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Vice President, Head of Product


This is a Full-time position in Vancouver, BC posted October 26, 2021.

About us

At WineDirect our mission is to help wineries thrive by providing the world’s best DTC-Wine ecommerce and retail sales platform.

Our legacy applications are transforming to a cloud-native, microservices-based architecture and we need a product organization that can rapidly scale and execute this project to completion over the next 24 months.

We have one clear goal, and that determines our focus each and every day – to be The Winery’s Champion.

Our SaaS platform will achieve that goal by creating new levels of engagement, performance and reliability for our customer

About the position

We are seeking an experienced product leader to help us build the next generation of our platform—The All-New WineDirect.

You will create a product vision and strategy that delivers significant business impact for our clients and is aligned with our long-term objectives.

You will convert this strategy into a prioritized product roadmap and collaborate with the VP Engineering to uncover solutions, while ensuring execution is on time, spec and budget.

If you relish responsibility and are constantly looking for opportunities to lead and make an impact, you’ll have the unique opportunity to deliver some of the most groundbreaking and essential software and services in our vertical.

The VP, Head of Product will be a visible leader responsible for building cross-functional coordination across the Executive, Sales, Marketing, and Engineering teams.

You will be hands on and customer-obsessed, while possessing the ability to make difficult trade-offs, and face issues head-on.

This leader should be entrepreneurially minded, have experience working in an agile organization and know how to leverage customer journeys to build amazing experiences.

Additionally, a proven history of building great products, driving adoption, making commitments and meeting timelines is a must.

While you’re uncompromising about execution, and love solving hard problems, you’re equally committed to individual mentorship and career development for your team.

Our product management team will need to grow to accomplish our near-term goals.

This will require recruiting, mentorship, and scaling expertise.

We believe there is much we can do to become stronger as a team and you will be a pivotal part of WineDirect’s evolution.

What you’ll be doing:

  • Own and drive all aspects of the product area from roadmap to delivery to customer adoption.
  • Collaborate with senior leadership to create and align on a product vision and strategy for new features and offerings based on user demand, data, and the experience of the WineDirect team.

    Develop a prioritized product roadmap and collaborate with the VP Engineering to drive execution of the roadmap, while optimizing our process.

  • Build strong partnerships with other teams internally and externally to solve problems, and ensure we deliver a cohesive customer experience.
  • Lead, coach, and develop a 5+ person team of talented product managers and product designers.

    Recruit, hire and retain exceptional talent as you scale your team.

  • Interface regularly with customers at events, during sales engagements, and through ad hoc opportunities to develop your product strategy and ensure customer success.
  • Remain on the leading edge of market requirements and strategic growth opportunities.
  • Other duties as assigned


  • 8+ years of software product management experience or history of entrepreneurial experience.
  • 4+ years in a leadership role within Product Management.
  • SaaS and ecommerce experience required.

    Start-up, marketing automation, fintech or DTC subscription experience a plus.

  • Proven track record of success managing all aspects of a successful product throughout its lifecycle.
  • Adept at working in an agile environment with talented engineering teams
  • You use data to inform and defend your decisions.

    You value market research and, when it comes to the competition, you have your finger on the pulse.

  • Ability to manage and balance and evolving priorities.

    There will always be more than you can do in a day, so you need continually make sure you have the right priorities and focus.

  • Strong verbal and written communication skills.

    Significant experience in presentations to internal and external executives.

  • A player-coach leadership mentality with proven success at developing product talent.

And finally, you:

  • Have a deep-seated entrepreneurial mindset that takes ownership of outcomes.
  • Are passionate about ecommerce, customer success, and the pursuit of excellence.
  • Thrive in ambiguous and dynamic environments and can roll-up your sleeves as needed.
  • Are excited to learn and always expand your knowledge.

    WineDirect has many new opportunities to pursue and there is always more to learn!

Why choose WineDirect over other opportunities:

  • You will have the autonomy and resources to build your team as you see fit.
  • Your work will be impactful to our clients, your peers, and the company.
  • You will own the roadmap and define interesting problems for our team of talented engineers to solve.
  • You will be put in a position to contribute right away, as you continue to learn and grow
  • You’ll get to work with and support a stellar group of people who work together to care for our clients and their customers

WineDirect by the Numbers:

  • Over $2B in sales enabled by our platform each year, growing >20% annually.
  • Over 3M consumer Monthly Active Users each.
  • Profitable, ambitious, and growth-oriented business.
  • Global reach, operating in 10+ countries.

WineDirect is an Equal Opportunity Employer.