The Scaling CEO

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 organization as they scale.

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 scale without simply adding more people.

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 alongside their organizations.

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 human touch.

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 era, and how AI is transforming both business operations and customer experiences.

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, successful CEO transitions, value creation, and how AI is beginning to transform supply chains and operations.

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 world's largest marketplace.

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, and business execution.

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 develops future CEOs. We also discuss carbon removal, climate technology, and where AI is creating new opportunities for industrial innovation.

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 on AI-generated marketing content and what Google's latest updates mean for businesses trying to grow online.

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 also dive into AI, cybersecurity, and how executives should think about governance as AI transforms the enterprise.

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 empower employees and automate operations before putting it in front of customers.

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, and the future of business operations.

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 future of technology companies.

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 company, this conversation is full of practical lessons you can apply immediately.

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 protecting governance, intellectual property, and long-term business value.

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 matter more than ever. This is an essential conversation for leaders preparing for what's next.

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're leading a business today, this conversation is full of practical ideas you can use immediately.

Building a successful company starts with the size of your vision. In this episode, I speak with Dan Hnatkovskyy, Co-Founder and CEO of Jome, about why ambitious goals attract better talent, investors, and customers. We also discuss lessons from multiple startups and exits, hiring exceptional people, scaling leadership, building AI-powered products, and why every executive should think bigger if they want to build a lasting company.

Most founders believe they need to reinvent everything to build a successful company. In this episode, I sit down with Travis Hedge, Co-Founder and CEO of Vouch, to discuss why that mindset can actually slow your growth. We talk about transitioning from CRO to CEO, leading through listening instead of assumptions, building strategic partnerships, scaling from startup to a $160M-backed company, and how AI is changing the way executives lead their teams and serve customers.

This article is a summary of what many different senior executives have told me about what they are doing with AI right now.As we enter July 2026, the state of AI in the executive office is defined by a striking paradox: executives are spending aggressively and taking personal control, yet most remain unable to prove clear financial returns.Roughly 72% of CEOs now identify as their company's main AI decision-maker - twice the share from last year (BCG, IBM). 83% of leaders are betting on the deployment of AI agents in full production (Business Wire), even as 56% of firms report no significant financial return and close to 90% report no measurable impact on productivity over three years (Fortune, NBER).While the macro-level data paints a picture of massive expenditure and structural uncertainty, the dispatches from the front lines tell a more nuanced story. Over the last month, I have sat down with sixteen CEOs on my podcast to discuss how they are navigating this moment. They aren't waiting for the ROI data to catch up to the hype. They are moving forward with five specific tactical shifts that redefine the executive's relationship with technology.

In this episode, I talk with Cleveland Brown, CEO and Co-Founder of Payscout, about building a culture that scales. We discuss why great leaders create environments for better decision-making, how to integrate culture during acquisitions, the importance of defining company values, fostering innovation, and how executives should think about adopting AI inside their organizations.

In this episode, I sit down with Neill Feather, CEO of Point Wild, to discuss leadership, scaling through acquisitions, and the growing impact of AI on cybersecurity. We explore how AI is changing cyber threats, what leaders should know about protecting their businesses, how to integrate acquisitions successfully, and why mentorship and continuous development remain essential as companies scale.

In this episode, I speak with Jennifer Rotner, Founder and CEO of Elite Creative, about scaling both yourself and your business. We discuss letting go as a founder, building systems that support growth, creating a thriving remote culture, and why human judgment is becoming even more valuable in the age of AI. Jennifer also shares how her company is embracing AI while keeping people at the center of every decision.

In this episode, I sit down with JR Butler, Founder and CEO of Shift Group, to explore what it really takes to build a high-performing sales organization. We discuss why the best salespeople challenge conventional thinking, how founders should transition from founder-led sales to scalable sales teams, lessons from building companies through hypergrowth, and how AI is changing the future of selling. If you're leading a growing company, this episode is packed with practical leadership and sales insights.

In this episode, I talk with Daniel Arbour, President and CEO of Oshawa Power, about leading culture change inside established organizations. We discuss transforming legacy systems, building a performance-driven culture, empowering frontline employees, managing large-scale operational change, navigating the future of energy, and preparing organizations for AI. Daniel shares practical lessons on leadership, feedback, execution, and how executives can create lasting change by challenging old assumptions.

