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Multimedia Advertising Sales Executives

 Beth’s comments are typical of our multimedia sales executives. If that sounds appealing to you, here’s what it takes to be an OMG multimedia sales executive:

  • Self-starter, energetic, unafraid, focused.
  • Impeccable integrity.
  • A people person. 
  • Great communicator, great listener.
  • High intelligence.
  • Creative.
  • Competitive.
  • Customer oriented.
  • Entrepreneurial.
  • An achiever.
  • Ability to thrive in a fast-paced environment.
  • Ability to find and engage new prospects and turn them into lasting customers.
  • Desire to succeed and win.

We offer competitive compensation with the opportunity for six-figure earnings. The plan includes base, commission, bonus opportunities, full benefits and a dynamic work environment.

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]


Sarasota Black Tie Reporter

Covering parties benefiting local charities; learning and writing about the leaders of Sarasota’s philanthropic scene; being the go-to person for the social calendar; and tirelessly taking pictures — lots of pictures — of the people, fashions and goings-on at local events: This is just the beginning of what it takes to cover the Black Tie beat for the Observer.

The Sarasota area is filled with active and generous philanthropists, which means there are many nonprofit organizations who benefit from their efforts. This results in a community that has more than 200 events a year (trust us, we counted) that raise money to aid these organizations in their missions. 

The black tie charity scene is at the heart of the community, which makes it a pillar of coverage for the Observer.

We are looking for our next social butterfly to cover all things Black Tie. This person should be a warm, outgoing personality who can chat up a soccer mom as easily as someone their grandparents’ age. Good with a camera, this person delights in meeting the variety of people who attend these events — from those who have amazing life stories to those who just like to wear amazing heels to every event (both have stories to tell). 

This person will be the keeper of the social calendar — a task we take seriously. She or he should be detail-oriented and highly organized: This job requires a lot of juggling, and you need to prioritize and multitask to make sure you are at the right place at the right time. Speaking of time, you must ensure you meet deadlines and post pictures promptly after each event. Once that’s completed, you will focus on pulling together content for print each week.

This job begs for creativity. Whether it’s taking pictures that give our readers something no one else has, or coming up with interesting ways to present events that people see every year, the opportunities are endless for the person with a clever eye and a witty sense of humor. Examples of this ingenuity could be pairing pictures with a timeline of an event or coming up with a fun fashion feature that highlights the best dressed of the weekend. At the Observer, we like to have fun with our content. This person should be passionate about creating new ways of entertaining and engaging readers of our Black Tie section.

And don’t forget about the fascinating people you’ll meet. From retired concert pianists to former CEOs of Fortune 500 companies, the area is full of interesting people. Don’t judge a book by its cover — just because these people have big wallets doesn’t mean they don’t have big hearts to match. We’re looking for someone who is willing to get to know these incredible people and who they are, not just who they’re wearing (though we do like to know where they shop).

This beat is a lot of fun, but it’s also a lot of work, particularly during the height of the social season. Be prepared to be busy from October through April — you’ll need the slower summer months to catch your breath (and catch up on sleep) and prepare for the next season.

Responsibilities include:

  • Compiling and keeping the black tie calendar up to date and error-free
  • Covering black tie events each week, which includes taking pictures and reporting for the weekly social column — requires lots of night and weekend work
  • Writing pithy, fun copy to go with events that will inform and entertain readers
  • Posting photo galleries to the website after each event
  • Maintaining the Black Tie Facebook, Instagram and Twitter social media pages
  • Planning and executing creative features for print and online based on the social beat (i.e. fashion reviews, “familiar faces” features, etc.)
  • Interviewing new couples and writing monthly Just Married stories
  • Fostering relationships with the philanthropists who attend most of these events
  • Getting involved in the philanthropic community, such as volunteering or serving on event committees
  • Occasionally writing stories for the Arts & Entertainment section, LWR Life Magazine and/or our special sections
  • Becoming the go-to person for all things social in Sarasota

Skills required:

  • An eye and passion for photography
  • Ability to write with voice and accuracy
  • Outgoing, warm personality
  • Organization and ability to multitask a must
  • A willingness to maintain an atypical work schedule — night owls will thrive
  • A desire to create content readers can’t wait to read
  • A curiosity to learn more about others around you
  • An interest (or interest in learning more about) fashion and writing style pieces
  • Knowledge of AP Style
  • Photoshop, Lightroom and video skills a plus

To see what the job looks like in action, check out our video of behind-the-scenes coverage of the Key to the Cure event:

The Black Tie section is inserted in all four weekly papers in our Sarasota-Bradenton market and is part of the Observer Media Group, a family-owned and operated multimedia company based in Sarasota, Florida. The company publishes 12 weekly newspapers throughout Florida, along with six websites. Altogether, our newspapers and websites reach more than 240,000 readers weekly.

While our print papers are weekly, we are a daily news operation, posting breaking news and features on our website, YourObserver.com. 

If you’re looking for a company in which to grow and continue to build your reporting skills, this is the place for you. We consistently win the Florida Press Association's general excellence award, and we have been named the best newspaper in North America three times in recent years. In everything we do, we strive for excellence, and we're GROWING — something not many news organizations can say these days.

Pay is competitive and commensurate with experience. Full benefits are included.

Please email your resume, including references, three to five clips, and a cover letter explaining why you’re the ideal candidate for the job to Executive Editor Kat Hughes at [email protected].  Please put "Black Tie reporter" in the subject line.

No phone calls, please.


News and feature writer

Do you love digging out the most engaging stories from your community? Can you share that story with your audience through the written word, photos and video? Are you comfortable navigating social media?

Those characteristics are essential, but only part of what it takes to join innovative, award-winning news teams at the Observer Media Group. 

When you become a reporter at the Observer Media Group, you join a close-knit, fun team that is building for the future. You would be working with experienced editors and a fun staff.

We’re looking for a self-starter who will quickly become the go-to person for all community news and events in the area.

Responsibilities include: 

  • Cover community events and take compelling, creative photos
  • Plan multimedia content to package with stories
  • Write weekly feature stories on community issues/events and residents
  • Cover news stories as needed and always be seeking story ideas
  • Upload photo events to the website/Facebook; help maintain the Observer’s social media pages
  • Contribute content, including photos and stories, to special sections throughout the year
  • Serve as an outstanding representative of the paper in the community

Requirements include:

  • Good photography skills; good eye for detail
  • Good writing and reporting skills
  • Great organizational skills
  • Detail-oriented
  • Creative
  • Ability to meet deadlines and multitask
  • Team player
  • Proficient in using social media as a news tool
  • Night and weekend availability is a must; however, you will work closely with your editor to balance your schedule with time off during the week.

The work environment is dynamic, innovative and fast-paced. Compensation is competitive and commensurate with experience. Full benefits are included.

Email your resume, including references, three to five clips and a note explaining why you’re the ideal candidate for the job to Executive Editor Kat Hughes, [email protected]. Please put “community reporter” in the subject line.

No phone calls please.