This Company Did Digital Transformation All Wrong. Here’s What Happened.
The Pitch Wasn’t Random. It Was Strategy.
I was invited to a private, ultra-conservative event. Jared Kushner was there. I was slightly uncomfortable—but not enough to keep me from doing business. Before attending, I asked my sponsor who would be there. Then I did the work. I researched everyone. I looked at companies’ digital footprints, branding strategies, and public visibility. I targeted the company I ended up pitching. I knew they were antiquated before I ever shook a hand.
When I met the CEO, I didn’t wait. I said, “Your brand needs a new strategy. One that strengthens your franchisees, helps them make more money, and connects you to the future.” He was intrigued. So he invited me in to present to his C-suite. I came with a signed proposal that outlined deliverables, outcomes, and a plan. They accepted.
What I Found When I Got In
Before I even opened a laptop, I reviewed their current messaging and branding materials. What I saw was outdated and misaligned with modern consumer expectations. They were still pushing messaging that hadn’t been refreshed in years—visually or strategically. They lacked a unifying voice, a sense of innovation, and any clear brand architecture that could be communicated across hundreds of locations. It was clear from the beginning that their brand had not kept up with the pace of change.
My audit went deep. I looked at everything:
Their corporate backend systems
Their franchise marketing systems
Their national digital presence
Their local Google visibility
Their social media (or lack of it)
And then I did something else. I ran a voice audit. I asked Alexa and Google about their business. Nothing came up. I asked about competitors. They came up. Live. In front of the C-suite. They were embarrassed.
Franchise locations didn’t show up in search. Most had no digital presence. Franchisees had no understanding of marketing or point-of-sale displays. The company provided no training, no support. The C-suite didn’t even realize how bad it was.
Resistance, Denial, and Fear
One woman in the room had fear in her eyes. I've seen that look before. My audit had exposed the failure of her department. She had been phoning it in. And she knew it. Most of the team resisted my findings. “Too expensive.” “Too complicated.” “Franchisees won’t do this—they’re old, rural, disconnected.”
That wasn’t my problem. It wasn’t my money to spend. But the CEO hired me to tell the truth. And I did.
What I Told Them to Do
I built a messaging and communications hierarchy to help their leadership and franchisees speak with clarity and consistency. I also audited their website’s backend code and performance. It was clunky and outdated. Slow load times, broken links, and poor mobile responsiveness made their brand look amateurish—especially in contrast to their competitors. I made clear recommendations to rebuild using modern responsive frameworks, and I flagged major SEO issues that were preventing them from showing up in even the most basic online searches.
I gave them an execution plan:
Hire someone focused solely on innovation and future tech
Build marketing systems that connected HQ to franchisees digitally
Create tools and in-person training for franchisees, especially those in rural areas
Establish a consistent, measurable Google, search and social media strategy
Offer ongoing education and marketing support
It was a basic digital foundation. The low lift was that everything I proposed was fundamental—basic Google Business Profiles, social media channels, training support. The big lift was the mindset. They didn’t believe it needed to be done.
I Proposed Even More
I followed up with another proposal to deliver training modules and workshops. I’d travel or offer virtual training. They declined. They said franchisees should pay for their own training. I told them: it’s your brand—you train your people.
What Happened to the Old Marketing Agency
The agency they had been using got pushed into design work. No more digital. From what I heard, they’d been coasting. My audit made that clear too.
Franchisees Wanted Help
The same outdated assets that hurt the parent brand were hurting local owners. I found inconsistent signage, poor design templates, and no scalable digital marketing support for local franchisees. Some had resorted to designing their own ads and most relying on word of mouth. This wasn’t just bad branding—it was bad business. I told leadership, if you don’t support your franchisees with real, usable marketing systems, you're failing them at every level.
When I interviewed franchisees, they told me they’d been asking for direct marketing help for over a year. They weren’t resistant. They were disconnected and unsupported.
The CEO Tried. But He Couldn’t Win.
The CEO brought me in. He didn’t understand the full picture, but he knew something was off. He trusted me to figure it out. But the rest of the leadership team didn’t. Eventually, he was left. I think they didn’t believe him either. They were protecting their jobs—not the company.
The Company Collapsed
I won’t name them. But they’re a shell of the company they were. Not just because of me—but because of the gaps I exposed that they chose to ignore. The lack of digital transformation wasn’t the only reason, but it was a huge one.
On the Flip Side: Navy Pier
Now, let’s talk about a company that did make it out alive! Navy Pier is a great example of what happens when leadership gets it right. I conducted a similar audit for them. But the difference was, they listened. They acted on all of my recomendations. They implemented a new digital brand strategy, invested in backend infrastructure, and rolled out a robust local search strategy. Their team was aligned. Curious. Courageous enough to change. I have a full case study on that work—and it’s proof that transformation is possible when people are willing to do the work.
Here’s What I Recommend
Audit Your Team’s Digital Readiness – Who’s ready to learn? Who isn’t?
Talk to Your Middle Managers – Make them part of the solution, not the resistance.
Commit a Budget and Timeframe – If you’re not ready to fund change, don’t ask for ideas.
Prepare to Let People Go – If someone’s blocking change, they have to move.
Soft Land the Departures – HR can help you do this with dignity.
Educate Yourself – Use Coursera, OpenAI, Google, Microsoft. Before you dive into AI, understand digital transformation.
Framework for Action
Discovery: Interviews, system audits, voice and search visibility
Strategy: Roadmaps, success metrics, timelines
Execution: Training, digital tools, backend connections
Leadership Alignment: Middle management coaching, innovation hires
Support: Ongoing advisory and brand monitoring
It’s Not Too Late—But You Have to Move
I get it. You’re overwhelmed. There are too many options. You don’t know where to start. The key is: start anyway. Embrace the fear and go.
Even I feel it. I’m watching AI agent acceleration unfold in real time. It’s intense. It’s fast. And it’s nerve-wracking. So I fight that fear by learning. I study Google, OpenAI, HuggingFace, Crunchbase. I download white papers. I track every update I can find. That’s how I move forward. That’s how I keep my edge.
So if you’re nervous? You’re not alone. But if you want to stay in business—you better start learning, too.