Commercial Insurance Team Lead - Medical Malpractice (Remote First)

Zensurance; Toronto; Remote; CAD 75,000 - 90,000; Full time

Benefits offered by this job

Remote-first

Home office allowance

Tech equipment

Half days before holidays

Health/dental plans

Health spending account

Parental leave top-up

Education assistance

Team-building events

Weekly huddles

Job summary

Zensurance is seeking a Team Lead for New Business in the Medical Malpractice vertical. You will mentor a team of Brokers, coach on sales strategy, and directly engage prospects and underwriters to close complex deals.

This role emphasizes leadership, collaboration, and the ability to scale revenue while maintaining exceptional client service in a fast-paced, digital brokerage environment. Remote-first with strong growth potential.

Qualifications

• 5+ years of commercial insurance experience (Medical Malpractice or allied health risk preferred).
• 3+ years of direct supervisory or team lead experience.
• Valid provincial broker’s license in good standing (RIBO preferred).
• Proven track record of driving sales metrics and achieving targets in a target-driven environment.
• Hunter mentality with a proactive, results-oriented approach.

Responsibilities

• Lead and coach a team of New Business Brokers to achieve ambitious GWP and sales targets.
• Close complex MedMal deals with prospects and underwriters while maintaining high service standards.
• Guide brokers on niche MedMal terms, risk profiles, and policy negotiations.
• Drive growth across core archetypes: Beauty & Wellness, Healthcare, Sports & Fitness, Pet Services.

Skills

Commercial insurance

People leadership

RIBO license

Job description

About Us:

Zensurance 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.

Zensurance 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 Zensurance, 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 Zensurance. 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 strongly preferred).


• 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.

$75,000 - $90,000 a year

At Zensurance, we hire for talent and potential.

The total cash compensation range including OTE for this role is $102,000 with a top earning potential of $115,000.

The annual base salary range provided for this position is a nationwide market range and represents a broad range of salaries for this role across the country. The actual salary for this position will be determined by a number of factors, including the scope, complexity and location of the role; the skills, education, training, credentials and experience of the candidate; and other conditions of employment. As part of our comprehensive compensation and benefits program, employees may also be eligible for performance-based case incentive awards.

Benefits & Perks at Zensurance:

At Zensurance, 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:

Zensurance 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.