Our client is a well-established insurance brokerage looking for an experienced Team Lead – Personal Lines / Private Client & Group to join their growing team.

This is a unique chance combining team leadership, business development, Group insurance, and Private Client support. You’ll lead a team of experienced Personal Lines Account Managers/CSRs while also acting as a key resource for Group opportunities and high-net-worth Personal Lines business.

The ideal candidate will be an established Personal Lines professional with robust communication skills, leadership experience, and a proactive approach to relationship management and business development.

What You’ll Do Team Leadership

Lead, support, and motivate a team of approximately 5 experienced Personal Lines Account Managers/CSRs

Serve as the escalation point for complex client, coverage, and service issues

Provide guidance and support to team members while promoting a collaborative and accountable environment

Monitor team performance, attendance, and vacation schedules

Communicate management initiatives and key information to the broader Personal Lines team

Support future recruitment, onboarding, and training initiatives

Help ensure high standards of client service, retention, and operational performance

Group Business Development

Manage and grow existing Group insurance relationships

Serve as a key liaison between the brokerage and Group clients

Handle Group quoting opportunities and coordinate submissions with insurers

Develop relationships with Group contacts and identify opportunities for additional business

Support inbound opportunities generated through existing relationships and referrals

Attend approximately 2–3 industry conferences and events per year to network, generate leads, and strengthen relationships

Identify opportunities for client retention, account rounding, cross-selling, and portfolio growth

Develop new Group relationships through referrals, networking,



and professional connections

Private Client / High-Net-Worth

Act as an internal resource for Private Client and high-net-worth Personal Lines opportunities

Coordinate submissions with specialty markets and insurers

Work with markets such as Chubb, Ovation, and Prestige

Review opportunities submitted by producers and determine the appropriate market

Obtain and communicate quotes and coverage options back to producers

Build and maintain relationships with high-net-worth markets and insurance partners

Support sophisticated insurance solutions for high-value homes, automobiles, recreational vehicles, collections, jewellery, art, watercraft, excess liability, and other complex personal assets

This is not a traditional cold-calling sales role. The focus is primarily on developing business through existing relationships, referrals, Group partnerships, and networking.

What We’re Looking For

5–7+ years of Personal Lines insurance experience

Active RIBO license

Previous team leadership or management experience

Strong understanding of Personal Lines products, underwriting practices, and insurance markets

Experience with Group quoting/business development is an asset

Exposure to Private Client / High-Net-Worth insurance is preferred

Experience working with multiple insurance carriers and markets

Strong relationship management and business development abilities

Excellent communication, presentation, negotiation, and interpersonal skills

Strong analytical, organizational, and problem-solving abilities

Comfortable managing multiple priorities in a fast-paced environment





Strong insurance management system and computer skills

Proactive, outgoing, entrepreneurial, and team-oriented personality

Compensation & Benefits

$80,000–$100,000 base salary, depending on experience

Additional earning potential through eligible personal new business

Employer-paid health and dental benefits

Long-term disability coverage

Hybrid work arrangement – 4 days in office / 1 day remote

Collaborative and supportive team environment

Opportunities for long-term growth opportunities

Why Consider This Opportunity?

Step into a leadership role without being removed from the insurance business

Lead an experienced Personal Lines team while maintaining strong industry exposure

Combine management, Group business development, and Private Client responsibilities

Work with respected high-net-worth insurance markets

Build and strengthen relationships with Group clients and referral partners

Opportunity to attend industry conferences and networking events

Strong autonomy and ability to make an impact within an established team

Growing brokerage with opportunities for future advancement The Ideal Candidate This role would be particularly well suited to a Senior Personal Lines Broker, Personal Lines Team Lead, Personal Lines Manager, or experienced Account Manager who is ready to take on greater leadership responsibility while remaining involved in client relationships, business development, and specialty insurance.

The client is ultimately looking for someone with the right leadership ability, personality, work ethic, and industry foundation. Specific systems such as Power Broker can be learned by the right candidate.

We believe diverse teams build stronger companies, and we welcome applicants from all backgrounds, experiences, and perspectives.

Accommodation is available upon request throughout all stages of the recruitment process.

📌 Team Lead – Personal Lines (Winnipeg)
🏢 David Aplin Recruiting
📍 Winnipeg