Director of Product Success

About this position

About Lookout Local

Lookout Eugene-Springfield’s mission is to provide fair, accurate, and non-partisan news, focusing on the role of business in shaping a community through taxes and jobs. We are committed to reviving local journalism and engaging with the community to reflect their needs and interests. Lookout Eugene-Springfield now approaches its first anniversary, having already achieved great traction -- audience, membership, advertising, and community trust -- It is part of Lookout Local, a now fast-growing, next-generation West Coast-based local news network.

Lookout Santa Cruz won the 2024 Pulitzer for Breaking News, and Lookout's fiercely mission-driven, business-driven model is winning wide national notice. Check out our network page:

Our workplaces are in-person, in-community, collaborative and collegial. We are building a diverse, highly skilled and mission-driven group of journalists, community builders and business people intent on maintaining our culture of learning, growth and community service.

About the role

Lookout is seeking a senior, mission-driven Director of Product Success to lead product strategy, experimentation, and business performance across our national platform. This is a high-impact leadership role with direct responsibility for the audience and revenue success of the products under its direction.

This role reports to the CEO and works in close partnership with the Chief of Staff and national leadership team. The Director of Product Success is accountable not only for building great products, but for ensuring those products materially advance Lookout’s growth, sustainability, and civic mission.

At its core, this role builds on top of Lookout’s newsroom-driven journalism—extending it into products that create deeper, more frequent, and more valuable daily relationships with readers.

What Product Success Means at Lookout

Product success at Lookout is defined by business outcomes, not just feature delivery. This role owns the performance of directed products in terms of:

Audience growth, engagement, and habit formation

• Revenue generation, including membership, advertising, and emerging product revenue
• Scalability, ensuring products can be replicated and adapted across markets

You will operate at two levels simultaneously:

• Platform-wide leadership — optimizing Lookout’s core product ecosystem for engagement, information utility, and revenue.
• News experimentation & next-stage products — leading the development, scaling, and monetization of new and evolving products that expand Lookout’s value beyond traditional news consumption.
• Core Product & Information Scope
• Native apps
• Newsletters
• Ask Lookout, our AI-powered local Answer Engine
• Guides, explainers, and local life resources
• Emerging reader-revenue and advertiser-supported products
• A central responsibility of this role is to strengthen Lookout’s position as a trusted local information hub, where journalism, service, and guidance work together.

Major Strategic Focus Areas

• Driving Daily Reader Engagement & Interaction
  Building on core newsroom journalism, you will:
• Increase daily and weekly usage across Lookout products
• Design products that invite interaction, return visits, and habit formation
• Extend journalism into formats that better match how people live, search, and decide
• Partner with newsroom leaders to ensure product choices reinforce editorial excellence
• Information as a Core Product (Ask Lookout)
  You will lead product strategy for Lookout’s emerging role as a metro information center, including:
• Product ownership of Ask Lookout, integrating AI-powered answers with trusted local reporting
• Ensuring information products meet standards of accuracy, transparency, and trust
• Using information demand signals to inform newsroom priorities and coverage
• Developing sustainable models for monetizing high-value information services
• Guides, Local Life Hacks & Service Journalism
  You will oversee the development of an ongoing suite of products designed to add daily, practical value, including:
• Evergreen and timely Guides (elections, housing, schools, transportation, health, local government)
• Local “life hacks” that help residents…