Commercial Insurance Team Lead - Medical Malpractice (Remote First)

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.
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.

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.

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.