Commercial Insurance Team Lead - Medical Malpractice

Accountabilities: Lead, coach, and develop a team of New Business Brokers specializing in Medical Malpractice and related commercial liability coverage. Improve sales performance and customer experience through structured coaching, call shadowing, call recording reviews, and actionable feedback. Conduct regular one-on-one meetings, provide constructive performance feedback, manage performance challenges, and foster a motivated, accountable, and resilient sales culture. Drive monthly and quarterly team sales targets, including Gross Written Premium (GWP), binding conversion rates, and response service-level agreements (SLAs). Lead daily team huddles, knowledge-sharing sessions, and ongoing development activities to strengthen technical expertise and sales effectiveness. Perform regular file audits and quality reviews to ensure accurate underwriting, regulatory compliance, and high service standards. Serve as the technical escalation point for complex Medical Malpractice, Professional Liability, and commercial liability risks, including specialized risk profiles, insurer concerns, and policy negotiations. Work directly with prospective clients and underwriters to assess complex cases, negotiate coverage, overcome objections, and close new business. Help brokers navigate niche policy terms, operational requirements, and specialized exposures across beauty and wellness, healthcare and allied health, sports and fitness, and pet services. Manage a fast-moving inbound sales pipeline, encouraging prompt responses and effective use of digital quoting tools, automated workflows, and insurer relationships. Monitor team performance using measurable sales and service metrics, identifying improvement opportunities while balancing growth, quality, and customer satisfaction. Requirements: At least 5 years of commercial insurance experience, with direct experience in Medical Malpractice, Professional Liability, or Allied Health risks strongly preferred. At least 3 years of direct supervisory or team leadership experience managing sales or service professionals. A valid provincial insurance broker license in good standing; a Registered Insurance Brokers of Ontario (RIBO) license is preferred. A demonstrated track record of achieving sales targets, improving conversion rates, and maintaining strong team accountability in a performance-driven environment. Strong consultative selling, negotiation, objection-handling, and customer relationship management skills. A proactive, resilient, and results-oriented approach to acquiring new business and overcoming sales challenges. The ability to coach brokers effectively, provide constructive feedback, manage performance, and motivate a high-performing team. Strong technical understanding of commercial insurance coverages, underwriting requirements, and complex risk assessment, particularly within Medical Malpractice and related liability lines. Excellent organizational skills and attention to detail, with the ability to prioritize competing demands in a fast-paced environment. A commitment to continuous learning, professional development, and staying informed about evolving insurance products, risks, and industry trends. Comfort working in a digital-first environment that uses proprietary brokerage management systems, automated workflows, and advanced quoting technology. Benefits: Base salary: $75,000–$90,000 per year, with actual compensation determined by factors including location, experience, qualifications, and role complexity. Total cash compensation: Target total cash compensation, including on-target earnings (OTE), of up to $102,000, with top earning potential of $115,000. Performance incentives: Potential eligibility for performance-based case incentive awards. Remote-first flexibility: A flexible working arrangement designed to support remote work. Home office support: Home office allowance and an equipment package providing the technology needed to work effectively. Flexible health coverage: Health and dental plans for employees and families, including mental health support. Wellness resources: Health and personal spending accounts to support individual wellness needs. Parental support: Parental leave top-up benefits. Professional development: Education reimbursement for eligible courses, conferences, books, and professional memberships. Career growth: Opportunities to learn from industry experts and continue developing professionally. Work-life balance: Half days before public holidays and a flexible, people-focused work environment. Team connection: Weekly team huddles and virtual and in-person team-building events.