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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]


Are you an innovative self-starter?  Are you persuasive, energetic and focused?  Do you build strong relationships?  We are looking for a strong sales candidate to sell our complete media offerings including print, digital and niche publications to local businesses in Sarasota and Manatee Counties. Top candidates will have a proven track record of overcoming obstacles and achieving goals. 

The Observer Media Group is a highly regarded, family-owned multimedia publisher serving a premier target audience in Sarasota and Manatee County. 

We are an innovative, growing company offering competitive compensation with the opportunity to grow into six-figure earnings. The plan includes base, commission and bonus opportunities as well as full benefits.


  • Prospect and hunt new business
  • Grow advertising revenue with new and existing clients
  • Coordinate and monitor ads and effectiveness across multiple products


  • 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.

Please send resume and cover letter to Penny DiGregorio at [email protected]

Advertising Sales Coordinator

This new position will be responsible for coordinating and supporting our dynamic, fast-paced sales team.

The ideal candidate will have strong administrative skills, attention to detail, excellent written and communication skills and possess an upbeat, positive attitude. 

  • ability to meet deadlines and work well under pressure.
  • work closely with sales reps to provide daily sales and  administrative support.
  • work closely with sales and creative department to execute social, digital and print ad creation.
  • eager to assist customers - both internal and external.
  • proficient in excel and word

We offer a competitive compensation plan, including full benefits and a dynamic work environment.

If you want to be a part of an innovative, growing company where you can make a difference, please send your resume to Penny Digregorio @ [email protected].

Marketing Coordinator

We are seeking an enthusiastic, creative, and hands-on Marketing Coordinator to join our Observer Media Group team and drive awareness for consumers and advertisers of our print and digital products across Florida.

The ideal candidate will possess a basic understanding of all marketing and advertising communication channels, the consumer experience, plus a burning desire to contribute as part of a team. This is an entry-level position with ample room for advancement.

The ideal candidate would be a college graduate with a degree in liberal arts or marketing-related program, along with some work or internship experience with a retail, advertising, or marketing business.

Job Details/Responsibilities:

  • Marketing and Advertising
    • Collaborate with the marketing director, internal teams, clients, and partners on marketing strategy.
    • Assist in developing marketing materials, including brochures, flyers, blog posts, posters, etc.
    • Traffic all advertisements to appropriate publications and online venues.
    • Coordinating with internal staff members on strategy, copy and creative needs.
    • Manages multiple projects and team efforts simultaneously in an effective and efficient manner under tight deadlines.
    • Create, maintain, and strengthen Company’s overall brand in all forms of media (online, print, out of home media).
    • Coordinate and fulfill sponsorship agreements with the advertising department.
    • Assist in key day-to-day marketing and product development functions.
    • Provide administrative support to the marketing director.
  • Events
    • Support the coordination and set up of trade expos, conferences, consumer and corporate events, and webinars.
    • Position may involve working nights and weekends as necessary to meet deadlines and participate in events.


  • BA or BS degree preferred.
  • Proficiency in Microsoft Word, Excel, and PowerPoint required.
  • Excellent writing skills required.
  • Time management skills required.
  • Strong interpersonal skills required.
  • Ability to attend outside events when called upon.


  • 1-3 years of customer-service oriented, marketing, event promotion, or outside sales experience considered.
  • Superior interpersonal and communication skills.
  • Possess the ability to thrive in a fast-paced environment with the ability to multi-task.
  • Ability to listen carefully and actively.
  • Excellent problem-solving skills.
  • Understand and demonstrate integrity, respect, and the ability to develop positive relationships with management, customers, and peers.
  • Flexible for scheduling including nights and weekends.
  • This is not a remote job.

To be considered, send a cover letter and resume to: [email protected]. No phone calls please.

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]