CEO 2 CEO - Conversations with Executive Leaders of The CEO Roundtable

Ep 25. The AI Lens: People Before Technology – Jason Dailey, Brandography – CEO 2 CEO

AI is everywhere, yet many business leaders still wrestle with the same question: How do you embrace it without disrupting your culture, overwhelming your team, or creating fear about the future?In this episode of CEO 2 CEO, Scott Sustacek sits down with Jason Dailey, Founder and CEO of Brandography, to explore what AI adoption really looks like inside growing companies. Rather than focusing on the latest tools (although he will name a few), Jason shares a different perspective—one centered on leadership, curiosity, and helping employees develop what he calls an "AI lens": a new way of looking at everyday work through the possibilities AI creates. Their conversation also explores Jason's philosophy of "forcing it to happen naturally"—creating opportunities for experimentation, discovery, and habit-building that encourage teams to embrace AI.  Along the way, Scott and Jason challenge common assumptions about adoption, innovation, and what it takes to build a future-ready organization. What if the biggest AI opportunity isn't the technology itself, but how your people learn to think differently?

Ep 24. 10X — From Incremental to Transformational Growth – Andy Siemens, Tailwind Voice and Data – CEO 2 CEO

In this episode of CEO 2 CEO, Scott Sustacek sits down with Andy Siemens, CEO of Tailwind Voice and Data, to explore what it really means to think—and lead—at a 10X level. But this isn’t about bold declarations or flashy growth goals. Instead, Andy shares a more subtle, strategic approach—one that quietly reshapes a business from the inside out. He reveals how focus, discipline, and the right people and team can drive exponential change.  This conversation challenges the way many CEOs think about growth. What if 10X isn’t about doing more… but focusing differently? If you’ve ever wondered how to accelerate a key part of your business without disrupting everything else, this episode offers a perspective you won’t want to miss. Be sure to subscribe to CEO 2 CEO and listen in on conversations where Scott connects the dots between the issues CEO’s face and the experience of remarkable guest leaders in upcoming episodes. And, be ready to be wiser from it.

Ep 23. Are You Ready for a Board — and Is There a Board Ready for You? – Anne Sample, Navigate Forward – CEO 2 CEO

Aspirations for a board seat can often be viewed through a glamorous lens — a prestigious, and perhaps cushy, gig as a next step in one’s career. In reality, true board work is very different than anticipated, board readiness is far more nuanced than many realize, and being good at it requires an approach unlike the one that made you successful operating a business.In this episode of CEO 2 CEO, Scott Sustacek sits down with Anne Sample, Owner and CEO of Navigate Forward, to unpack what board readiness and successful service truly means. Anne draws on experience as she explains the mindset shift from operator to governor, the real time commitment involved, and why the first board seat matters so much.   The conversation examines common missteps executives make, how boards evaluate fit, and how this type of search differs from a job search.If you're considering board service as a next chapter, this episode offers candid insights — and maybe an important reality check — on how to approach the journey with clarity and credibility. The CEO Roundtable is comprised of executives representing many fast-growing Minnesota companies who desire to share their ideas, experiences, and insights. Our CEO Roundtable leadership development groups include entrepreneurs interested in growing their companies by leveraging the knowledge of their peers.

Ep 22. Stepping Into the Seat: A New CEO’s Candid Debrief – Ann Houser, The Bailey Group – CEO 2 CEO

Stepping into the CEO seat for the first time can feel like walking into a room where every light switches on at once — the ability to change the trajectory of a company through the decisions made and direction set; the tension between immediate business pressures and long-term strategy; and the surprising duality of feeling connected to the organization and isolation. This episode is a candid conversation with Ann Houser, CEO of The Bailey Group, who went from seasoned HR and coaching leader to owner and board member to first-time chief executive.  Ann reflects on what motivated her to take the reins, why early assumptions quickly gave way to humility and the moment she realized she needed her own community of peers for outside perspectives.  You'll hear her insights on the importance of setting priorities and giving yourself grace to grow in and into the CEO role that will surely resonate. Whether you're a first-time CEO or a seasoned leader, Ann’s candor offers honest insights and valuable reminders that becoming a great CEO is a never ending —and very human—journey for all of us.

Ep 21. Supercharging Marketing and Driving Revenue Growth with AI – Nick Archer, Industrial Tool – CEO 2 CEO

Artificial intelligence is continuously evolving and rapidly redefining how middle-market companies can operate — far beyond the early days of experimentation with ChatGPT. In this episode of CEO 2 CEO, Scott Sustacek sits down with Nick Archer, CEO of Industrial Tool, who shares how he and his leadership team moved beyond cautious Chat GPT use to embed AI into their sales and marketing efforts. What began as tentative exploration became a catalyst for productivity and a differentiator with customers. Nick discusses the turning points that transformed skepticism into strategy — from automating meeting follow-ups and building purpose-driven knowledge bots to creating a data-driven marketing engine that pinpoints real buyer intent. He also outlines a practical game plan any leader can follow to start harnessing AI’s potential within their own organization. It’s an inside look at how a manufacturing company is reshaping its business models through smart, intentional use of technology.