The Scaling Executive

I sit down with Michael “Hutch” Hutchison, Co-Founder and CEO of inGroup International, to explore what it takes to scale a people-first business across nearly 200 countries. We talk about building a global company from the ground up, dividing leadership responsibilities, creating trust with customers, and leading with vision and transparency. Hutch also shares how he uses AI as a CEO thought part...

I sit down with Dylan Serota, CEO and Co-Founder of Terminal, to talk about what happens when rapid growth suddenly reverses. We discuss leading through a major downturn, moving from Chief Strategy Officer to CEO, building remote and hybrid teams, hiring globally, and how AI is changing the skills companies need. Dylan also shares why companies must rethink how they approach talent as AI reshapes...

In this episode, I sit down with Rajiv Parikh, CEO of Position2, to discuss the personal growth required to become a better CEO. We explore why leaders need to be open to difficult feedback, how listening can transform relationships with boards and teams, why the right communities can accelerate leadership growth, and how AI can help entrepreneurs and companies turn ideas into reality faster.

In this episode, I sit down with Mario Di Dio, CEO of Helium, to explore what happens when great technology meets the realities of the market. We discuss why a great idea is not enough, how leaders can recognize when a technology is too early, how to find the right market for innovation, and why CEOs need to become increasingly aware of how their words, decisions, and behavior affect the entire or...

In this episode, I sit down with Fred Voccola, technology entrepreneur, board director, and CEO of Simpro Group, to explore accountability, scaling, and AI-driven operations. We discuss why waiting for final results to hold people accountable is too late, how leaders can track leading indicators, why CEOs need to stay close to the details of the business, and how AI is changing the way companies s...

In this episode, I sit down with Will Jones, President and CEO of THOMPSON Child & Family Focus, to talk about what it really takes to scale an organization responsibly. We discuss why leaders need the discipline to say no, how to evaluate growth opportunities, why leadership capacity matters before expansion, and how coaching, peer groups, humility, and lifelong learning help executives grow...

In this episode, I speak with David Gilbert, Founder and CEO of FairSquare, about leading a multi-brand enterprise through growth and transformation. We discuss building culture across multiple organizations, earning trust through clear communication, hiring and developing great leaders, knowing when to let go, embracing AI across the business, and helping customers adapt to a changing world.

In this episode, I sit down with Mark Seeger, Founder and Co-CEO of Glydways, to explore what it really means to scale yourself as an executive. We discuss letting go of the skills that made you successful, building ownership instead of dependency, creating mission-driven cultures, partnering instead of building everything yourself, and using AI to increase productivity across the organization.

In this episode, I speak with Byron Duncan, COO of FieldPulse, about the leadership mistakes that create unnecessary stress inside organizations. We discuss lessons from handling over 25,000 customer interactions, designing systems that help employees succeed, making difficult scaling decisions, saying no to the wrong opportunities, and using AI to improve customer experience without losing the hu...

In this episode, I sit down with Diaz Nesamoney, Founder and CEO of DaVinci Commerce and co-founder of Informatica, to discuss why great products are no longer enough, how partnerships create lasting competitive advantages, and why today's CEOs must rethink their entire scaling playbook. We also explore founder mode, knowing when to let go, leading major company pivots, rebranding in the AI er...

Over the past few months, I’ve been speaking with CEOs who are no longer debating whether to use AI. In this episode, I break down why AI spending is up in 2026 but headcount and ROI aren't moving, and what the CEOs actually winning with AI do instead. Includes real examples and a simple 30 day action plan.

In this episode, I sit down with Andy Unanue, Founder and Managing Partner of AUA Private Equity Partners and former COO of Goya Foods. We discuss why founders must stop doing everything themselves, how to build leadership teams that can scale without you, what private equity firms look for before investing, lessons from growing family businesses, operational excellence, manufacturing efficiency,...

