“If you don’t draw a hundred thumbnails first, was it even real design?” That’s how The Content Crowd host Trevor Grimes kicks off this deeply personal and professional conversation with longtime friend and creative peer Jessica Jackson Tait, now VP of Business Operations at WITH.

What unfolds is part origin story, part playbook for how creative minds can build meaningful systems without sacrificing heart. Jessica shares how her background in graphic design and art direction shaped her transition into creative operations—and how she’s redefining leadership by respecting both creative time and business goals.

You’ll hear why WITH dropped “agency” from their name, how they structure timelines around real data (not guesswork), and why project managers are the unsung heroes of creative work. Jessica also breaks down her move from agency ops to business ops, including how she helped launch a strategic advisory model with major clients like Coca-Cola and AT&T.

This episode is a guide for anyone trying to balance artistic integrity with sustainable, human-centered strategy.

👤 Guest Bio

Jessica Jackson Tait is VP of Business Operations at WITH, a strategic and creative firm based in Atlanta. Starting her career in graphic design and art direction, Jessica brings a rare blend of creative intuition and operational precision to her role. With over a decade at WITH, she now oversees systems, tools, and business decisions that help teams do great work—on time and with purpose.

📌 What We Cover

• Why WITH stopped calling itself an “agency”—and what that shift unlocked
• How to build project plans around real creative timelines (not just client deadlines)
• The power of time tracking as a creative growth tool—not a policing tactic
• Tips for bridging the gap between creatives and project managers
• What it actually means to operationalize value-driven content strategy
• The human reason behind WITH’s new advisory offering
• How to balance efficiency with empathy when managing creative teams
• Why content must earn trust—not just attention

🔗 Resources Mentioned

• monday.com (project management tool used by WITH)
• Harvest (time tracking tool)
• QuickBooks
• Jessica’s LinkedIn: https://www.linkedin.com/in/jessicajacksontait/
• WITH on LinkedIn: https://www.linkedin.com/company/with-agency