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AE

Digital Account Executive

Playfly Sports logoPlayfly Sports$70,000–$100,000/yrChicago, Illinois, United StatesListed 1mo ago

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The posting

DIGITAL ACCOUNT EXECUTIVE

Chicago, IL

Hybrid

THE RUNDOWN

Playfly Sports is looking for a Digital Account Executive to join our team in Chicago.

The Digital Account Executive (AE) for Playfly Media (formerly known as Home Team Sports) will be responsible for driving revenue across Playfly Media’s digital portfolio of assets through consultative selling and relationship building with agencies and client stakeholders throughout the Midwest. They will work closely with their Integrated AE counterparts to build cross platform packages across Linear TV and Digital that address client needs and maximize revenue for Playfly. They will also be tasked with identifying and closing digital revenue that is not directly tied to a Linear TV buy.

WHAT YOU’LL ACCOMPLISH

· Pursue, cultivate, and grow business relationships with key agency and client decision makers throughout the Midwest.

· Prospect new business and assist in the development of net new accounts for Playfly Media.

· Gain a deep understanding of Playfly’s digital offering (video, programmatic, social, branded content, display) so that you can effectively communicate the value proposition to clients and build customized solutions that help them accomplish their goals.

· Collaborate and work closely with Sales counterparts and other internal divisions (Insights, Marketing, etc) to bring compelling and impactful opportunities to market.

· Serve as a Digital subject matter expert and resource for the Playfly Chicago/Detroit Media team, as well as our agency and client partners.

· Other job-related duties as assigned.

WHAT YOU’LL BRING

· Bachelor’s degree required, with preference in Sports Media, Communications, Marketing or related fields.

· 3-5 years of digital, sales and/or agency experience in advertising is required.

· Interest in and general understanding of the sports digital advertising industry, and current contacts within the aforementioned business sectors is strongly recommended.

· Strong oral and written communication skills are necessary.

· Strong organizational, presentation and public speaking, and project management skills are imperative to this role.

· Knowledge of Microsoft Office computer applications, including Word and Outlook is necessary.

· Ability for analytical reasoning of sales and research data (CPM, impressions, site metrics, data analysis, etc.)

· Must be technologically savvy with propensity for understanding new technology platforms and how they apply to our business model.

· A proven ability to develop and maintain successful internal and external business relationships is essential.

TRAVEL, LIFTING, PHYSICAL REQUIREMENTS

· This role takes place in an office setting and is a sedentary role. Desks can convert to standing desks, as needed or desired.

· AE is expected to travel regularly throughout the Midwest to meet with agencies and clients.

COMPENSATION

Actual compensation packages are based on several factors that are unique to each candidate, including but not limited to skill set, depth of experience, certifications, and specific work location. This may be different in other locations due to differences in the cost of labor.

The base pay range for this role is

$70,000 - $100,000 USD

WHAT WE DO

Playfly Sports is the full-service, leading sports marketing and media company that enables brands to engage with sports fans on a local, regional, and national level through scaled linear, digital, and experiential assets. Playfly Sports drives outcome-based solutions into 90-million households via more than 7,800 live U.S. broadcasts of MLB, NBA, and NHL games; and influences sports fans of all ages through the management of college and high school multimedia rights, uniform branding, and high-profile sports sponsorship platforms. Playfly Sports has the unique ability to partner, innovate, and advance the aspirations of athletes, brands, academic institutions, and sports fans across the U.S. Playfly Sports is Powered by Partnership. Visit Playfly Sports online at playfly.com

WHAT WE STAND FOR

At Playfly, we know that a diverse, equitable, and inclusive company is a more innovative and successful one, but more importantly, we believe it’s just the right thing to do. Through conversations, company initiatives, community events and partnerships, policy changes, data analysis, workshops, and support groups, we are dedicated to creating a workplace where everyone can thrive. We are here for the long haul and to do the meaningful work that creates true institutional change within our workplace, with our partners, and in the communities we serve.

EEOC & DIVERSITY STATEMENT

Playfly Sports affirms that inequality is detrimental to our associates, our clients, and the communities we serve. Our goal is to impact lasting change through our actions. Together, we unite for equality and equity. Playfly Sports is committed to equal employment opportunities regardless of any protected characteristic, including race, color, genetic information, creed, national origin, religion, sex, affectional or sexual orientation, gender identity or expression, lawful alien status, ancestry, age, marital status, or protected veteran status and will not discriminate against anyone on the basis of a disability. We support an inclusive workplace where associates excel based on personal merit, qualifications, experience, ability, and job performance.

ACCOMMODATIONS

Playfly Sports is committed to the full inclusion of all qualified individuals, and as part of this commitment, Playfly Sports will ensure that persons with disabilities are provided reasonable accommodations. If reasonable accommodation is needed to participate in the job application or interview process, to perform essential job functions, and/or to receive other benefits and privileges of employment, please contact recruiting@playfly.com .

We are unable to sponsor or take over sponsorship of an employment visa for this role at this time

Equal Opportunity Employer This employer is required to notify all applicants of their rights pursuant to federal employment laws. For further information, please review the Know Your Rights notice from the Department of Labor.

For California and UK Residents, please read our Privacy Policy

Taken from Playfly Sports's own posting, last seen live on 13 Nov 2026.

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The application

Your details and CV, then 4 questions.

Have readyCVCover letter (optional)LinkedIn (optional)Website (optional)
  1. 1.
    When can you start?Short answer
  2. 2.
    Are you willing to undergo a background check, in accordance with local law/regulations?Yes or no
  3. 3.
    Will you now or in the future require sponsorship for employment visa status?Yes or no
  4. 4.
    ​If you provided a phone number, do you consent to receiving follow-up communication via text message (or SMS message) regarding your application status?Yes or no

From Playfly Sports's apply page, checked 5 Nov 2026.

About Playfly Sports

Sells sponsorships, broadcast and digital advertising, season tickets and premium seating on behalf of pro teams, college athletic departments and high school associations, to local, regional and national brands and to fans.

Pay schedule: Salaried staff whose postings state base pay only and tie the job to individual and team revenue targets; the careers page points to a company benefits package.

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