Senior Underwriter, Personal Umbrella

Location: Remote

About Monoline

Monoline is redefining the standalone personal umbrella insurance market with an unwavering focus on underwriting excellence, disciplined risk selection, and long-term profitability. Founded by proven entrepreneurs with a track record of successful ventures, Monoline is built on the principles of curiosity, innovation, and customer-centric solutions. We believe in challenging the status quo, bringing fresh perspectives to a traditional industry, and designing intuitive, straightforward, and consistent products. Our philosophy is rooted in empathy – understanding customer needs to create truly helpful solutions. We lead with gratitude, valuing every detail and the relationships we build along the way.

Our core values guide everything we do:

• People First – We build meaningful relationships, treating our team, partners, and customers with respect and care.
• Positive Presence – We bring energy and optimism to every challenge, fostering a supportive and motivated team culture.
• Batteries Included – We take initiative, think independently, and execute at a high level without waiting for direction.
• Always Curious – We seek knowledge, challenge assumptions, and continuously refine our approach to be the best at what we do.

About the Role

We are seeking an underwriting professional who evaluates risk thoughtfully, makes sound decisions, and thrives in a collaborative, client-facing environment. This hire will join our senior underwriter as we build out the team to meet the demands of our high submission volume and strengthen our agency relationships. With our current programs growing and additional products on the horizon, you'll be joining at a pivotal point in Monoline's underwriting evolution. Smart risk selection matters as much as ever with efficiency and automation becoming a priority as we scale.

This role will be responsible for underwriting personal umbrella liability risks across both admitted and non-admitted markets, including primary and excess layers. You will be interacting directly with agency partners, over the phone and face-to-face, to clearly explain coverage structure, eligibility, guidelines, and the rationale behind underwriting decisions. This reflects Monoline's commitment to relationship-oriented underwriting: giving agents access to real underwriters, not just decisions in an inbox. This individual must be comfortable leveraging new technology and live systems. They'll also bring an aptitude for AI-driven projects, such as owning prompt improvement initiatives to keep underwriting tools sharp.

Responsibilities

Underwriting & Decision-Making

• Evaluate and underwrite personal umbrella insurance risks across both admitted and non-admitted markets, including complex cases.
• Adhere closely to company policies and underwriting guidelines, with an emphasis on disciplined risk selection.
• Ensure all underwriting decisions are fully documented and able to withstand internal and external audits.
• Identify risks beyond individual authority and collaborate with management on complex case approvals.
• Manage renewals strategically to support profitable retention and portfolio stability.
• Monitor trends and patterns in day-to-day work to inform underwriting strategy and operational efficiency.
• Contribute to refining underwriting rules, eligibility criteria, and guidelines over time.
• Analyze performance metrics and participate in data-driven initiatives to bind and retain desirable business.

Collaboration & Product Support

• Partner with the AVP of Underwriting during product launches, and contribute ongoing process improvements for existing product offerings.
• Serve as a dedicated underwriting contact for a set of agency partners, answering questions on quotes, underwriting decisions, coverage, or eligibility.
• Work closely with the Support team to respond to inbound calls and chats, providing expert underwriting guidance in real time.
• Partner cross-functionally to ensure alignment with current underwriting guidelines.

Automation & AI-Enabled Underwriting

• Identify opportunities where automation can enhance routine underwriting tasks, freeing time for complex risk judgment.
• Use AI-assisted tools for data analysis, prompt refinement, and improvements to the submission review process.
• Keep underwriting decisions clear and well-documented, feeding a continuous feedback loop that strengthens AI tools.

Requirements

• 5+ years of underwriting experience in personal lines and/or commercial insurance, with a proven track record in risk analysis and decision-making.
• Carrier or MGA-side experience is preferred; personal umbrella and/or high net worth experience is a plus.
• Demonstrated ability to confidently assess risk and apply underwriting guidelines in support of smart, disciplined risk selection.
• Strong analytical and critical thinking skills, with sound judgment on complex, escalated risks.
• Exceptional written and verbal communication skills, capable of conveying complex information clearly and effectively.
• Proficient with underwriting systems, quote platforms, and data tools; able to leverage technology to support efficient decision-making.
• Comfortable picking up new AI-assisted tools and prompt techniques quickly, with genuine curiosity for how they can improve the work.
• Self-starter with an entrepreneurial mindset, able to work independently while collaborating effectively across teams.
• Detail-oriented, organized, and adaptable to a fast-paced underwriting environment.
• Open to feedback and continuous improvement.
• Insurance designation or certification is a plus.
• Limited travel required.

Why Monoline?

• Join a forward-thinking, underwriting-first insurance company committed to excellence in risk selection and profitability.
• Take on a critical role that shapes Monoline's underwriting future and the broader E&S personal umbrella market.
• Work with a team that values expertise, execution, and long-term thinking over volume-driven growth.
• Be at the forefront of tech-enabled underwriting innovation in a high-impact role.

Benefits

• Health, dental & vision insurance plans
• 401K match
• Equity - Stock Options
• Unlimited time off
• Paid parental leave
• Flexible schedule & work from home options