“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

What if your next podcast episode closed a $500K deal?

In this inaugural episode of The Content Crowd, host Trevor Grimes sits down with Joseph Lewin, Head of Podcast Strategy at Scrappy ABM, to talk about why creating content with people you want to know is the fastest way to meaningful results.

Joseph breaks down the mindset shift that changed everything: stop chasing audience growth and start building real relationships—with future clients, partners, collaborators, even employers. From account-based podcasting to low-lift live shows, he shares the strategies that helped clients close over $2M in deals through conversation-first content.

If you’ve been stuck thinking your show needs a massive following to be valuable, this one’s your permission slip to go live, go scrappy, and start building something real—one guest at a time.

👤 Guest Bio

Joseph Lewin is Head of Podcast Strategy at Scrappy ABM, where he helps B2B companies launch and scale relationship-driven shows. He’s launched 25 shows in the past year alone, with clients closing over $2 million directly from their podcasts and live shows. He’s a champion of account-based podcasting and believes content should start conversations—not just collect views.

📌 What We Cover

• What makes a podcast “account-based” and why that matters for B2B
• The myth of needing an audience before you can start a show
• How to use your podcast as a strategic re-engagement tool for pipeline
• The difference between audience growth and network growth
• Real ways to turn your show into a referral engine
• Why hosting guests is the ultimate shortcut to job offers, deals, and trust
• How to show up consistently—even if you're just getting started
• The “set the table” mindset that flips traditional podcasting on its head

🔗 Resources Mentioned

• Scrappy ABM
• LinkedIn Live
• Apple Podcasts Marketing Chart