Jump to: Politics, Policy and Power Correspondent / Arts, Culture & Entertainment Reporter / Executive Editor / Senior Correspondent / Marketing Manager (National) / Director of Product Success (National)

Browse more open positions at Lookout Eugene-Springfield here.


Lookout Santa Cruz seeks colleagues to join our evolving and growing team. Since launching, Lookout Santa Cruz has surpassed audience, membership and advertising goals. Most importantly, we are meeting our mission each day to provide all in Santa Cruz County a new, trustworthy source of news and information.

This page lists our current openings, and we are always open for inquiries from those who see themselves excelling in our new model. 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 and growth.

We’ve built a lively, mobile-first, built-for-the-2020s model that is quickly winning wide reader, civic and business community adoption as a primary news source, one that is successfully competing with hedge-fund-depleted daily journalism. We’ve found a formula that is working, a new combination of traditional and contemporary, a model that is getting national attention.

We’re traditional, in the best sense of the word, becoming a strong local journalistic and business presence, serving local-first, high-quality, non-partisan news, information and connect-the-dots analysis.

We’re contemporary in the best sense. Our model is digital-born, embracing the phone as a primary means of delivery, and just beginning to exploit all the things that a local digital news-plus platform can uniquely do for and with our communities.

Founded by news industry veteran analyst Ken Doctor, we support one of the largest newsrooms per capita in the nation and we cover Santa Cruz County’s a full spectrum of news, entertainment and opinion coverage. We now serve a second community, with Lookout Eugene-Springfield launched and rapidly growing. See our positions open there.

Application Process: Please send your resume and cover letter to jobs@lookoutlocal.com and put Santa Cruz, [Job Title] in the subject line.

What We Offer:

  • Competitive salary and performance-based incentives.
  • Full-time benefits include highly competitive medical, dental, and optical benefits, and 401(k) with matching.
  • Good PTO allowances.
  • Stock options in our growing company.
  • An opportunity to make a significant impact on and contribute to the revival of local journalism.
  • A collaborative and mission-driven work environment.

Equal Opportunity Employer: Lookout Santa Cruz is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, or veteran status.

Politics, Policy and Power Correspondent

As Pulitzer Prize-winning Lookout Santa Cruz enters its sixth year, we’re looking for an experienced government and public policy reporter, able to break news, provide near-immediate context and write engagingly and clearly on the many local issues of the day. Santa Cruz County is a vital, active civic community and readers have looked to Lookout for first and best coverage, here mainly focused on the county and the city of Santa Cruz. Have you proven you get under these stories of politics, policy and power and feed reader interest and engagement with Lookout and with the wider communities we serve? We’ve told these stories well for half a decade, with a Pulitzer a pinnacle, but more importantly with every-day, every-week incisive, explanatory journalism distinguishing ourselves.

We prize versatility in storytelling and format and our collegial correspondent team are fast becoming comfortable video creators. We tell our best stories through people, whether dailies or the kind or accountability work that has increasingly sets us apart: https://lookout.co/lookout-santa-cruzs-growing-impact. We are an-person newsroom, now growing from 10 to 12, seeking a new colleague who will immerse themselves in all things Santa Cruz, while knowingly understanding national trends and context.

You are well-versed in data and records, and have begun to use the modern AI tools of the day to aid your work. We’d appreciate seeing your best narrative storytelling, a key part of what readers expect.

About Lookout Local: Earlier this year, we launched our second site with Lookout Eugene-Springfield, to great immediate reception and success. Key in that is the work of Ben Botkin, who has already broken statewide investigative work and established himself as the leading voice in Lane County politics. That work provides a template of what we will produce in Santa Cruz in 2026. Overall, we are building a modern company of journalists and friends in a collaborative, in-office, community-centric environment. As we now plan Lookouts 3-5, we are building a pipeline of ambitious talent.

