Senior Underwriter, Workers Compensation

Pie Insurance; United States; Remote; USD 95,000 - 120,000; Full time

Benefits offered by this job

Competitive cash compensation

Comprehensive health plans

Generous PTO

Future focused 401k match

Parental and caregiver leave

Job summary

Pie Insurance is seeking a Senior Underwriter to lead complex commercial underwriting with a focus on policy quality and timely decisions. You’ll mentor teammates, collaborate across departments, and drive improvements in underwriting workflows. Remote in the United States, the role requires strong analytics, risk assessment, and communication skills.

Join a fast-paced team that values speed, accuracy, and partnership with our growth‑oriented culture and competitive compensation.

Qualifications

• High school diploma required; associate/bachelor preferred.
• 5+ years of property and casualty commercial underwriting experience preferred.
• Advanced underwriting, pricing, risk selection, agency relations/management.

Responsibilities

• Lead by example in daily underwriting output and meet goals.
• Ensure quality of deliverables and decision points in underwriting.
• Respond to coding information questions and inquiries.
• Support leadership to relieve workflow pressure and assist with referrals.

Skills

Underwriting

Pricing

Risk assessment

Interpersonal skills

Excel

G-Suite

Communication

Team leadership

Industry knowledge (P&C)

Education

High school diploma (required)

Associate or bachelor degree preferred

Tools

Excel

G-Suite

Job description

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 Underwriter is a pivotal team member when it comes to supporting the department with functional and operational tasks in order to help the team achieve their target deliverables. In addition to their own production requirements, the Senior Underwriter serves as the go‑to representative for the team when other departments and teams are looking for additional expertise and knowledge regarding underwriting. As a Senior level contributor, this person is able to represent the underwriting team in a variety of capacities and step in for other leaders when needed.

How You’ll Do It

Act as a Senior Level expert:

• Lead by example in daily underwriting output by meeting or exceeding the daily required goals.
• Responsible for quality of deliverables and decision points made under the underwriting umbrella.
• Respond to questions and inquiries for coding information.
• Support the Leadership Team to relieve pressure points in their workflow and daily activities.
• Assisting and approving referrals when the Leadership Team is not available.
• Deeper reviews for areas for opportunities for improvement on loss meetings.
• Responsible for meeting with team members from other teams to help them understand the role of underwriting and be able to tie together how interdepartmental workflows operate.
• Interviewing with other department candidates.

Ad Hoc Departmental Responsibilities

• Act in place of the Leadership Team in departmental meetings.
• Manage operational tasks and help with decision making for both internal department and external department needs.
• Create documentation around new processes and procedures and act as a liaison with other departments to help with functional direction guidance.
• Act as the initial point of contact for new projects and new tools to be used in the organization and how it impacts underwriting - Pilot Group.
• Document processes and procedures for basic operational needs.
• Focus on specialty programs to work through the underwriting process in general.
• Actively engage with other departments around project-based process and product improvement initiatives.
• Own and manage projects to agreed upon timelines and resource allocation.
• Act as the underwriting contact in key partnership relationships for the organization.

Provide Coaching, Mentoring And Training Functions

• Design and manage onboarding and training programs for team members in the department, and awareness training for team members outside the department.
• Provide feedback to the Mentorship Team about the progress of new team members.
• Conduct Work and Watch sessions to help with efficiencies for both new and existing team members.
• Formally and informally guide, mentor, and coach underwriters in both technical and professional skills.
• Collaborate together to organize monthly department training sessions.

The Right Stuff

• A high school diploma is required for this position. An associate or bachelor degree is preferred.
• 5+ years of property and casualty commercial underwriting experience is preferred.
• Advanced-level knowledge of underwriting, pricing, risk selection, agency relations/management.
• Ability to manage partner relationships, including travel as needed.
• Intermediate to advanced knowledge of workers’ compensation class codes.
• Ability to apply underwriting/appetite, tools, systems, and resources to achieve goals.
• Strong interpersonal skills and can establish and maintain healthy working relationships.
• Advanced problem solving skills, ability to analyze an issue, research possible solutions and take action swiftly.
• Advanced technical skills and analytical skills.
• Intermediate level Excel skills (include: managing pivot tables, navigating and interpreting existing information and data sets, sorting, filtering).
• Basic skills with G-Suite (google docs, google sheets, gmail).
• Ability to communicate (written and verbal) at all levels in a professional manner.
• Strong Interdependence: Ability to multitask and prioritize basic to complex tasks, desk management, and prioritization of deliverables.
• Ability to manage a desk in an underwriting capacity to include quoting, declining, exposure review, binding, issuance support, transactional communication and relationship development.
• Ability to sell our product while simultaneously discerning risk characteristics within the direct to business market.
• You thrive in a fast‑paced, deadline‑driven environment.
• CPCU, ARM, or Agent’s P&C License 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.

Base Compensation Range

$95,000—$120,000 USD

Compensation & Benefits

• Competitive cash compensation
• Comprehensive health plans
• Generous PTO
• Future focused 401k match
• Generous parental and caregiver leave

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.

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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.

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