CTO2CTO Podcast Guests

Technology leader with deep experience in private equity-backed companies and portfolio transformation. Former CTO at Envision Capital, a private equity firm investing in lower middle market manufacturing and B2B services companies. Currently CIO at Salute, a data center services company owned by New Mountain Capital. Previously spent significant time at GE in both IT roles and running software and electronics businesses. Specializes in bringing enterprise-grade technology to traditionally low-tech companies and enabling AI adoption at scale.

Eashwer Srinivasan is the Chief Technology Officer at Sonny's Car Wash, the vertically integrated car wash equipment, chemistry, and software company founded in 1949. Before joining Sonny's, he served as VP Engineering at Wind River and held senior technology roles at GE Digital and Rockwell Automation, building industrial software platforms across some of the world's most demanding operational environments. He also led software delivery for NASA projects, an experience that sharpened his instinct for high-reliability, mission-critical engineering. That background now shapes how he approaches platform modernization, predictive maintenance, and AI adoption in what most people assume is a simple industry.

Kit Colbert spent nearly two decades at VMware, ultimately serving as company CTO and managing 2,400 engineers, while also doing foundational individual-contributor work on technologies like vMotion and Storage vMotion. His hands-on engineering career spanning low-level systems work, cloud-native architecture, and enterprise product leadership gives him a uniquely grounded perspective on innovation at scale. Today he is Platform CTO at Invisible Technologies, where he leads development of AI-powered enterprise solutions and human data labeling infrastructure, putting him at the frontier of agentic AI and the evolving economics of software teams.

Robert Stewart is the Chief Technology Officer at Arbital Health, a platform that reduces administrative burden in value-based care contracts by ingesting fragmented healthcare data, applying actuarial models, and delivering clear visualizations for payers and providers. With a background in physics and philosophy from Rice University, his unusual career path took him through underwater acoustics research and early machine learning implementation at Castlight Health before landing him at the intersection of AI and healthcare finance. He is perhaps best known for pioneering the concept of the "actuarial engineer," teaching credentialed actuaries to write production code, rather than training engineers to understand healthcare actuarial science.

Anoop Tripathi is the Chief Technology Officer at Sauce Labs, where he leads platform, infrastructure, and innovation strategy for one of the world's largest software testing and automation cloud environments. His career spans networking, security, virtualization, and enterprise platforms, with senior leadership roles at Citrix, Netgear, and Automation Anywhere. A consistent theme across his work is the argument that software complexity is largely self-inflicted, and that AI, rather than replacing quality engineering, will dramatically amplify the need for it as code volumes rise.

Christopher Penido is the Chief Technology Officer at Louis Vuitton, one of the world's most iconic luxury brands, where he has spent over 12 years architecting and overseeing network, operations, business, and security projects in a follow-the-sun global environment. Growing up in Queens and studying Romance languages, he found that multilingualism and the empathy that comes with it became the foundation of his leadership philosophy. At Louis Vuitton, he has driven security-as-culture initiatives and pioneered the use of blockchain to capture product provenance, reinforcing brand storytelling and supply chain trust.

Ro Mohindroo is a veteran technology executive who has held CTO, CIO, and CDO roles across enterprises, leading large-scale digital transformation programs before transitioning to advising startup and scaleup CTOs. Her advisory work is shaped by a core insight: that technical excellence and operational excellence are not the same thing, and that many companies stall when they conflate the two. She is particularly focused on helping founders and tech leaders connect their work to measurable business outcomes, build reference architectures grounded in business capability, and adopt AI where it creates quiet, structural value rather than headline-grabbing demos.

Gajus Kuizinas is the Co-founder and CTO of Contra, the independent work platform, and one of the most prolific open-source contributors in the JavaScript ecosystem. His libraries receive over 20 million downloads each week and are relied on by Fortune 500 companies including Amazon, Microsoft, Oracle, and IBM. At Contra, he has built a high-trust engineering culture that operates without mandatory code reviews, relying instead on async Loom walkthroughs and radical ownership. His approach to hiring is equally distinctive: the single interview question he uses, "Do you consider yourself lucky?", has become something of a legend in engineering hiring circles.