What is expected of you:

Our reporters will provide timely, useful, and connect-the-dots reporting that distinguishes the Lookout model. Readers know our reporters through the bylines and photos and look to them for reliable news and information.This role involves working deeply into Politics, Policy and Power, collaborating with colleagues on both breaking news and in-depth pieces, and excelling at narrative storytelling. The ideal candidates will provide fair, accurate, and non-partisan news, work at the cadence of digital publishing, and be enthusiastic about the responsible use of newer technologies. We’re looking for journalists who see the power of revived local journalism and have the skills and enthusiasm to be part of a new team doing it.

Responsibilities:

  • Reporting and Storytelling:
    • Provide timely, useful, and connect-the-dots reporting on assigned beats.
    • Create narrative stories that give readers a fair, accurate, and non-partisan sense of the news that matters most to them.
    • Collaborate with colleagues on breaking news and in-depth pieces.
    • Conduct thorough research and investigations, verify facts and cross-check information to ensure reliability.
    • Write clear, concise, and compelling stories in various styles, from breaking news to in-depth features. 
    • Look for ways to help readers participate in their communities and to be of service to them.
  • Digital Proficiency:
    • Work at the cadence of digital publishing, ensuring timely updates and responsiveness to breaking news.
  • Collaboration and Teamwork:
    • Collaborate with fellow journalists and editors to share insights, story ideas, resources, and expertise.
  • Community Engagement:
    • Engage with the community to understand their needs and interests, reflecting this in reporting.
    • Build and maintain a network of sources and contacts. Develop relationships with key community members, officials, and experts.
    • Represent Lookout Santa Cruz at community events and forums.

Qualifications:

  • Proven, relevant experience as a journalist with a track record of timely and impactful reporting.
  • Strong narrative storytelling skills with a commitment to fair, accurate, and non-partisan journalism.
  • Proficiency with digital publishing tools and a keen interest in emerging technologies.
  • Deep understanding of beat reporting and the ability to develop and maintain a network of sources.
  • Demonstrated ability to serve readers’ news and information needs.
  • Excellent communication and interpersonal skills.
  • Ability to thrive in a fast-paced, dynamic environment.
  • Passion for Lookout’s mission and a deep understanding of the local community.

Application Process: Please send your resume and cover letter to jobs@lookoutlocal.com and put Santa Cruz, Politics, Policy and Power Correspondent in the subject line.

Arts, Culture & Entertainment Reporter

As Pulitzer Prize-winning Lookout Santa Cruz enters its sixth year, we’re looking for an energetic, skilled reporter and storyteller enthused and able to cover this wide-ranging in the small cultural mecca, Santa Cruz. Though a community of only 250,000, Santa Cruz is home to many creatives in all lines of performance and wider culture. We’ve told these stories well for half a decade and now as our moves to “emeritus” status, we look for a proven culture writer and reporter to join our expanding team of 12 in the newsroom.

We prize being on top of high and low culture and everything between, and increasingly tell those stories using video and audio as well as text. We are a collegial, in-person newsroom seeking a new colleague who will immerse themselves in all things Santa Cruz, while knowingly understanding national trends and context.

We want a reporter who will go beyond just telling readers what is happening, but tells the stories behind the events and productions. We want a reporter who shines a light on the organizations and culture of Santa Cruz County. You know these people because you talk with them and attend their events. We don’t want a critic, but someone who looks at the community with a critical eye. You will help readers find the best things they’ll want to do and know about, writing guides, profiles and breaking news on this very newsy beat.

You are a storyteller who has or will build a robust database of diverse source. You are passionate about art galleries, dance, classical music and theater as well as the offbeat or non-traditional activities that keep people busy at night and on weekends.

About Lookout Local: We’ve just launched our second site with Lookout Eugene-Springfield, to great immediate reception and success. Key in that is the work of Annie Aguiar, who has hit the ground running and provides a template of what we will produce in Santa Cruz in 2026. We are building a modern company of journalists and friends in a collaborative, in-office, community-centric environment. And as we plan Lookouts 3-5, we are building a pipeline of ambitious talent.

