Senior Manager, Underwriting

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 Manager, Underwriting is the operational leader of the New Business Underwriting team, responsible for translating strategic direction from the Director of New Business Underwriting into day-to-day execution. This role owns team performance, service delivery, and underwriter development — ensuring the team operates with consistency, quality, and efficiency.

The Senior Manager is a seasoned underwriting professional whose technical expertise is sought out by team members, and who can make sound, independent decisions in complex or ambiguous situations without waiting for direction.

How You'll Do It

Lead Day-to-Day Underwriting Operations

• Own team adherence to service levels, underwriting guidelines, and quality standards; proactively surface and resolve operational bottlenecks before they escalate.
• Serve as the primary internal escalation point for complex submissions, risk evaluations, and underwriting judgment calls within the team.
• Manage workload distribution and capacity across the team to maintain SLA performance during volume fluctuations or staffing changes.
• Oversee training and SOP currency; ensure team members are up to date on appetite, product changes, pricing models, and industry developments.

Develop Underwriting Talent

• Directly manages a team of underwriters that may include senior individual contributors, Team Leads, and/or other managers depending on organizational structure.
• Coaches and develops team members with a focus on building independent decision-making, accountability, and technical proficiency — creating the conditions for others to operate with greater autonomy over time.
• Partners with the People team and the Director throughout the full team member lifecycle, including performance management, coaching plans, hiring, and offboarding.
• Identifies hiring needs and leads recruiting for high-quality underwriters; shapes team composition with a view toward future capability needs.

Execute on Operational Process and Improvement

• Identify, develop, and implement process improvements that drive efficiency, underwriting quality, and conversion within the team.
• Gather feedback from underwriters and internal partners to surface operational gaps; bring forward well-scoped recommendations to the Director.
• Provide reporting and performance data to the Director and leadership; use data to frame team results and highlight trends requiring action.
• Support implementation of new underwriting tools, best practices, and product or pricing changes as directed by the Director and cross-functional partners.

Support Partner and Stakeholder Relationships

• Serve as an operational point of contact for partner agents on day-to-day underwriting matters, escalating relationship-level issues to the Director as appropriate.
• Partner with Business Development to support retention and partner engagement at the team level.

The Right Stuff

• High school diploma/GED required; Bachelor's degree or equivalent experience preferred.
• Minimum 8 years of commercial insurance experience required; workers' compensation underwriting experience strongly preferred.
• Minimum 4 years of progressive leadership experience in commercial insurance underwriting; experience leading managers or team leads is a plus but not required.
• Disciplinary expertise sought out by peers and team members; strong technical underwriting judgment with the ability to handle complex risks independently.
• Proven ability to manage operational execution across a team, balancing throughput, quality, and team development simultaneously.
• Skilled at translating strategic direction into operational plans and guiding a team through execution — including during periods of change or ambiguity.
• Strong data fluency: able to track team performance metrics, identify trends, and communicate findings clearly to leadership.
• Effective cross-functional communicator; builds trust with internal partners and escalates appropriately without over-relying on the Director.
• Advanced problem-solving skills with the ability to navigate multi-layered situations and anticipate downstream impacts.
• Experience with performance management, coaching plans, and talent development.
• Knowledge of insurance underwriting best practices, service metrics, and customer experience operations.
• Progress toward or attainment of a professional designation (CPCU, ARe, or equivalent) is a plus and encouraged as a development milestone for those on a Director-track trajectory.
• Proficiency in G-Suite tools and collaboration platforms (Slack preferred).

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.

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