Director of Product Success (National)

Location: Best situated in either Santa Cruz, CA or Eugene–Springfield, OR, with partial remote possible
Reports to: Chief Executive Officer
Works closely with: Chief of Staff, national leadership team, local newsroom leaders, growth, revenue, and engineering partners
Time horizon: Supporting two current Lookout cities and building scalable playbooks for the next three Lookout launches through 2028

About Lookout

Lookout is building the next generation of local news—independent, digital-first, community-rooted, and financially sustainable. We are a modern replacement for the legacy newspaper: mission-driven, membership-supported, and built to reach a significant majority of each community we serve.

Lookout’s ambition extends beyond traditional news consumption. We aim to become each community’s trusted metro information center—the place people turn to daily not only for journalism, but for answers, guidance, context, and practical help navigating local life.

Our product ecosystem is intentionally broad and evolving. Today it includes browser experiences (desktop and mobile), native apps, newsletters, and live events. Next up: a local Answer Engine (Ask Lookout) and a growing suite of AI-assisted products designed to deepen engagement, expand reach, and unlock new revenue opportunities—while strengthening local journalism.

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

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

1. 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

2. 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

3. 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

4. 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

This role sits at the intersection of journalism, product, and business strategy. You will help define:

How local news evolves beyond the article
How trusted information becomes a daily utility
How product excellence fuels both civic impact and financial sustainability
How Lookout scales into a national network without losing local soul

This role combines:

Editorial adjacency: working directly with newsroom leaders to extend journalism into new, high-impact formats
Product ownership: setting strategy, priorities, and roadmaps across core and emerging products
Business accountability: driving measurable audience growth, engagement, and monetization
Experimentation at scale: turning successful pilots into repeatable playbooks for a growing national network
AI-forward thinking: responsibly integrating AI into information products and workflows that increase value without eroding trust

You will help Lookout evolve from a great local-news organization into each community’s daily information utility—a role legacy newspapers once played, but no longer can.