Our mission is to repopulate news deserts, not by protesting financially driven chains, but by creating better local news and local news products, ones that earn both membership and advertising dollars every day. We are building robust local news companies — meant to serve their communities and last. We stand for trustworthy, local, independent journalism. Apply today to join the team.

Position Overview: 

Our reporters will provide timely, useful, and connect-the-dots reporting that distinguishes the Lookout model. Readers know our reporters through the bylines and photos and look to them for reliable news and information.This role involves working deeply into the Arts, Entertainment and Culture community, collaborating with colleagues on both breaking news and in-depth pieces, and excelling at narrative storytelling. The ideal candidates will provide fair, accurate, and non-partisan news, work at the cadence of digital publishing, and be enthusiastic about the responsible use of newer technologies. We’re looking for journalists who see the power of revived local journalism and have the skills and enthusiasm to be part of a new team doing it.

Responsibilities:

  • Reporting and Storytelling:
    • Provide timely, useful, and connect-the-dots reporting on assigned beats.
    • Create narrative stories that give readers a fair, accurate, and non-partisan sense of the news that matters most to them.
    • Collaborate with colleagues on breaking news and in-depth pieces.
    • Conduct thorough research and investigations, verify facts and cross-check information to ensure reliability.
    • Write clear, concise, and compelling stories in various styles, from breaking news to in-depth features. 
    • Look for ways to help readers participate in their communities and to be of service to them.
  • Digital Proficiency:
    • Work at the cadence of digital publishing, ensuring timely updates and responsiveness to breaking news.
  • Collaboration and Teamwork:
    • Collaborate with fellow journalists and editors to share insights, story ideas, resources, and expertise.
  • Community Engagement:
    • Engage with the community to understand their needs and interests, reflecting this in reporting.
    • Build and maintain a network of sources and contacts. Develop relationships with key community members, officials, and experts.
    • Represent Lookout Santa Cruz at community events and forums.

Qualifications:

  • Proven, relevant experience as a journalist with a track record of timely and impactful reporting.
  • Strong narrative storytelling skills with a commitment to fair, accurate, and non-partisan journalism.
  • Proficiency with digital publishing tools and a keen interest in emerging technologies.
  • Deep understanding of beat reporting and the ability to develop and maintain a network of sources.
  • Demonstrated ability to serve readers’ news and information needs.
  • Excellent communication and interpersonal skills.
  • Ability to thrive in a fast-paced, dynamic environment.
  • Passion for Lookout’s mission and a deep understanding of the local community.

Qualifications:

  • At least five years experience at a daily newspaper, magazine or digital outlet as an editor or reporter
  • Experience as a story editor, capable of spotting red flags, reporting holes, buried leads, structural problems and missed opportunities in stories
  • Must be more than a copy editor, with excellent news judgment and great writing skills
  • Excited about – and experienced with – editing younger journalists. Patient and collegial
  • Ability to be flexible in a fast-paced digital news environment
  • Highly collaborative with reporters, editors, photographers and able to work cross-functionally with business and community teams

Application Process: Please send your resume and cover letter to jobs@lookoutlocal.com and put Santa Cruz, Arts, Culture & Entertainment Reporter in the subject line.

Executive Editor

Reports to the CEO 

Position Overview: 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 from our Pulitzer to our fast-ramp launch  and model-building in 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 judgment 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 with the managing editor and community and student engagement manager on a scheduled, steady, and strategic, stream of Lookout Listens and issue-oriented forums. Nationally, becomes another key spokesperson for Lookout’s success and expansion strategy. 

