Pie Engineering Jobs

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. The Vendor Management & Sourcing Specialist is the operational backbone of Pie’s Claims Vendor Management and Procurement function, owning end-to-end work across both sourcing/procurement execution and vendor relationship and performance management. In this senior individual contributor role, you will lead the full sourcing lifecycle by translating business needs into RFx processes, conducting market research, spend analysis, benchmarking, and competitive bid evaluations, and delivering data-backed vendor selection recommendations. You will also manage the Claims vendor portfolio by coordinating stewardship meetings, monitoring scorecard performance, handling day-to-day vendor communications, and driving issues through the escalation log from identification to resolution. This role operates within a lean team and requires independent judgment, strong follow-through, and proactive delivery of leadership-ready outputs with minimal oversight. How You’ll Do It Sourcing & Procurement Execution Lead end-to-end sourcing activities: needs intake, market research, RFx development and management, bid evaluation, and vendor selection recommendation packages. Conduct spend analysis and competitive benchmarking across the active vendor portfolio to identify cost optimization, consolidation, and renegotiation opportunities. Prepare comparison matrices, commercial term analyses, and leadership-ready recommendation summaries that enable vendor decisions based on data, not assumptions. Support contract negotiations by conducting pre-negotiation research: identi

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 Staff Attorney, you’ll report directly to the VP of Legal & Compliance and serve as a key legal resource across the organization. Your primary focus will be commercial contract review and negotiation on behalf of all business partners at Pie, managed through our contract lifecycle management platform, LinkSquares. You’ll own the full contracting workflow — from intake through execution — while building strong relationships with internal stakeholders who rely on your guidance to move work forward. You’ll also lead Pie’s legal collections function, supporting accounts receivable recovery through demand letters, coordination with outside counsel, and resolution of disputed accounts. This role will likely expand to include corporate compliance and governance support, as well as other legal matters across the organization. How You’ll Do It Contract Review and Negotiation Draft, review, and negotiate commercial agreements, vendor contracts, NDAs, and service agreements on behalf of all business partners at Pie. Serve as the primary point of contact for contract intake and workflow management in LinkSquares, our contract lifecycle management platform. Identify legal risks and propose practical revisions that protect Pie’s interests without creating unnecessary friction for the business. Partner with internal stakeholders across Technology, Finance, Operations, and other teams to understand their contracting needs and provide responsive, business-oriented guidance. Manage the executed contract repository, including tracking key dates, renewal windows, a

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 an Inside Sales Rep, you’ll serve our direct customer channel by working with small business owners and giving them the support they need. The sales team is flexible and adaptable — we navigate challenges and problem-solve quickly in service of our mission. Pie is a highly collaborative team that communicates constantly. You’ll work across teams and with stakeholders, so strong communication and coordination skills are essential. You’ll be in regular contact with customers by phone and email to sell and build relationships. How You’ll Do It Build relationships and sales with Direct customers You will be calling inbound leads from our lead database, setting appointments, and maintaining our lead and prospect systems. You will take inbound calls (and some outbound) from warm leads, prospects who want to talk to us (no cold calling). Further qualify prospects through a series of questions to understand their business needs. Policy, sales and closing Partner with the underwriting team to ensure policy can be written. Present policy and close deal. The Right Stuff 1 year of Inside sales experience is required. 1 year of experience in high transactional environments is preferred. An active property & casualty license. 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 v

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

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. The Medical Only Claims Adjuster will play a vital role in delivering quality claim file management and an industry-leading customer claims experience. This will be completed by adhering to Pie’s Claims Best Practices and complying with regulatory and statutory requirements. This role will work with internal and external partners to deliver best in class performance, identify and pursue claim mitigation opportunities and deliver favorable claim outcomes for Pie’s customers. How You’ll Do It Claims Technical Management: Independently handle all aspects of the workers’ compensation medical only claims from set-up to closure. Conduct timely 2-point contact investigation, with focus on continued medical management, potential for lost time benefits, and claim closure as facts of the case change. Mitigate claim exposure while achieving the best outcome. Determine timely and accurate compensability decisions within statutory requirements. Set and adjust timely/accurate reserves within authority limits to ensure reserving activities are consistent with the case facts and company best practices. Timely administration of statutory medical benefits throughout the life of the claim. Use Utilization Review where appropriate and pay medical bills within the allotted timeframes Comply with all applicable statutory guidelines, rules, and regulations. Proactively identify and timely escalate claims that meet indemnity claim conversion criteria Consistent and timely resolution of medical treatment to resolve and close claims Maintain a split inve

