If your content feels bland or forgettable, this might be why: you're playing it safe. In this episode, Trevor Grimes sits down with Phil Pilalas, a fellow “content dork” and messaging strategist at Scrappy ABM, to talk about the one thing too many brands overlook—point of view.

Phil unpacks why content that tries to “be a friend to everyone” often ends up resonating with no one. He shares how safe messaging erodes brand voice, why marketers must fight to keep the founder’s original intent intact, and how to translate brain dumps from subject matter experts into content that actually says something.

Whether you're building a brand guide or trying to write one strong LinkedIn post, this conversation reminds us that meaningful content starts with a clear perspective—and the courage to stick to it.

👤 Guest Bio

Phil Pilalas is a messaging and content strategist at Scrappy ABM. He helps companies say important things to important people—by turning subject matter expertise into clear, compelling content. With a background in broadcast communications and leadership roles in marketing, Phil’s known for distilling messy brain dumps into tight, audience-ready narratives.

📌 What We Cover

• Why content needs a clear point of view to matter
• How trying to “stay safe” waters down your message
• What to ask when building a brand voice (that actually reflects your brand)
• How to distill hours of SME talk into a week’s worth of content
• The role of the CEO’s voice in brand communication
• Why marketers need face time with product and sales teams
• How to validate your tone with real customer language
• What “dying on the wrong hill” looks like for content distribution

🔗 Resources Mentioned

• Simon Sinek – Start With Why
• LinkedIn (as a key content platform)
• TikTok, YouTube – as examples of finding the right hill for your content
• “Brand archetypes” (mentioned, not followed)

Low-Tech, High-Impact Account-Based Marketing

If you’re ready to trade expensive, tech-heavy account-based marketing for a repeatable, revenue-driving ABM program, check out Scrappy ABM. Led by a team of Scrappy ABM experts, they specialize in low-budget plays and programs that deliver high impact—no shiny tools required. Scrappy ABM has built account-based programs that have delivered millions in revenue, and you can build your first successful ABM program with their help.

Start with a pilot program or launch an account-based podcast. Learn more at scrappyabm.com. Let's get scrappy.

“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