Executive Editor

The Executive Editor, working with the Managing Editor as the newsroom leadership team, will shape the next generation of multiple news and information products offered by Lookout Santa Cruz and Lookout more widely, applying and growing the Lookout Local journalism model, making sure we meet both our mission and business performance needs.

At Lookout Local, we’ve figured out a bunch of things well – real and early-on community engagement, multi-stream revenue, local advertising and bedrock breaking news-to-accountability through the day local journalism. And we appreciate the national recognition of our work fromour Pulitzer to ourfast-ramp launchandmodel-buildingin Oregon. But that’s just a beginning in Santa Cruz and in Eugene‑Springfield, and as we plot next communities to serve.

For this position, we’re seeking a
spirited, top editor/news product innovator ready to work with great colleagues to take Lookout Santa Cruz specifically and Lookouts overall to next levels of journalism, community service and revenue generation. We understand the fast‑evolving connections in that holy trinity, and believe that harnessing the latest tech/thinking (including mastering local AI application, on which we’ve laid a great foundation already) is fundamental to our future.

At this point, we focus on three key types of products: site, app and newsletter, and this leader, working with both our senior team and newsroom will build on those — and what’s to come.

At our two Lookouts, now approaching 40 strong people in number, we pride ourselves on being both fiercely mission‑driven and fiercely business‑driven, and know that only those local news organizations (like our friends and cohorts in the Knight Growth Challenge Fund, with Texas Tribune now the eighth member after we joined as the seventh) will prosper in the now‑faster changing ways all of us find and consume news.

We’re ready for the task, and seek a collaborative, accomplished audience‑and product‑focused colleague to join us in this adventure.

Ideally, we’d like the candidate to be located and (relocatable) to the Bay Area, if not Santa Cruz itself, able to join us in person at least a couple of days a week. The ideal candidate possesses a good understanding of the differentiation of Lookout’s model and a passion for building atop it, with the well‑demonstrated experience to be successful at a high national quality level.

We’re asking a lot – both a history of newsroom leadership excellence and a proven product orientation that matches with the tech of our times.

This is a newly created position, and it encompasses four main initiatives:

1) Building on the successful, Pulitzer Prize‑winning Lookout Santa Cruz start of four years

Builds on Lookout’s already impactful new product creations – including Neighborhood Newsletters, Briefs, Story Maps, Events integrations and more – proactively assesses, innovates and tests new ways of creating news and information that will serve and delight audiences. Builds upon the Lookout Playbook, applying both audience strategy and judgement that maximizes the best use of now‑emerging technologies. Working with the managing editor, focuses on the next phase of our coverage plans, as we increase staffing, leading to the updating of a 2025‑2026 community news and information plan.

In this strategic content and product analysis, and product development, works as a member of Lookout’s overall senior leadership team as well as with its product and revenue teams as well.

2) Leading, along with colleagues, Lookout’s expansion efforts to other cities.

Patterned on Lookout’s highly successful fundraising, planning, hiring and deployment for Lookout Eugene‑Springfield, strategizes next markets.

3) Serving as a prominent public face, with publisher‑like interaction, in the wider Santa Cruz County community and nationally

Become a familiar face in civic and business circles, a company presence that augments what our correspondents, ad salespeople and community engagement people do. Include creating useful community partnerships, talks to civic groups, moderation of events, 1:1 lunches with elected, business and non‑profit leaders. Works…