Director of Product, WooCommerce Checkout

WooCommerce is the most popular eCommerce platform on the web. We’re looking for a Product Director that will shape the future of the WooCommerce checkout and our branded consumer wallet experience.

As the Product Director covering this major product area, you will drive the strategic direction and roadmaps for our checkout and express payments experiences. Leading from concept to launch, you will collaborate on discovery, prioritize customer problems, guide product planning, and partner with go-to-market teams to launch. Your approach should both be transformational and iterative – with a passion for challenging the status quo and removing blockers.


  • Are customer focused; passionate about optimizing (and innovating) cart, checkout, and payments flows for merchants, developers, and shoppers.
  • Have experience building both consumer facing and merchant facing products, and using network effects of the two sided market between the two to create new, uniquely valuable products for both groups.
  • Have a deep understanding of industry best practice that will help to drive higher checkout conversion rates, with the right level of customization.
  • Bring rich subject matter expertise in B2B and B2C payments and financial services.
  • Are outcome focused and measure the success of your work based on results.
  • Know how to break down a problem or project into small pieces; can plan iteratively and have an experimental approach, responding to customer or market changes as needed.

Primary Responsibilities

  • Collaborate with Woo Leadership, Engineering, and Design Directors to set product strategy and vision for the checkout and express payments product area. Drive toward ambitious OKRs aimed at establishing our products as the top option for Woo users.
  • Manage Engineering teams in a high-growth business and organization. Define and execute efficiently on a focused product roadmap. Facilitate debate; influence prioritization; inspire contribution.
  • Talk to our customers – merchants, developers, and shoppers – to understand their most important checkout needs. Leverage interviews, internal data, market feedback, and your intuition to define the most valuable problems worth solving. Maintain product and discovery backlogs. Validate product direction through testing and MVPs.
  • Successfully launch new features and drive adoption, with a constant focus on improving attach rates and increasing usage.
  • Rally team input and cross-functional alignment through quarterly planning processes. Maintain an efficient cadence for collaborating with other Leads throughout the product life cycle. Advocate for projects, secure the right resources for success, and work with leadership when goals are at risk.
  • Own product performance, track metrics, and report progress.


  • 10+ years in the tech industry, with 4+ years of experience focused on payments and Fintech.
  • 4+ years of experience in payments/FinTech. Leading large scale and/or global launches is a plus.
  • 3+ years of people management experience, with hiring and growth responsibilities.
  • A consistent track record of owning and driving results.
  • Ability to balance multiple priorities and projects simultaneously, at the right level of detail.
  • Strong written and verbal communication skills, especially when it comes to articulating and unpacking customer problems.
  • Comfort with decision-making in both data-rich and data-poor situations.

About Automattic

We are the people behind, WooCommerce, Tumblr, Simplenote, JetpackLongreads, Day One, PocketCasts, and more. We believe in making the web a better place.

We’re a distributed company with more than 1900 Automatticians in 96 countries speaking 120+ different languages. We democratize publishing and commerce so anyone with a story can tell it, and anyone with a product can sell it, regardless of income, gender, politics, language, or country.

We believe in Open Source and the vast majority of our work is available under the GPL.

Diversity, Equity, and Inclusion at Automattic

We’re improving diversity, equity, and inclusion in the tech industry. At Automattic, we want people to love their work and show respect and empathy to all. We welcome differences and strive to increase participation from traditionally underrepresented groups. Our DEI committee involves Automatticians across the company and drives grassroots change. For example, this group has helped facilitate private online spaces for affiliated Automatticians to gather and helps run a monthly DEI People Lab series for further learning. Diversity, Equity and Inclusion is a priority at Automattic, though our dedication influences far more than just Automatticians: We make our products freely available and translate our products into and offer customer support in numerous languages. We require unconscious bias training for our hiring teams and ensure our products are accessible across different bandwidths and devices. Learn more about our dedication to diversity, equity, and inclusion and our Employee Resource Groups.

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