Regional Sales Manager II

Company Overview

Recognized as a Milwaukee Journal Sentinel Top Workplace for 14 consecutive years, including three years of being honored as number one! Join us at West Bend, where we believe that our associates are our greatest asset. We hire talented individuals who are conscientious, dedicated, customer focused, and able to build lasting relationships. We create and maintain an environment where you feel a sense of belonging and appreciation. Your diversity of thought, experience, and knowledge are valued. We’re committed to fostering a welcoming culture, offering you opportunities for meaningful work and professional growth. More than a workplace, we celebrate our successes and take pride in serving our communities.

Job Summary

Develop and execute strategic plans to maximize business opportunities through independent insurance agencies within the assigned territory. Support, measure, and monitor internal and external sales efforts including short-term promotions, social media opportunities, rollovers, co-op, etc.

Work Location

This is a fully remote/work from home role where you will spend 50% of your time in the field, servicing the Chicago territory. On occasion you may be asked to travel to an office location for in-person engagement activities such as team meetings, training and corporate events.

 

This is a fully remote/work from home role. On occasion you may be asked to travel to an office location for in-person engagement activities such as team meetings, training and corporate events.

 

 

Responsibilities & Qualifications

Shape the future of agency partnerships. Drive meaningful growth.

At West Bend, we believe sustainable success is built on strong, trusted agency relationships – and the people who know how to cultivate them.

We’re looking for a Senior Regional Sales Manager who brings both strategic vision and a relationship-first mindset to the table. In this role, you won’t just manage a territory – you’ll shape it. You’ll partner closely with independent agencies, underwriting, and sales leadership to identify opportunities, strengthen performance, and drive profitable growth.

If you’re energized by being in the field, building meaningful partnerships, and turning market insight into action, this is an opportunity to make a real impact.

 

Why West Bend

At West Bend, our associates truly are our greatest asset. We’re intentional about creating a culture where people feel valued, supported, and connected to the work they do. Here, your voice matters, your contributions are recognized, and your growth is part of the plan.

 

What you’ll do

As a Senior Regional Sales Manager, you’ll lead the strategy and execution behind territory growth – working through independent agency partnerships to drive results that align with our long-term business goals.

In this role, you will:

• Design and implement targeted territory strategies that unlock growth opportunities across your agency network
• Strengthen and expand agency partnerships, while identifying and onboarding new agencies
• Partner with sales leadership to consistently meet or exceed production goals
• Serve as a trusted advisor to agents, providing guidance, support, and responsive service
• Collaborate closely with underwriting to align market insights with decision-making and identify areas of opportunity or risk
• Analyze territory and agency performance, using data to inform strategy and drive continuous improvement
• Develop and lead trainings, sales programs, and engagement initiatives (virtual and in-person) that help agencies grow profitably

 

What you bring

You bring a balance of business acumen, industry expertise, and relationship-building strength. You’re comfortable operating independently, influencing across teams, and navigating both strategy and execution.

We’re looking for:

• 5+ years of property & casualty insurance experience
• Strong knowledge of products, underwriting, and regulatory landscape
• A track record of achieving or exceeding sales goals
• Excellent communication, negotiation, and analytical skills
• Experience collaborating across cross-functional teams
• Proficiency in Microsoft tools and data/CRM platforms
• Bachelor’s degree in a related field (preferred)
• CIC or CPCU designation
• Valid agent’s and driver’s licenses

 

Who thrives in this role

This role is well-suited for someone who enjoys being both strategic and hands-on – someone who builds trust quickly, spots opportunity where others don’t, and takes ownership of outcomes. If you’re