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City reporter

At the Observer Media Group, we believe the most important news is the news closest to our readers. After all, despite the noise national news generates, the issues that impact us most are local.

If you agree, you might be the perfect fit to join our team here in sunny Sarasota, Florida. We are looking for a news reporter with at least five years' experience in government reporting to cover our most high-profile beat: the city of Sarasota and all its happenings.

The Sarasota Observer is looking for an enterprising reporter who will become embedded in the community — someone who can pluck a story from a City Commission agenda just as aptly as they can write a heartwarming tale about a member of the community.

The right candidate will quickly become the go-to person for all news related to the city beat. That includes covering city government, transportation, business and development, which is a hot topic with the pace of the area's growth. In addition to reporting on what's happening, this reporter will need to take the next step in the story to write about what it means for readers and how it will affect their lives — and their pocketbooks. 

Our new city reporter must be able to develop a network of sources that ranges from elected officials to neighborhood residents. With our hyperlocal coverage, we need a reporter who can become a part of the community to discover and report what matters most to our readers. This person should also be handy with a camera to shoot their own photos and tell stories visually. Video skills are a plus.

If you like challenges, high standards and beating the pants off your competition, this is the place for you. Our goal is to grow and improve ourselves while serving up exceptional local content for our readers. The ideal candidate is enthusiastic and has a strong desire to continue to learn and be a part of a young, energetic team. Although our papers publish weekly, we are a digitial-first news operation, and we are focused on posting continously on our website,


The Observer Media Group is a family-owned and operated multimedia company based in Sarasota, Florida. The company publishes 10 newspapers throughout Florida, two quarterly lifestyle magazines and six websites. Altogether, our newspapers and websites reach more than 350,000 readers each week. And we are GROWING!

The Observer Media Group's newspapers are consistently recognized as some of the best publications in the state and the nation. We are dedicated to being a leader in innovation in our industry and we take our work — but never ourselves — seriously.

Interested? Email a resume, cover letter and 3-5 clips to Managing Editor Eric Garwood at [email protected]. Please put "news reporter" in the subject line. No phone calls please. Salary is $40,000-$50,000, depending on experience. Full benefits are included.

Marketing Specialist

Sarasota, FL, USA

We are seeking an enthusiastic, creative, and hands-on Marketing Specialist 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 an understanding of all marketing and advertising communication channels, the consumer experience, plus a burning desire to contribute as part of a team. The candidate would be a college graduate with a degree in liberal arts or marketing-related program, along with 2+ years of work experience with advertising, marketing, or membership-based business.

Job Details/Responsibilities:

Marketing, Membership and Advertising:

  • Collaborate with the marketing director, internal teams, clients, and partners on marketing and membership projects and strategies.
  • Assist in developing marketing materials, including brochures, email campaigns, flyers, social media posts, posters, etc.
  • Coordinate membership campaigns to include direct mail, print and digital tactics.
  • Assists with membership registration, events, and provides customer service via phone or email to members.
  • Traffic all advertisements to appropriate publications and online venues.
  • Maintain and strengthen the 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 membership functions.
  • Provide administrative support to the marketing director.


  • Participate, set up and break down 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. Occasional travel may be required.
  • Must occasionally lift or move up to 25 lbs. Stand comfortably for extended periods.


  • BA or BS degree preferred in either marketing/communications, English, journalism, graphic design, or related field.
  • The ideal candidate should have a minimum of 2+ years of professional experience in corporate marketing, communications, event promotion, or membership services experience.
  • Experience in MS Office Suite and Adobe Creative Cloud (Indesign, Illustrator, Acrobat) software packages are strongly preferred. MailChimp, Facebook, Twitter, Instagram, Google Analytics skills are a plus.
  • Strong graphic skills are a must, as are excellent communications, interpersonal and time management skills.
  • Customer service experience. Must be comfortable receiving and making outbound phone calls.


  • Ability to be a self-starter and work independently.
  • Possess the ability to thrive in a fast-paced environment with the ability to multi-task.
  • 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 your resume and cover letter to: [email protected]. No phone calls please.


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 Nowicki, Advertising Sales Manager,
1970 Main St., 3rd Floor
Sarasota, FL 34236 
[email protected]


The Observer Media Group is looking for an entry level, inside sales candidate to sell classified and service directory advertising.

Advertising and marketing experience not required. We provide on-going training to help ensure success and high earning potential. The successful candidate will manage, maintain and grow the existing client base - with many of the businesses advertising with us for many years.

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


  • Maintain Relationships with Key Accounts
  • Identify prospects and be comfortable selling over the phone
  • Provide customer service to ensure highest level of customer satisfaction


*Self-starter, creative, and goal-oriented personality

*Great communicator - great listener

  • Thrive in our collaborative, team environment
  • Need to be punctual and responsible and have impeccable integrity
  • Ability to excel in unsupervised environment

Please send resume and cover letter to [email protected].


We are looking for an Advertising Assistant who will be responsible for supporting our dynamic, fast-paced sales team, trafficking ads across several platforms and assisting salespeople while they are in the field. We offer a competitive compensation plan, including full benefits, a dynamic work environment. and opportunity to grow into a larger role.

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

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