Head of Product

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.

As our Head of Product, you'll be a visionary leader, developing product strategy, driving innovation and growth in a dynamic and fast-paced environment. You'll be instrumental in defining and delivering products that not only meet our customers' needs but also leverage cutting-edge technologies like Generative AI. A deep understanding of user experience (UX) and user-centric design principles will be critical to ensure these innovations are intuitive and impactful for our users.

What You'll Do:

• Strategic Product Leadership & Bold Innovation:

Develop and articulate a compelling product vision, strategy, and roadmap aligned with our business goals, with a strong emphasis on bold innovation and leveraging emerging technologies.

Drive the next wave of products, with a core focus on strategically integrating Generative AI and other AI capabilities to achieve outsized growth in the US market by creating differentiated value propositions and superior user experiences.

Synthesize and translate quantitative and qualitative insights into actionable product strategies.




• AI-Powered Product Development & Execution with Exceptional UX:

Create and deliver customer-centric products that meet user needs and drive business objectives, with a strong emphasis on leveraging Generative AI and broader AI to enhance user experience, personalize interactions, and improve efficiency.

Champion user-centered design principles and ensure a seamless and intuitive user experience across all product touchpoints, particularly as we integrate new AI/GenAI features.

Construct scalable and configurable technical solutions, ensuring future adaptability and growth.

Partner closely with cross-functional teams to effectively communicate and execute the product vision, ensuring initiatives are well-understood and implemented.




• Team Leadership & Development in an AI-Driven Landscape:

Build, manage, and scale the product organization, fostering a collaborative and high-performance environment..

Mentor and develop Product Managers, empowering them to bring bold and innovative concepts to life and enhance user experiences through intelligent features.

Nurture a team focused on delivering our customer proposition, and help the team grow into positions of influence and scale within an increasingly AI-integrated product landscape.

Your Skills:

• Superior business judgment, combining intuition, experience, and data-driven insights, with a keen understanding of the potential of AI/GenAI.
• Strong understanding of commercial imperatives and how to translate opportunities into successful products with strong UX.
• Proven ability to define and execute a bold product vision, strategy, and roadmap, with a keen awareness of emerging and AI technologies, and their application to enhance value proposition and customer experience.
• Excellent team motivator, able to effectively manage and inspire a high-performing product team to embrace AI-driven innovation and user-centric design.
• Strong negotiation, communication, and stakeholder management skills, including the ability to articulate the value and implications of pivots initiatives.
• Deep understanding of the capabilities and implementations of Generative AI and broader AI product development within a product framework.
• Ability to identify cross-program dependencies.

Your Experience:

• Extensive experience running a product team and managing staff.
• Extensive experience working with agile projects at scale, managing multiple streams and stakeholders.
• Proven experience implementing Generative AI and broader AI into products, with a demonstrable understanding of user experience considerations.
• B2C experience, e-commerce and marketplace experience preferred

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/