Inside Sales Representative

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.

As an Inside Sales Rep, you’ll serve our direct customer channel by working with small business owners and giving them the support they need. The sales team is flexible and adaptable — we navigate challenges and problem-solve quickly in service of our mission. Pie is a highly collaborative team that communicates constantly. You’ll work across teams and with stakeholders, so strong communication and coordination skills are essential. You’ll be in regular contact with customers by phone and email to sell and build relationships.

How You’ll Do It

Build relationships and sales with Direct customers

You will be calling inbound leads from our lead database, setting appointments, and maintaining our lead and prospect systems.

You will take inbound calls (and some outbound) from warm leads, prospects who want to talk to us (no cold calling).

Further qualify prospects through a series of questions to understand their business needs.

Policy, sales and closing

Partner with the underwriting team to ensure policy can be written.

Present policy and close deal.

The Right Stuff

1 year of Inside sales experience is required.

1 year of experience in high transactional environments is preferred.

An active property & casualty license.

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 $26.50 — $32 USD

Compensation & Benefits

Competitive cash compensation

Comprehensive health plans

Generous PTO

Future focused 401k match

Generous parental and caregiver leave

Our 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

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