Sales District Leader – Field

Jobtailor; Milwaukee (WI); On-site; USD 90,000 - 130,000; Full time

Job summary

Jobtailor in Wisconsin seeks a field-based coach to support independent contractor agency owners. You will drive profit growth, advise on district plans, and recruit owners to captive roles, spending most time with clients in the field.

The role requires licensing in Property & Casualty, Life, and Health, plus strong project management, budgeting, and financial analysis. Travel up to 50% is expected; NDA and background check are required.

Qualifications

• Experience delivering customer-driven solutions and strong service orientation.
• Knowledge of business systems and using them to improve efficiency.
• Prior management or project-team leadership experience.
• Strong understanding of project management methodologies and tools.
• Experience with financial analysis, budgeting, and reporting.
• Licensed Insurance: Property and Casualty, Life, and Health.
• Valid driver's license and clean driving record.
• Residence in Milwaukee, WI district; up to 50% travel.
• Background check and NDA required.
• Sponsorship not offered unless specified.

Responsibilities

• Support agency business owners who operate as independent contractors.
• Coach and advise agency business owners on profit growth plans and sales execution.
• Recruit agency owners to become captive agents.
• Influence performance results for independent contractors.
• Connect corporate strategy with agency practices and results.
• Coach on sales results and state sales plan execution.
• Assist with district profit understanding while preserving owners' business control.
• Manage district programs for the district.
• Help agency owners target and prioritize sales activities and opportunities.
• Provide business expertise to support successful agency operations.
• Source and select agency business owners for openings.
• Build relationships with agency owners and staff.
• Work primarily in the field, spending ~70% of time directly with customers, agents, and staff.
• Report to the Wisconsin State Director.
• Attend occasional office-based meetings, trainings, and culture events.

Skills

Project Management

Financial Analysis

Insurance Licensing

Customer-Driven Solutions

Operational Planning

Tools

Business Systems

Job description

• Support agency business owners who operate as independent contractors
• Coach and advise agency business owners on district profit and growth plans
• Recruit agency owners to become captive agents
• Influence performance results for independent contractors
• Connect corporate strategy with agency practices and results
• Coach and advise agency owners on sales results and state sales plan execution
• Assist with district profit understanding while preserving owners' business control
• Manage company programs for the district
• Help agency owners target and prioritize sales activities and opportunities
• Provide business expertise to support successful agency operations
• Source and select agency business owners for openings
• Build relationships with agency owners and staff
• Work primarily in the field, spending approximately 70% of time directly with customers, agents, and agency staff
• Report to the Wisconsin State Director
• Attend occasional office-based meetings, trainings, and culture events

Requirements

• Demonstrated experience providing customer-driven solutions, support and service
• Basic knowledge and understanding of business systems and leveraging them for efficiency
• Prior management experience or demonstrated experience leading project teams
• Solid knowledge of project management methodologies, practices, techniques and tools
• Solid knowledge and understanding of financial analysis and reporting
• Prior experience developing and executing operational business plans and marketing plans
• Solid knowledge and understanding of budget management concepts
• Required insurance licensing: Property and Casualty (personal lines authority does not qualify), Life, and Health
• Valid driver's license and acceptable driving record
• Must reside in the district, ideally Milwaukee, WI and surrounding
• Up to 50% travel
• Background check required
• Non-disclosure agreement required
• Sponsorship will not be considered unless specified in the posting

Core Competencies

Demonstrates expertise in coaching and advising agency business owners on profit growth, sales execution, and operational efficiency. Possesses strong project management skills and a solid understanding of financial analysis, budget management, and customer-driven solutions.

Highest-signal resume keywords

• Project Management
• Financial Analysis
• Insurance Licensing
• Customer-Driven Solutions
• Operational Business Plans

ATS Optimization Keywords

Hard Skills

• Project Management Methodologies
• Financial Reporting
• Budget Management
• Operational Planning
• Sales Strategy Execution

Soft Skills

• Coaching
• Relationship Building
• Advising
• Influencing Performance

Certifications & Qualifications

• Property and Casualty Insurance License
• Life Insurance License
• Health Insurance License

Industry Keywords

• Agency Operations
• Independent Contractors
• District Profit
• Sales Activities
• Recruitment

Tools & Technologies

• Business Systems