Lookout Santa Cruz Positions:

Lookout Eugene-Springfield Positions:

National Team Positions:

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.

Managing Editor

Position Overview

The Managing Editor is a central newsroom leader responsible for driving editorial excellence across Lookout Santa Cruz’s coverage of Santa Cruz County and, secondarily, the surrounding region. This role requires a proven editor with a track record of elevating ambitious journalism and leading teams of reporters across multiple beats to produce distinctive, high-impact work.

The ideal candidate brings exceptional news judgment, sophisticated story ideation, and rigorous line editing skills — along with a demonstrated ability to coach reporters to do their best work. Just as important, this editor thrives in a fast-paced, digital-first environment and is deeply committed to building a consistently excellent, seven-day-a-week report.

At Lookout, excellence is not occasional — it is expected throughout the day, every day. We serve readers with a mix of investigative and accountability reporting, authoritative beat coverage, breaking news, and service journalism that answers real community questions. The Managing Editor ensures that this work meets a high bar for relevance, clarity, and impact.

We prioritize reporting that connects the dots, explains complex issues, and delivers insight with authority and precision. Whether a story is 500 or 2,500 words, it should be deeply reported, well sourced, and clearly written. We embrace a range of formats — from narrative and explanatory stories to Q&As, reader-driven formats, and multimedia — always matching the format to the journalism.

Lookout Santa Cruz serves as the founding site of Lookout Local, now serving both Santa Cruz County and Lane County, Oregon, with Lookout Eugene-Springfield, launched in April, 2025.

As illustrated by a 2024 Pulitzer win, Lookout Local newsrooms focus on impactful stories, quickly becoming the go-to local news source in their communities. More up-to-date background on us, and related media coverage, here: https://lookout.co/network

Key Responsibilities

Editorial Leadership & Team Development

  • Work with the Executive Editor to set the daily and long-term editorial agenda.
  • Lead and manage a team of reporters covering a range of beats, providing clear direction from idea generation through publication.
  • Edit stories with rigor and precision, ensuring clarity, depth, fairness, and distinctiveness.
  • Coach reporters to elevate their reporting, sharpen their focus, and produce ambitious, high-impact journalism.
  • Foster a culture of accountability, creativity, and continuous improvement across the newsroom.

Story Ideation & Execution

  • Drive a strong pipeline of enterprise, investigative, and beat-driven stories.
  • Ensure daily coverage is urgent, relevant, and aligned with audience needs.
  • Elevate storytelling through structure, framing, and the use of compelling supporting elements (data, visuals, multimedia).
  • Maintain high standards for sourcing, reporting depth, and narrative clarity.

Community-Centered Journalism

  • Ensure coverage reflects and engages the full diversity of Santa Cruz County.
  • Work with reporters to surface community concerns, questions, and undercovered issues.
  • Collaborate on audience engagement efforts, using feedback and insights to inform coverage.

Standards & Trust

  • Uphold the highest standards of accuracy, fairness, and independence.
  • Ensure all content is nonpartisan, transparent, and trustworthy.
  • Maintain consistency in voice, tone, and editorial quality across the report.

Innovation & Digital Execution

  • Embrace and advance digital-first storytelling, distribution, and audience strategies.
  • Work closely with product and audience teams to optimize reach and impact.
  • Use modern tools and platforms to enhance reporting, editing, and presentation.
  • Experiment thoughtfully with new formats, including video and reader-driven journalism.

Qualifications

  • At least 7+ years of journalism experience, including 3+ years in a significant editing or newsroom leadership role.
  • A proven track record of journalistic excellence, particularly in editing and elevating reporters across multiple beats.
  • Demonstrated success leading teams to produce impactful enterprise, investigative, and beat reporting.
  • Exceptional news judgment, story sense, and editorial instincts.
  • Strong line-editing skills, with the ability to bring clarity, structure, and authority to complex stories.
  • Experience managing reporters, providing constructive feedback, and developing talent.
  • Deep understanding of — or ability to quickly immerse in — Santa Cruz County and its communities.
  • Fluency in digital-first journalism and content management systems (Newspack or similar).
  • Ability to balance speed with quality in a deadline-driven environment.
  • Commitment to inclusive, community-centered journalism.
  • Comfort working in a startup environment that values agility, collaboration, and innovation.
  • Strong visual and storytelling instincts, with the ability to collaborate on multimedia presentation.

Pluses:

  • Bilingual skills
  • Experience with data journalism
  • Audio/video production experience

Additional Details

The Managing Editor position is a full-time, on-site position based in Santa Cruz, California. We pride ourselves on our in-person, in community local news daily presence.

Application Process

Please send your resume and cover letter to jobs@lookoutlocal.com with “Santa Cruz, Managing Editor” 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 Eugene-Springfield 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.

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.

Managing Editor (Eugene-Springfield)

Position Overview:

The Managing Editor applies the Lookout Local journalism model. The ideal candidate will demonstrate well-experienced news judgment, excellent story ideation and line editing skills and most of all be committed to creating a great seven-day-a-week news report. 

