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

Position Type

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

Target Openings

What Is the Opportunity?

What Will You Do?

• Product Vision: You clarify the purpose of our product goals, ensuring they focus on providing peace of mind and choice for small businesses. You drive a roadmap that balances customer ease with business health.

• Delivery & Agile: You own the full product lifecycle. You build the business case for new features and lead the team through "test-and-learn" cycles.

• Compliance: You act as the bridge between departments, navigating complex filings and carrier requirements to keep us moving safely.

• Market Intelligence: You dive deep into competitor pricing and features, ensuring Simply Business stays relevant and attractive to our customers.

How you’ll do it 

• You’re a bridge-builder. You align different teams (Tech, Marketing, Legal) behind a single, actionable plan.

• You’re a persuasive storyteller. You break down big, complex ideas into clear messages for stakeholders at all levels.

• You help others grow. You mentor junior team members and find ways to make our internal processes better and faster.

What Will Our Ideal Candidate Have?

• Experience with SQL and data visualization software like Looker and Amplitude to provide clear insights that help us make better decisions for our customers. 

• 7+ years in P&C with 5+ years in Product. Have successfully managed state portfolios and a strong understanding of what drives profitable growth.

• Degree in Finance, Economics or Statistics. Professional certifications and insurance expertise preferred.

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.