4) Leads, with managing editor, next plans for development and training in the newsroom, creating a development program for journalists, individually, and collectively, setting up a steady cadence of learning/training programs. The executive editor role requires a demonstrated, collegial leader, with substantial newsroom management, well-tested digital and audience experience, and one who excels in building further on both a set of products and a culture of excellence and collaboration. Working with the managing editor, who will direct the newsroom day to day, the ideal candidate both values Lookout’s early success and offers a vision of its next steps, steps that are both mission- and business-building. Deeply using audience analytics, the ideal candidate will proactively assess and recommend initiatives that do both, using emerging digital tools to their optimal points, and work closely with both the newsroom and Lookout’s senior team to advance quickly the work that must be done to push forward Lookout locally and nationally. 

Responsibilities:
● Leadership and Team Management: 

● Lead, along with the managing editor a growing newsroom of skilled journalists, fostering a culture of excellence, innovation, collaboration and reader service. 

● Become a key public presence of Lookout in the civic, business and non-profit communities 

● Mentor and develop journalistic talent, with programs of learning and training, ensuring high standards of reporting and storytelling. 

● Engage with the community to understand their needs and interests, ensuring the newsroom’s work reflects and serves the community. 

● Represent Lookout Santa Cruz at public events and forums, building strong relationships with community members. 

● Aim to build local media partnerships around content and promotion. 

● Editorial Direction: 

● Shapes and guides the next generation of editorial vision and strategy for Lookout Santa Cruz, applying Lookout’s overall model and high standards of reporting, editing and presentation. 

● Reviews current product set and lead adjustments in it with renewed strong focus on audience and analytics, working with managing editor, newsroom team and Lookout’s leadership team. Includes, website, apps, metro, niche and neighborhood newsletters, email alerts, notifications, forums. 

● Proactively innovates touchstone series for which Lookout can claim – and fulfill coverage – on topics of known audience interest

● Puts into effect a story/series planning regimen that maximizes productive work, improves workflow and is of visible use to the Commerce & Community team. 

● Ensures the production of high-quality, engaging, and 

reader-centric news and information products that drive both mission and business results. Shapes expanded “Info Central” vision of positioning Lookout as a center for many kinds of information as well as news. 

● Maximizes regional, state and national content partnerships that add depth to Lookout Santa Cruz’s local-first position. 

● Digital Expertise: 

● Eagerly apply current digital tools and emerging technologies that grow our impact in news delivery and reader engagement. 

● Drive innovation in digital storytelling, ensuring content is optimized for various platforms and devices, and reaches diverse audiences, including increasing integration of video and audio storytelling. 

● Collaboration with Business Side and in Building Lookout Network: 

● Partners, along with the managing editor, with the business team to align editorial and business goals. 

● Work collaboratively to create products and initiatives that meet the needs of readers and support business objectives. 

● Drives larger Lookout network expansion through both Santa Cruz and innovations beyond 

● Editorial Integrity and Standards: 

● Uphold the highest standards of journalistic integrity and ethics. 

● Ensure all content is accurate, fair, and non-partisan. 

Qualifications: 

● Proven, substantial leadership and management experience in a similar role within a news or media organization. 

● Strong background in digital journalism and audience/product-focused analysis and familiarity with current digital tools and platforms. 

● Excellent editorial judgment, great editing chops from daily to investigative storytelling. 

● Demonstrated ability to create and sustain a collaborative, high-performing newsroom culture. 

● Experience working closely with business teams to align editorial and business strategies. 

● Passion for Lookout Santa Cruz’s mission and a deep understanding of the local community. 

● Exceptional communication and interpersonal skills. 

● Ability to thrive in a fast-paced, dynamic environment.

Application Process: Please send your resume and cover letter to jobs@lookoutlocal.com and put Santa Cruz, Executive Editor in the subject line.

Senior Correspondent

Reports to the Managing Editor

This Senior Correspondent position will focus both on their own work and on working with the full team of correspondents, enhancing meaningful, in-depth reporting across our full range of coverage.