In this episode, I sit down with Ali Wing, CEO of Oobli, to explore one of the biggest challenges leaders face as their companies grow: becoming the bottleneck. We discuss building teams that can operate without constant executive involvement, scaling through systems and frameworks, leadership growth, board governance, consumer-focused innovation, the future of food technology, and how AI is transforming organizations. Ali also shares lessons from Nike, startup leadership, and leading businesses through periods of rapid growth.

In this episode, I speak with Sriram Subramanian, CEO of Link ToAny, about the challenges of scaling a company without losing confidence in your own vision. We discuss transitioning from developer to founder, building a unique go-to-market strategy, hiring mistakes, creating your own leadership playbook, transparency with employees, and how AI is reshaping the future of commerce. Sriram shares why founders and executives sometimes need to trust their instincts instead of blindly following conventional advice.

In this episode, I sit down with Daniele Horton, Founder and CEO of Verdani Partners, to discuss what it takes to scale a business when the systems, skills, and strategies that got you here are no longer enough. We talk about building a fractional team model, scaling sustainability across thousands of properties, embracing AI, making the leap from expert to executive, and why leaders must constantly evolve if they want their organizations to keep growing. Daniele also shares her journey from architect to entrepreneur and the lessons she's learned scaling a global company.

In this episode, I sit down with David Ly, founder, chairman, and CEO of Iveda, to discuss what it takes to lead a company through more than two decades of technological change. We talk about building trust, scaling globally, communicating across cultures, why leaders must personally verify execution, and how David turned operational challenges into AI-powered innovations long before AI became a trend. This conversation is packed with lessons on leadership, accountability, resilience, and long-term growth.

In this episode, I sit down with Diana Steinhoff, President and CEO of Renaissance Life and Health Insurance Company of America. We discuss the power of asking better questions, creating psychological safety, scaling leadership without getting lost in the weeds, balancing digital transformation with empathy, and using AI to improve customer experiences while keeping humans at the center. Diana also shares how her clinical background shaped her leadership philosophy and why understanding how customers feel is critical to building great organizations.

In this episode, I sit down with Grant Bowen, founder and CEO of Peak Projects, to discuss one of the hardest transitions every founder faces: letting go. We talk about building trust in your team, scaling a service business without sacrificing quality, developing future leaders, creating repeatable processes, and using AI to improve efficiency without losing the human judgment clients depend on. Grant also shares lessons from growing Peak Projects into a nationally recognized firm serving high-profile clients across the country.

In this episode, I sit down with Jay Rosenzweig, CEO of Rosenzweig & Company, to discuss what separates scalable leaders from those who get stuck. We explore why humility, curiosity, and integrity are essential leadership traits, how CEOs should think about building leadership teams, when founders need to let go of control, and what Jay has learned from placing hundreds of executives and advising high-growth companies. We also discuss AI, talent, succession planning, and the future of leadership in a rapidly changing world.

In this episode, I sit down with Zach Papenhausen, President and CEO of Apollo Corporation. We discuss the dangers of overbuilding products, why customer research can still lead you in the wrong direction, and how CEOs can avoid falling in love with features instead of customer needs. Zach shares lessons from acquiring a company just before COVID, scaling with limited resources, balancing data with human impact, and using AI to help small businesses compete with much larger organizations.

In this episode, I sit down with Dan Turner, President and CEO of Xperigo. We explore why trust is the foundation of great leadership, how strong culture drives business performance, and why CEOs must learn to let go and empower their teams. Dan shares lessons from leading through uncertainty, overcoming imposter syndrome, building one of Canada's most admired workplace cultures, and using AI to support people without losing the human touch that customers value most.

In this episode, I sit down with Mike Winterfield, Founder and Managing Partner of Active Impact Investments. We discuss the biggest mistakes founders make when trying to scale sales, why CEOs should stay close to customers longer than they think, and how to transition from founder-led sales to a scalable sales organization. Mike also shares insights from evaluating dozens of startups, coaching founders, servant leadership, venture capital, and how AI is changing productivity, hiring, and company growth.

