VP, Product Development at Legacy.com

| Chicago
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Company and Opportunity

Legacy.com is the place where life stories live on. We are the leader in online obituaries; a top-50 website in the United States, and a destination for over 40 million unique visitors each month. Founded in 1998, Legacy.com is honored to help consumers express condolences, share direct support for families, and celebrate the people who have touched their lives. We continue to broaden our offerings in our mission to help people seeking information and guidance on all aspects of end-of-life. Our leadership is actively investing in the growth of the organization, expanding our business model and helping more people as our culture’s relationship with end-of-life evolves. Our vision is to become a full-service end-of-life and memorialization resource.

Position Overview

The Vice President of Product Development sits at the center of Legacy’s efforts to make that vision a reality by managing the organization’s product sets, acting as a product champion, and assuming responsibility for the product strategy, customer experience, and user experience design. Reporting to the Chief Technology Officer, the role requires a unique blend of business acumen, design skills, technology expertise, and a strong drive to exceed growth expectations.

This is a growth-stage product leadership role, requiring both the development of the products and the development of product development capabilities. Success for the Vice President of Product Development means achieving not only commercial success through product/market fit, but by generating scale in the product development process from design to technical implementation through ongoing support. Achieving scale requires an entrepreneurial, experimental and growth mindset, strong cross-functional facilitation and motivation skills, and most importantly, a consistent focus on team and talent development.

The Vice President of Product is a key hire for the organization as it positions itself for ambitious audience and revenue growth through iterative product enhancement, business model innovation, and new product development. The role serves as part of a senior leadership team driven to scale a business in a category with tremendous opportunity, supported by focused and committed investors. Together, the team will transform the business.

The role represents a rare and unique opportunity to participate in a conversation about changing attitudes and practices around the end of life. It requires a true product leader with sensitivity, a thoughtful, empathetic design approach, and the ability to balance a diverse set of perspectives in bringing the company’s vision to life.


Team Development

  • Develop a strong, self-sustaining team with rich and comprehensive talent development practices, while nurturing team health and team development. Maintain an open and transparent set of management practices for clear communication, collaboration and continuous improvement.

Roadmap and Vision

  • Partner with key senior leadership team members to evaluate commercial viability of product concepts and prioritize product development activities.
  • Use customer, market and competitive data to analyze product/market fit, operational and commercial feasibility, and growth opportunity across the product set. 
  • Establish a clear, easy to understand vision, strategy, and product roadmap providing opportunities for continuous optimization.

Product Development

  • Employ lean methods to identify problems and solutions for key customer segments.
  • Work with stakeholders to define business hypotheses for products, translating them into a defined commercial scope, and a series of epics, backlogs, user stories, and releases.
  • Adopt a growth mindset approach to product development, using hypothesis-driven experimentation to assess segment, product and feature-level performance.

Customer and User Experience Design

  • Identify key customer experiences and associated business value, articulating clear cross-functional goals, design considerations, operational ramifications, and technical scope.
  • Adopt a DesignOps approach incorporating distinct tracks of understanding on top of Agile discovery and delivery tracks to product high-quality designs with solid craft and methods.
  • Elevate User Experience through prototyping, iterative design and testing, developing consistent, adaptive design systems integrated with standard technical implementations.


  • Work with CEO, COO, CTO and VP Marketing to realize new business models and products.
  • Work with Marketing, Advertising, Operations, and Support teams to drive revenue, audience, profit and engagement from all revenue channels.
  • Work with Technology team to identify, design and build scalable platform components for delivering product capabilities, and the mechanisms for supporting them at scale.

Required Skills

  • Ability to identify/recruit talent, develop talent, and coach teams to greater health and performance while managing change across the organization. 
  • Proven track record of identifying, attracting and recruiting product and design talent
  • Proven ability to get things done, in strategy, design and cross-functional implementation
  • Proven ability to work effectively in fast-paced, ever-changing, growth-stage organizations
  • Proven ability to inspire, motivate by example, and manage change across the organization
  • Proven skills in product strategy, customer identification, customer and product discovery
  • Proven skills in product development, including planning and roadmap development
  • Proven skills in stakeholder management, strategic prioritization, consensus and evangelism
  • Demonstrated technical acumen and grasp of constraints and opportunities for scale
  • Demonstrated experience in hypothesis-driven, continuous learning and experimentation
  • Entrepreneurial mindset, bias for action, and demonstrated ability to make hard calls
  • Superior visual, verbal and textual communication, presentation and storytelling skills


  • 8-10 years’ experience in product development, software, digital media or publishing
  • 6-8 years’ experience managing and developing teams across the growth/scale lifecycle
  • Strong preference for candidates with a mix of start-up and/or growth-stage experience
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