Major issues we’ve covered demand deeper and wider coverage, including deeper dives into the criminal system, law enforcement agencies and the courts. There are real issues of jail treatment, opioid overdose response and the familiar mental health challenges that communities face.  

Affordability, the kind and nature of housing and economic development and homelessness head the list of issues the senior correspondent will help report and lead on. Further, the issues of our day – the local impacts of dramatic change in federal funding – pervades and will continue to dominate much coverage going forward. 

The senior correspondent brings a fair, experienced, inventive and nuanced approach to these issues, surfacing fresh reporting. We expect a successful candidate to bring a rich background of accountability and watchdog work, including a knowledge of public records and data journalism, showing the ability to take on broader issues as well as breaking impactful news. The ideal candidate must have demonstrated a command of the reader-focused, people-driven, data-centric reporting that provides readers and communities what they want.

The correspondent will work both independently and collaboratively with editors and fellow correspondents to deepen and broaden our coverage. The demonstrated ability to collaborate is a must. 

If you are interested, please respond with a cover letter describing your capabilities, demonstrating relevant experience and drive to this work, and include relevant examples of it. 

Responsibilities: 

  • Lead our accountability agenda, working with editors to identify and prioritize opportunities for investigative, enterprise and in-depth reporting across the newsroom.
  • Produce quick-turn and long-term accountability stories that meet the needs of a fast-paced newsroom.
  • Work with and mentor other reporters to develop in-depth stories on their beats and spanning multiple beats, including assisting with records requests and source development.
  • Be a newsroom leader on investigative tools, such as Nexis, public records and datasets (publicly available or compiled) that can be mined for stories.
  • Track an ongoing newsroom-wide database of FOIA and public records requests.

Essential Skills:

  • Eight to 10 years of experience as a daily news reporter, demonstrating significant accountability work.
  • Demonstrated proficiency with open records laws and libel laws.
  • Ability to work in a fast-paced environment and handle multiple and changing priorities simultaneously.
  • Excellent news judgment and outstanding writing and editing skills, including an ability to turn investigative reporting into compelling narratives.
  • Data journalism skills, particularly data collection and data analysis.
  • Comfort with the format of Lookout’s correspondent-focused model, and the personality it brings to the work.
  • Desire to work in an entrepreneurial, fast-growth startup environment, embracing the agility and flexibility required to thrive within a new business.

Nice to have:

  • Bilingual abilities in Spanish and English.
  • Editing abilities are a plus.
  • Ability to create visualizations that aid storytelling. 
  • Evolving applied knowledge of AI use.

Application Process: Please send your resume and cover letter to jobs@lookoutlocal.com and put Santa Cruz, Senior Correspondent in the subject line.

Marketing Manager (National)

Lookout Local
Location: Santa Cruz, CA or Eugene, OR (Hybrid or Remote within Pacific Time preferred)

Reports to: Chief of Staff

About Lookout

Lookout Local is growing — fast. We’re expanding a network of independent, community-first newsrooms across the West, starting with Lookout Santa Cruz and Lookout Eugene-Springfield. We’re looking for a Marketing Manager to help lead the next phase of our audience growth.

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.

This role sits at the intersection of growth marketing, PR, and execution. You’ll be responsible for strengthening Lookout’s local and national profile and driving top-of-funnel audience growth, maximizing our earned, owned and paid channels. This is a hands-on role for someone who loves building, testing, measuring, and refining — from strategy through design, copy, launch, and reporting. You’ll work closely with our energetic teams of business-side managers and newsrooms as Lookout accelerates its success and growth.

What You’ll Do

This role sits at the intersection of growth marketing, PR, and execution. You’ll be responsible for strengthening Lookout’s local and national profile and driving top-of-funnel audience growth, maximizing our earned, owned and paid channels. This is a hands-on role for someone who loves building, testing, measuring, and refining — from strategy through design, copy, launch, and reporting. You’ll work closely with our energetic teams of business-side managers and newsrooms as Lookout accelerates its success and growth.

