TSR Team Lead

Overview

Cheep Insurance isn’t your typical insurance brokerage. As Atlantic Canada’s first and only fully digital insurance broker, we’ve been shaking things up in the industry since 2016!  Our mission is to make insurance simple, convenient, and accessible to everyone. We specialize in personal insurance solutions with an emphasis on specialty segments and are committed to ensuring that all individuals can secure the insurance they need.  Cheep is the brokerage of choice for many Atlantic Canadians and joining the Southampton Group of Companies has opened the door to meeting the needs of Canadians in Ontario, British Columbia & Alberta as well.  The journey of expanding our reach across Canada means we are also growing our fantastic team of service professionals!

We’re looking for a TSR TEAM LEAD to guide and support our TSR (Transactional Service Representative) Team – ensuring efficient workflows, accurate data, and compliance with all internal processes and regulatory requirements. From coaching team members and managing day-to-day operations to improving systems, leveraging automation, and partnering with leadership on new initiatives, this role combines leadership, problem-solving, and innovation.

This is a remote position, Monday to Friday during standard business hours, and requires a reliable home workspace with consistent availability throughout your shift. Ideally, the candidate would be based in Nova Scotia for added convenience, but this is not a requirement. We are open to exceptional candidates from other locations and wouldn’t want to miss out on great talent simply due to geography.

You’ll also take the lead on exciting initiatives like our Cheep Apartment Protection Program (CAPP) and contribute to streamlining processes that help the entire team work more efficiently.

If you enjoy variety, love collaborating with others, and want to make a real impact in a supportive, tech-forward environment – we’d love to hear from you!

Key Accountabilities

• Lead, manage, and hold the TSR Team accountable to achieve operational excellence.
• Coach, mentor, and develop team members through training, guidance, and recognition.
• Foster a positive, growth-oriented team culture that aligns with company values.
• Manage scheduling, workload distribution, and TSR shared inboxes to maintain service levels.
• Oversee BMS activities, ensuring accuracy, timeliness, and compliance with workflows.
• Monitor KPIs and turnaround times, providing leadership with performance reports and driving improvements.
• Champion workflow efficiency by identifying opportunities to streamline processes and reduce inefficiencies.
• Collaborate with leadership, IT, and vendors to enhance technology, automation, and AI tools.
• Identify operational gaps or bottlenecks, design solutions, and support rollout of new systems.
• Promote continuous improvement by balancing execution with innovation in daily operations.
• Act as the primary liaison between the TSR Team and other departments, insurer partners, finance partners, and vendors.
• Support EOS initiatives and special projects, ensuring accountability for Rocks, Scorecards, and timelines.
• Ensure compliance with licensing, regulatory, and contractual requirements across the organization.
• Oversee corporate insurance needs and maintain accurate staff licensing and continuing education records.
• Implement and enforce data privacy, security protocols, and support insurer or regulatory audits.

Qualifications and Skills

• CAIB or CIP designation, post-secondary education, or equivalent combination of industry experience and professional development.
• 5+ years of insurance industry experience, ideally in a brokerage, with at least 2 years in a leadership or team lead role.
• Strong organizational skills and attention to detail, with the ability to manage compliance requirements, documentation, and reporting accurately.
• Solid understanding of insurer partner products, underwriting guidelines, binding authority, and operational processes.
• Comfortable with technology, process automation, and workflow optimization tools.
• Excellent communication skills, with the ability to build trust, motivate a team, and collaborate across departments.
• Demonstrated ability to coach, develop, and hold team members accountable while maintaining a positive, growth-focused culture.

Compensation

Salary to be determined by education, experience and qualifications.

About Cheep Insurance

Our Mission:

We believe insurance should be simple, convenient, and accessible to everyone.

We help find personal insurance & payment plans that work for everyone – even if you don’t have the best driving record, credit, or payment history.

Our Core Values

Our company culture is very important to us – we’re looking for team members who align with our core values:

• People First – We believe in teamwork, empowerment, empathy, & open communication.
• Innovation & Simplicity – We work smarter, not harder.
• Professionalism – We take pride in our work, act with integrity, and lead with accountability.
• Good Vibes – We strive to bring positive energy to the world of insurance.
• Growth-Focused – We take initiative to #GSD (if you know, you know) and make our vision a reality.

Highlights of Working at Cheep Insurance

• Work from home full time to maximize work-life balance
• Opportunities for growth and development
• Positive work culture and relationships, including a formal employee recognition and appreciation platform
• Simplified workflows to make life as easy as possible for our team (in the insurance broker world, this can be hard to come by!)
• Our fun team culture and fast-paced environment make the work day enjoyable!

Working at the Southampton Financial Group of Companies

Cheep Insurance is a proud member of the Southampton Financial Group of Companies.

Our aim is to create a workforce that is diverse, promotes positivity, and demonstrates the values of equality, fairness, and respect in everything we do. We are dedicated to an antidiscrimination approach and provide equal opportunity for employment regardless of gender, race, ethnicity, national origin, age, sexual orientation or identity, education, or disability. We respect and value diverse life experiences and cultures and ensure that all voices are valued and heard.

Southampton Financial Inc. welcomes and encourages applications from people with disabilities. Accommodations are available on request for candidates taking part in all aspects of the selection process.

Apply Now

Interested? Send your resume and cover letter to [email protected] to apply.

We thank all applicants for their interest; however, only those selected to be interviewed will be contacted.