In this episode of So You Think You Can Dev, we sit down with Charles Sims, also known as The Hurricane CTO, for a powerful conversation on navigating disruption, AI, and the human side of innovation.

With over 15 years of experience and more than $1.5 billion in acquisitions in the sports and entertainment industries, Charles shares his unique journey from the world of film production to leading transformative tech initiatives at organizations like the LA Clippers. Now an investor and tech evangelist, he offers a candid look at how today’s AI disruption differs from past waves of innovation, why many businesses still struggle with understanding their own systems, and how leaders can identify true opportunities amid the hype.

He also introduces his “Hurricane Method,” a framework designed to bring chaos to calm through better leadership, communication, and process design.

Whether you're a tech leader, founder, or just curious about where AI is heading, this episode is packed with practical insights and thought-provoking takeaways.

Check out KMS Technology:⁠⁠⁠ ⁠https://kms-technology.com/⁠⁠⁠⁠

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Learn more about Charles and the Hurricane Method at ⁠hurricanecto.com⁠

In this episode of So You Think You Can Dev, we sit down with Tory Bjorklund, Digital Transformation Specialist and CEO of Victoria Fide Consulting, to explore a pressing question: why do so many digital transformation projects still fail, even in 2025?

With decades of experience leading complex tech initiatives across industries, Tory unpacks the disconnect between better tools and persistently poor outcomes. From misaligned business goals to constantly shifting requirements and underprepared teams, this episode dives deep into the human and organizational challenges behind tech failures.

We also discuss the evolving role of AI, especially agentic AI, and how companies can lay the right data and infrastructure foundations to take full advantage of emerging technologies.

Whether you’re a developer, a CTO, or a business leader navigating change, Tory offers actionable insights on how to align your teams, manage up effectively, and make digital transformation stick. Tune in for a no-nonsense conversation that reframes success around business outcomes, not just technical execution.

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In this episode, we chat with Naveen Krishnan - AI Architect at Microsoft. Naveen is a recognized voice in the AI community at the forefront of leveraging cutting-edge technologies to solve real-world problems, with a deep passion for artificial intelligence and cloud computing.

Listen in as Naveen shares cutting-edge insights on the latest AI trends, from the evolution of large language models to the rise of Agentic AI. He discusses the challenges and opportunities in implementing AI, especially for regulated industries, and how it's creating competitive advantages.

We explore practical use cases, real-world challenges in industries like fintech and healthcare, and how organizations can start small and scale responsibly.

Check out KMS Technology:⁠⁠ ⁠https://kms-technology.com/⁠⁠⁠

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In this episode of So You Think You Can Dev, we sit down with AI entrepreneur and investor Dilip Dubey, Founder of Sutra AI, to explore how companies - especially mid-market players can unlock transformative business value through AI.

With over two decades of experience as a founder, investor, and mentor, Dilip offers a unique 360° perspective on leveraging generative and agentic AI for operational efficiency, revenue growth, innovation, and customer experience. He shares real-world examples of companies doubling their profitability through AI, explains why traditional digital transformation is no longer enough, and breaks down how businesses can start small and scale fast.

Whether you're a tech leader or business executive, this episode is packed with strategic insights and practical steps to help you build a future-ready organization with AI.

Check out KMS Technology:⁠⁠ ⁠https://kms-technology.com/⁠⁠⁠

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In this episode of So You Think You Can Dev, we sit down with Dave Sobel, the Host of Business of Tech and longtime expert in the managed services space. From IT infrastructure refresh cycles to the growing role of AI and data engineering, Dave breaks down where the tech services market is heading in 2025 - and what that means for SaaS companies.

The conversation explore why internal hiring is becoming more challenging, how co-managed outsourcing models are helping companies scale smarter, and what separates a good service partner from a great one. Dave also shares insights on measuring ROI, the evolving role of generative AI, and why outcomes—not just output—should drive your decisions.

