Lead the underwriting engine that keeps small businesses protected and partner agents confident. This role owns team performance, service levels, and process improvements, while helping Pie grow its partner channel through smarter underwriting strategy, training, and operational discipline.
About Pie Insurance
Pie’s mission is to empower small businesses to thrive by making commercial insurance affordable and easy to use. They leverage technology to modernize how small businesses buy and experience commercial insurance, backed by a team that values speed, integrity, and customer outcomes.
Schedule
Remote (United States only; territories excluded)
Full-time leadership role requiring reliable high-speed internet
Cross-functional collaboration with Business Development, Product, Compliance, and People teams
What You’ll Do
- Manage underwriting team performance, ensuring policies are issued efficiently and SLAs are consistently met
- Serve as the escalation point for underwriting questions and risk evaluations, providing clear guidance and decision support
- Coordinate load balancing across underwriting teams to maintain service levels
- Lead regular training and ensure SOPs stay updated on appetite, pricing models, and industry trends
- Act as the primary operational representative to channel partners and support partner agent success
- Gather partner and internal feedback to improve conversion, operations, and underwriting workflows
- Collaborate across departments to implement partner-channel processes, products, and service improvements
- Provide reporting, benchmarking, and insights to leadership, including competitor and trend research
- Coach and develop Team Leads, create growth plans, and partner with People on performance management
- Identify hiring needs, act as hiring manager, and scale the team to meet growth targets
- Monitor the underwriting book of business and contribute to national/regional underwriting plans and OKRs
- Partner with Business Development leadership to drive retention and partner engagement
What You Need
- High school diploma or GED (bachelor’s preferred or equivalent experience)
- 6+ years of commercial insurance experience
- 2+ years leading a commercial underwriting team (or equivalent leadership experience)
- Strong understanding of underwriting operations, customer experience best practices, and service metrics
- Advanced problem-solving skills with ability to manage complex, multi-layer situations independently
- Strong analytical skills to translate data into clear decisions, deliverables, and action plans
- Ability to set goals, forecast headcount, and make hiring decisions that improve productivity and efficiency
- Strong communication skills (written and verbal) with the ability to tailor messaging by audience
- Comfort with Google Workspace and collaboration tools (Slack preferred)
- Advanced knowledge of rate making, book management, and strategic prioritization
Benefits
- Base salary range: $110,000–$140,000 (USD)
- Competitive cash compensation plus equity (“a piece of the pie”)
- Comprehensive health plans
- Generous PTO
- Future-focused 401(k) match
- Generous parental and caregiver leave
- Discretionary bonuses may be available based on company performance
This is a real leadership seat with accountability and influence. If you’ve led underwriters, know how to run the book, and can build partner trust while improving ops, move on it.
Happy Hunting,
~Two Chicks…