Team Lead - Commercial Insurance Sales (Remote First)

About Us

The company is redefining commercial insurance for Canadian businesses.

As a leading InsurTech, we make getting the right coverage simple, fast, and accessible through a digital-first experience. Our platform combines advanced technology with deep industry expertise to deliver tailored insurance solutions that help businesses thrive.

The company has been recognized for its rapid growth and industry impact:

✅ Deloitte’s Technology Fast 50 (2023, 2024, 2025)

✅ Deloitte’s Technology Fast 500 (2024, 2025)

✅ Top Insurance Employers (2022)

At the company, we value ownership, collaboration, and innovation. Our team thrives on solving complex challenges, challenging the status quo, and making a real impact in an industry ready for change.

If you're looking to build something meaningful in a fast-growing, customer-focused company, we’d love to hear from you!

We’re looking for a Team Lead, New Business - Medical Malpractice to join our growing commercial brokerage team at the company. If you’re passionate about people leadership, sales coaching, and the fast-paced world of digital brokerages, this is an incredible opportunity for you.

Reporting directly to the Practice Leader, you'll play a critical role in expanding our revenue, driving conversion rates, and scaling our team quickly without compromising quality.

In this role, you will specifically champion and lead brokers supporting our Medical Malpractice (MedMal) vertical, driving growth across core industry archetypes including:

Beauty & Wellness

Healthcare & Allied Health

Sports & Fitness

Pet Services

As the Team Lead, you'll serve as the technical and operational anchor for MedMal coverages, helping your brokers navigate niche policy terms, complex operational indexes, and specialized risk profiles.

This is a player/coach role. You'll mentor a dedicated team of New Business Brokers to help them hit ambitious sales goals, while also working directly with prospects and underwriters to close complex deals yourself.

The New Business Workflow

• Inbound Qualified Leads: Brokers engage with 15+ warm, inbound leads per day—no cold calling required.

• Pure Sales Focus: We’ve eliminated administrative drag. Your brokers focus strictly on new business acquisition; renewals, endorsements, and mid-term changes are handled by dedicated support teams.

• Speed to Market: In our world, responsiveness wins deals. You will coach your team to manage a fast-moving sales pipeline, leveraging relationships with 50+ insurer partners to bind coverage rapidly.

• Tech-Driven Environment: We leverage a proprietary BMS, automated workflows, and advanced quoting tech to deliver custom, real-time insurance solutions.

• Data-Driven Outcomes: Performance is transparent and measurable. You'll hold direct accountability for your team’s Gross Written Premium (GWP), binding conversion ratios, and response SLAs.

Responsibilities

• Sales Coaching: Be obsessed with customer experience and consultative selling. Elevate team performance through structured shadow sessions, call recordings, and actionable, real-time feedback.

• Leadership Excellence: Commit to the craft of people management: leading meaningful 1:1s, delivering constructive feedback, navigating performance management, and fostering a resilient, high-energy sales culture.

• Target Achievement: Keep team energy and motivation high to consistently hit and exceed monthly and quarterly team GWP targets.

• Quality Assurance & Development: Conduct daily team huddles, knowledge-sharing sessions, and regular file audits to ensure strict compliance, accurate underwriting, and high service standards.

• Complex Risk Guidance: Act as an escalation point to help brokers navigate complex MedMal and commercial liability risks, underwriter pushback, and policy negotiations.

Requirements

• Industry Experience: 5+ years of commercial insurance experience (direct experience with Medical Malpractice, Professional Liability, or Allied Health risks is a bonus).

• People Leadership: 3+ years of direct supervisory or team lead experience managing sales or service professionals.

• Licensing: Valid provincial broker’s license in good standing (RIBO licensed preferred).

• Track Record of Performance: Proven history of driving sales metrics, conversion rates, and team accountability in a target-driven environment.

• Hunter Mentality: Agile, resilient, and persistent approach to winning business and overcoming objections.

• Execution & Detail: Exceptional attention to detail with the ability to triage competing priorities in a fast-paced setting.

• Growth Mindset: Strong commitment to continuous learning, professional self-development, and keeping pace with evolving insurance trends.

Benefits & Perks at the company

At the company, we know that when our people thrive, so does our business. That’s why we offer a flexible, people-first work environment designed to support your well-being, growth, and success.

If you're looking for a team that values learning, collaboration, and impactful work, we’d love to meet you!

💻 Work Your Way

• Remote-first setup for added flexibility
• Home office allowance to create a comfortable workspace
• Top-tier tech: "Office in a box" with all necessary tech equipment
• Half days before public holidays: Enjoy half days before long weekends

❤️ Your Health, Your Way

• Flexible health and dental plans for families, including mental health support
• Health & personal spending accounts to invest in wellness your way
• Parental leave top-up, because family comes first

🚀 Investing in Your Growth

• Education assistance reimbursement for courses, conferences, books, and memberships
• Opportunities to learn from industry experts and grow your career

🤝 Staying Connected

• Weekly Friday huddles to share updates and connect across teams
• Virtual & in-person team-building events to strengthen our culture

AI Tools and Your Interview

We know AI is a valuable tool, and you're welcome to use it to prepare for your interview. However, please don't use AI assistants during the live interview itself. We want to have an authentic conversation with you, and using AI during the interview could affect our evaluation of your suitability for the role.

Just so you know, we use an AI scribe to help us take notes and review interviews, ensuring a fair and clear process.

Diversity & Inclusion

The company celebrates diversity and is committed to creating an inclusive environment. We welcome applications from all backgrounds and provide accommodations throughout the hiring process. If you need support, let us know, we’re here to help.