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. The Payroll Partner Service Advocate is a key role for Pie's Payroll Partner team. This is a mid-level customer service team member who focuses on routine to advanced customer issues and resolves concerns and requests from payroll partners and insureds. How You’ll Do It Provide responsive, timely, and relevant service to payroll partners: Handles email, and platform-based communication with payroll partners and cross-functional stakeholders to provide excellent customer service, Maintains SLA’s set by Payroll Partner Ops team in a consistent and efficient manner. Works as a team member to handle: Policy Issuance General questions Follow-Up Communication Respond within 24 hours or less to requests from payroll partners Cancellation requests from insureds and partners Renewal policy management Urgent payroll partner customer and partner escalations. Complex payroll partner customer and partner questions. Model the behaviors and strategies necessary to successfully interact with and resolve routine to advanced issues for payroll partners in all channels: Applies advanced level of Workers Comp training and knowledge to policy, billing and agency questions, concerns, and production. Build relationships with partners and internal teams to provide consistent, excellent communication with customers. Seek resolutions to issues while also anticipating ways in which to prevent future issues. Voices the payroll partner’s needs and advocates for the customer and their perspective. Lead ongoing training and on-boarding for personal and

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. At Pie, our “employees” are team members, and we call ourselves Pie-oneers. The Principal People Partner ensures the successful contribution of our Pie-oneers by driving people and organizational strategies that enable and empower our leaders to lead their teams to achieve their highest-impact goals and drive success across the business. As Pie’s People team evolves, we are seeking a highly strategic yet execution-focused Principal People Partners to serve as a trusted advisor to senior leaders, driving people and organizational strategies that enable our leaders and teams to achieve their highest-impact goals and drive business success. These highly collaborative roles partner with executive leadership to design and implement talent strategies, foster high-performing teams, and build a culture of performance, agility and integrative thinking. The Principal People Partner role reports directly to the Chief People Officer and works cross-functionally across the PTE team and senior managers (primarily Director+), including the CEO and Pie’s Senior Leadership Team (SLT). As a senior level individual contributor, the Principal People Partner brings considerable leadership influence and is responsible for aligning people strategy with business objectives, leading change management, and providing expert consultation on all aspects of the team member lifecycle. How You’ll Do It Strategic Business Partnership Lead senior management in translating business strategy into a talent strategy that embeds and reinforces our culture and d

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. The Complex Claims Adjuster will play a critical role in delivering quality claim file management and an industry-leading customer claims experience, by providing hands-on adjudication of catastrophic and large loss claims. This will be completed by adhering to Pie’s Claims Best Practices, complying with regulatory and statutory requirements, and applying advanced knowledge and experience with complex negotiation strategies, structured settlements, Medicare Set-Aside requirements, and overall risk evaluation and mitigation. This role will work with internal and external partners to deliver best in class performance, identify and pursue claim mitigation opportunities and deliver favorable claim outcomes for Pie’s customers. Additionally, the Complex Claims Adjuster will collaborate with the Complex Claims Practices Consultant and Claims leadership to continually seek out ways in which to improve claims processes and protocols. How You’ll Do It Claims Technical Management: Independently handle all aspects of catastrophic and large loss workers’ compensation claims from set-up to closure. Conduct timely 3-point contact investigation, with focus on continued investigation as facts of the case change. Determine timely and accurate compensability decisions within statutory requirements. Set and adjust timely/accurate reserves within authority limits to ensure reserving activities are consistent with the case facts and company best practices. Ability to present claims to senior management, internal and external

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 agr

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. The Senior Claims Adjuster will play a critical role in delivering quality claim file management and an industry-leading customer claims experience., This will be completed by adhering to Pie’s Claims Best Practices and complying with regulatory and statutory requirements. This role will work with internal and external partners to deliver best in class performance, identify and pursue claim mitigation opportunities and deliver favorable claim outcomes for Pie’s customers.. How You’ll Do It Claims Technical Management: Independently handle all aspects of the workers’ compensation claims from set-up to closure. Evaluate and handle high dollar, high exposure, complex claims. Conduct timely 3-point contact investigation, with focus on continued investigation as facts of the case change. Mitigate the complex exposure while achieving the best outcome. Determine timely and accurate compensability decisions within statutory requirements. Set and adjust timely/accurate reserves within authority limits to ensure reserving activities are consistent with the case facts and company best practices. Ability to present claims to senior management, internal and external stakeholders. Timely administration of statutory medical and indemnity benefits throughout the life of the claim. Comply with all applicable statutory guidelines, rules, and regulations. Control legal activity with defense counsel through the litigation process while managing legal fees and costs. Prioritize early resolution opportunities, evaluate claim exposure and negotiate settleme

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 Vice President of Claims Adjudication, reporting to the Chief Claims Officer, your purpose will be to collaborate in the design and execution of Pie's claims strategy and programs. In this role, you will lead Pie's claims adjudication function, ensuring the delivery of optimal claim outcomes and exceptional customer experiences. You are responsible for strategically building and leading a claims adjudication organization that executes on the overall claims strategies. You will be fostering relationships at every level both internally with team members and other senior leaders, as well as externally, working to build relationships with key partners in the industry. How You'll Do It Claims Adjudication Leadership Lead and oversee Pie's claims adjudication function across all jurisdictions. Plan and direct all aspects of claims adjudication operations, overseeing daily and long-term activities. Responsible for implementing claims programs for workers' compensation. Serve as the lead claims adjudication authority, bringing expert claims experience to the Pie Executive Team. Direct the quarterly review and settlement of large loss and catastrophe claims. Develop and guide claims adjudication procedures and policies to enhance the processing, investigation, and settlement of claims. Claims Strategy Collaboration Collaborate with the Chief Claims Officer in the design and execution of Pie's overall claims strategy. Contribute claims adjudication expertise and insights to inform enterprise-wide claims initiatives. Partner with Claims leadership on strat