At Lookout Local, our revival of local journalism starts by producing excellence every day, throughout the day, serving readers’ evolving needs with a wide range of meaningful and local/personal journalism, responsive to our diverse communities’ changing needs. The managing editor must be comfortable and enthusiastic about the wide range of content we will deliver, from investigative and accountability work, to best-in-class beat stories, breaking news and service journalism that answers readers’ questions.

As illustrated by a 2024 Pulitzer win, Lookout Local newsrooms focus on impactful stories and, while being a primary news source, keep our readers briefly updated on step-by-step governmental proceedings and other actions. We are high on explanatory, connect-the-dots reporting and pointed knowing writing. Whether in 500 or 2,500 words, we tell the readers what we know, well-sourced and well-told. We fit the formats to the content, using Q&As and Ask Lookouts, and other emerging formats – including video – in addition to narrative journalism.

We need a Managing Editor with extensive story-editing experience and a track record of leading teams of journalists. The ideal candidate brings deep knowledge of the Eugene-Springfield area, Oregon and/or the Pacific Northwest.

Responsibilities:

  • Editorial Direction:
    • Working with the Executive Editor, the Managing Editor will help direct the daily newsroom, working with correspondents in planning, reporting, sourcing and first-line editing.
    • The managing editor will ensure we are producing high-quality, trustworthy, non-partisan stories and community information, working with Lookout colleagues on multiple evolving products to distribute that content.
  • Community Engagement:
    • Help lead Lookout’s overall community engagement work, working with both correspondents and the wider Lookout team.  
    • Look for ways, in digital and in person, to gain reader insights and feedback.
    • Represent Lookout Eugene-Springfield at community events, strengthening its role as a trusted local institution.
  • Maintain and Strengthen Standards:
    • Ensure content meets the highest journalistic standards of fairness, accuracy, and clarity, delivered with trustworthiness and lack of partisanship.
  • Innovation and Growth:
    • Apply the full toolbox of modern digital creation and distribution tools, working closely with colleagues especially in audience analysis.

Qualifications:

You should have at least seven years of journalism experience, and at least three as a newsroom manager. The position is on-site, in our collaborative office in downtown Eugene.

  • Rock-solid journalism judgment, intuition and taste. 
  • Demonstrated experience, with references to match, on story editing, news publication and deadline experience as well as proven ability to edit with painstaking clarity, providing readers with the context they need. 
  • Adept at using Newspack or modern content management systems and tools.
  • Desire to work in an entrepreneurial, fast-growth startup environment, embracing the agility and flexibility required to thrive within a new business. 
  • Experience and comfort with the pace of digital-first journalism, and the digital technologies that power it. 
  • Ability to engage diverse local communities in Lookout’s work. 
  • Ability to think through visuals that will aid storytelling and work with colleagues to activate them. 
  • Demonstrated adaptability, especially with new topical coverage areas and communities.
  • Comfort learning new technology and experience working in content management systems, producing, editing and dressing stories with related media (photos, videos, etc).
  • Comfort with the format of Lookout’s correspondent-focused model, and the personality it brings to the work. 
  • Plusses: Bilingual abilities, data, and audio/video.  

The Managing Editor position is a full-time Lookout Local employee. We offer competitive employee benefits.

Hiring process
As part of our process for senior editorial leadership roles, we ask finalists to complete a short leadership and work-style assessment.

The assessment focuses on how candidates collaborate across teams, make decisions under pressure, and lead in complex environments. It is not a clinical or diagnostic test, and there are no “right” personality types.

We use results as one input among several, alongside interviews, references, and past work.

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

Photojournalist

Position Overview

At Lookout Local, our revival of local journalism starts by producing excellence every day, throughout the day, serving readers’ evolving needs with a wide range of meaningful and local/personal journalism, responsive to our diverse communities’ changing needs. The managing editor must be comfortable and enthusiastic about the wide range of content we will deliver. That includes investigative and accountability work, best-in-class beat stories, breaking news and service journalism that answers readers’ questions.

As illustrated by a 2024 Pulitzer win, Lookout Local newsrooms focus on impactful stories and while being a primary news source, keep our readers briefly updated on step-process governmental proceedings and other actions. We are high on explanatory, connect-the-dots reporting and pointed knowing writing. Whether in 500 or 2,500 words, we tell the readers what we know, well-sourced and well-told. We fit the formats to the content, using Q&As and Ask Lookouts, and other emerging formats – including video – in addition to narrative journalism. See more on Lookout here.

Lookout Eugene-Springfield has an opening for a community-focused photojournalist with sports proficiency and experience shooting and editing social video to join our outstanding collegial team

We need a visual storyteller who goes beyond taking images to accompany stories and understands that a photojournalist creates images that expand our correspondents’ storytelling.

Lookout staff is engaged in the community both through the work we do as well as by participating in tabling at community events, school visits and Lookout Listens sessions with members.

The University of Oregon is a significant part of our coverage, so a demonstrated proficiency in sports photography is a must for the ideal candidate.

