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 Category

Underwriting

Position Type

Permanent

Compensation 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

$109,300.00 - $180,200.00

Target Openings

1

What Is the Opportunity?

As a pivotal member of the Managing General Agent (MGA) team, you will be responsible for comprehensive portfolio management and underwriting oversight across all MGA lines of business. You will regularly collaborate with internal stakeholders across Product, Pricing, Customer Service Center, and Insights teams to drive program profitability, growth, and long-term sustainability. Additionally, this position requires external representation with reinsurers and fronting carriers to drive initiatives for improved growth and profitability.

What Will You Do?

• Actively monitoring the flow, health, and profitability of the entire book of business, including a deep focus on new business, renewals, geographic concentration, industry/class results, and product profitability across lines of business, distribution channels, state and territory, and industry/class-specific segments.

• Collaborating with MGA colleagues to research and interpret complex data, identifying growth opportunities through optimization and mitigating loss potential. Support Product Managers, Underwriters, and Actuaries in strategic execution.

• Collaborating closely with the Claims Program Manager to gather insights that inform Product and Underwriting teams for strategic portfolio action.

• Leading underwriting projects and making independent decisions to strengthen and develop the MGA portfolio.

• Supporting underwriting innovation and automation through strategic partnerships with digital product and insurance product teams.

• Serving as a Subject Matter Expert (SME) for partnership distribution, including marketing, coverage, and underwriting guidance on all lines of business.

• Building and maintaining strong relationships with key external stakeholders, including capacity providers and fronting carriers.

• Empowering and mentoring less experienced underwriters through active support, knowledge transfer, and continuous educational opportunities.

What Will Our Ideal Candidate Have?

• An entrepreneurial spirit who thrives in an insurance start-up environment.

• Extensive underwriting experience with commercial P&C products, including General Liability, Inland Marine, Property, and BOP, is required across various lines of business.

• Bachelor's degree with 8+ years of relevant work experience.

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

• Advanced knowledge of product offerings, insurance lifecycle processes, underwriting guidelines.

• 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.

• You are passionate about the customer and the customer's 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.

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.