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The Senior Underwriter will manage underwriting quality and profitability, analyze trends, develop product recommendations, and collaborate with internal and external teams for growth.
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.
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.
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.
Simply Business is an equal opportunity employer. We’re committed to welcoming and helping employees grow within an inclusive & diverse culture. And that commitment starts with our interview process.
Once you apply, your info will be reviewed by a team with a mix of levels and experiences. We pride ourselves on fostering a sense of community, which is only made stronger by each individual at SB, so you’ll have the opportunity to meet a variety of people throughout the process. Get excited!
Most of our first round interviews will take place over Zoom. In subsequent interviews, there may be an opportunity/expectation to meet team members in person.
If it looks like you could be a good fit for the role, we’ll ask you to interview on Zoom first regardless – you’ll need WiFi and a laptop, or a 4G-enabled smartphone. If you don’t have access to either of these, or you need support with your application, get in touch with us at [email protected].
Please email us with any questions or if you want to pause your application for a bit – we’ll be happy to keep you updated on future opportunities like the one above. Want more info on working at Simply Business? Check out our careers page: simplybusiness.com/careers/
Top Skills
Data Analysis
Insurance Technology
Underwriting Software
Simply Business Boston, Massachusetts, USA Office
We are located in downtown Boston, accessible to every line on the T and surrounded by a lot of history and a lot of great places to grab lunch.
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