For Jason, hosting “On the Right Stack” is a deliberate strategy to constantly fuel and sharpen technology-enabled business acumen applied to the work of his team’s advisory services.
His unfiltered dialogues with enterprise founders, operators, and builders who are actively connecting people, processes, and platforms serve as a masterclass in current execution, unpacking technology-driven strategies and what is actually working and what is failing across industries today.
Not every technology decision gets made in Silicon Valley, and that is exactly the gap this podcast was built to close. Host Jason Cohen sits down with Craig Walker, founder and CEO of Dialpad, bringing a veteran operator’s perspective to a conversation about unified communications, early AI adoption, and what it takes to lead technology transformation at any scale. Real experience. Real insight. No hype.
The gap between AI ambition and execution isn’t a technology problem. It’s a leadership problem.
Tools are not the issue. Access is not the issue. Clarity is.
Where should AI create value?
What does success look like?
What gets prioritized?
When those answers are clear, execution follows.
That was a major theme in our latest On the Right Stack Podcast conversation with Andy Roach.
The best CTOs don’t just build systems.
They build understanding. When a CEO consistently gets clear, outcome-driven communication:
Decisions happen faster
Priorities stay aligned
Trust builds over time
It’s not about simplifying the work. It’s about making sure the work can be supported at the level where it actually gets funded and prioritized.
That’s leadership. This was a big theme in our latest On the Right Stack Podcast conversation with healthcare CEO Jeff Stamps—especially around how technical leaders show up in executive discussions.