In this episode, I sit down with Dr. Shalabh Gupta, Founder and CEO of Unicycive Therapeutics, to discuss what it really takes to scale a company in a high-stakes industry. We talk about prioritizing when everything feels urgent, creating a culture where employees are not afraid to take risks, identifying your blind spots as a leader, and continuously upgrading yourself as a CEO. Shalabh also shares lessons from taking a biotech company public, working with investors, and using AI to accelerate growth and commercialization.

In this episode, I sit down with Bryan House, CEO of Elastic Path, to discuss scaling software companies through multiple growth stages. Bryan shares why customer success teams often outperform traditional sales teams, how leaders must let go to scale, lessons from helping build Acquia into a billion-dollar success story, and why staying close to customer problems matters more than ever. We also explore AI-driven commerce, developer adoption, open-source growth strategies, customer relationships, and how CEOs can scale themselves as their organizations grow.

In this episode, I speak with Gregory Shepard, founder of Startup Science and serial entrepreneur who has built and sold 12 companies. Greg shares what his research revealed after interviewing more than 1,200 founders, why most startups fail in the first 18 months, and how founders often build through their own lens instead of the market's reality. We discuss product-market fit, delegation, startup frameworks, founder mindset, competitive positioning, meditation, and how structure can dramatically improve a company's chances of success.

In this episode, I talk with Eric Edelson, CEO of Fireclay Tile, about scaling a craft-based business into a high-growth platform. Eric shares how his team transformed manufacturing complexity into repeatable systems, why bringing order to chaos is the key to growth, lessons from acquiring Fox Marble, and the challenges of scaling service businesses. We also discuss leadership, company culture, continuous learning, AI adoption, operational excellence, and how great businesses create structure without losing craftsmanship.

In this episode, I sit down with Ed Kopko, CEO of Bold Business and former CEO of Butler International, to discuss what it really takes to scale a company through decades of growth and change. Ed shares why CEOs struggle to find time for strategic thinking, the costly leadership mistakes he would avoid if starting again, the importance of benchmarking against the best, and how AI is reshaping workforce solutions. We also explore organizational change, leadership instincts, global scaling, and what it means to build an AI-first company in today's rapidly evolving business environment.

The signal this month is clear. The companies winning with AI have stopped running pilots and started scaling what pays. New data shows that 80% of enterprises running AI agents now report measurable return. Firms stuck on chatbots fall behind. The difference comes down to execution.This month McKinsey told CEOs to move past productivity demos and ask a harder question: how will AI change the economics of your business? IBM found that companies redesigning core functions around AI are four times more likely to hit their goals. The message to the corner office is blunt. AI is now a board-level value lever, and your P&L is where the proof lives.I host The Scaling CEO podcast. I just finished interviews with 19 leaders across industrial manufacturing, software, and private equity backed hospitality. They have settled the question of whether AI works. Now they decide faster, scale what pays, and kill what stalls. Here are the five things they do to drive ROI and protect their lead.

In this episode, I talk with Ross Meglathery, CEO of Integra Tech and former Marine Corps officer, about leadership under pressure and what CEOs get wrong when scaling companies. Ross explains why leaders fail when they refuse to acknowledge their weak spots, how military leadership shaped his approach to business, and why building trust matters more than authority. We also discuss operational discipline, company culture, AI in business operations, and how CEOs can build resilient teams during periods of rapid growth.

In this episode, I sit down with Stacey Epstein, CEO of Structured and former executive at SuccessFactors, ServiceMax, and Freshworks, to talk about the realities of scaling as a CEO. Stacey shares the leadership lessons she learned moving from CMO to CEO, why founders often neglect the areas they think they already understand, and how culture changes as companies grow fast. We also discuss AI, partner ecosystems, leadership pressure, scaling teams, and why AI should act as a thought partner, not a replacement for people.

In this episode, I talk with Steve Harmon about the hidden pressure that comes with leadership. Steve shares lessons from scaling a family business into a multi-company operation managing millions of square feet of industrial space. We discuss stress management for CEOs, leading with culture, balancing growth with people leadership, building service businesses, and how AI is increasing productivity across operations and logistics.