From the Dot-Com Boom to AI: How Tech Buying Has Evolved
In this episode of “Ahead of the Heard,” Olive Technologies’ CEO, Chris Heard, sits down with Howard Holton, CTO at Gigaom, to discuss the changing landscape of buying technology over the past 20 years. With a career spanning more than 35 years and over $5 billion in tech purchases, Howard shares his unique perspective on the parallels between the dot-com boom and today’s hype around AI and crypto.
The Wild West of Tech Buying
Howard describes the early 2000s as a time of unbridled opportunity and chaos in the tech industry. “It was like the Wild West. Everyone knew they needed tech, but nobody knew how to manage it.” He draws a comparison between the dot-com era and the current excitement around AI and crypto, noting that both periods were marked by a lack of understanding and a rush to capitalize on new technologies.
The Importance of Due Diligence
Reflecting on the lessons learned, Howard emphasizes the importance of thorough evaluation before making tech purchases. “We often engage in ‘shoot, ready, aim’—we buy technology before fully understanding how it will benefit our business.” He stresses the need for businesses to carefully assess how new technology aligns with their operations, rather than being driven by fear of missing out.
Complexity and Security
Howard discusses the increasing complexity of technology and the corresponding rise in cybersecurity threats. “Cybersecurity is a combat sport. It’s not optional, and it’s always reactive.” He underscores the importance of maintaining robust security practices, as vulnerabilities will always exist in any system.
The Role of Sales and Customer Success
The conversation also touches on the dynamics between buyers and vendors. Howard highlights the importance of trust in vendor relationships,
You’re not selling a product, you’re selling trust. Once that trust is broken, the relationship is over.”
He also discusses the value of customer success managers (CSMs) in ensuring long-term satisfaction and addressing issues that arise after the sale.
The Future of Tech Buying
Looking ahead, Howard identifies key areas where businesses should focus their attention. He mentions hyper-automation and identity management as two critical technologies that could reshape business operations in the coming years.
We need to evolve our operating models to align with cloud-first and fully distributed environments.
Chris Heard’s “Ahead of the Heard” podcast continues to provide insightful discussions on the future of technology. This episode with Howard Holton offers a deep dive into the evolving landscape of tech buying, the lessons learned from the past, and the critical considerations for the future. As businesses navigate these changes, these conversations serve as a guide to making informed and strategic decisions.
