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Head of Product Development

Head of Product Development

4MATIV TechnologiesBoston, MA, US
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Head of Product Development

ABOUT 4MATIV TECHNOLOGIES, INC.

4MATIV Technologies is transforming student transportation through technology, ensuring every child has access to the learning opportunities that maximize their potential. We manage multi-modal mobility for school systems nationwide, streamlining operations and expanding service options.

We currently support 50+ school districts in major cities such as Houston, Indianapolis, Minneapolis-St. Paul, and Phoenix, overseeing 22,000+ student trips daily across 1,000+ routes. Our flagship SaaS product, TOMS (Transportation Operations Management System), is central to our mission—empowering schools to efficiently manage transportation, improve service reliability, and expand transportation options for families.

At 4MATIV, we are committed to :

  • Building user-centered products that create lasting impact for students and districts
  • Working shoulder-to-shoulder with clients as a mission-aligned, trusted partner
  • Valuing diverse perspectives and experiences
  • Caring deeply about outcomes and continuous improvement

POSITION OVERVIEW

4MATIV is seeking a Head of Product Development to lead the evolution of TOMS, our SaaS-based transportation management platform. This leader will be responsible for shaping and executing the product roadmap, driving innovation, and ensuring that development efforts align with customer needs, business strategy, and market demands.

As Head of Product Development, you will work closely with the founding CEO, leadership team, and key stakeholders to define priorities and bring our vision to life. You will oversee a highly skilled, integrated development team, balancing UX, UI, software engineering, and software delivery expertise to deliver a world-class product.

Leadership Scope

This role will also serve as the strategic and operational leader for engineering and data operations / analytics, unifying the product vision across departments. Key responsibilities include :

  • Strategic management of the development teams and contracted resources / partners, to ensure seamless collaboration and delivery.
  • Driving cross-functional product alignment, ensuring data-driven innovation and a seamless integration of analytics, engineering, 4MATIV’s consulting group, internal operational user needs, and client & partner needs.
  • Developing a structured pipeline for prototypes and operational tools created by the Data Ops / Analytics team, ensuring they contribute to client services and operational success.

    • This role requires a strategic mindset, strong execution capabilities, and deep experience in both SaaS product management and software development. The ideal candidate has successfully led teams in SaaS product development, understands the intersection of business needs and technical feasibility, and has a track record of delivering user-centered solutions in a fast-paced environment.

    RESPONSIBILITIES

    Product Strategy & Leadership

  • Work with the CEO and leadership team to define and execute a product roadmap that aligns with market needs and business priorities.
  • Translate strategic priorities into actionable product features, ensuring they address user needs, customer expectations, and stakeholder goals.
  • Maintain a clear, scalable product roadmap, balancing short-term execution with long-term innovation.
  • Ensure alignment between software design, business needs, and user experience, making strategic trade-offs as necessary.

    • Engineering & Data Operations Leadership

  • Oversee the Engineering and Data Ops / Analytics departments, ensuring that technical execution aligns with business and product strategy.
  • Directly manage and support key leaders, including the VP of Data Ops / Analytics, Senior Engineering Manager, and Software Engineer.
  • Lead the integration of data analytics and engineering efforts
  • Develop a structured process for prototypes and tools developed by Data Ops / Analytics to transition into fully realized product features.

    • Technology & Process Management

  • Ensuring that all engineering efforts align with internal development and business priorities.
  • Establish best practices for Agile software development, sprint planning, and cross-team collaboration.
  • Allocate responsibilities and resources effectively, ensuring the successful implementation of product features and engineering initiatives.
  • Drive continuous improvement, implementing scalable development processes and data-driven decision-making frameworks.

    • Execution & Hands-On Involvement

  • Take a hands-on role in areas where you have direct expertise, ensuring high-impact contributions.
  • Oversee key product development milestones, ensuring smooth execution from design to release.
  • Facilitate feedback loops with internal teams and clients, iterating on the product based on real-world usage and insights.

    • QUALIFICATIONS

    Required Qualifications

  • 10+ years of experience in software product development, ideally spanning multiple roles across the product lifecycle.
  • 5+ years of experience managing teams, with a proven track record of building and leading high-performing development teams.
  • 3+ years of experience working with stakeholders to set strategic product goals.
  • 2+ years working on web platforms in a leadership or senior product role.

    • Preferred Qualifications

  • Experience in web UX / UI development (2+ years).
  • Experience scaling product development teams and hiring for UI / UX and technical roles.
  • Deep knowledge of software development processes, including best practices for Agile, Scrum, and Lean methodologies.
  • Strong understanding of software architecture trade-offs, including different approaches to development, deployment, and scalability.

    • Bonus Qualifications

  • Experience working with Ruby on Rails projects.
  • Familiarity with React-based front-end development.
  • Knowledge of web design frameworks / libraries.
  • Deep understanding of agile software development methodologies, including their strengths and limitations.
  • A strong grasp of pragmatism vs. principles in software development decision-making.

    • WHY JOIN 4MATIV?

  • Lead the development of a SaaS product with real-world impact – TOMS is transforming school transportation, creating more efficient, reliable, and accessible systems for students.
  • Own the full product lifecycle – Guide engineering, data operations, and product development as part of a fast-growing, mission-driven company.
  • Work closely with a visionary CEO – Help shape product strategy at a high level while working hands-on to drive execution.
  • Build and scale a high-performing team – Play a key role in growing and mentoring a talented software development team.
  • Make a lasting difference – Your work will directly improve how school systems manage transportation, ensuring better access to education for thousands of students.

    • Requirements

    Required Qualifications

  • 10+ years of experience in software product development, ideally spanning multiple roles across the product lifecycle.
  • 5+ years of experience managing teams, with a proven track record of building and leading high-performing development teams.
  • 3+ years of experience working with stakeholders to set strategic product goals.
  • 2+ years working on web platforms in a leadership or senior product role.

    • Benefits

  • Health Care Plan (Medical, Dental & Vision)
  • Retirement Plan (401k, IRA)
  • Life Insurance (Basic, Voluntary & AD&D)
  • Paid Time Off (Vacation, Sick & Public Holidays)
  • Family Leave (Maternity, Paternity)
  • Short Term & Long Term Disability
  • Training & Development
  • Work From Home
  • Free Food & Snacks
  • Wellness Resources
  • Stock Option Plan
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