Careers - O'Rourke Media Group

Career Opportunities

At O’Rourke Media Group, our people are what makes us different. If you thrive in a fast-moving, results-driven environment with no BS, politics or red tape in the way of making things happen, we’d love to hear from you.

Why work for us

Fun, collaborative, open work environment
Meaningful, mission-driven work that makes a difference in the communities we serve
Great benefits
Opportunity for advancement
Industry-leading results and a winning culture

If you are interested in any current job openings or would like to be considered for future opportunities, please email your resume and letter of interest to the hiring manager listed on job opening or Jim O’Rourke at jorourke@orourkemediagroup.com.

Sales Director - Delaware

O’Rourke Media Group is recruiting for a results-driven Sales Director for our business in Delaware, Maryland and Virginia. The ideal candidate will bring a proven track record of achieving revenue growth, will have strong digital acumen and will be effective with building trusted relationships with local businesses. We’re looking for someone that works well with people to get stuff done. This position is a hybrid arrangement but required to spend time at our office in Seaford DE and must live in our market area.

The Guide is Delmarva’s premier advertising niche product, casting a wide print distribution and engaged online audience. Sussex Printing has been Delmarva’s leading printer since 1959. O’Rourke Media Group also brings a fast-growing, internal full-service digital agency, offering everything from website development, SEM, SEO, Facebook advertising, content marketing services and much more. We’re truly a one-stop shop, providing advertising, marketing and promotions support for local businesses.

Job Responsibilities

Manage and motivate a team of account executives to effectively sell print and digital, multichannel advertising and marketing solutions to local businesses.
Recruit, hire and train Account Executives.
Individual account management and new business development.
Grow digital revenue in and outside our core business footprint.
Experienced and proven skills with prospecting, getting appointments, presenting, and closing.
Effective building relationships with customers, account executives, fulfillment team members, and other stakeholders in OMG.
Drive Printing & Design sales.
Provide superior service that transcends to excellent retention with advertisers.
Network, engage and be active in the communities we serve.

Job Requirements

Minimum five years of sales experience.
Minimum five years of management experience.
Strong communication and time management skills.
Negotiating experience.
High proficiency in MS Excel and other technology applications.

Compensation Package Details

Competitive base plus commissions.
Car allowance.
Medical benefits, vision, dental and PTO.
401 (k) savings plan.
Will consider reasonable reimbursement for relocation.
Opportunity for career advancement and earnings growth.

About the Parent Company

O’Rourke Media Group is a family-owned, diversified media company that was formed in 2018. Originally just a holding company that owned a few newspapers, O’Rourke Media Group (OMG) has established itself as an industry-leading, digital media company comprising a cutting edge digital agency and an impressive group of award-winning, hyper-local print newspapers and niche magazines. OMG now operates in eight states, 36 markets with over 50 publications and hyper-local websites.

Interested candidates should send their resume to: Jorourke@orourkemediagroup.com

Reporter - Pagosa Springs, CO

O’Rourke Media Group is searching for a talented reporter to fill a full-time position in Pagosa Springs, Colorado, at The Pagosa Springs SUN.

Our journalists are driven to find stories that matter to our community and are dedicated to fairness, accuracy, and ethics. The successful candidate for this position is someone who knows how to cover hard news but also loves to write about people and their passions. They know that a good interview is often a good conversation and know when to ask the tough questions, but also when to listen. The ideal candidate has exceptional writing skills and is willing to put in the extra effort and research to deliver an engaging story.

Preferred qualifications for this position include:

Degree or diploma in journalism, or a related field;
At least 1-3 years of experience as a reporter with experience covering hard news and feature stories or experience at a college newspaper;
The ability to meet tight deadlines and report the news as it happens;
Superior language, writing and editing skills;
Strong photography skills;
Able to work a variety of schedules, including evenings, nights and weekends;
Excellent critical thinking and problem-solving skills;
Ability to work in a fast-paced environment;
A valid driver’s license and a reliable vehicle;
Willingness to live in or near Pagosa Springs, Colorado.

If this sounds like the perfect position for you, we would love to hear from you! To apply, please send your resume, letter of interest and relevant samples of your work to Chad Richardson, Vice President of News, crichardson@orourkemediagroup.com.

Company Benefits

We offer competitive compensation plans and employees are eligible for medical, dental, vision, life insurance benefits, paid time off and our 401 (k) savings plan. This is an excellent opportunity for career development and growth within the company.

