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Professional Sales Executives

Beth’s comments are typical of our multimedia sales executives. If that sounds appealing to you, we’re looking for more energetic, entrepreneurial achievers who are outgoing and money-motivated.

  • If you can talk with confidence to business owners to identify their goals …
  • If you are willing to prospect and meet new people to learn about their business objectives …
  • If you have high self-esteem and confidence …
  • If your presentation skills separate you from the pack …
  • If you are not easily intimidated by business owners who may be “old school” …
  • If you are articulate and looking for the highest quality in your employer and in yourself …

… This is the place for an exciting and rewarding sales and marketing career!

We offer competitive compensation with the opportunity for six-figure earnings, full benefits and a culture that encourages innovation and entrepreneurism.

With Observer Media Group, you find a company that offers rewarding work that makes a difference in the community. It’s a place where the company’s leaders value all their associates and are committed to helping them grow and succeed — professionally, personally and financially. It’s a place where everyone strives for excellence.

We have immediate openings in Sarasota, Winter Garden-Windermere, Winter Park, Palm Coast, Port Orange and Jacksonville.
Please send resume and cover letter to:
Penny DiGregorio, Advertising Sales Manager,
1970 Main St., 3rd Floor
Sarasota, FL 34236 
[email protected]

Graphic Designer

Our graphic designers not only win Addys for their advertising designs, but they also are award-winning designers of special dog couture.

The #1 trait of our graphic designers is creative flair. But they also understand the principles of effective advertising design — being able to work with our advertising sales team to conceptualize and execute print and digital ads that generate response and create memorable brands for our customers.

Our designers must have a thorough grasp and flair for style and proportion; and how type, fonts and color work with images. In addition to advertising design, our designers also create brochures, media kits, posters, letterhead; business cards; and all varieties of digital ads — animated, videos, interstitial, etc.  

Ideal candidates have a positive attitude; are able to work in a collaborative, team environment; and must be able to meet deadlines and work under deadline pressure. 

We offer a competitive compensation plan, including full benefits, dynamic, fast-paced work environment; and the opportunity to grow professionally.

We currently have openings for a graphic designer in the Sarasota and Winter Garden locations. 

Please send cover letter, resume and five samples of recent work to:
Caleb Stanton, Creative Director
[email protected]

IT technician / Help Desk

Wanted: An IT technician who loves computers — and people

Have you been a computer nerd since childhood? Do you love the rush you get when  coworkers cheer you for saving the day? Have we got the job for you. 

The Observer Media Group is looking for someone who is as passionate about helping people as he or she is about computers. This is not an IT help desk where you sit in a cubicle answering calls. It is an interactive, high-paced and versatile work environment where no two days are the same.

We are a growing publishing company packed with interesting and complex IT challenges. That means we need someone who is flexible, curious, willing to learn and who loves to solve problems and be the hero for their colleagues. The right individual will thrive on juggling multiple responsibilities and prioritizing tasks to attack and complete projects. He or she will be a talented plate-spinner who approaches requests with a sense of urgency and a smile. The right candidate will also be resourceful, looking proactively to find solutions and answer questions on their own.

The job entails fielding and responding to IT issues internally in a responsive and comprehensive way. This could range from setting up a work machine for a new employee to figuring out a networking issue with one of our servers. This position also acts as the liaison with our third-party IT provider. You’re the one who can solve the problem, or if not, you’ll find who can. 

Requirements of the position include:

  • Two years’ experience preferred;
  • Excellent customer service skills;
  • Hardware and software support and troubleshooting for Windows PCs and OSX Macs;
  • Understanding backups;
  • Knowledge of network administration; and
  • Experience with active directory administration

Don’t have all of these? We’re happy to teach if you’re ready to learn. 

About the Observer Media Group
The Observer Media Group is a family-owned and operated multimedia company based in Sarasota, Florida. The company publishes 13 weekly newspapers throughout Florida, along with seven websites. Altogether, our newspapers and websites reach more than 400,000 readers weekly. 

Please send your cover letter and resume to [email protected].  Please put "IT technician" in the subject.

Realty-Builder Managing Editor

If you know anything about Florida business, you know that everything revolves around dirt — real estate.

That’s where the money is. And you know what they say: “Follow the money.”

In this case, we’re looking for someone to follow the development. Specifically, follow residential home building and selling in Jacksonville and Northeast Florida.

We have an immediate opening for the managing editor position of our nearly 20-year-old specialty monthly, Realty-Builder. 

Realty-Builder is one of 14 newspapers, three magazines and eight websites that make up the Observer Media Group, a family-owned company based in Sarasota, Fla., with 125 employees and operations in 12 Florida markets. Realty-Builder is also a sister publication to the 105-year-old Jacksonville Financial News & Daily Record, also part of the Observer Media Group.

With a circulation of 20,000, Realty-Builder is the leading publication in Northeast Florida for home builders, Realtors and the associated industries that serve them. That audience relies on Realty-Builder to keep it abreast of the trends, changes, companies and people influencing the fast-growing residential real estate market Jacksonville.

As managing editor of Realty-Builder, you will be part of the company’s Jacksonville editorial team and will work in tandem with the editors and reporters at the Daily Record.

Specifically, you’ll be responsible for the whole shebang, including: 

  • Creating an annual editorial calendar;
  • Conceptualizing and plannig the editorial content for each edition;
  • Assigning stories to freelancers; 
  • Writing major stories; 
  • Editing and helping edit the stories;
  • Working with the editorial designer on the look of the publication;
  • Coordinating editions with the Advertising Department;
  • Networking in the community with Realtors and home builders.
  • Finally: Producing an engaging, must-have, must-read publication for the region’s real estate and home building industries.

It sounds like a lot, and it is. But it’s essentially yours to make a difference.

We’ll make it worth your while with highly competitive compensation (and standard benefits — health, dental, life, 401k, vacation).

If you think you would have fun and find it rewarding being a leading voice and a leader in two of the most important industries in Greater Jacksonville; and if you think you have the right stuff and enthusiasm, then show us: Send an email that inspires us to pick up the phone and call you. Accompany that email with a resume, too.

Send to: Karen Mathis, Editor, Jacksonville Daily Record, [email protected]. No phone calls please.