Digital Sales Account Executive

Position Summary: Chicago Sports Network (CHSN) is seeking a driven and results-oriented Digital Sales Account Executive to generate advertising revenue across the network's digital portfolio. This role is responsible for developing new business opportunities, growing existing client relationships, and delivering innovative advertising solutions that connect brands with CHSN's highly engaged sports audiences across digital, streaming, and emerging media platforms.

The Digital Sales Account Executive will sell a broad range of advertising and sponsorship opportunities, including digital display, video, social media, branded content, Connected TV (CTV), Over-the-Top (OTT) streaming, and integrated marketing programs. This position will collaborate with internal teams to create customized, data-driven campaigns that meet clients' marketing objectives and drive measurable results.

In addition to digital advertising sales, the role will support revenue growth through sponsorship activations, experiential marketing opportunities, special events, and cross-platform programs that leverage CHSN's media assets throughout its regional footprint. The ideal candidate is a strategic, consultative seller with experience in digital media, strong relationships within the advertising community, and a proven track record of exceeding sales goals in a fast-paced, evolving media environment.

·Drive digital advertising revenue growth through the sale of CHSN's digital media portfolio, including display, video, social media, branded content, Connected TV (CTV), Over-the-Top (OTT) streaming, and integrated marketing solutions. 

·Develop and execute strategic sales plans to identify, prospect, and secure new business opportunities while expanding existing client relationships. 

·Build and maintain strong relationships with advertisers, agencies, sponsors, and key decision-makers throughout the Chicago market and designated CHSN territories. 

·Create customized, cross-platform advertising and sponsorship solutions that align with client objectives and leverage CHSN's digital, streaming, social, experiential, and broadcast assets. 

·Present compelling sales proposals and negotiate advertising agreements to achieve or exceed individual and departmental revenue goals. 

·Collaborate with marketing, content, ad operations, and production teams to develop and execute innovative client programs and sponsorship activations. 

·Educate clients on the value of digital advertising products, audience targeting capabilities, campaign measurement, and performance analytics. 

·Monitor campaign performance and provide clients with insights, reporting, and recommendations to optimize results and maximize return on investment. 

·Maintain an active sales pipeline and accurately track account activity, forecasts, and revenue opportunities within CRM systems. 

·Stay current on industry trends, market conditions, digital advertising technologies, programmatic advertising, CTV/OTT developments, and competitive offerings. 

·Represent CHSN at industry events, networking functions, client meetings, and hospitality events to strengthen relationships and generate new business opportunities. 

·Work collaboratively across departments to ensure successful campaign execution, customer satisfaction, and long-term client retention. 

·Consistently meet or exceed established sales goals, revenue targets, and performance metrics.

·Bachelor's degree in Business, Marketing, Communications, Advertising, or a related field, or an equivalent combination of education and experience. 

·Minimum of 3-5 years of experience in digital media sales, advertising sales, sponsorship sales, or account management. 

·Proven track record of generating new business, growing existing accounts, and consistently achieving or exceeding revenue goals. 

·Experience selling digital advertising solutions, including display, video, social media, streaming/OTT, programmatic, sponsored content, and integrated marketing programs. 

· Strong understanding of digital marketing metrics, audience targeting, media analytics, campaign performance reporting, and ROI measurement. 

·Excellent communication, presentation, negotiation, and relationship management skills. 

·Ability to manage multiple client accounts, priorities, and internal stakeholders in a fast-paced environment. 

·Proficiency with Microsoft Office Suite (Excel, PowerPoint, and Word) and CRM platforms such as Salesforce or similar sales management tools. 

·Willingness to work flexible hours, including occasional evenings and weekends, for client events and networking opportunities.

Preferred Qualifications:
·Experience selling CTV/OTT, streaming video, digital video, sports media, or integrated advertising solutions. 

·Experience developing and executing cross-platform advertising campaigns that incorporate digital, social, streaming, broadcast, sponsorship, and experiential assets. 

·Knowledge of programmatic advertising, ad-serving platforms, audience measurement tools, and digital analytics platforms. 

·Existing relationships with Chicago-area advertisers, media agencies, and marketing decision-makers. 

·Experience working in a major media market, regional sports network, professional sports organization, or sports media environment. 

·Familiarity with the Chicago sports landscape and the fan bases of CHSN partner teams.

What We Offer: We believe great work happens when people feel supported, valued, and inspired. Here’s what you can look forward to as part of our team:

·Competitive salary that recognizes your experience and impact.

·Comprehensive Medical, Dental, and Vision insurance to keep you and your family well.

·Life Insurance plus Short‑Term and Long‑Term Disability for added peace of mind.

·A robust 401(k) retirement plan to help you plan for your future.

·Generous PTO so you can recharge and show up at your best.

·Paid Parental Leave to support you during life’s most important moments.

·Exclusive access to sports and entertainment events—because fun matters.

·Complimentary catered lunch every Monday through Friday (yes, really!).

·Free on‑site parking, keeping your commute stress‑free.

The total expected compensation range for this role is $75k/yr. - $150k/yr. which includes base salary and commission. Final compensation will be influenced by factors such as the candidate’s skills, relevant experience, degrees and certifications, job responsibilities, market conditions, and the position’s location.

About Us

Chicago Sports Network (CHSN) is the premier regional sports network and the exclusive television home of the Chicago Blackhawks, Bulls, and White Sox. We deliver more than 300 live games annually, along with comprehensive, year‑round programming designed for one of the most passionate sports markets in the country.

With a commitment to first‑class production, innovative storytelling, and in‑depth coverage, CHSN connects fans to the teams they love across connected TVs, mobile devices, and web platforms throughout our five‑state footprint. Beyond live broadcasts, we produce high‑quality digital content and behind‑the‑scenes storytelling that deepens fan engagement and elevates the local sports experience.

At CHSN, we are driven by a shared mission: to bring the heart of Chicago sports to life while delivering exceptional value to fans, partners, and communities. We foster a collaborative, fast‑paced environment where creativity, excellence, and a passion for sports come together to shape the future of regional sports media.

We are an equal opportunity employer and all qualified applicants will receive consideration for employment without regard to race, color, religion, national origin, sex, sexual orientation, age, disability, gender identity, marital or veteran status, or any other protected class.