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Senior Underwriter, Workers Compensation

Pie Insurance - Remote - Remote - posted 2026-10-09

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Salary: USD 95,000 - 120,000 / annual

Pie Insurance is seeking a Senior Underwriter for Workers Compensation to serve as a pivotal team member supporting the underwriting department. This role combines individual underwriting production with leadership responsibilities, positioning the Senior Underwriter as the go-to expert for the team and other departments seeking underwriting guidance. Key Responsibilities: As a Senior Level Expert, you will lead by example in daily underwriting output, meeting or exceeding daily production goals. You are responsible for the quality of deliverables and underwriting decisions. You respond to coding inquiries, support the leadership team to relieve workflow pressure points, assist and approve referrals when leadership is unavailable, conduct deeper reviews for improvement opportunities, meet with cross-functional teams to explain underwriting's role and interdepartmental workflows, and participate in interviewing candidates from other departments. Ad Hoc Departmental Responsibilities include acting in place of leadership in departmental meetings, managing operational tasks and decision-making for internal and external needs, creating documentation for new processes and procedures, serving as the initial point of contact for new projects and tools (pilot group), documenting processes for operational needs, focusing on specialty programs, engaging with other departments on process and product improvement initiatives, owning and managing projects to agreed timelines, and acting as the underwriting contact for key partnership relationships. Coaching, Mentoring and Training: You will design and manage onboarding and training programs for department members and awareness training for other departments. You provide feedback to the mentorship team on new member progress, conduct work-and-watch sessions for efficiency improvements, formally and informally guide and mentor underwriters in technical and professional skills, and collaborate to organize monthly department training sessions. Pie Insurance leverages technology to transform how small businesses buy and experience commercial insurance, with a mission to make commercial insurance affordable and accessible. Requirements: - High school diploma required; associate or bachelor degree preferred - 5+ years of property and casualty commercial underwriting experience preferred - Advanced-level knowledge of underwriting, pricing, risk selection, and agency relations/management - Intermediate to advanced knowledge of workers' compensation class codes - Ability to manage partner relationships, including travel as needed - Ability to apply underwriting appetite, tools, systems, and resources to achieve goals - Strong interpersonal skills and ability to establish and maintain healthy working relationships - Advanced problem-solving skills with ability to analyze issues, research solutions, and take swift action - Advanced technical and analytical skills - Intermediate-level Excel skills (pivot tables, data interpretation, sorting, filtering) - Basic G-Suite skills (Google Docs, Sheets, Gmail) - Professional written and verbal communication at all levels - Strong multitasking and prioritization abilities - Ability to manage an underwriting desk including quoting, declining, exposure review, binding, issuance support, transactional communication, and relationship development - Ability to sell products while discerning risk characteristics in the direct-to-business market - Thrives in fast-paced, deadline-driven environments - CPCU, ARM, or Agent's P&C License preferred

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