*Sheryl Underwood’s recent signing with Creative Artists Agency/CAA marks a significant new chapter for the comedian, television host, and media personality. But according to communications strategist Tonya McKenzie, the deal should not be viewed as the result of a single breakout moment.
Writing in a recent edition of her “CTRL the Narrative” Substack column, McKenzie argued that Underwood’s addition to one of Hollywood’s most influential talent agencies is the culmination of decades spent building a brand, audience, and business infrastructure across multiple platforms.
“CAA did not discover her,” McKenzie wrote. “She made them ready for her.”
While many observers connected the agency signing to Underwood’s recent Netflix roast appearance, McKenzie argues the real story began decades earlier.
“What happened is that Sheryl Underwood spent decades building a catalog, a brand, a business, and a following,” McKenzie wrote. “And then she stepped on a Netflix stage and reminded everyone who she is.”
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Why the Signing Resonates Beyond Hollywood
CAA is one of entertainment’s most influential agencies. For Underwood, the signing represents another step forward in a career that spans stand-up comedy, daytime television, radio, podcasting, and national touring.
McKenzie believes that too much attention is often placed on the moment an opportunity arrives, while the years of work behind that opportunity receive little recognition. In her view, Underwood’s recent visibility did not create her value; it simply reminded audiences and industry leaders of it.
“That is the difference between luck and strategy,” McKenzie wrote. “And if you are not paying attention, you will miss the lesson entirely.”
The Value of Strategic Visibility
One of McKenzie’s key lessons for public relations and marketing professionals is that a single appearance can change a career trajectory when it is placed before the right audience.
Using Underwood’s roast performance as an example, she argues that communications professionals often spend too much time pursuing volume and not enough time creating meaningful opportunities with lasting impact.
“A single well-placed appearance can do what 100 posts cannot,” McKenzie wrote. “Stop posting for volume. Start positioning for impact.”
McKenzie also pointed to Underwood’s ability to build a presence across multiple platforms. Throughout her career, Underwood has worked in comedy, television, radio and live events, creating a diversified foundation that allowed her to capitalize when a major opportunity arrived.
According to McKenzie, platform diversity is one of the most effective forms of career insurance because it prevents public figures from becoming dependent on a single outlet, format or audience.
Building Credibility Beyond Entertainment
Another point emphasized in McKenzie’s column is the importance of community engagement. She highlighted Underwood’s work through Black Radio Solidarity, which has organized national radiothons focused on voter engagement, HBCU fundraising and public-health initiatives.
Rather than viewing civic involvement as a publicity exercise, McKenzie described those efforts as long-term investments in reputation and trust.
“Community impact creates the kind of credibility that no press release can manufacture,” she wrote.
McKenzie also pointed to Underwood’s decision to add CAA while maintaining her relationship with Innovative Artists for personal appearances. Instead of replacing her existing team, Underwood expanded her support structure as new opportunities emerged.
“Momentum is not the time to manage down,” McKenzie wrote. “It is the time to scale up.”
Lessons for Speakers and Communicators
McKenzie devoted a portion of her analysis to what speakers and communicators can learn from Underwood’s performance style. She emphasized the importance of preparation, audience awareness and composure under pressure.
McKenzie argues that audience awareness, credibility and specificity are often what separate memorable communicators from forgettable ones. She also noted that the way speakers handle unexpected challenges can become part of the message audiences remember most.
Ultimately, McKenzie sees Underwood’s latest career milestone as evidence that preparation remains one of the most valuable assets in entertainment and business.
“Virality is a door,” McKenzie wrote. “Preparation is what walks through it.”
For McKenzie, Underwood’s latest milestone reinforces a simple lesson: years of preparation often make success appear sudden.
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