About Rainbow

Rainbow is a program administrator modernizing small-to-middle market business insurance through technology-driven underwriting and data-informed decision making. We are adding a production-oriented Regional Underwriter who thrives in a collaborative, fast-paced environment and consistently delivers high-quality underwriting outcomes.

Our underwriting team evaluates risks across admitted and non-admitted commercial multi-peril products in more than 40 states. With a continuously expanding product portfolio, Rainbow offers ongoing opportunities to broaden expertise and learn new underwriting disciplines.

About the Role and Team

As a Regional Underwriter, you own new business underwriting decisions for your region and help grow our commercial portfolio there. Our underwriting team is organized into three regions (West, Central, and East) to facilitate more intimate knowledge within each territory, allowing for more confident, quicker decisions. 

You will partner closely with your regional peers and your Regional Sales Managers, sharing the same quarterly new business goals, with coaching from our Underwriting Manager and support from dedicated strategy and operations leaders. Our technology handles routine work and surfaces agency and risk insight at the point of quote, freeing you to analyze the accounts that need real judgment: grey-area risks, exception requests, and complex referrals.

What You'll Do

• Analyze and decision underwriting referrals from agents in your region, bringing sound judgment to grey-area accounts rather than defaulting to guidelines or system output alone.
• Review and respond to exception requests, working with sales to confirm that they come from a reasonable place and are supported by the risk.
• Build strong relationships with agency partners in your region, communicating decisions and underwriting standpoints in a way that drives repeat business.
• Use proprietary data to prioritize your time, giving top-performing agencies and high-potential risks the attention they merit.
• Share in the results of your region, collaborating with regional peers to grow production while maintaining underwriting profitability.
• Collaborate with sales, service, and product to improve the efficiency of our underwriting process and the quality of our products.
• Maintain thorough underwriting file documentation that meets our standards and the requirements of regulators and capacity partners.
• Use our continuous underwriting model to identify risks that warrant further consideration.
• Compile and moderate agency feedback, turning it into action items that support continuous improvement.
• Help design underwriting functions and processes as we scale our offerings, and support business development and product needs as they arise.

What You Need

• 3+ years of small and middle market commercial underwriting experience, including hospitality or real estate business.
• Demonstrated judgment: you weigh the full picture of a risk and make confident decisions on accounts that do not fit neatly within guidelines.
• Comfort working directly with independent agents and moving quickly without sacrificing quality.
• Superior organization, prioritization, and desk management skills.
• A service-first, collaborative mindset, including a willingness to share accountability for regional results.
• Detail orientation, with superb written and oral communication skills.
• Alignment with our values: problem solving, iteration, and care.

What We Value 

Our values shape how we hire, how we evaluate growth, and how we work together every day. For an underwriter, here is what they look like in practice:

• We are problem solvers: We proactively address obstacles, turning them into opportunities.
• We are tenacious and iterative: We refine approaches to achieve the best outcome.
• We take ownership without ego: We focus on the greater good and act responsibly.
• We act quickly: We act with intention and speed for success.
• We care: We operate with empathy for work, relationships, and impact.

Compensation and Benefits

Compensation

• Base salary: $85,000 - $115,000, set by experience and benchmarked against comparable technology and insurance companies.
• Quarterly performance bonus: paid quarterly instead of annually, so you see the rewards of your work four times a year. Your bonus is tied to company premium growth, underwriting results (including loss ratio), new business production in your region, and your individual performance.
• Aligned with sales: Regional Underwriter targets include new business production in your territory, the same goals your Regional Sales Managers work toward.
• Meaningful equity: every employee is a shareholder. Stock options are granted at hire and vest over four years, with a one-year cliff.

Benefits

• Health coverage: Rainbow pays 90% of medical and dental premiums for you and your dependents, and 100% of vision, life and disability premiums.
• Flexible time off: no annual cap, plus paid company holidays.
• Parental leave to bond with new family members.
• Remote setup: a company-issued laptop and equipment, plus a monthly internet and phone stipend.
• Travel covered: flights and lodging for company meetings, agency visits, and industry events.
• Professional development: annual reimbursement allowance for certifications, designations and continuing professional education.
• Wellness: Company-sponsored mental wellness tool subscription, plus monthly stipend for additional wellness purchases and memberships.

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