Regional Sales Manager II

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.

Responsibilities

• Shape the future of agency partnerships. Drive meaningful growth.
• Lead the strategy and execution behind territory growth – working through independent agency partnerships to drive results that align with our long-term business goals.
• 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

Qualifications

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

Benefits

• Medical & Prescription Insurance
• Health Savings Account
• Dental Insurance
• Vision Insurance
• Short and Long Term Disability
• Flexible Spending Accounts
• Life and Accidental Death & Disability
• Accident and Critical Illness Insurance
• Employee Assistance Program
• 401(k) Plan with Company Match
• Pet Insurance
• Paid Time Off
• Enhanced PTO may be available for experienced candidates
• Bonus eligible based on performance

Pay

The salary range for this position is $100,000-$120,000. The actual base pay offered to the successful candidate will be based on multiple factors, including but not limited to job-related knowledge/skills, experience, business needs, geographical location, and internal equity.

Schedule

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.

Benefits

• Medical & Prescription Insurance
• Health Savings Account
• Dental Insurance
• Vision Insurance
• Short and Long Term Disability
• Flexible Spending Accounts
• Life and Accidental Death & Disability
• Accident and Critical Illness Insurance
• Employee Assistance Program
• 401(k) Plan with Company Match
• Pet Insurance
• Paid Time Off
• Enhanced PTO may be available for experienced candidates
• Bonus eligible based on performance