Senior Underwriter, MGA

Who Are We?

Simply Business is a digital insurance brokerage that specializes in one thing: protecting the businesses our customers are working hard to build. We’re doing this by simplifying the insurance-buying process for all small businesses, blending together a combination of technology, data, and insurance knowledge. Our proprietary technology platform allows small business owners to easily search and compare quotes from over 20 top-rated insurance providers, customize their coverage, and purchase and access their policies – all online.

Founded in the UK in 2005, Simply Business is an insurtech pioneer with nearly 20 years of experience supporting small businesses. Simply Business is passionate about building an outstanding product for our customers – one that empowers their entrepreneurial spirits.

More importantly, we’re doing it all while taking care of our people. We’ve consistently been named a best place to work, including most recently ranking in Built In’s 2025 Best Companies to Work for in the US (Top 100), and Best Places to Work in Boston.

We want team members who have the drive to challenge boundaries. If you’re smart and passionate about delivering brilliant customer experiences, we’d love to hear from you.

Job CategoryUnderwritingPosition TypePermanentCompensation Overview

The annual base salary range provided for this position is a nationwide market range and represents a broad range of salaries for this role across the country. The actual salary for this position will be determined by a number of factors, including the scope, complexity and location of the role; the skills, education, training, credentials and experience of the candidate; and other conditions of employment. As part of our comprehensive compensation and benefits program, employees are also eligible for performance-based cash incentive awards.

Salary Range$85,600.00 - $141,200.00Target Openings1What Is the Opportunity?Are you an experienced underwriter who wants to help grow and scale a direct-to-consumer insurance product? Simply Business (SB) is looking for a Senior Underwriter to join our Managing General Agent (MGA) team. This isn't your average underwriting role—you'll have the exciting opportunity to help manage a growing insurance program for small business owners in the fast-paced, direct-to-consumer space. This role reports to the Director of Underwriting and is for an underwriting expert who is passionate about combining traditional underwriting expertise with a modern, data-driven approach. You will be a key part of our team, focusing on portfolio management, profitability, and product development. You'll use your sharp analytical skills to identify trends, analyze performance, and make strategic recommendations that help us scale our programs and drive profitable growth.

What You'll Do:

• Managing the underwriting quality and profitability of our MGA book, ensuring adherence to reinsurance guidelines and regulatory requirements.

• Working within our Underwriting Workbench to review risk alerts and document decision-making.

• Actively analyze key trends across new business and renewal cycles, and the performance of various products across lines, geographic regions, and distribution channels within the book of business, collaborating closely with the underwriting, product, and analytics teams.

• Using internal and external data to develop product recommendations that help us grow our programs.

• Working cross-functionally with insurance product, marketing, service, and other SB teams to optimize our products and processes.

• Your underwriting expertise will be critical to influencing change with internal and external partners, challenging norms, and thinking outside the traditional underwriting box.

• You will actively collaborate with and influence our external stakeholders—from reinsurers to claims administrators—to drive strategic changes that support the continued growth and profitability of our MGA.

What We're Looking For:

• Education & Underwriting Experience: Candidates should possess a Bachelor's degree or at least 8 years of relevant work experience. Additionally, 5+ years of experience in commercial lines underwriting is required, with expertise in Professional Liability and Property considered a strong plus. A solid understanding of core Property & Casualty lines, including BOP, Package, General Liability, and Professional Liability, is essential. A CPCU or similar insurance designation is considered a plus.

• Analytical Mindset: You are comfortable working in a data-driven environment and have a solid understanding of pricing models, insurance workflows, and underwriting guidelines.

• Strong Communicator: You can clearly communicate complex underwriting and marketplace concepts to both technical and non-technical stakeholders.

• Customer-First Orientation: You are dedicated to providing solutions that are easy for our customers to understand and that truly meet the specific needs of small business owners.

• A Challenger: You are not afraid to challenge the status quo, ask tough questions, and contribute to the future of our business.

• Collaborative and Independent: You have the ability to work independently as well as with others in a team environment and manage competing priorities.

$81,300 - $147,600 a year the annual base salary range provided for this position represents a broad range of salaries for this role across the country. The identified range is what Simply Business reasonably and in good faith expects to pay for this position. The actual salary offered within this range for this position will be determined by a number of factors, including the geographic location of the successful candidate; the skills, education, training, credentials and experience of the successful candidate relative to the requirements of the role; the market data for this position in the specific work location; and other conditions of employment. As part of our comprehensive compensation and benefits program, employees may also be eligible for performance-based cash incentive awards.

What Will Our Ideal Candidate Have?

• Insurance designation(s) and/or insurance education are preferred (CPCU, AU, ARM, AAI, and/or MBA/MA degree)

• Experience working with US commercial P&C products in an underwriting capacity

• Advanced knowledge of product offerings, insurance lifecycle processes, underwriting guidelines and pricing systems

• Advanced understanding of insurance workflows and concepts, including limits, coverages, pricing models, ISO and form/rate rules

• Excellent communication, analytical, quantitative and problem-solving skills.

• Experience with project management is preferred

• You are passionate about the customer and the customers’ user experience

• The ability to challenge us! We want people who can come in and shape the future of this business and not be afraid to raise questions and help us improve

• An entrepreneurial spirit who wants to be part of insurance start-up

What is a Must Have?

• Bachelor's degree with over 8 years or more relevant work experience

• Insurance designation(s) and/or insurance education are preferred (CPCU, AU, ARM, AAI, and/or MBA/MA degree)

• Experience working with US commercial P&C products in an underwriting capacity

What Is in It for You?

Here are some of the great benefits and perks that come from being a Simply Business employee:

• Group plan for medical, dental, vision, and prescription drug coverage.

• Short term disability, long term disability, and life insurance coverage.

• Participation in the Company’s bonus program-Participation in 401(k) plan with a 5% employer match.

• Commuter benefits to help cut down on parking and public transit costs.

• 25 days of vacation time plus 10 sick days and 10 company holidays.

• A genuine investment in your learning and development-Regular team outings and volunteer opportunities. 

• An awesome office space.

• A hybrid working model, giving our employees great choice and flexibility to work in a way that’s best for their particular job, their teams, and their lives.

Employment Practices

Simply Business is an equal opportunity employer. We’re committed to welcoming and helping employees grow within an inclusive & diverse culture.