The Scaling Executive

In this episode, I sit down with Jaspreet Singh, Founder and CEO of Druva, to discuss what it takes to build and scale a successful organization. We explore the challenges of transitioning from a technical founder to a business leader, finding product-market fit, hiring the right executives, defining roles, and developing the leadership skills needed to manage a growing company. We also discuss wh...

The executives pulling ahead with AI are building it into how their companies run. In this episode of The Scaling Executive Podcast, Glenn Gow, The Scaling Executive Coach, breaks down the top five things leaders are doing with AI right now, based on conversations with senior operators in retail, aerospace, law, cybersecurity, finance, and software: keeping humans accountable for output, building...

In this episode, I sit down with Ben Little, CEO of Bridger Photonics, to discuss the leadership lessons he has learned from scaling businesses, leading turnarounds, and growing organizations across different industries. We explore how CEOs can avoid becoming bottlenecks, the qualities every great executive needs, why bad news should travel faster than good news, and how understanding unit economi...

In this episode of The Scaling Executive Podcast, I speak with Adam Povlitz, President and CEO of Anago Cleaning Systems, about leadership, business growth, and the challenges executives face as their responsibilities expand. Adam shares how he helped grow the company beyond $100 million in system-wide revenue in just 19 months, why leaders need to learn to delegate effectively, and how testing id...

In this episode of The Scaling Executive Podcast, I speak with Prabhakar Tadepalli, Co-Founder, President, and COO of Tyfone, about what it really takes to build and scale a business. We discuss why customers care more about results than your vision, how to recognize when your business needs to pivot, and why listening to customers is essential for survival. Prabhakar also shares lessons from his...

In this episode, I sit down with Daniel Cohen, VP of Customer Success at CodeRabbit, to explore how leaders can scale customer operations, build accountable teams, and use AI effectively. Daniel shares lessons from his early engineering career, his approach to high trust and high accountability, and why leaders need to give people ownership while holding them responsible for outcomes. We also disc...

In this episode, I sit down with Lauren Antonoff, CEO of Life360, to discuss what it takes to grow as an executive and lead through major change. Lauren shares lessons from her time at Microsoft, including helping transition SharePoint from on-premises software to the cloud, and explains why organizations must be willing to continually reinvent themselves. We also discuss how leaders can overcome...

In this episode, I sit down with Janet Grondin, CEO of Stellar Solutions, to talk about what it really takes to scale as a leader. We discuss her transition from the U.S. Air Force to corporate leadership, how her leadership style changed during the pandemic, and why understanding what employees need can make you a better leader. Janet also shares how she learned to move from doing the work hersel...

In this episode, I sit down with Clay Cowan, CEO of IRA Financial, to discuss the challenges executives face as their companies grow. We talk about moving from functional leadership to the CEO role, making better decisions, knowing what deserves your attention, delegating to the right people, and bringing in outside expertise when necessary. We also explore customer acquisition, long-term brand bu...

In this episode, I sit down with Dr. Aleksandr Yampolskiy, co-founder and CEO of SecurityScorecard, to discuss what happens when technical expertise turns into executive leadership. We talk about scaling through hypergrowth, building a strong company culture, creating customer-focused organizations, developing leaders, and learning to step into new roles as the business grows. We also discuss coac...

In this episode, I sit down with Michael McCready, founder and managing partner of McCready Law, to discuss what it really takes to scale a business beyond the founder. We talk about building leaders, delegating effectively, creating systems and culture that support growth, and expanding a business without keeping every decision centralized. We also explore AI adoption, governance, employee concer...

Senior executives are past the chatbot hype and are now building AI into how they actually run their companies. In this episode of The Scaling Executive Podcast, Glenn Gow, The Scaling Executive Coach, breaks down the top five things leaders are doing with AI right now, based on conversations with C-suite operators and growth equity investors: using AI as a co-pilot, automating mundane work, build...

In this episode, I sit down with Bob Root, Operating Partner at Southfield Capital, to discuss scaling businesses, developing leaders, and using AI strategically. Bob shares lessons from his time at Procter & Gamble and Microsoft, explains how he approaches founder-led businesses and CEO transitions, and discusses why he believes cost savings alone isn't a strategy for AI. We also explore...

