Simply Business

Senior Product Manager

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Boston, MA, USA

Hybrid

Fintech • Information Technology • Insurance • Software

We Protect The Small Businesses You Love.

The Role

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.

We are seeking a highly motivated and experienced Senior Product Manager to join our dynamic Digital Product team. As part of a forward-thinking Digital Product Management group, you will be instrumental in shaping the future of our online customer experiences, driving innovation, and leveraging cutting-edge technologies to unlock hyper-growth in the online small business insurance space. We are committed to delivering intuitive, impactful, and innovative digital solutions that empower our customers to easily research, buy, and manage business insurance online.

As a Senior Product Manager, you will be leading a dedicated cross-functional team through the entire product development lifecycle. Your role will be pivotal in delivering outcomes that support our ambitious company growth plans, with a strong emphasis on customer-centricity, technological advancement, and improving Customer Lifetime Value.

What you'll do:

Strategic Product Development & Innovation: Lead the ideation, discovery, and delivery of innovative digital experiences and solutions. You will contribute to the product vision and strategy for your area, ensuring alignment with broader team and company goals. Proactively identify and champion opportunities to integrate novel technologies, particularly AI and Generative AI, to create more personalized, flexible, and component-based online sales journeys that cater to diverse customer segments.
Problem Solving & Roadmap Ownership: Shape the approach to solve critical customer problems and business challenges in collaboration with cross-functional stakeholders. You will formulate and own the roadmap for your product area, including a discovery and delivery backlog, making data-driven trade-off decisions that maximize value and align stakeholder needs.
Customer-Centric Execution with UX Focus: Champion user-centered design principles, ensuring a seamless and intuitive user experience across all product touchpoints, especially as we integrate new AI/GenAI features. Your focus will be on improving the online purchase experience for complex, misunderstood products, making finding, buying, and updating small business insurance as hassle-free as possible for customers.
Stakeholder Engagement & Influence: Proactively engage and align people with different objectives and agendas to a common goal, keeping stakeholders abreast of the latest learnings and results. You will partner closely with cross-functional teams to effectively communicate and execute the product vision.
Continuous Improvement & Accountability: Champion a "Build, Measure, Learn" culture, fostering continuous improvement within the product management discipline, particularly in discovery methodologies. You will be accountable for delivery against Value Stream OKRs, primarily focusing on conversion-to-purchase metrics, and will own, measure, and report on key product metrics.

Your Skills:

Customer Focus: A deep commitment to understanding customer needs and pain points, with a proven ability to translate insights into impactful product solutions that enhance the online purchase experience.
Product Expertise: Extensive experience in iterative product development, from discovery and ideation to launch and continual optimization. Familiarity with frameworks that ensure a steady flow of work, delivery, learnings, and value. Experience with agile/lean/value streams is a strong plus.
Data-Driven & Analytical: Strong analytical skills with a data-driven and evidence-based approach to decision-making and prioritization. Experience with analytics tools (e.g., Amplitude, Mixpanel, Looker, Tableau) and ensuring the capture of relevant data to inform product strategy and roadmap.
Technological Acumen: Experience and a strong desire to leverage new, novel technologies such as AI and Generative AI to provide superior customer experiences. A deep understanding of the capabilities and implementations of Generative AI and broader AI product development within a product framework is highly desirable.
Influence & Collaboration: Proven ability to influence and align diverse stakeholders to a common goal. Strong collaboration skills, able to iterate on a product and strike the right balance between technical, design, and commercial trade-offs.
Leadership & Motivation: An inspirational leader who can lead by example, motivate cross-functional teams to push through challenges, and foster a passion for elevating product management practices. You understand technical and design trade-offs and can work with your team to find creative solutions that balance speed and quality.
Business Acumen: 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.

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/

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Simply Business

Simply Business is dedicated to making small business insurance simple and accessible. Our robust digital marketplace allows small business owners to find and buy the insurance they need online, matching them with coverage from multiple top insurers to offer choice, transparency, and value. We have nearly 20 years of experience supporting small businesses, with over 1 million customers worldwide. Founded in the U.K. in 2005, Simply Business launched its U.S. operations in 2017 and today employs over 1,000 people across offices in London and Northampton in the U.K., and in Boston and Atlanta in the U.S.Simply Business is more than our name. It’s how we approach small business insurance.

Why Work With Us

Here at Simply Business we have five core values that we uphold in everything that we do: Learning, Empowerment, Authenticity, Pioneering, and Simplicity. Utilizing these values and embedding them into our culture makes SB a unique and great place to work, a place where every person is valued, a place where we get things done and have fun doing so.