Coffee with Bob Howland — A Boardroom Voice for the Future
It’s a bright morning in Boston’s Seaport District, and I’m weaving my way through the sleek glass buildings and harborside walkways toward a coffee spot that’s quietly popular with local entrepreneurs. On the surface, this area is all modern polish — but there’s a grittiness under the surface that feels right for the conversation I’m about to have. I’m meeting Bob Howland, a seasoned executive known for turning complex, siloed companies into future-ready organizations.
On my way there, I think about what makes Bob different. He’s not a typical tech guy. And he’s not just a strategist either. He calls himself a connector — someone who sees the full landscape of a business and knows how to bring the right pieces together. He’s been described as T-shaped: broad in perspective, but deep where it counts — especially in digital transformation.
I step into the café and spot him right away. Bob’s already there, seated at a table near the front, casually dressed, sipping his coffee with the calm confidence of someone who’s led billion-dollar shifts but doesn’t need to say it out loud.
We say hello, and after a few minutes of casual talk, I dive in.
“Bob, how do you describe what you bring to a board?”
He pauses briefly, then leans forward. “I help companies become future-ready. That means more than adopting the latest tech — it’s about aligning people, process, and purpose to navigate what’s coming. I’ve led transformations that go beyond strategy decks. I’ve built systems, teams, and operating models that let companies move faster and smarter.”
“And do you see yourself as a technologist?”
He smiles. “That’s a great question — and no, not really. I didn’t come up through IT. I started on the P&L side. I’ve run marketing teams, built digital platforms, managed full business units. So I can talk to the CIO, sure. But I can also talk to the CFO, the general counsel, the board chair. That’s where I bring value — I connect the dots across the business.”
“You mentioned ‘future-ready’ — what does that mean in a governance context?”
“It’s about helping boards look around corners. Many boards focus heavily on oversight, which is important — but the best boards also think about foresight. How is the company evolving? Are we prepared for the next wave of disruption? That’s where I come in. I’ve been the person executing that change, and I know what works — and what falls apart.”
As Bob takes another sip of his coffee, I ask one last question.
“Why board service now?”
“I’ve been part of some once-in-a-generation changes — at Vanguard, at Dawn Foods, at Blueport. I’ve seen the pressure executives face. And I’ve seen the gap that sometimes exists between boards and management, especially around digital decisions. I want to help bridge that gap. Not by being the loudest voice in the room, but by asking the right questions and seeing what others might miss.”
The conversation winds down, and I walk back into the bustle of Boston, reminded that future-ready leadership isn’t about tech for tech’s sake — it’s about clarity, courage, and connection. And that’s exactly what Bob brings to the table.
Maarten Schaefer
Chief Storyteller CoolBrands