Leon Kuperman is the Chief Technology Officer at CAST AI, a cloud cost optimization and automation platform for Kubernetes workloads, where he brings over 20 years of experience spanning product management, software design, and production deployment. He is one of the most direct voices on the economics of AI infrastructure, specifically the GPU scarcity trap that forces enterprises into 3-year cloud contracts at tomorrow's prices, and has built CAST AI's philosophy around automating infrastructure decisions so engineers can focus on problems that actually require human intelligence. A brown belt in Brazilian jiu-jitsu, he draws an explicit parallel between mat resilience and engineering leadership: the goal is calm minds, not busy ones.

Jason Blackman is the Chief Information Officer at CAR Group, where he leads global technology strategy across a portfolio of digital automotive marketplaces spanning Australia, the United States, South America, and beyond. His background is unusually broad: he began in control systems and hardware design, moved through software engineering and product leadership, and eventually added governance and cybersecurity to his mandate before stepping into the CIO role. This multidisciplinary lens shapes his pragmatic view on AI adoption, separating use cases into "no regrets" and "watch carefully" buckets, and his conviction that normalizing AI tools is a culture challenge as much as a technology one.

Jeff Miller is the Vice President of Engineering at LinenMaster, a mission-critical SaaS platform for the commercial laundry industry, where he leads the modernization of 30-year-old infrastructure using a deliberate strangler-fig approach. With over two decades of experience, including CTO roles at Yello and NCSA, he specializes in scaling engineering teams, navigating legacy codebases, and applying AI pragmatically in environments where downtime has real-world consequences. He is a vocal advocate for Jocko Willink's Extreme Ownership philosophy and an active mentor who believes that leadership style, not just technical skill, is the true differentiator in senior engineering roles.

John Higginson is the Chief Technology Officer at Curriculum Associates, the leading EdTech provider in the United States, where he oversees a product and engineering team of 400+ people serving 14 million students and 1 million educators. His executive career includes serving as CPTO at Groupon, CTO at Enova, CPTO at FTD, and CTO at Applied Systems. A literature and law graduate before becoming a CTO, he brings an unconventional view to AI in education, particularly around speech-based reading assessment and student privacy, and is known for his conviction that AI literacy is now a baseline expectation for every engineer, not an advanced specialization.

Vinay Kapoor is the Chief Product Officer and Interim CTO at Expana, an AgriFood data and market intelligence platform, where he leads product strategy, design, and roadmap for customers making high-stakes commodity pricing decisions. With 20 years of progressive experience in software product development, he has now held the combined CPO/CTO role twice and has become a practitioner-voice on when to split those functions and why. He is also a sharp critic of AI strategy that skips fundamentals, data quality, governance, and clear ROI models, and advocates for product teams that can speak the language of EBITDA rather than just features.

Derek Wise is the Chief Product and Technology Officer at Civica, a global provider of software and technology services for public sector organizations. Before Civica, he served as Chief Product Officer at Oracle and Grapeshot and as VP of Engineering at Benevolent AI, a career arc that began with a tour as a US Marine. That military foundation is not incidental to his leadership philosophy: he has developed a set of heuristics for building high-performance tech teams that draws directly on Marine Corps decision-making frameworks, emphasizing psychological safety, fast iteration, and the discipline to document why decisions were made as well as what was decided.

Jo Wickremasinghe is the Chief Product and Technology Officer at BPP, the UK professional education group, where she unified engineering, digital platforms, and product strategy under a single vision, a structure she proposed herself when the role was originally framed as Chief Digital Officer. With over 20 years in digital product management, her career spans some of the most prominent digital organizations in the world: Microsoft, BBC, News UK, Babylon Health, and Zoopla. An aerospace engineer by training who pivoted to tech during the dot-com boom, she brings a uniquely cross-disciplinary perspective on org design, digital transformation, and the evolving demands on modern engineering teams.

CJ Montano is the CTO and founder of MyHockeyIQ, an AI-powered sports management platform for hockey, and serves as a board member at Forte Group. A software development veteran, he was the inaugural guest of CTO2CTO, chosen deliberately for his ground-level perspective on what it actually looks like to build a software-first startup on a $7/month AI stack. He is a candid voice on the real learning curve of generative AI tools, including their "last-mile" problems, the myth that AI will replace developers, and why junior engineers who learn to use AI as a thinking partner rather than just a code generator will outcompete those who treat it as either a threat or a crutch.