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Operational Overload: What CEOs Can Learn from Auntie Tab, Jesseca (Judy), and Kevin

Writer's picture: Yolanda K. ChurchwellYolanda K. Churchwell

In the ever-changing world of DEI, corporate responsibility, and the economy, CEOs are facing challenges they may not have anticipated. Recently, Wal-Mart and Target made big moves by shifting their DEI efforts—an economic and political pivot that could change entire industries. At the same time, three remarkable CEOs—Tabitha Brown, Jesseca Dupart-Harris, and Kevin Hart—are navigating these waters in their own unique ways.


Photos of Jesseca, Tabitha and Kevin with their brands under title "what do they have in common"
Photo Credit: CEOs' social media accounts

Tabitha Brown: The Strategic Auntie


Tabitha Brown is an entrepreneur and actress whose branded products are sold exclusively in Target. But with the recent shifts in corporate policies, she’s asked fans not to boycott Target. Instead, she encourages us to support Black-owned brands within the store.


Tabitha’s situation highlights a valuable lesson for every CEO: the importance of diversifying your revenue streams. Relying on a single partner—like Target—is risky. To build a resilient business, developing additional sales channels is essential.


This is where a Fractional COO can make all the difference. A COO can help implement the systems needed to diversify income, manage ongoing projects, and guide your business to new heights.



Jesseca Harris-Dupart: The Independent CEO


Jesseca Harris-Dupart, CEO of Kaleidoscope, is a model of independence. Her products are thriving in big retail chains like Target and Wal-Mart, but even with her success, she faces the same challenge that any rapidly growing business does: building systems.


For Jesseca, the next step is ensuring her operational processes are well-documented and scalable. As she grows, she’ll need to expand her team and replicate the systems that are currently driving her success.


Jesseca also gave us a powerful reminder: “It’s okay to not be okay.” This message is a reality check for every entrepreneur. Scaling a business isn’t always smooth sailing. It requires resilience and the ability to take a step back when needed.


A Fractional COO can support Jesseca—or any CEO—by documenting processes, aligning team efforts, and ensuring smooth, scalable growth.



Kevin Hart: A CEO Rebuilding After Leadership Challenges


Kevin Hart, CEO of Hartbeat, has faced some serious leadership challenges. After the resignation of two CEOs in less than 15 months and the difficult decision to lay off employees, Kevin found himself running the day-to-day operations.


This situation is a reminder that no matter how big or successful your brand, you need solid systems in place to navigate tough times.


Like Tabitha and Jesseca, Kevin needs a Fractional COO to help him rebuild the infrastructure, implement Standard Operating Procedures (SOPs), and transition back to his visionary role without getting stuck in the weeds of daily operations.



The Takeaway: What Every CEO Can Learn


The challenges faced by these high-profile CEOs serve as a wake-up call for entrepreneurs everywhere. Whether you’re building your brand like Tabitha, scaling like Jesseca, or managing leadership transitions like Kevin, one thing is clear: Your business will only thrive in 2025 if you build systems to support it.


Here’s how a Fractional COO can help:

  • Tabitha’s Business: Diversify revenue and create operational strategies beyond reliance on one partner.

  • Jesseca’s Business: Document processes, build systems, and prepare for sustainable growth.

  • Kevin’s Business: Implement systems and SOPs to rebuild and scale with minimal personal involvement.


No matter where you are in your entrepreneurial journey, you need the right systems in place to grow, scale, and manage your operations. A Fractional COO can partner with you to step away from the day-to-day grind, focus on your visionary role, and scale your business with confidence.



Ready to Scale Your Business? Next Steps...


If you're a CEO who’s ready to transition from feeling overwhelmed to strategically thriving, I invite you to my Profit Pipeline Masterclass on February 22 at 10 am EST. In this free masterclass, I’ll share how to streamline your operations, eliminate bottlenecks, and reclaim your time as a Visionary CEO.


Spaces are limited, so register today to secure your spot and start building the systems that will carry your business to success in 2025 and beyond.



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