Walter Rogers
CEO of MONTYCLOUD
GET TO KNOW WALTER...
Hometown:
Rome, Italy
Alma Mater:
The University of Texas at Austin
Walter A. Rogers, CEO of MontyCloud, has built a career at the intersection of sales excellence, technical innovation, and entrepreneurial grit. From launching his first business as a college student to leading multiple successful exits, Walter brings a unique blend of go-to-market expertise and visionary leadership to the evolving world of CloudOps.
Q: Tell us a little about you and your background.
A: Born in Rome, Italy, and raised in Houston, I’ve always balanced curiosity with a bias for action. During my college years at the University of Texas, that meant opening a bar on Sixth Street—a crash course in marketing, finance, operations, and human nature. After two years, it was time to pivot into consulting, where I spent six years studying how some of the most successful companies in the US sold, ran, and scaled. My consulting work with IBM in the early 90’s hooked me on technology. That inevitably led me to where I am today.
Q: You’ve built and scaled multiple companies. What first sparked your interest in entrepreneurship?
A: I came straight into the world knowing I’d run my own business, but the bar I opened in college with my roommates was the catalyst. We were regulars there, and one day we heard the owner had landed in jail. We tracked down the landlord, showed up with a check for next month’s rent, and walked away with the keys—profitable by the first month. That early lesson in timing and risk-taking shaped everything that came after. I went on to consult in sales effectiveness, moved to Asia to lead marketing for Marcam, and later started my first software company after landing a contract with BMC Software. That venture, which aggregated demand for technical education, was acquired within a few years. From there, I built and sold a server consolidation software firm to VMware, bought back my sales business, helped Amazon Web Services train more than 30,000 sellers worldwide, and launched CloudChomp to automate cloud migration assessments—ultimately selling it to VMware in 2021.
Q: As someone with both technical and sales expertise, how do you bridge the gap between engineering innovation and customer-facing storytelling?
A: My superpower is go-to-market strategy, but I’ve always surrounded myself with brilliant technical partners. I start by listening—really listening—and asking questions until I know exactly what customer need is being solved and why. From there, I translate that complexity into simple, relatable language that connects. I’ve found that if you approach customers with genuine curiosity, they will tell you everything you need to know. Most of the time, they’ll chart their own path to a decision—you just need to know when to lean in and when to listen.
Q: What is the best advice you have ever received?
A: “Listen more than you talk”, “be fifteen minutes early; if you are not early you are late,” and “complexity is the enemy of execution.” For me, it all comes down to insight, preparation, and action.
Q: What core challenge was MontyCloud built to solve—and how is that challenge evolving as cloud complexity increases?
A: Managing the cloud is far more complicated than most realize. When companies move from on-premises data centers to hyperscalers like AWS or Azure, they’re not escaping complexity—they’re simply trading one kind for another. They gain agility, scalability, and speed to innovate, but also inherit new challenges around cost visibility, security, compliance, and governance. Without the right systems in place, these challenges can quickly lead to cost overruns, misconfigurations, or even breaches.
What we do, is ensure cloud management is simpler, safer, and more predictable, especially for managed service providers (MSPs) who oversee dozens or even thousands of customer environments. Our platform gives them a single pane of glass to operate, optimize, and even monetize their cloud environment. Overall, it helps MSPs reduce operational overhead, identify cost savings, and uncover new service opportunities for their customers.
With our latest MCP Server release, we’ve taken that a step further. Our customers can interact with their entire cloud environment through natural language—asking questions like, “Show me my customer’s cost profile” or “Where are the compliance risks?” and get tailored insights. It makes CloudOps as intuitive as having a conversation, without losing the depth and control enterprise teams need.
Q: As AI continues to evolve, how do you see the role of human operators shifting in cloud operations? Are we moving toward AI-assisted governance as the norm?
A: Absolutely. We’re shifting from do-ers to directors. AI agents will increasingly handle routine monitoring, diagnostics, and fixes, while humans will focus on creativity, innovation, and problem-solving.
Q: Are there any ‘AI Scares’ or myths you would like to debunk?
A: There’s a lot of fear about AI displacing jobs. But with every shift comes new opportunity. And I’ll give you an example—when textbooks were first introduced, teachers worried they’d no longer be needed because all the knowledge was suddenly… in a book. Yet education didn’t disappear; it evolved and improved. It’s the same with AI. If we fear new technology, we risk becoming the ones left behind. The advice I would give is to keep learning new tools and use them to do better work—because the minute you think you know it all is the minute you start falling behind.
Q: What do you think the future of CloudOps looks like five years from now, especially with increasing multi-cloud complexity and AI-driven environments?
A: Cloud operations are evolving much like modern car maintenance. Years ago, you could pop the hood and fix things yourself. Today, cars diagnose issues automatically and even schedule their own service. Soon cars will go one step further and even drive themselves to repair shops. CloudOps is heading the same way—AI will manage the monitoring and fixes, while humans bring oversight, creativity, and trust that technology can’t replace.
Q: If we gave you a ‘CEO Recharge Button’ you could hit once a month, what would it trigger?
A: A boat ride with family, friends and of course Kona, my Husky, on Lake Austin—nothing fancy, just cruising and recharging. A few quiet hours on the water always brings perspective. Either that or live music at any one of the may venues in Austin. I am blessed to live in such a wonderful city.
MontyCloud simplifies cloud operations with no-code automation cutting costs, improving security, and giving teams time back to innovate.
More info: montycloud.com
“If we fear new technology, we risk becoming the ones left behind.”