Senior Manager, Operations

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 a Senior Manager, Operations, you will play a central role in building a scalable, high-performing operations organization. Reporting to the Director of Customer Service & Operations, you will own the performance of our vendor partnerships and customer service operational model — driving accountability, efficiency, and continuous improvement across the function.

This role is well-suited for an operator who sees a landscape of manual processes not as a limitation, but as a clear roadmap for impact. You will design and implement scalable systems and workflows — leveraging modern tools, including AI — while building the business cases that justify continued investment in operational excellence. If you are motivated by the challenge of building something that lasts and believe that finding a way forward is always possible, we want to hear from you.

How You’ll Do It

Vendor Relationships

• Lead all aspects of the operations vendor relationships — including weekly business reviews, quality calibration sessions, performance scorecards, and quarterly business reviews (QBRs) with senior vendor leadership.

• Serve as the incident owner for escalated vendor-originated service failures — including outages, quality breakdowns, and SLA misses — by triaging quickly, coordinating resolution across internal and external stakeholders, and ensuring a documented path to prevention.

• Maintain and evolve vendor performance scorecards; track SLAs, quality scores, AHT, and other KPIs continuously.

• Own vendor volume forecasting and headcount planning; ensure accuracy ahead of each planning cycle.

• Manage vendor onboarding and offboarding, including knowledge transfer and transition planning.

• Maintain vendor risk registers; surface compliance gaps proactively and drive remediation.

• Serve as the cross-functional connector when system issues or process changes affect vendor teams.

Operational Metrics

• Maintain deep familiarity with the full CS metric suite — SLA adherence across teams and contact types, AHT, quality pass rate, reopen rate, forecast accuracy, cost per contact, and net sentiment, etc.

• Identify negative trends early and engage the CS Director to co-create action plans. Don't wait to be asked.

• Deliver operational reporting to SLT on a regular cadence; bring context, next steps, and clear action plans — not just numbers.

• Take ownership of CS KPI reporting deliverables on a monthly basis.

• Build and refresh team and rep scorecards that ladder up to CS and company goals; recommend adjustments as trends shift.

Continuous Improvement and Automation

• Continuously evaluate existing workflows for streamlining opportunities; implement improvements and document them.

• Identify automation and self-service opportunities across CS operations; partner with the CS Director and VP to develop and prioritize the business case pipeline.

• Leverage available technology — including AI tools — to reduce manual effort, improve throughput, and elevate the team's capacity for higher-value work.

• Collaborate cross-functionally with Product and Engineering to advance automation and self-service