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. No insurance experience required — full training and RIBO licensing provided.
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 full-training track: strong B2B outside sales professionals who are new to insurance. Our client provides full training in commercial insurance product, sales process, and RIBO licensing, including exam prep and booking.
COMPENSATION & BENEFITS
- $70,000 to $80,000 (draw against commissions, guaranteed for 2 years to help you build your book of business), plus bonuses
- Year 1 Total Compensation at Target: draw plus commission as the rep ramps through structured training and licensing
- 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, approximately 3 months of onsite training, through a longer structured ramp that includes product training, sales onboarding, and RIBO licensing preparation and exam
- Post-training: work from home, with visits to the office as required. Specific cadence agreed with the VP Commercial Sales.
EXPERIENCE, BACKGROUND & EDUCATION REQUIREMENTS
- Proven B2B outside sales track record selling to business owners, CEOs, CFOs, or VP-level decision makers
- No insurance industry experience required. Our client provides full training, including RIBO licensing support. Preference is given to candidates with prior experience selling to construction, manufacturing, technology, food and beverage, life sciences, not-for-profit, transportation, and related sectors.
- Experience with long sales cycles (6+ months) and multiple stakeholders is a strong asset
- Ability and willingness to commit to 5 days per week in-office during the full training period
- 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
- Full structured onboarding in-office, 5 days per week, including commercial insurance product training, sales process training, and RIBO licensing preparation
- RIBO licensing exam support: prep resources, online exam booking, and dedicated study time during the training period
- Formats include in-house training, carrier-based training, and external courses
- Servant-leadership coaching from a Sales Manager with three years in the role, plus direct access to the VP Commercial Sales
- Longer ramp period with a structured progression into independent selling as licensing and product mastery are completed
- Ongoing professional development budget available through the education reimbursement program
WHY YOU SHOULD APPLY
- A real path into commercial insurance for proven B2B hunters from outside the industry. Full training and RIBO licensing are provided.
- Uncapped earnings. Renewal commissions on your book compound year over year, creating meaningful long-term income on the accounts you closed years earlier.
- 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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