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Head of Product
Head of Producthackajob • Boston, MA, United States
Head of Product

Head of Product

hackajob • Boston, MA, United States
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Head of Product

Hackajob is collaborating with Simply Business to connect them with exceptional tech professionals for this role.

Simply Business is a digital insurance brokerage that specializes in protecting the businesses our customers are working hard to build. We simplify the insurance‑buying process for all small businesses by blending technology, data, and insurance knowledge. Our proprietary technology platform allows small business owners to search and compare quotes from over 20 top‑rated insurance providers, customize coverage, and purchase and access policies—all online.

Founded in the UK in 2005, Simply Business is an insurtech pioneer with nearly 20 years of experience supporting small businesses. We build an outstanding product that empowers entrepreneurial spirits. We are consistently named a best place to work, 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.

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.
  • Who You Are

    You’re a builder at heart, passionate about creating products that make a real difference. You thrive on solving complex problems and overcoming challenges. You’re a natural leader, able to inspire and motivate teams, and you’re deeply committed to delivering exceptional and innovative customer experiences, with a strong understanding of how technology and AI can transform them.

    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 and 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.
  • #J-18808-Ljbffr

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    Head Of Product • Boston, MA, United States

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