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.

As the Team Lead, Collections, you own the end-to-end process for past-due receivable collections — installment payments, short-rated policies, claim deductibles, audit surcharge fees, and additional premium from mid-term endorsements or end-of-policy audits. You are accountable for Pie's overall bad debt recovery rate and for driving collection, litigation, and settlement outcomes against internal targets. You lead a team of individual contributors alongside BPO and offshore partners, set the strategy for how every dollar of exposure gets pursued, and continuously find upstream improvements that reduce Pie's exposure before receivables ever reach collections.

You set and enforce service-level agreements across the collection lifecycle and are accountable for the performance of your team, your vendors, and your BPO and offshore partners against defined KPIs. You partner with Accounting to establish and maintain allowance processes and month-end financial close recommendations and documentation. You are the decision-maker for collection referrals and vendor preference, and you make sure collection progress is visible and tracked across Pie's systems and vendor systems. This is a role for someone who wants to own a function, build it, and be measured on results.

How You’ll Do It

Own recovery outcomes across every policy in collections

Own Pie's bad debt recovery rate. You're accountable for driving collection success against internal collection-rate and recovery targets, and for the outcomes of litigation and settlement.Set and enforce service-level agreements across the full collection lifecycle — from receivable handoff and outreach cadence through referral timing and final closeout — and hold your team, vendors, and BPO and offshore partners accountable to those SLAs and KPIs.Own and continuously improve the collection assignment process and vendor preference lists, including placement for unpaid installment invoices, surcharge fees, and final invoices following audit close.Prioritize collection effort on a risk basis, focusing attention on the large and jumbo balances that drive the majority of exposure.Make sure every call, letter, and text complies with the FDCPA, Regulation F, the TCPA, and applicable state debt-collection laws. Partner with Compliance and Legal on consent, opt-out, and disclosure requirements.Serve as the top-level point of contact for collection issues, complaints, and escalations, acting as subject matter expert and business stakeholder advocate within Pie.Partner with Product and Engineering to build the systems and automations that streamline collections — automated ordering, tracking data, KPI reporting, and automated action triggers and process steps.Track and drive continuous improvement for bad debt allowance processes, in partnership with Accounting.Coordinate dispute resolution cross-functionally and identify upstream process improvements that reduce bad debt exposure.Ensure timely closeout for all receivables at the end of collections or litigation.Partner cross-functionally to ensure trackability, visibility, and assignment inclusion for policy and collection-handling data — the source that powers Collections KPI tracking and management.Monitor collection progress and make or propose escalation approvals based on defined debt-amount thresholds.


Manage collection vendors and litigation

Partner with Legal to drive litigation and settlement strategy and outcomes, and establish fast-track referral criteria for high-risk accounts — explicit refusal to pay, payment-plan default, or flight risk — so accounts are pursued before they age out of viability.Manage litigation decisions, billing, documentation, and judgment readiness.Create and maintain vendor scorecards covering recovery rates, timeliness, and other key data points.Partner with vendors to design and implement quality improvements based on scorecard findings.Review and update vendor guidelines regularly, and communicate any changes, additions, or deletions to vendor partners in a timely manner.Manage vendor billing.Serve as the primary point of contact for vendors on escalations and approval requests.Research, propose, and vet potential new vendor partners.


Lead and grow the collections team

Lead, develop, and manage the performance of the collections team, including BPO and offshore resources — setting clear benchmarks, coaching to them, and actively managing underperformance through improvement plans up to and including off-boarding.Develop and maintain SOPs for collections processes to ensure timely handling, dispute management, and proper receivable closeouts.Establish benchmarks and KPIs for the team and individual contributors, and manage business performance and productivity.Drive process improvement and optimization of existing processes through Agile methodology.Manage onboarding, ongoing training and development, and offboarding for team members. Coordinate training strategy and identify growth areas in partnership with Enablement and Learning and Organizational Development.Serve as an escalation point for complex customer inquiries, questions, and disputes, and skillfully handle follow-up.


The Right Stuff

A high school diploma or GED is required. An Associate's or Bachelor's degree is preferred.3+ years of team leadership or people management experience, including managing performance, required.1+ year of Premium Audit experience preferred.Experience in commercial insurance preferred.2+ years of vendor management experience required.1+ year of experience managing BPO or offshore teams preferred.1+ year of experience with data analysis and an understanding of workers' comp operational practices required. A strong understanding of Pie's products and systems is required.LEAN Certification preferredWorking knowledge of debt-collection regulations — the FDCPA, Regulation F, and the TCPA — and applicable state laws required.Communicate clearly and convincingly in writing and out loud, present your own views, and make requests directly and openly. You close the loop, and you give and receive feedback with empathy. You bring professional maturity, customer empathy, and an owner's attitude. You can build bad debt allowance formulations complete with financial close documentation and back-testable, documented assumptions.Analyze and solve simple to complex problems independently and use data to make informed decisions. You design win-win solutions with creativity and good judgment, challenge the status quo, and apply agile thinking — testing ideas, iterating on findings, and refining before you launch the full solution.Learn from mistakes, aim to be better tomorrow than today, and raise the performance bar. You seek to understand, stay open to new information and change, and question assumptions while applying new context.Demonstrate interpersonal awareness — considering the needs of others, building collaborative relationships, and respecting individual and cultural differences. You gain cooperation by delivering results and building buy-in.Comfortable with G-Suite tools, Salesforce, collaboration tools (Slack preferred), and basic office machines.Take responsibility for your own tasks, deliverables, and timelines with strong self-direction.Intermediate data reporting and analytic skills — enough to pull vendor scorecard data, analyze it, and bring recommendations to vendor partners and the Premium Audit team.Intermediate organizational skills to track progress against vendor expectations and pivot between platforms frequently.


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

$70,000—$90,000 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

