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Wayfair is a technology leader, reinventing the way people shop for their homes

Director of Product Management, Driver Technology & On Road Execution

$75k – $110k AngelList Est.
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Wayfair is looking for a senior product leader to build an industry-leading over-the-road technology platform that maximizes customer and business outcomes through application of technology to our transportation operations. As part of the Wayfair Transportation & Delivery teams, your platforms will optimize how our network of drivers and third-party carriers execute pickup and delivery of billions of dollars worth of big & bulky packages ensuring terrific outcomes for Wayfair suppliers, carriers, and customers. This role will drive step change improvements in Wayfair’s speed, customer experience, and supply chain costs across the millions of packages flowing through our proprietary supply chain network.

The Director of Product Management for Driver Technology & On Road Execution will own several core work streams:

  • Dispatch & Tracking: Create unified, holistic platforms for dispatch, as well as track and trace applications. Build and maintain best-in-class service that powers data-driven insights about truck movement and arrival, while building tools that empower front-line dispatchers and driver service managers to handle real-time exceptions in day-to-day operations. Work with carrier partners to improve tracking data provided by third parties.
  • Customer Reservations: Evolve technologies that enable customers to schedule pickups and deliveries efficiently and effectively. In close partnership with Storefront, Marketing and Customer Service, create a delivery and return reservation experience that creates durable retention and competitive advantages while improving operational efficiency of our trucks and routes.
  • Driver Applications: Empower hundreds of Wayfair drivers (both employees & contractors) to deliver exceptional supplier- and customer-facing experiences by putting the necessary information and actions into their hands with fully-integrated Android mobile applications. Contribute to ongoing creation of a world-class mobile platform for Supply Chain functions.
  • Customer Exception Management: Working closely with customer service, provide all Wayfair customers with the best possible outcome when things don’t go according to plan. Orchestrate responses to on-road exceptions across Transportation Technology, Operations, and Customer Service.
  • Customs & Cross-border - Work in close partnership with our International Supply Chain and European Operations teams to ensure all in-land transportation can cross international borders freely, complying to all legal regulations, as well as ensuring our drivers have the support they need on the road.

You will lead a team of product managers to define and execute the product strategy and roadmap for our Driver Technology & On Road Execution teams, building a scalable technology platform for over-the-road operations and customer exception management. Technologies will be operated across Wayfair’s network in North America and Europe. You will own the overarching vision, driving product prioritization, requirement creation, and execution of product development with Engineering, Design, and Operations teams. This role is highly strategic, requiring close partnership with many internal stakeholders including other transportation technology teams, operations research, finance, procurement, carrier management, customer service, storefront experience, and others.

This role reports to the Head of Product for Wayfair Transportation & Delivery and presents significant technical, analytical, and leadership opportunities with enormous potential for business impact. Successful candidates will be entrepreneurial and creative problem solvers who are able to lead high-performing cross functional teams that bring their vision to reality. They’ll also be able to dive deep into the technical details of their platform while simultaneously defining and communicating front-line vision as a key leader within our organization. They will also serve as part of the overall Supply Chain Technology leadership team.

What You’ll Do:

  • Partner with senior leaders to define and align business and product vision and strategy for Driver Technology & On Road Execution
  • Develop and maintain a product platform roadmap and regularly update to key partners and stakeholders
  • Lead, develop, and mentor a team of 5-7 product managers with indirect responsibility for 30-40 additional cross-functional scrum members.
  • Lead cross-functional teams in planning, prioritization, and product delivery including engineering, operations, operations research, and storefront experience.
  • Counsel leaders in business, operations and other departments on strategy, optimization, process definition, and execution
  • Define and measure business impact, and monitor performance of initiatives and communicate performance metrics to key stakeholders
  • Leverage data to understand risks, impacts, scope and priorities of our business objectives, and enable the team to drive results
  • This position will require frequent travel to sites through North America and Europe.


  • 10+ years’ Product Management experience, with preference for candidates with a mix of start-up and large-company experience (and/or candidates who have started new products/initiatives within large companies).
  • 5+ years’ experience successfully leading and improving teams that are highly effective both in terms of impact and team culture.
  • Excellent analytical skills with demonstrated experience with hypothesis-driven problem solving and turning data into actionable insights.
  • Deep understanding of business strategy and metrics.
  • Superior communication skills with demonstrated ability to navigate a complex organization and generate buy-in for ideas and plans.
  • Strong technical background, with demonstrated ability to partner effectively with both engineering and operations research / data science
  • Transportation industry experience preferred, but not required.
  • Entrepreneurial mindset, with a bias for action and ability to deal with extreme ambiguity and rapidly changing environments.

About Us:

Wayfair is one of the world’s largest online destinations for the home. Whether you work in our global headquarters in Boston or Berlin, or in our warehouses or offices throughout the world, we’re reinventing the way people shop for their homes. Through our commitment to industry-leading technology and creative problem-solving, we are confident that Wayfair will be home to the most rewarding work of your career. If you’re looking for rapid growth, constant learning, and dynamic challenges, then you’ll find that amazing career opportunities are knocking.

No matter who you are, Wayfair is a place you can call home. We’re a community of innovators, risk-takers, and trailblazers who celebrate our differences, and know that our unique perspectives make us stronger, smarter, and well-positioned for success. We value and rely on the collective voices of our employees, customers, community, and suppliers to help guide us as we build a better Wayfair – and world – for all. Every voice, every perspective matters. That’s why we’re proud to be an equal opportunity employer. We do not discriminate on the basis of race, color, ethnicity, ancestry, religion, sex, national origin, sexual orientation, age, citizenship status, marital status, disability, gender identity, gender expression, veteran status, or genetic information.

Wayfair at a glance

Wayfair is a technology leader, reinventing the way people shop for their homes

Wayfair focuses on E-Commerce, Home & Garden, Home Decor, and Furniture. Their company has offices in Boston and Berlin. They have a large team that's between 501-1000 employees. To date, Wayfair has raised $358M of funding; their latest round was closed on October 2014 at a valuation of $2.4B.

You can view their website at http://www.wayfair.com/ or find them on Twitter, Facebook, and LinkedIn.

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