKERS

• Small-to-medium businesses, typically 20 to 100 employees, with annual revenues in the $5 million to $10 million range
• Target industries: construction and developers, manufacturing, technology, food and beverage, life sciences and pharma, not-for-profit, transportation and logistics, electrical contractors and landscapers
• Geographic focus: GTA and surrounding areas of Ontario
• Primary decision makers: business owners, CEOs, CFOs, VPs of Operations, and senior finance or operations leaders

SALES CYCLE, ORDER VALUE, ACCOUNT SIZE

• Average sales cycle: 12 to 18 months for ideal commercial accounts
• Average number of calls to close: 4 to 6
• Target account size: businesses with $5 million to $10 million in annual revenue
• Renewal commissions on the producer's book form the long-term income base. A renewing book of business is the primary wealth-building engine of this role.

COMPETITIVE ADVANTAGES

• Full-service brokerage with a 360 degree, holistic, multi-disciplined approach (specialists in every major practice area)
• Proactive, ongoing service model with strong claims advocacy
• Competitive pricing backed by deep carrier relationships
• Risk management approach that goes well beyond basic policy placement
• Recognized as one of Canada's Top Small and Medium Employers
• 40+ years of market presence and an established book of long-tenured clients
• Servant-leadership sales management and a supportive, participatory culture

TYPICAL DAY & DUTIES

Year 1 activity split:

• 100% New Business Development (Year 1)
• 0% Account Management (Year 1)

On a typical day you will be building and working a pipeline of self-sourced prospects: attending networking events, making outbound calls, sending outbound emails, leveraging referrals, meeting with prospective clients in person, presenting and quoting commercial insurance programs to business owners and senior decision makers, collaborating with internal specialist and service teams, and maintaining accurate pipeline records in the CRM.

Approximately 75% of your pipeline will be self-generated; approximately 25% will come from warm or list-supplied leads.

In Year 2, as your book of business grows, the role transitions to a mix of continued new business development and early account management on your renewing accounts.

LEADS

• Approximately 75% of leads are self-generated through cold outreach, networking events, referrals, and self-built target lists
• Approximately 25% of leads are warm or list-supplied through internal specialist referrals, existing relationships, and marketing activity
• This is a hunter role. Expect to own your own prospecting and pipeline from Day 1.

OVERNIGHT TRAVEL

• None required. The territory is GTA and surrounding areas, and all client activity is day-trip accessible.

SUPPORT & TRAINING

• Structured onboarding in-office, 5 days per week, for approximately 1 to 3 months depending on experience depth
• Formats include in-house training, carrier-based training, and external courses
• RIBO licensing support if the candidate is finalizing their licence: prep resources and online exam booking
• Servant-leadership coaching from a Sales Manager with three years in the role, plus direct access to the VP Commercial Sales
• Ongoing professional development budget available through the education reimbursement program

WHY YOU SHOULD APPLY

• Uncapped earnings. Renewal commissions on your book compound year over year, creating meaningful long-term income and personal wealth.
• Established, respected, 42+ year brokerage. One of Canada's Top Small and Medium Employers, with a culture built on support, transparency, and long tenure.
• Open GTA territory, no overnight travel, and a servant-leadership sales management team focused on setting producers up to win
• Deferred Compensation program and profit sharing. Compensation and benefits designed for long-term wealth building, not just a short-term paycheque.

EQUAL OPPORTUNITY EMPLOYER

Just Sales Jobs and our clients are equal opportunity employers. We do not discriminate. All candidates are evaluated solely on performance merit and organizational fit.

NOT THE RIGHT FIT? WE MAY HAVE OTHER ROLES FOR YOU.

If this particular role isn’t the right match, we encourage you to browse our other open positions at https://justsalesjobs.ca/jobs-opening/ and apply for any that interest you. Our recruiters review every resume we receive — and if we have another role that could be a great fit for your background, we will reach out to you directly.

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