In this eye-opening episode of My Biggest Marketing Mistake, Kacy Maxwell, CMO of Provisions Group, sits down with Jessica Walker, founder and CEO of Care Sherpa, to unpack a misstep that’s far more common and costly than most business leaders realize: investing in the right technology at the wrong time.

With marketing and tech deeply intertwined, it’s easy to believe the next shiny tool will be the solution to all your problems. But what happens when the promise of efficiency turns into a costly distraction? Jessica reflects on a decision that many leaders make with the best intentions, only to face unintended consequences.

You’ll hear about:

🔥 The hidden cost of jumping into new tools too soon

🔥 Why the timing of a tech investment can matter more than the tool itself

🔥 How to assess your readiness beyond just technical capability

This conversation is a must-listen for business owners, marketing leaders, and anyone making decisions about technology investments. If you’re navigating the endless wave of new platforms and wondering when (or if) to buy in, this episode offers a candid look at what can go wrong and how to get it right.

We Want YOU on the Show!

🎙 Submit to Be a Guest

We’re looking for CEOs and Founders who’ve made big marketing mistakes and are open to sharing what they’ve learned in a full episode. Interested? Email us to start the conversation.

🎙 Get Featured on the Show

Are you a marketer with a story to tell? Record a 30-second voice memo about your marketing mistake and the lesson you learned and email it to us. We may feature your clip on the podcast.

📩 Send all submissions to: mbmm@provisionsgroup.com with the subject line 'Marketing Mistake Submission'.