At Pie Insurance, our mission is simple: make small business insurance affordable and as easy as pie. We specialize in workers' compensation and commercial auto insurance for small businesses across the U.S. 

With our data-driven approach, small businesses can get a workers’ comp quote in just three minutes and save up to 30% on premiums.* 

At Pie, culture isn’t just a buzzword; it’s what drives us. We’re obsessed with giving our customers the best experience, always curious, and never afraid to tackle challenges head-on. We believe that diversity fuels innovation and we aim to foster an inclusive environment where everyone has an opportunity for impact and growth.

🏆 Pie has been named to: Forbes’ America’s Best Startup Employers 2025, Purpose Jobs’ Best Places To Work Remote in 2025, BuiltIn's Best Places to Work in Colorado (2025), Best Remote Midsize Places to Work (2025), among others. 

⚠️ Safety First ⚠️ 
Pie is committed to your security during the recruitment process. Verify the identity of recruiters before sharing personal or financial details. Protect yourself from job scams and report suspicious activity.

* Individual savings and quote time may vary. Discounts and savings not available for workers’ compensation policies in Wisconsin.


Pie Insurance

Pie's mission is to empower small businesses to thrive by making commercial insurance affordable and as easy as pie. We leverage technology to transform how small businesses buy and experience commercial insurance.

Like our small business customers, we are a diverse team of builders, dreamers, and entrepreneurs who are driven by core values and operating principles that guide every decision we make.

This role serves as the connector for customer success with responsibilities to onboard/offboard agencies, ensuring they are using the self-service tools for easier support, and coordinating our systems to match when our customers change. In addition this team will assist with backoffice tasks as needed that can include agency document requests and troubleshooting questions regarding agency commissions.

How You’ll Do It

Resolve customer emails requests (cases) with accuracy and timeliness:

Provide specific assistance related to agency commission questions and common issues, such as account updates and financial information.Manage final resolution for specific document requests that generate from other teams.

Assist customers with technical issues & pursue long-term internal solutions when possible:

Assist customers with technical issues, working with Engineering to represent and troubleshoot the immediate issue while also identifying broader trends and opportunities to leadership.

Ensure Technical Success For Agencies

Support new agency partner setup that can include CRM and portal configurations, as well as reverse engineering for offboarding steps.Assist with the set of tasks to change business relationships across agencies (consolidation or restructure).Manage headcount process ensuring data alignment, accurate job descriptions, and process continuity.

General Customer Support

Assist other teams with similar customer case and phone support as needed .

The Right Stuff

Educational Background

High school diploma or equivalent experience is required. 

Experience

1 year in a high-volume customer contact environment preferred.Emerging ability to apply analytical and critical thinking skills for roles when required.Ability to solve simple problems within the team with guidance and apply creativity and challenge the status quo.Emerging ability to consider the needs of others on the team while working with others on projects in a productive fashion to accomplish the team goals. Ability to develop and sustain collaborative working relationships and fully commit to a decision once it's made.G-Suite Tools, Salesforce, Collaboration tools (slack is preferred), basic office machinesBasic self-direction and responsibility for own tasks, deliverables and timelinesRegular attendance and punctuality are essential requirements for this role. Success in this position relies on the ability to adhere to a consistent work schedule and meet attendance expectations. Dependability in this area ensures team collaboration, supports operational effectiveness, and delivers exceptional service to our customers.

The use of AI in Application Review: To support a fair, efficient, and consistent hiring process, we use AI-powered tools to assist in the initial screening of applications. These tools help us identify qualifications and prior work experiences that align with the requirements of the role. We may also use AI assistant video tools during interviews to support note-taking and candidate evaluation. All AI-powered outputs are still subject to human oversight and decision-making at multiple stages of the process. By submitting your application, you acknowledge and consent to Pie utilizing these AI technologies to assist in our evaluation process.

Base Compensation Range

$21 - $25 USD

Compensation & Benefits

Competitive cash compensationComprehensive health plansGenerous PTOFuture focused 401k matchGenerous parental and caregiver leaveOur core values are more than just a poster on the wall; they’re tangibly reflected in our work 

Making every part of working with us "Easy as Pie" - including our offer process. When we find someone we'd like as a Pie-oneer (a member of our team), we move quickly to put together a fair offer based on your skills, experience, location, and compensation expectations.

Each year Pie reviews company performance and may grant discretionary bonuses to eligible team members.

Location Information 

Unless otherwise specified, this role is remote. Remote team members must live and work in the United States (territories excluded) and have access to reliable, high-speed internet.

Additional Information

Pie Insurance is an equal opportunity employer. We do not discriminate on the basis of race, color, religion, sex, sexual orientation, gender identity, marital status, age, disability, national or ethnic origin, military service status, citizenship, or other protected characteristic.

Pie Insurance participates in the E-Verify program. Please click here, here and here for more information.

Pie Insurance is committed to protecting your personal data. Please review our Privacy Policy.

Safety First: Pie Insurance is committed to your security during the recruitment process. We will never ask you for credit card information or ask you to purchase any equipment during our interview or onboarding process.

Pie Named to 2025 America's Best Startup Employers

Pie Insurance 2025 State of Workplace Safety Report

#BI-REMOTE



CS Specialist, Service Support Team United States

What the job involves