At Lookout, we believe that photojournalism is not just complementary and our journalist should have a genuine curiosity and willingness to cover assignments solo, delivering compelling visuals, informative cutlines and written reports. Check out the best of our first year’s impact work and photojournalism, here. 

The demands of the position include fast-paced daily journalism and long-term storytelling. There is a great deal of independence and all Lookout journalists are expected to be expert planners, teammates and communicators.

Lookout Eugene-Springfield is home to a cyclorama photo studio, which should be a playground for our photojournalist and our ideal candidate will have ideas for how to use this space to create visuals that engage our community.

Our ideal photojournalist has a drone license and ideas for integrating aerial photography into our regular coverage.

Mentoring is a key part of this position, and the photojournalist will work with correspondents on best practices in visual storytelling as well as with a summer photography intern.

The position is expected to start June 22, 2026.

Responsibilities:

  • Document breaking news, features, sports, business, arts and community events through still and video journalism
  • Produce social-first video content for platforms including Instagram and YouTube
  • Capture and edit short-form video, interviews, reels and behind-the-scenes content
  • Develop strong relationships within the community to identify visual storytelling opportunities
  • Cover high school and Division I college sports with an emphasis on action photography and storytelling
  • Work collaboratively with correspondents and editors to develop multimedia coverage plans
  • Quickly edit and transmit photos and video on deadline
  • Develop individual enterprise visual projects 
  • Write accurate captions, gather basic reporting information and contribute to story development
  • Help grow audience engagement through compelling visual journalism and active community presence
  • Represent the organization professionally at public events and in community settings
  • Maintain and organize photo and video archives
  • Be an adept problem solver
  • The photjournalist position is a full-time, on-site position based in Eugene, Oregon. We pride ourselves on our in-person, in-community presence in daily local news.

Qualifications:

  • Experience in photojournalism, visual storytelling and multimedia reporting
  • Strong photography skills with knowledge of composition, lighting and action photography
  • Experience shooting and editing social video content
  • Familiarity with Adobe Creative Suite, Photo Mechanic and mobile editing tools
  • Ability to work independently and manage multiple assignments on deadline
  • Strong communication and interpersonal skills
  • Comfortable engaging with community members, public officials, athletes and event organizers
  • Understanding of social media trends and audience engagement strategies
  • Be flexible: Willingness to work evenings, weekends and non-regular hours as news and events require
  • Valid driver’s license and reliable transportation required
  • Have complete photojournalist gear, including lenses needed for sports photography and lighting for studio work
  • Experience covering sports photography at the high school or collegiate level
  • Drone license and aerial photography experience
  • Knowledge of AP Style caption writing
  • Experience working in a digital-first newsroom
  • Familiarity with live social coverage and real-time publishing workflows

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 Eugene-Springfield 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.

About Lookout Eugene-Springfield:

In one year, Lookout Eugene-Springfield has become the largest local newsroom in Lane County and is the destination for local news and information for this community. Known for journalism that goes beyond the superficial, Lookout staff always put the community at the center of our coverage.

Lookout is a full-time, in-person newsroom with an office located in downtown Eugene.

If you believe local journalism is built through relationships and visibility in the community, if you are curious, approachable, creative and eager to experiment with new storytelling formats while maintaining strong journalism standards, you could be the right fit for Lookout.

Application Process:

Please send your resume and cover letter to jobs@lookoutlocal.com with “Eugene Photojournalist” in the subject line.

Business and Development Correspondent (Eugene-Springfield)

Position Overview:

Lookout Eugene-Springfield’s Business and Development Correspondent will approach the beat with a broad lens, focusing on issues and trends as much as what is opening and closing. The ideal candidate understands the role of business in shaping a community through taxes and jobs as well as the cost of doing business in Lane County and greater Oregon.

An interest in how the business culture in the state impacts the local economy and the desire to tell these larger stories is important.  While this is an inherently local beat, we understand that statewide factors impact the local economy and telling this story is important. This correspondent has the potential to impact the local and statewide business culture with their coverage.

Finally, the heart of all stories are people, those who are impacted by decisions being made and this correspondent will seek out voices of real people as the foundation for our coverage.

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.
    • Comfortable with social media platforms and integrating them into how we tell stories.  This includes on-camera video work.
  • 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.
    • Enthusiastically represent Lookout Eugene-Springfield 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 Eugene-Springfield’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 “Eugene, Business Correspondent” 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

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

How to Apply

Please send your resume and cover letter to jobs@lookoutlocal.com and put PRODUCT SUCCESS 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
  • An opportunity to make a significant impact on and contribute to the revival of local journalism.
  • A collaborative and mission-driven work environment.

Hiring process
As part of our process for senior editorial leadership roles, we ask finalists to complete a short leadership and work-style assessment.

The assessment focuses on how candidates collaborate across teams, make decisions under pressure, and lead in complex environments. It is not a clinical or diagnostic test, and there are no “right” personality types.

We use results as one input among several, alongside interviews, references, and past work.

Equal Opportunity Employer: Lookout Eugene-Springfield 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.