Senior Manager, Operations

Pie Insurance

1d•$115,000 - $140,000•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 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.

Requirements

Bachelor's degree.
5+ years of experience in customer service, CS operations, or insurance operations — with demonstrated experience managing external/BPO vendors.
Proven track record holding vendors accountable to performance standards, running QBRs, and driving measurable improvement.
Strong command of CS and insurance operational metrics — SLA adherence, AHT, quality scores, net sentiment, cost per contact, forecast accuracy — and the ability to translate data into clear narratives and action plans.
Experience identifying operational trends early and mobilizing stakeholders around solutions.
Demonstrated ability to build and present business cases to leadership.
Proficiency with data analysis, spreadsheets, and basic modeling.
Experience in the P&C insurance industry — specifically workers' comp, policy lifecycle, and multi-line support.
Ability to travel up to 20%.

Responsibilities

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.
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.
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 capabilities for agents, insureds, and internal teams.
Lead or contribute to process redesign as new products, tools, or priorities shift how the team operates.
Recommend and develop best practices within your function; drive consistency across inbound support teams.
Lead and develop direct reports; provide clear role expectations, performance goals, and ongoing feedback.
Facilitate monthly leadership training with TLs and managers alongside the training team.
Build quarterly team plans that tie to company direction and help your team translate vision into action.
Align with WFM weekly on volume, staffing, and forecasting.
Partner with Training and Quality to ensure processes and content are current.
Represent CS in IT meetings; manage tickets and track resolution.
Serve as the primary escalation point for vendor-originated issues — triage, coordinate resolution, and close the loop with affected stakeholders.
Synthesize and share DM feedback weekly to drive continuous quality improvement with the vendor.