Simply Business is hiring: Head of Product (Boston) in Boston

Join to apply for the Head of Product role at Simply Business

This range is provided by Simply Business. Your actual pay will be based on your skills and experience talk with your recruiter to learn more.

Base pay range

$153,400.00/yr - $278,400.00/yr

Simply Business is a digital insurance brokerage that specializes in one thing: protecting the businesses our customers are working hard to build. Were doing this by simplifying the insurancebuying 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 toprated 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, were doing it all while taking care of our people. Weve consistently been named a best place to work, including most recently ranking in Built Ins 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 youre smart and passionate about delivering brilliant customer experiences, wed love to hear from you.

What Youll Do

• 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.
• Create and deliver customercentric 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 usercentered 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 crossfunctional teams to effectively communicate and execute the product vision, ensuring initiatives are wellunderstood and implemented.
• Build, manage, and scale the product organization, fostering a collaborative and highperformance 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 AIintegrated product landscape.

Your Skills

• Superior business judgment, combining intuition, experience, and datadriven 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 highperforming product team to embrace AIdriven innovation and usercentric 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 crossprogram 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, ecommerce and marketplace experience preferred.

Benefits and Perks

• Group plan for medical, dental, vision, and prescription drug coverage.
• Shortterm disability, longterm disability, and life insurance coverage.
• Participation in the Companys 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 thats best for their particular job, their teams, and their lives.

Simply Business is an equal opportunity employer. Were 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 youll 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, well ask you to interview on Zoom first regardless youll need WiFi and a laptop, or a 4Genabled smartphone. If you dont have access to either of these, or you need support with your application, get in touch with us at uscareers@simplybusiness.com.

Please email us with any questions or if you want to pause your application for a bit well 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/

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 performancebased cash incentive awards.