O’Rourke Media Group is a fast-growing company that owns and operates hyper-local, community newspapers, websites, niche publications and a full-service digital agency. We are family-owned and mission-driven to save newspapers and local media companies by investing in the people, resources and technology needed to thrive for many years to come. We believe that every community can benefit from a well-run, properly resourced, local newspaper and website. Our News teams produce hyper-local, high interest local news and accurate and trustworthy reporting. Our Sales and Digital Fulfillment teams bring omnichannel advertising solutions to local businesses in the communities we serve.

O’Rourke Media Group now operates in nine states and 38 markets with 51 publications and hyper-local websites. We started from ground zero in December 2018, totally bootstrapped, confident and with an entrepreneurial mindset.

Salary: $38,000 to $39,000

Account Executive - Greater Phoenix Area, AZ

O’Rourke Media Group is helping businesses in the Greater Phoenix area grow with powerful advertising solutions across multiple platforms. Our City Sun Times brand offers businesses the ability to reach engaged local audiences through a monthly print publication, dynamic news site, newsletters, and engaging social platforms, while the Queen Creek Sun Times provides a loyal and growing readership ideal for targeted marketing. With digital advertising, sponsored content, and customized marketing strategies, we connect businesses with the right customers, helping them thrive in an ever-evolving market.

We are seeking a proactive and results-driven Account Executive to serve as the primary liaison between our media organization and our clients in the greater Phoenix area. The ideal candidate will be responsible for managing client relationships, developing strategic advertising campaigns, and driving revenue growth by identifying new business opportunities within the Phoenix, Scottsdale, Tempe & Chandler areas.

Key Responsibilities:

New Business Development: Identify and pursue opportunities to acquire new clients, expanding our portfolio and driving revenue growth.
Client Relationship Management: Act as the main point of contact for clients, understanding their advertising needs, and providing strategic guidance to achieve their marketing objectives.
Campaign Planning and Coordination: Collaborate with clients and internal teams to develop comprehensive advertising strategies across various media platforms, ensuring alignment with clients’ brand guidelines and goals.
Performance Monitoring and Reporting: Analyze the effectiveness of advertising campaigns, providing clients with detailed reports and insights to inform future strategies.

Qualifications:

Experience: Proven success in media sales or advertising account management, with a track record of meeting or exceeding revenue targets. We are willing to consider candidates from outside of the media industry that have b2b sales experience.
Communication Skills: Exceptional verbal and written communication abilities, capable of articulating ideas clearly and persuasively to clients and internal teams.
Analytical Skills: Proficiency in analyzing market trends and campaign performance metrics to make data-driven decisions.
Technical Proficiency: Familiarity with digital marketing tools, social media platforms, and customer relationship management (CRM) software.
Education: A bachelor’s degree in marketing, advertising, communications, or a related field is preferred.

At O’Rourke Media Group, we value innovation, collaboration, and a commitment to customer excellence. We offer a competitive salary, comprehensive benefits package, and opportunities for professional growth within a supportive and dynamic work environment.

Interested candidates are encouraged to send their resume and a cover letter detailing their relevant experience and explaining why they are a good fit for this role to COO, Caleb Anderson at canderson@orourkemediagroup.com.

Sales Director - Vermont

O’Rourke Media Group is recruiting and will be offering excellent, above market compensation for a results-driven Sales Director at our business in Vermont. The ideal candidate will bring a proven track record of achieving revenue growth, will have strong digital acumen and will be effective with building trusted relationships with local businesses. We’re looking for someone who works well with people to get stuff done. This position is a hybrid arrangement but required to spend time at our office in St Albans, VT and must live in our market area (Franklin or Chittenden County).

The St. Albans Messenger is a very strong paid, community newspaper and website serving Franklin County, VT. The Essex Reporter and Milton Independent are excellent hyper-local, free monthly newspapers distributed to 100% of the households in their respective communities. Currently, the Colchester Sun is online only. We have an ambitious plan to expand and add more monthly print newspapers and local news sites in Chittenden County.

In addition to selling advertising to local businesses, our Vermont team offers a full range of printing and design services. We’re truly a one-stop shop, providing advertising, marketing and promotions support for local businesses.

Job Responsibilities

Manage and motivate a team of account executives to effectively sell print and digital, multichannel advertising and marketing solutions to local businesses.
Recruit, hire and train Account Executives.
Individual account management and new business development.
Grow digital revenue in and outside our core business footprint.
Experienced and proven skills with prospecting, getting appointments, presenting, and closing.
Effective building relationships with customers, account executives, fulfillment team members, and other stakeholders in OMG.
Drive Printing & Design sales.
Provide superior service that transcends to excellent retention with advertisers.
Network, engage and be active in the communities we serve.

Job Requirements

Minimum five years of sales experience.
Minimum five years of management experience.
Strong communication and time management skills.
Negotiating experience.
High proficiency in MS Excel and other technology applications.