Tune in for a thoughtful conversation that connects industry trends with real business value.

Check out KMS Technology:⁠⁠ ⁠https://kms-technology.com/⁠⁠⁠

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In this episode of So You Think You Can Dev, we sit down with Tom Altman, Fractional CTO at Altus CXO - to explore the evolving world of technology and its impact on modern business. Drawing on over 25 years of experience in web development, e-commerce, and tech leadership, Tom offers a candid discussion on the shift from hands-on coding to strategic technology management.

The conversation delves into the transformative influence of Generative and Agentic AI on business processes and the crucial role of systems mapping, process documentation, and data governance. He shares real-world insights on managing technical debt and boosting efficiency in an AI-driven future.

Whether you’re a tech veteran or an aspiring leader, this episode promises an engaging journey into the future of technology.

Check out KMS Technology:⁠⁠ ⁠https://kms-technology.com/⁠⁠⁠

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In this episode of So You Think You Can Dev, we sit down with Tamara Adlin—author, speaker, and UX strategist—to explore the critical role of alignment in product development and startup success. From her early days at Amazon to consulting for startups and enterprise companies, Tamara shares insights on how misaligned teams impact products (aka “corporate underpants”) and why getting your executive team on the same page can make or break a project.

We also dive into disruptive technologies like AI and blockchain—should companies rush to adopt them or take a more strategic approach? Plus, Tamara shares valuable advice for women in tech and job seekers looking for support through Never Search Alone.

Tune in for real-world stories, practical strategies, and a candid discussion on what it really takes to build great products and resilient teams.

This episode is a part of our Women in Tech series, where we spotlight inspiring women in the tech industry.

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Philip Massey is a Director & CPA at Dean Dorton, a leading professional services firm specializing in accounting, business advisory, and technology solutions

At Dean Dorton, Philip focuses on cloud-based financial software, helping businesses streamline operations, enhance decision-making, and integrate ERP and financial systems for greater efficiency.

Having been in the industry since 1994, Philip is most passionate about the intersection of finance and technology. With deep expertise in software implementation, integration, and business process optimization, he helps organizations navigate cloud transformation and align technology adoption with long-term business goals.

In this episode, Philip shares insights on the challenges of cloud adoption, security considerations, and how businesses can make smarter technology decisions to stay competitive in a rapidly evolving digital landscape.

Check out KMS Technology:⁠⁠ ⁠KMS Technology

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In this episode of So You Think You Can Dev, we welcomeKathleen Lorey, VP of Strategic Services atRESICAP. With her extensive experience in product development, Kathleen shares invaluable insights into the complexities of enhancing product adoption and managing change effectively.

RESICAP is a leading vertically integrated solution for institutional owners of single-family residential assets in the United States. Their extensive range of services includes asset valuation, property sourcing, general contracting, construction management, maintenance, property preservation, leasing, property management, dispositions, and title services. 

Join us for an engaging conversation that highlights the intersection of technology, project management, and strategic services. Along with how to foster a culture of innovation and collaboration within your organization.

This episode is a part of our Women in Tech series, where we spotlight inspiring women in the tech industry.

Check out KMS Technology:⁠⁠ KMS Technology

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This is Part 2 of our conversation with ⁠Janie Longfellow⁠⁠, CPO & CTO at Nicus Software, continuing our Women in Tech series.

In Part 2, Janie discussed the importance of effective communication, collaboration, and empathy in building successful cross-functional teams. Including specific cases from her own experience as a tech leader.

She also highlighted the role of data-driven decision-making and the potential of AI in shaping the future of product, technology, and customer success. Such as the increased collaboration between different teams and leveraging AI to streamline processes, and improve efficiency.

This episode is a part of our Women in Tech series, where we spotlight inspiring women in the tech industry.

Check out KMS Technology:⁠⁠⁠ ⁠KMS Technology⁠

Follow us on LinkedIn:⁠⁠⁠ ⁠KMS Technology