About the roleLookout 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 LookoutProduct 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
Lookout's macro product ecosystem includes:- Browser experiences (desktop and mobile)
- 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 navigate their communities
- Systems and workflows that allow service journalism to scale sustainably
- Revenue strategies tied to these products, including sponsorships, membership value, and advertising
- Ownership of Key Next-Stage & Revenue Products
You will serve as product owner for a portfolio of high-priority products, including: - Neighborhood newsletters and hyperlocal formats
- Obituaries as a reader- and advertiser-supported product
- Legal advertising and public-notice products
For each, you are accountable for: - Clear product strategy and success metrics
- Audience usage and revenue performance
- Iterative improvement based on data and community feedback
- Scalable playbooks for future Lookout launches
- News Experimentation & Organizational Leadership
This role incorporates the mindset and practice of a Director of News Experimentation, including: - Targeted research to understand community needs and opportunities for deeper engagement
- Designing and scaling systems and workflows that support journalism about, for, and with audiences
- Developing new forms of information delivery and storytelling aligned with sustainability goals
- Cultivating a culture of experimentation around information, in partnership with newsroom, revenue, and technology teams-and directly with community members
- The ultimate goal: to connect Lookout's journalism more closely to the daily lives, experiences, and habits of community members, growing total addressable audience and monetizable value.
- AI & Process Innovation
Lookout is committed to responsible, practical use of AI in local journalism. In this role, you will: - Lead AI-enabled process improvements within selected products
- Help integrate AI thoughtfully into newsroom and product workflows
- Identify opportunities where automation and augmentation improve speed, quality, or sustainability
- Ensure AI adoption aligns with Lookout's editorial standards and public trust
What You'll Bring- Senior-level experience leading digital products tied directly to audience and revenue growth
- Background in media, news, marketplaces, SaaS, or consumer platforms
- Demonstrated success launching and scaling new products or workflows
- Comfort working across editorial, business, and technical functions
- Strong product intuition grounded in data and community research
- Experience with experimentation, service journalism, or information products a plus
- A deep belief in the civic importance of strong, sustainable local journalism
