Account Executive, Ontario Regional Sales

Account Executive, Ontario Regional Sales

Established in 2014, Sterling Brokers is growing rapidly and looking for talented individuals to join our team.

The Account Executive Role requires licensed insurance sales professionals who are self‑described “hunters”. The expectation of this role is that you will actively hunt for new business prospects while also being skilled at cultivating relationships with existing clients in the Employee Benefits space.

To be considered for this role you should demonstrate a knack for identifying potential clients, initiating contact, and effectively pitching solutions that meet their needs. This combination of prospecting and relationship‑building is crucial for sustained success in the competitive field of insurance sales.

Sterling Brokers’ Ontario regional sales team is disrupting the Group Benefits and Retirement landscape in Canada. The power of Sterling is our innovative Benefits Management Platform, Unique Multi‑Employer Plan Solutions, and Full‑Service Support and Technology Teams. Working together, we design and support unique, streamlined solutions for businesses while integrating with the largest insurance carriers in Canada and global HRIS platforms. Apply now to join our team and kick off your 2026.

• Manage the entire sales process, from initial contact to the close of the deal.
• Understand client needs and present tailored solutions, effectively demonstrating the value of our insurance products and services.
• Collaborate with internal teams to ensure seamless implementation and delivery of solutions to clients. This role is supported by a dynamic implementation team that will take the sale through implementation and onboarding, ensuring a smooth and seamless transition for the client and their employees.
• Expand your knowledge of our offerings and industry trends to stay ahead of the competition.
• Retain organized records and track progress toward business goals and quotas using Salesforce.
• Leverage Excel, Salesforce, and Salesloft to streamline your sales activities, track progress, and optimize your performance.
• Strategic planning with your manager to constantly fine‑tune your territory approach to improve overall sales results on a weekly, monthly, & quarterly basis.
• Generate new business opportunities on your own, in addition to leads received from a variety of sources (BDR’s, Marketing, Partnerships).
• Collaborate with our internal GRS team to support client requirements for financial planning support services and/or retirement/investment plans as part of their Group Benefits solution. This role is supported by a Group Retirement Planning team that specializes in this field.

• Mandatory requirement: licensed insurance advisor – LLQP (Life, Accident and Sickness License) and E&O Coverage in force and in good standing in Ontario.
• Nice to have – Extra Provincial Licenses or willingness to be licensed in other provinces in the future.
• Nice to have but not required – Segregated funds experience, CFP, CP, CEBS designations or other.
• Proven experience as a successful Account Executive or in a comparable sales role within the insurance industry specifically in group benefits.
• Experience working in a business‑to‑business sales environment with a multi‑stage sales process.
• Strong track‑record of independently generating leads, qualifying prospects, and closing deals.
• Proficiency in utilizing Excel for data analysis and reporting.
• Experience with Salesforce and Salesloft, or similar CRM and sales automation tools.
• Excellent communication and negotiation skills, with the ability to build rapport and establish trust with clients.
• Self‑motivated and target‑driven, with a passion for exceeding sales goals.
• Strong organizational and time‑management abilities to effectively prioritize tasks and meet deadlines.
• It is our company policy and an insurance regulation that you are licensed in the province in which the customers’ business is headquartered to earn commission income.

This is a fully remote role with the opportunity to work out of a local Toronto office if you prefer.

• Entry level

• Full‑time

• Sales and Business Development

• Insurance Agencies and Brokerages

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