In this episode, I sit down with Stevan Popovich, President and Chief Retail Officer of Cycle Gear, to discuss what it takes to scale a business and its leadership team. We talk about building trust among high performers, coaching employees through personal and professional growth, leading through rapid expansion, improving communication and prioritization, and balancing technology with the human...

In this episode, I sit down with Adam Harris, CEO and co-founder of Cloudbeds, to explore what it really takes to scale a global technology company. We discuss the lessons he learned from finance and consulting, the challenges of scaling across 41 countries, knowing when to say no, and how CEOs can scale themselves without becoming the bottleneck. We also take a deep look at AI, from using it as a...

In this episode, I sit down with Augustin Prot, co-founder and CEO of Weglot, to discuss how to build and scale a company without losing focus. We explore why he and his co-founder deliberately kept the team small, how they approach hiring and profitability, and why managers at Weglot are still expected to contribute operationally. We also discuss company culture, the four-day workweek, hybrid wor...

In this episode, I sit down with Lindsay Glassco, President and CEO of Plan International Canada, to discuss what it really takes to scale an organization. We talk about letting go of control, building trust, creating a resilient organization, aligning employees around strategy, and knowing when to step back as a CEO. Lindsay also shares her perspective on AI, organizational culture, leadership, a...

In this episode, I sit down with César Cabrera, Co-Founder and CTO at Ualett, to explore how technical leaders can scale themselves and their teams. We discuss why technology should serve the user, how to build from the outside in, the importance of delegation, and how leaders can avoid becoming the bottleneck. César also shares how his team uses AI to accelerate coding, testing, prototyping, and...

In this episode, I sit down with Brian Rich, Managing Partner at Catalyst Investors, to discuss what it really takes to scale a company and make the difficult decisions that come with growth. We talk about how CEOs and their teams need to evolve, managing boards, investment strategy, AI, and the challenge of predicting where technology is heading. Brian also shares how he thinks about AI-enabled b...

I speak with Brian R. Smith, Managing Director at S3 Ventures, about what it really takes to scale a company, from finding product-market fit to building a team that can see what the CEO cannot. We discuss why leaders need to let go, how boards and CEOs can better understand each other’s incentives, when to bring in a coach, and why the right team is critical to growth. Brian also shares his persp...

I speak with Dan Corrigan, co-founder and CEO of Organic 3, about the lessons he learned from building businesses through persistence, mistakes, customer feedback, and personal growth. We discuss why CEOs need to stop trying to do everything themselves, hire earlier, build a strong leadership team, and ask “who” instead of “how.” Dan also shares lessons from international partnerships, coaching, p...

I speak with Jonathan Snow, the co-founder, Chief Innovation Officer, and Managing Director at Avenue Z, about the leadership challenges that appear when a company grows faster than its infrastructure. We discuss delegation, managing your energy, knowing what only you should be doing, and recognizing when growth is creating a “house of cards.” Jonathan also shares lessons from scaling marketing bu...

I speak with Vic Yeh, co-founder and CEO of Cara, about what happens when a technical founder becomes a CEO and the company begins scaling rapidly. We discuss why leaders must reinvent themselves, move from doing to empowering, build the right team and processes, and use AI to increase productivity without replacing the people who make the business work. Vic also shares lessons from scaling an ins...

I sit down with Ankur Ahlowalia, CEO of Chronus, to discuss how executives can scale a company without simply scaling costs and headcount. We explore how to identify and empower top talent, improve sales win rates, build systems around learning from losses, and develop people through mentorship and coaching. Ankur also shares how he is leading an AI transformation at Chronus and using AI agents to...

I sit down with Larry Weber, founder of Weber Group and Racepoint Global, to explore the leadership and communication lessons he learned from building multiple major companies. We discuss hiring people you can trust, scaling through strong talent, communicating a company’s value through a simple story, leading through rapid growth, and building influence as an executive. Larry also shares his pers...