Compensation Package Details

Competitive base plus commissions.
Car allowance.
Medical benefits, vision, dental and PTO.
401 (k) savings plan.
Will consider reasonable reimbursement for relocation.
Opportunity for career advancement and earnings growth.

About the Parent Company

Interested candidates should send their resume to: Jorourke@orourkemediagroup.com

Account Executive - Ripon, WI

O’Rourke Media Group is looking for an Account Executive to help grow our business in Ripon, Green Lake, and surrounding areas in Wisconsin. We have an excellent brand and engaged print and digital audience with the Ripon Commonwealth Press, the paid weekly newspaper of record in Ripon, along with the seasonal Green Laker, which is published 10 times a year, from May to September. We’re also expanding our digital agency in Green Lake County, offering local businesses website development, content marketing, SEM, SEO, Facebook Advertising, targeted email marketing, and much more.

If you’re driven, confident, and love talking to people, this is your shot to break into a career with excellent earning potential and career growth.

What You’ll Do:

Sell Ads + Marketing: Help local businesses grow with smart advertising across multichannel platforms.
Make Connections: Build relationships with clients in our market area.
Manage Campaigns: Work with our creative team to build advertising plans that deliver results.
Track Success: Show clients how their ads are working and keep upselling.

What We’re Looking For:

Sales experience (B2B or media sales is a plus—but if you’ve got hustle, we’ll teach you!).
Great communication skills—you’re confident, friendly, and know how to get people’s attention.
A curious mind—interested in marketing, local business, and learning fast.
Comfortable with tech tools like social media, email, and CRMs.

What’s in It for You:

Excellent earning potential – Base pay + commission
Training + growth – Career development in media and marketing
Awesome team vibe – We win together and support each other
Benefits – PTO, health, dental, vision, and more

O’Rourke Media Group is a family-owned, diversified media company that was formed in 2018. Originally just a holding company that owned a few newspapers, O’Rourke Media Group (OMG) has established itself as an industry-leading, digital media company comprising a cutting-edge digital agency and an impressive group of award-winning, hyper-local print newspapers and niche magazines. OMG now operates in eight states, 36 markets, with over 50 publications and hyper-local websites.

To be considered, email your resume and a quick intro to Jade Lewandowski, VP of Sales at jade@orourkemediagroup.com

Account Executive – Sheboygan, WI

O’Rourke Media Group believes a digital-first approach to sharing information helps communities thrive, and we’re bringing this approach to Sheboygan through the Sheboygan Sun and other platforms. By delivering local news quickly and accessibly, while offering innovative digital marketing solutions, we’re supporting community growth and helping local businesses connect with their audience. Through partnerships with organizations like the Sheboygan Chamber of Commerce, we’re fostering a vibrant, connected community.

We are seeking a proactive and results-driven Account Executive to serve as the primary liaison between our media organization and our clients in Sheboygan, Wisconsin. The ideal candidate will be responsible for managing client relationships, developing strategic advertising campaigns, and driving revenue growth by identifying new business opportunities within the Sheboygan area.

Key Responsibilities:

New Business Development: Identify and pursue opportunities to acquire new clients, expanding our portfolio and driving revenue growth.
Client Relationship Management: Act as the main point of contact for clients, understanding their advertising needs, and providing strategic guidance to achieve their marketing objectives.
Campaign Planning and Coordination: Collaborate with clients and internal teams to develop comprehensive advertising strategies across various media platforms, ensuring alignment with clients’ brand guidelines and goals.
Performance Monitoring and Reporting: Analyze the effectiveness of advertising campaigns, providing clients with detailed reports and insights to inform future strategies.

Qualifications:

Experience: Proven success in media sales or advertising account management, with a track record of meeting or exceeding revenue targets. We are also open to candidates from outside the media industry with B2B sales experience.
Communication Skills: Exceptional verbal and written communication abilities, capable of articulating ideas clearly and persuasively to clients and internal teams.
Analytical Skills: Proficiency in analyzing market trends and campaign performance metrics to make data-driven decisions.
Technical Proficiency: Familiarity with digital marketing tools, social media platforms, and customer relationship management (CRM) software.
Education: A bachelor’s degree in marketing, advertising, communications, or a related field is preferred.

At O’Rourke Media Group, we value innovation, collaboration, and a commitment to customer excellence. We offer competitive compensation, health, dental, and vision benefits, a 401(k) retirement plan, ongoing training, and a fun, supportive team culture.

Interested candidates are encouraged to send their resume and a cover letter detailing their relevant experience and explaining why they are a good fit for this role to VP of Sales, Jade Lewandowski, at jade@orourkemediagroup.com.