About Rainbow

Rainbow is a program administrator modernizing small business insurance through technology-driven underwriting and data-informed decision making. As we grow, we’re expanding our underwriting leadership and adding a Commercial Insurance Underwriting Manager to help oversee daily execution, ensure quality and consistency, and develop our underwriting team.

Our underwriting organization supports admitted and non-admitted commercial multi-peril products across the US. With a continuously expanding product portfolio, this role offers the opportunity to lead through growth—strengthening underwriting standards while expanding into new products and jurisdictions.

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The Role

As a Commercial Insurance Underwriting Manager at Rainbow, you are responsible for the day-to-day management of the underwriting team, serving as a hands-on leader who ensures underwriting decisions are consistent, compliant, and aligned with strategy. While this role includes underwriting complex referrals and escalations, its primary focus is team leadership, quality control, and operational execution.

You will oversee underwriting workflows, provide coaching and performance feedback, and act as an escalation point for nuanced risks—particularly within hospitality-focused accounts. You will also own internal quality assurance efforts, including underwriting file audits and ongoing reviews to ensure adherence to guidelines, regulatory requirements, and capacity partner expectations.

This is a high-volume, fast-paced environment that requires strong judgment, organization, and adaptability. You’ll partner closely with sales, service, and technology teams to continuously improve underwriting processes as Rainbow scales. As a growing startup, we value an all-hands-on-deck mindset, and this role will play a key part in shaping how underwriting operates as we grow.

This position is remote, with occasional travel for company meetings and industry events.

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What You’ll Do

• Manage the day-to-day operations of the underwriting team, ensuring consistent execution of underwriting standards and service levels
• Serve as the primary escalation point for complex underwriting referrals and non-standard risks
• Conduct regular underwriting file audits and quality reviews, identifying trends, gaps, and improvement opportunities
• Provide coaching, feedback, and guidance to underwriters to support performance and professional development
• Partner with sales, service, and product teams to improve underwriting efficiency and agent experience
• Communicate underwriting decisions and expectations clearly to agents and internal stakeholders
• Ensure underwriting files meet internal documentation standards, regulatory requirements, and capacity partner guidelines
• Support training and onboarding of underwriters as the team grows
• Contribute to the evolution of underwriting workflows, controls, and processes as new products and programs launch
• Demonstrate ownership and flexibility in supporting a coast-to-coast underwriting operation as needed

What You Need

• 5+ years of commercial underwriting experience, with exposure to food service risks
• E&S underwriting experience strongly preferred
• Experience reviewing, auditing, or overseeing underwriting files for quality and compliance
• Prior people management experience preferred (or demonstrated experience leading and mentoring underwriters)
• Strong organizational skills and attention to detail
• A collaborative, team-first leadership style
• Adaptability and comfort operating in a fast-changing environment
• Excellent written and verbal communication skills
• Strong ownership mindset and work ethic, including the ability to support a multi-time-zone underwriting operation

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