Territory Development Manager- Chicago, IL

Gainsco; Chicago (IL); Remote; USD 85,000 - 115,000; Full time

Benefits offered by this job

Medical and dental insurance

Vision insurance

Life insurance

Disability insurance

401K with company match

PTO + holidays

Company vehicle

Laptop provided

Parental Leave

Job summary

GAINSCO is seeking a Territory Development Manager to drive growth within a defined geographic area, partnering with Independent Agencies to increase policy production. You will use consultative sales techniques in a B2B setting, employing email, calls, virtual meetings, and in-person visits to execute a comprehensive contact strategy.

The role requires at least 2 years of sales experience, with a preference for insurance-specific background.

Qualifications

• Bachelor’s degree required or preferred.
• 2+ years of successful sales experience.
• Experience with insurance sales is a plus.
• Ability to influence agents to increase territory production.
• Salesforce experience is a plus.

Responsibilities

• Achieve defined daily, weekly, and monthly production goals.
• Make contacts through multiple channels (email, calls, virtual meetings, in-person visits).
• Review and coach on agency performance for continuous improvement.
• Manage agency contests and quarterly bonus programs.
• Set and communicate goals for each agent and develop strategies to reach them.
• Conduct commission conversations with agency owners to optimize commission levels.
• Review commission statements and agency footprint targets.
• Identify markets and execute sales strategies based on market data.
• Review reports and adjust actions to meet goals.
• Appoint agents in desired areas and manage travel/field activities.
• Ensure compliance with sales, contact requirements, and documentation in Salesforce.

Skills

Bachelor’s degree

Sales experience

Agents coaching

Negotiation

Presentation

Analytical skills

Time management

Education

Bachelor’s degree preferred

Tools

Salesforce

Job description

Posting Details

• Posted on November 12, 2026

Locations

Showing 1 location

• Chicago, IL, USA
• Remote
• Field Operations
• Full-Time
• Requisition #: TERRI003325

Description

About GAINSCO

Founded in 1978, GAINSCO offers property and casualty insurance with an emphasis on non-standard personal auto policies. It serves drivers nationwide by providing minimum-limits personal auto coverage, making insurance more accessible to a broader market. In 2020, GAINSCO, Inc. and its subsidiaries were acquired, making a significant milestone that strengthened GAINSCO’s ability to grow and expand its reach in the personal auto industry market while continuing to build on its decades of specialized expertise.

Join a team that is dedicated to supporting your professional growth and long-term success.

Who We Are

At GAINSCO, we are a team driven by passion, creativity, and a commitment to excellence. We celebrate achievements, encourage innovative thinking, and recognize the unique strengths each person brings. Our people truly set us apart.

We are seeking an energetic and results-driven Territory Development Manager to join our dynamic team. They will be responsible for driving growth in a defined geographic area, partnering with the Independent Agency Market to increase insurance policy production. The successful candidate will leverage proven consultative sales techniques in a Business-to-Business environment, employing a mix of email, phone calls, virtual meetings, and in-person visits to implement a comprehensive contact strategy plan.

What does a Territory Development Manager do at GAINSCO?

• Achieve defined daily, weekly, and monthly production goals.
• Make a targeted number of contacts each day through various channels, including email, phone calls, virtual meetings, and in-person visits.
• Review and provide coaching on agency performance, ensuring continuous improvement and responsiveness to feedback.
• Effectively manage agency contests and quarterly bonus programs.
• Set and communicate goals for each agent, developing strategies and tactics to support goal achievement.
• Conduct effective commission conversations with agency owners to maintain or earn higher commission levels.
• Review commission statements and manage agency footprint targets.
• Based on market-specific information, identify and execute sales strategies.
• Review available reports and adjust actions to achieve goals.
• Identify and appoint agents in desired areas.
• Manage low-hanging fruit, incline/decline reports, and zero producers to change behavior.
• Ensure compliance with best practices, sales, contact requirements and documentation of activities within Sales Force.

What is required?

Education

• Bachelor’s degree preferred.

Experience

• 2 or more years of successful sales experience.
• Experience with insurance sales is a plus.
• Ability to positively influence agents to increase territory production.
• Salesforce experience is a plus

Other skills and abilities

• Ability to learn and promote products and services.
• Rapport-building skills with agents.
• Excellent verbal and written communication skills.
• Effective sales, negotiation, and presentation skills.
• Analytical skills to interpret product data and identify market trends.
• Disciplined follow-up and organizational skills.
• Ability to manage multiple projects simultaneously.
• Ability to effectively manage your own time and coordinate various tasks simultaneously.
• Works independently, possesses a high energy level, and pays attention to detail.

What else do you need to know?

• Field-based role, responsible for managing Chicago, IL.
• Overnight travel around 25% (6-7 overnights per month) depending on proximity to agency population
• Must have valid Driver License
• Competitive salary based on experience, with bonus opportunity.
• Company provided equipment, including laptop, cell phone, printer/scanner/fax.
• Company vehicle included for Field role.
• Excellent benefits package: medical & dental, vision insurance, life insurance, short term and long-term disability insurance
• Parental Leave Policy
• 401K + Company Match
• PTO + Paid Company determined Holidays.

Applicants are required to be eligible to lawfully work in the U.S. immediately; employer will not sponsor applicants for U.S. work authorization (e.g. H-1B visa) for this opportunity

All offers are contingent upon a successful background investigation (including employment, education, criminal and DMV verification- when applicable) and a pre-employment drug test with results satisfactory to GAINSCO.

GAINSCO is an Equal Employment Opportunity Employer

Equal Opportunity Employer This employer is required to notify all applicants of their rights pursuant to federal employment laws. For further information, please review the Know Your Rights notice from the Department of Labor.