Top-of-Funnel Audience Growth (Core Focus)

  • Own Lookout Local’s top-of-funnel growth strategy across current and new markets, meeting growth goals
  • Drive awareness, reach, and first-touch engagement with new readers, newsletter subscribers, and app users
  • Identify who our next best audiences are in each market and how their needs, habits, and entry points differ
  • Grow newsletter signups, app installs, and first-time readers with a focus on quality, not just volume
  • Ensure Lookout’s value proposition is clear to people who have never heard of us before
  • Work seamlessly with Membership Growth Manager in working the entire funnel toward sustained conversion and retention 

Audience Intelligence & Analytics

  • Lead audience learning across markets: who is coming to our platforms (website, app+), where they’re coming from, and what converts
  • Track and report on top-of-funnel KPIs (reach, acquisition sources, engagement signals, cost efficiency)
  • Partner with editorial, membership, and leadership to connect acquisition behavior to downstream outcomes (engagement, retention, conversion)
  • Use GA4, newsletter data, campaign performance, and platform insights to identify patterns and opportunities
  • Turn insights into action — refining messaging, channels, audience targeting, and timing
  • Help leadership understand what’s working, what’s scalable, and what’s not worth repeating

Campaign Strategy & Demand Generation

  • Design and execute multi-channel acquisition campaigns (email, social, partnerships, paid, earned media)
  • Continuously test messaging, formats, and channels to improve acquisition efficiency
  • Identify high-performing growth loops (newsletters, events, referrals, app, SEO, social) and help scale them
  • Work with leadership staff to create repeatable growth playbooks that can be adapted and reused as Lookout enters new markets
  • Balance experimentation with discipline — learning fast while avoiding one-off or unsustainable wins

Brand, PR & Market Expansion Support

  • Strengthen Lookout Local’s brand locally and nationally as a growing network of newsrooms
  • Support launches of new sites, products, newsletters, and major milestones with clear go-to-market strategies
  • Lead or support earned media and partnership outreach to expand reach and credibility
  • Ensure consistent positioning across markets while preserving each newsroom’s local voice and relevance

Execution & Cross-Team Collaboration

  • Own campaigns end-to-end: planning, creative coordination, launch, optimization, and reporting
  • Collaborate closely with newsroom leaders, membership, product, and community engagement teams
  • Translate editorial priorities and product launches into audience-facing growth opportunities
  • Manage multiple campaigns across multiple markets without losing clarity or momentum
  • Balance experimentation with discipline, building a sustainable growth engine rather than one-off wins

What We’re Looking For

  • 5+ years of experience in growth marketing, audience development, or digital marketing
  • Proven ability to own campaigns end-to-end, from strategy to execution to reporting
  • Strong writing and editing skills, with an eye for clear, effective messaging
  • Experience with email marketing platforms (ActiveCampaign or similar)
  • Comfort working in CMS-driven websites (WordPress/Newspack a plus)
  • Analytical mindset with experience using data to drive decisions
  • Highly organized, detail-oriented, and comfortable managing multiple campaigns at once
  • Excited by local journalism, civic engagement, and building something meaningful

Bonus Points

  • Experience working in media, journalism, or subscription-based businesses
  • Smart, evolving use of AI
  • Familiarity with Broadstreet, Newspack, Firebase, or newsroom workflows
  • Experience supporting multi-market or networked organizations
  • Background in PR, partnerships, or brand marketing

Application Process: Please send your resume and cover letter to jobs@lookoutlocal.com and put MARKETING MANAGER in the subject line.

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

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:

  1. Platform-wide leadership — optimizing Lookout’s core product ecosystem for engagement, information utility, and revenue.
  2. 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

Application Process: Please send your resume and cover letter to jobs@lookoutlocal.com and put PRODUCT SUCCESS in the subject line.