Team Lead, Collections

Pie Insurance

7h•$70,000 - $90,000•Remote

About The Position

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.

Requirements

A high school diploma or GED is required.
3+ years of team leadership or people management experience, including managing performance, required.
2+ years of vendor management experience required.
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.
Working 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.

Nice To Haves

An Associate's or Bachelor's degree is preferred.
1+ year of Premium Audit experience preferred.
Experience in commercial insurance preferred.
1+ year of experience managing BPO or offshore teams preferred.
LEAN Certification preferred

Responsibilities

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.
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, 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.