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 (commercial auto experience is highly preferred)
- 1 year of experience in high transactional environments is preferred.
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.
- 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 InformationUnless 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 InformationPie 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.
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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
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Skills Required
- 1 year of inside sales experience
- Commercial auto experience
- 1 year of experience in high-transactional environments
- Must live and work in the United States, excluding territories
- Access to reliable, high-speed internet
What the Team is Saying
Pie Insurance Compensation & Benefits Highlights
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Healthcare Strength — Healthcare coverage is employer-paid for full-time employees from day one across medical, dental, and vision, with HSA/FSA options and company HSA contributions. This breadth meaningfully reduces out-of-pocket exposure and anchors the package as comprehensive.
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Parental & Family Support — Parental leave is fully paid for the first three months, paired with a generous return-to-work plan and separate caregiver leave. These provisions indicate strong support for growing families and caregiving needs.
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Leave & Time Off Breadth — Time off is described as generous and flexible, with additional sick time noted in some summaries. Such breadth gives employees latitude to manage rest and personal obligations.
Pie Insurance Insights
What We Do
Pie is transforming small business insurance. Our team of seasoned technology and insurance experts are on a mission to empower small businesses to thrive by making insurance affordable and as easy as pie.
Why Work With Us
Our team of seasoned technology and insurance experts is on a mission to make insurance less expensive, simpler, and more transparent for small business owners. In the process, we’re creating a workplace where people thrive and ideas become actions.
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Pie Insurance Teams
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Remote Workspace
Employees work remotely.
As a fully remote company, Pie supports our Pie-oneers in working in a U.S. location that’s best for them.
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