The Role

We’re looking for a Sales Executive to join our growing team and help drive new business opportunities. Our company provides a digital core platform to property & casualty and specialty insurance companies in Tier III+ (up to $500m in premium). We serve a highly addressable market of niche and growing insurers who need modern technology to compete and scale. Our solution, ISI Enterprise, helps insurance those companies better manage risk, uncover insights, and streamline operations — all in one platform built for sustainable growth.

The ideal candidate has a hunter mentality, focused on creating early-stage connections, both virtually and in person, that can be handed off to our core enterprise sales team once qualified. If you’re naturally outgoing, proactive, and comfortable starting conversations, whether at industry events, conferences, or through virtual outreach, this position is for you. You’ll be the person who uncovers active opportunities while also instigating demand for new solutions at companies where a project is on the horizon. If you’ve worked as an insurance agent or in a client-facing role within the industry, this could be a strong next step in your career.

This role includes sales administration responsibilities and offers a salary forward compensation plan with commission earned for generating qualified pipeline, not just closed deals.

Key Responsibilities

• Prospect actively across multiple channels (email, LinkedIn, in-person events, and industry conferences) to identify and engage potential leads
• Make meaningful connections and establish early rapport with decision-makers and influencers
• Qualify leads based on fit, intent, and strategic alignment with our offerings
• Hand off warm, qualified leads to the enterprise sales team for deeper engagement and closing
• Attend industry events and conferences as a brand ambassador, initiating conversations and making connections on the ground
• Build and maintain a CRM database of industry contacts
• Support sales administration tasks (e.g., coordinating introductory meetings, helping prep materials)
• Collaborate closely with the sales and marketing team to optimize outreach strategies and messaging

About You

• A naturally outgoing personality, someone who isn’t shy about walking up to someone and starting a conversation
• Previous experience in a client-facing, prospecting, or relationship-building role
• Strong communication skills, both verbal and written
• Comfort with sales tools and CRM platforms
• The ability to work independently and manage time effectively across a hybrid work environment
• Bonus: Background as an insurance agent or within the insurance industry

Compensation Plan:

This role is structured with a salary first compensation model and includes a performance-based commission plan designed to reward pipeline stage success:

• Base Salary: Competitive
• Commission Structure:
• Commission is earned when a prospect reaches a key milestones in the sales funnel (e.g., Finalist stage)
• This model ensures you’re recognized for generating quality pipeline, even if you’re not the one closing the deal

Why Join Us

With a recent investment from NexPhase Capital, a PE firm specializing in scaling businesses like ISI, we will be redefining its go-to-market approach to scale the business. You’ll be a key part of a newly established sales team, where your work has a clear and measurable impact. If you’re energized by meeting people, building connections, and helping open doors, this role is built for you.

Job Type: Full-time

Pay: $55,000.00-$100,000.00 per year

Additional pay:

• Commission pay

Benefits:

• Casual dress
• Company events
• Dental care
• Extended health care
• Life insurance
• On-site parking
• Paid time off
• Tuition reimbursement
• Wellness program
• Work from home

Schedule:

• Monday to Friday

Work Location: Hybrid remote in Etobicoke, ON M8Z 1S4