Insurance Sales Representative

The Grumley Agency; Wauwatosa (WI); On-site; USD 70,000 - 95,000; Full time

Benefits offered by this job

Base salary + commission

PTO

Mon-Fri schedule

Hands on training

Retirement plan

Evenings off

Job summary

The Grumley Agency in Wauwatosa, WI is seeking an experienced Insurance Sales Representative who thrives in a positive, supportive environment. You’ll help local families and businesses choose coverage that protects their futures, while growing the agency through service conversations and proactive outreach.

You’ll work directly with the agency owner, receive ongoing coaching, and enjoy a schedule that supports work-life balance with a Monday–Friday routine and opportunities for advancement

Qualifications

• Active Property and Casualty Insurance License in Wisconsin.
• Proven success in building and maintaining client relationships.
• Clear and articulate communication, both on the phone and in person.
• Proficiency with standard office software and agency management systems.
• High school diploma or equivalent.
• Experience in an independent insurance agency is a plus.

Responsibilities

• Connect with local families and businesses to assess insurance needs.
• Develop customized coverage plans for peace of mind and protection.
• Manage inquiries and proactively reach out to potential clients in the Wauwatosa area.
• Explain policy details in plain language so clients can decide confidently.
• Regularly review accounts to ensure coverage keeps pace with changing life circumstances.
• Foster a welcoming office environment where visitors feel valued and heard.

Skills

Client relationships

Communication skills

Sales experience

Business development

Education

High school diploma

Tools

Agency management systems

Office software

Job description

Job Description

Experienced Insurance Sales Representative — Support, Opportunity, and a Team You Can Count On

You know insurance. You know how to earn trust, recognize opportunities, and help clients make important decisions. You also know how much the right agency environment matters.

At The Grumley Agency in Wauwatosa, we’re looking for an experienced Insurance Sales Representative who wants to grow in a positive, inclusive workplace where people share ideas, work through challenges together, and treat one another with respect.

Support here is personal and practical. You’ll have direct access to the agency owner, help navigating difficult cases, and ongoing coaching to strengthen your skills. Your experience will be respected, your questions welcomed, and your ideas heard.

You’ll have opportunities to develop new business and work with existing clients through service conversations, coverage reviews, and changing insurance needs. We recognize the value of staying connected to clients—and the opportunities those relationships create to provide better protection and grow your business.

We value initiative, thoughtful follow-through, and pride in your work. We also believe your workplace should offer encouragement, collaboration, and recognition for what you contribute.

If you enjoy insurance and want an agency where you can contribute, keep growing, and feel supported along the way, we’d like to meet you.

Let’s talk about what you want from your next agency.

Benefits

• Annual Base Salary + Commission + Bonus Opportunities
• Paid Time Off (PTO)
• Mon-Fri Schedule
• Hands on Training
• Retirement Plan
• Evenings Off

Responsibilities

• Connecting with local families and businesses to understand their unique insurance needs and concerns.
• Developing customized coverage plans that provide real peace of mind and protection.
• Managing a steady flow of inquiries and proactively reaching out to potential clients in the Wauwatosa area.
• Explaining complex policy details in plain, easy-to-understand language so our clients feel confident in their decisions.
• Regularly reviewing accounts to ensure that our clients' coverage keeps pace with their changing lives.
• Cultivating a welcoming office environment where every visitor feels valued and heard.

Requirements

• Active Property and Casualty Insurance License in Wisconsin.
• Strong track record of success in building and maintaining client relationships.
• Clear and articulate communication style, both on the phone and in person.
• Proficiency in standard office software and agency management systems.
• High school diploma or equivalent.
• Previous experience working within an independent insurance agency is helpful but not strictly required.

Company Description

Allstate's best-in-class products and services help provide innovative protection and retirement solutions to millions of households nationwide. Our evolving business strategies and solutions continue to reinvent the industry standards, helping our customers better protect what they have today and prepare for a brighter tomorrow.