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. The Claims Adjuster will play a vital role in delivering quality claim file management and an industry-leading customer claims experience. This will be completed by adhering to Pie’s Claims Best Practices and complying with regulatory and statutory requirements. This role will work with internal and external partners to deliver best in class performance, identify and pursue claim mitigation opportunities and deliver favorable claim outcomes for Pie’s customers. How You’ll Do It Claims Technical Management: Independently handle all aspects of the workers’ compensation claims from set-up to closure. Conduct timely 3-point contact investigation, with focus on continued investigation as facts of the case change. Mitigate claim exposure while achieving the best outcome. Determine timely and accurate compensability decisions within statutory requirements. Set and adjust timely/accurate reserves within authority limits to ensure reserving activities are consistent with the case facts and company best practices. Timely administration of statutory medical and indemnity benefits throughout the life of the claim. Comply with all applicable statutory guidelines, rules, and regulations. Control legal activity with defense counsel through the litigation process while managing legal fees and costs. Prioritize early resolution opportunities, evaluate claim exposure and negotiate settlement. Claims Customer Service: Serve as a point of contact for our partner agents and customers to provide general claim guidance and help set claim process expectations. Ass

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. The Senior Claims Adjuster will play a critical role in delivering quality claim file management and an industry-leading customer claims experience., This will be completed by adhering to Pie’s Claims Best Practices and complying with regulatory and statutory requirements. This role will work with internal and external partners to deliver best in class performance, identify and pursue claim mitigation opportunities and deliver favorable claim outcomes for Pie’s customers. How You’ll Do It Claims Technical Management: Independently handle all aspects of the workers’ compensation claims from set-up to closure. Evaluate and handle high dollar, high exposure, complex claims. Conduct timely 3-point contact investigation, with focus on continued investigation as facts of the case change. Mitigate the complex exposure while achieving the best outcome. Determine timely and accurate compensability decisions within statutory requirements. Set and adjust timely/accurate reserves within authority limits to ensure reserving activities are consistent with the case facts and company best practices. Ability to present claims to senior management, internal and external stakeholders. Timely administration of statutory medical and indemnity benefits throughout the life of the claim. Comply with all applicable statutory guidelines, rules, and regulations. Control legal activity with defense counsel through the litigation process while managing legal fees and costs. Prioritize early resolution opportunities, evaluate claim exposure and negotiate settlemen

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. The VP, Field Underwriting owns Pie's underwriting P&L and the execution engine behind it. Reporting to the Chief Underwriting Officer and operating as a member of the executive team and peer to the VP of Insurance Product and Pricing, this leader is accountable for portfolio results, team performance, and the operating model that delivers them. The VP shapes company priorities alongside functional accountability — that means making enterprise-first calls when function and enterprise are in tension. They define how Field UW operates for the next several years: who it hires, how the onshore/offshore model evolves, what the AI-enabled underwriting function looks like at scale, and what underwriting excellence means for Pie's customers. This role partners closely with Corporate Underwriting on the automation roadmap, providing the field execution perspective that drives what gets built next. Someone who has managed a steady-state function will not thrive here. Someone who has built and restructured will. How You'll Do It Own Underwriting Results and Portfolio Performance Own loss ratio outcomes across New Business and Renewal. Drive underwriting strategy in partnership with the VP of Insurance Product and Pricing and the CUO, including appetite, authority standards, and risk selection philosophy. Partner with Corporate Underwriting on appetite, eligibility, and underwriting best practices development; anchor those decisions in field execution experience and portfolio loss data. Establish portfolio monitoring frameworks that surface emerging trends bef

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. Overall, the Total Rewards Manager is responsible for the strategy and execution of that strategy for base compensation, short term incentive compensation, long term incentive compensation, equity, benefits, and wellness. The work requires partnership with People Partners and Recruiters as well as the executive team, including the Director of People Operations, SVP of People and Talent, CEO, and CFO. How You’ll Do It Serve as the Compensation Partner to deliver strategic compensation support to the organization: Provide consultation and guidance to key stakeholders (Director of People Operations, Chief People Officer, CEO, and CFO) as well as other leaders and People Partners regarding compensation strategy, programs, and communications. Partner with People Partners and Talent Acquisition for all compensation activities related to their functions. Assist with ad-hoc requests and reporting needs. Compensation analysis: Ensure salary and equity structures remain market competitive as the market changes throughout the year. Work with People Partners to recommend any necessary off-cycle increases and market adjustments. Audit for pay gaps and ensure equitable pay. Maintain Pie’s job architecture: Prepare and/or review job descriptions reflecting job responsibilities, activities, duties, and requirements and recommend appropriate alignment within our job architecture. Ensure consistent application of job architecture throughout the organization thereby protecting equitable practices in job levels and compensation Assist in maintaining systems to ensure accu