Director of Product Management at Penrose Hill

Penrose Hill

Director of Product Management

  • Location: Remote Remote US

Penrose Hill is building the next generation of premium wine brands. Collaborating with famed winemakers and sourcing from distinguished vineyards around the globe, we make award winning wines of pedigree. As the worlds first data-first winery, were part of the wine business from grape to glass: not just making the wines but getting it directly into the hands of customers. Our largest and most profitable distribution channel is our wine club business, Firstleaf, which uses machine learning technology to match the perfect wine selections to each customer based on their preferences and ratings.

The Director of Digital Product Management will own the digital customer experience for Firstleafs direct-to-consumer wine club and eCommerce platform. They will be responsible for setting the product vision, implementing and managing a robust prioritization and roadmapping process, owning end-to-end execution, and ensuring a best-in-class user experience. They will also be responsible for making our brand story, rich data assets, and other differentiators come to life on our owned properties.

This seasoned leader will manage and expand the team from a small set of designers to a team of digital product managers, designers, UX copywriters, and UX/UI researchers.

This role will have a track record of successfully building and leading digital product teams, doing the right things (and doing them well) to drive the business, all while fostering relationships across the entire organization and distilling the needs of a complex web of stakeholders into an ambitious product roadmap.


  • Lead the Product team and own product strategy definition and execution across the product lifecycle. Develop an organizational design aligned with delivering on key business objectives, and expand the team additional product managers, UX/UI designers and copywriters, and UX researchers.
  • Develop Firstleafs digital product vision and drive focus on objectives across multiple departments (Marketing, Customer Service, etc) with a goal of delivering a world-class consumer-facing experience.
  • Work with Firstleaf executive team to define the company roadmap for digital product. Prioritize initiatives on an ongoing basis in line with strategy, business KPIs, and customer value.
  • Develop and implement communications architecture to drive stakeholder alignment, manage expectations, and continually incorporate feedback.
  • Lead the UI / UX product design team in ideating and evaluating new features from product viability and UX perspective, and taking roadmap items from planning through to engineering handoff
  • Collaborate with Engineering leadership to allocate resources effectively and define a process with tooling that enables clear communication, accountability, and ownership
  • Drive ongoing conversion rate optimization efforts through data-driven hypothesis generation, design and execution of AB and multivariate testing, and communicate key learnings from tests to other parts of the organization
  • Provide thought leadership, innovation and process optimization initiatives such as build vs buy decisions, implementing e-commerce software and other industry best practices
  • Reinforce a strong product culture based on data driven decision making, testing and short iterations.


  • 8+ years’ experience in a senior product management position involving a B2C product, ideally e-commerce or subscription service based.
  • 3+ years Experience in leading a UI / UX product design team
  • Proven ability to define, clearly communicate, and lead the execution of a digital product strategy and roadmap, stemming from a clearly articulated product vision
  • Demonstrated leadership skills with a rich blend of analytical, creative, and strategic talents in order to effectively communicate, motivate, and inspire cross-functional teams with professionalism and clarity.
  • Ability to define and analyze numerous product metrics (from Google Analytics and other tools), ability to think strategically and know when and how to apply each in order to influence the success of new features and review performance of existing ones
  • Detail orientated; superior problem solving and organizational and skills; and an ability to conceptualize, prioritize, and manage multiple projects.
  • Track record of designing, growing, developing and nurturing distributed teams


Working with the best wine team in the world isn’t enough?

But seriously, we offer some great benefits – from competitive compensation (base + bonus), remote work arrangements, to flexible work hours, plus stock option grants, multiple options in medical/dental/vision plans, 401k, life insurance, a world class employee assistance program, flexible spending accounts, and a discount on our wine club, Firstleaf…just to name a few.

See all Product Manager Jobs >

Sign up for Daily Remote Job Alerts!

Want Access to 25,000+ More Remote and Flexible Jobs?

More Jobs

More Jobs

Part-time to full-time,
freelance to employee

More Career Fields

More Career Fields

50+ flexible
job categories

More Resources

More Resources

Q&A's, webinars,
career coaching & more

Learn More About Our Premium Service