In this episode, I speak with Spencer Jacobs, Co-Founder and President of Neato. We explore why many brands fail to understand their true Amazon profitability, how technology became Neato's biggest competitive advantage, building custom AI tools, scaling operations, creating leverage through systems, leading high-growth companies, and the operational lessons every executive can learn from the...

In this episode, I sit down with Adam Hasemeyer, CEO of Valtech Americas. We discuss why every leader needs a personal board of directors, how to align teams around a shared mission, integrating acquisitions, scaling company culture, building management systems that drive execution, using executive coaching for growth, and how AI is reshaping both business operations and digital transformation.

In this episode, I talk with Jeff Cates, CEO of ContactMonkey and former CEO of Achievers and Intuit Canada. We explore building high-performance cultures, defining excellence across teams, scaling through clear operating systems, leading organizational transformation, creating better workplace communication, learning from private equity, and using AI to improve leadership, employee communication,...

In this episode, I talk with Brent Constantz, Founder and CEO of Blue Planet, about commercializing deep technology, building companies around innovation, and leading through disciplined execution. Brent shares why businesses shouldn't be designed around regulations, how operating plans create alignment across an organization, and why giving young professionals real leadership responsibility d...

In this episode, I sit down with Andrew Palosi, CEO of Ad Leverage and Datacube.ai, to discuss scaling an agency, building a SaaS company from customer feedback, and evolving as a leader. Andrew explains why CEOs must learn to delegate, how listening to clients creates new business opportunities, and why authentic leadership matters more than ever. We also explore the risks of relying too heavily...

In this episode, I speak with Jason Veiock, Founder and CEO of Bearing, about building a culture where honest feedback drives better decisions. Jason shares lessons from the Air Force, federal law enforcement, GoDaddy, and now his own startup. We discuss why humility is a competitive advantage, how mission-first leadership creates stronger teams, and why consistent habits shape company culture. We...

In this episode, I sit down with Todd Greenbaum, President and CEO of Input 1, to discuss the leadership lessons he's learned over four decades of scaling. Todd shares why knowledge transfer is essential for growth, how building strong middle management unlocks scale, and why CEOs must invest in teaching instead of becoming bottlenecks. We also explore his practical approach to AI, using it to...

Growth doesn't happen by accident, it happens because you're prepared for it. In this episode, I speak with Garth Coleman about leading through hypergrowth, building scalable systems, writing playbooks instead of waiting for them, making the right hiring decisions, and preparing your business before rapid growth arrives. We also dive into how AI is changing software, product development, a...

Scaling a company requires more than growing revenue, it requires growing as a leader. In this episode, I talk with venture capitalist Krishna Srinivasan about how founders must evolve, build leadership teams, work effectively with their boards, preserve culture through growth, and make smarter decisions as their companies scale. We also explore how AI is changing investing, startups, and the futu...

In this episode, I sit down with Keith Zubchevich, CEO of Conviva, to explore the leadership shift from creating strategy to owning every outcome. We discuss building companies from startup to IPO, creating a leadership framework that fits you, why culture is a CEO's greatest responsibility, and how AI is transforming productivity and customer experience. If you're leading a growing compan...

The hardest part of an acquisition isn't the deal, it's the people. In this episode, I sit down with Colby Durnin to discuss scaling through acquisitions, why culture determines whether integrations succeed, building strong relationships with your board, learning to delegate as a CEO, and leading through growth. We also explore how executives should approach AI strategically while protecti...

As AI makes it easier for everyone to build products, what will actually make your company stand out? In this episode, I speak with Ezra Menaged, CEO of Hometalk, about the future of competitive advantage in the AI era. We discuss scaling from growth leader to CEO, developing executive judgment, empowering teams with AI, building data-driven businesses, and why taste and decision-making will matte...

AI is changing leadership faster than any technology before it. In this episode, I sit down with Jascha Kaykas-Wolff, CEO of Visiting Media, to discuss why executives must personally lead AI adoption instead of delegating it. We explore agile leadership, scaling from CMO to CEO, building AI-first organizations, empowering teams with AI agents, and preparing employees for the future of work. If you...