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Director, Field Underwriting

Pie Insurance

Pie Insurance

United States
Posted on Sunday, April 2, 2023
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.

Under limited supervision, serves as underwriting subject matter expert and leader of the Field Underwriting Team. Drives strong underwriting performance through oversight of authority delegation, underwriting execution, and active management of the portfolio results. Partners with the VP of Underwriting, Product Line Management, Business Development, and others in the development and execution of business strategies to support profit and growth, along with the development of underwriting talent. Participates/Leads countrywide initiatives to support continued evolution of underwriting. Serves as local change agent to ensure adoption of new strategies, models and practices.

How You’ll Do It

  • Responsible for oversight and influence of underwriting execution through portfolio and individual risk collaboration

    • Underwriting Subject Matter Expert holding highest level of authority in the Field
    • Partner with Sales and Business Development Leadership, Corporate Underwriting and Product Line Management to monitor trends, emerging issues, production and underwriting results for the book of business. Partners with management to take action as needed.
    • Partnering in the management of authority delegation
    • Evaluation of UW and quality program execution.
  • Shared leadership accountability for the development of underwriting talent and skill set. Accountable for underwriting talent development and skill set

    • Coach and mentor for Underwriting Managers, Team Leads, and Individual Underwriters
    • Identification and delivery of training
    • Deepening the team's underwriting to support independent thinking, and thoughtful judgment
    • Partner with other UW Directors/Management in staff calibration activities and evaluation of performance.
  • A member of the Underwriting Leadership team to influence, design and drive regional business strategies, operating practices, and pricing strategies to support profit and growth objectives

    • Lead/Participate in underwriting projects and initiatives across Pie
    • Partners with the Director of Corporate Underwriting in the ongoing development of Underwriting capabilities, including underwriting best practices and tools, appetite and eligibility.
    • Leads execution of new underwriting tools & best practices, product and pricing strategies.
  • Perform other duties as assigned.

The Right Stuff

  • Bachelor’s degree or equivalent work experience.
  • 15+ years underwriting and underwriting program development experience.
  • 5+ years underwriting leadership experience
  • Advanced Ability to develop managers and individuals
  • ARe, CPCU, FLMI, FALU or CLU accreditation or progress towards accreditation
  • Intermediate Word, SQL/Query and Excel skills
  • Advanced ability to comprehend and interpret insurance and contract documents.
  • Highly advanced oral and written communication skills, demonstrating the ability to convey business terminology that is meaningful and well received by all stakeholders, including customers and associates.
  • Advanced knowledge of broad business practices
  • Advanced persuasion and negotiating skills when working with clients to present quotes and/or solutions and to resolve issues/problems.
  • Advanced ability to lead change management.
  • Advanced ability to liaise with individuals across a wide variety of operational, functional and technical disciplines.
  • Highly advanced investigative, analytical and problem solving skills utilizing experience, research, guidelines and internal resources.
  • Advanced ability to manage multiple tasks and/or projects simultaneously, including the ability to handle changing priorities and deliverables.
  • Advanced ability to comprehend, analyze and apply vast amounts of underwriting and financial information quickly to make sound financial underwriting and risk assessments.
  • Advanced knowledge of insurance principles, underwriting policies and procedures and guidelines for dealing with risk analysis
  • Advanced knowledge of medicine, law, accounting, finance as applied to the evaluation of workers’ compensation risks
  • Ability to work well within a team environment and participate in department projects
  • Ability to work online, either at home or remote
  • Occasional travel required


Base Compensation Range
$155,000$215,000 USD

Compensation & Benefits

  • Competitive cash compensation
  • A piece of the pie (in the form of equity)
  • 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

Our goal is to make all aspects of working with us as easy as pie. That includes our offer process. When we’ve identified a talented individual who we’d like to be a Pie-oneer , we work hard to present an equitable and fair offer. We look at the candidate’s knowledge, skills, and experience, along with their compensation expectations and align that with our company equity processes to determine our offer ranges.

Each year Pie reviews company performance and may grant discretionary bonuses to eligible team members.

Location Information

Unless otherwise specified, this role has the option to be hybrid or remote. Hybrid work locations provide team members with the flexibility of working partially from our Denver or DC office and from home. 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.

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