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 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 Team

• 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.

Partnership

• 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.

The Right Stuff

• 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%.

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

$115,000—$140,000 USD

Compensation & Benefits 

• 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 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

#LI-REMOTE

#BI-REMOTE