Software Without Borders
Software Without Borders is the essential listen for technology leaders and business owners in the software sector who crave insights from the industry’s top minds. Picture a relaxed, coffee-driven chat where tech veterans discuss cutting-edge projects and business strategies shaping their industry. Tune in to join conversations that traverse the intersections of technology and business, helping you stay ahead in a rapidly evolving industry.
Episodes
In this episode of Software Without Borders, Andy and Scott sit down with Kristina Crane, transformational executive, fractional COO/CSO, and CEO of The Canyons Group, to unpack what it really takes to lead organizations through AI-driven change. Kristina draws on 25+ years across SaaS, government tech, and operational transformation to explain how companies can embrace AI without losing their people, culture, or strategic focus. F...
In this episode of Software Without Borders Podcast, Andy Hilliard sits down with Olivier Poulard, Accelerance’s Head of Global Software Engineering Strategies, to unpack one of the biggest myths in global software delivery: that adding more people solves delivery problems. Olivier shares what really drives predictability—clear alignment across people, process, technology, and data—and why so many organizations unknowingly “scale c...
On today's episode, we sit down with Raja Musunuru, CPO at Tiffin and a seasoned leader with over 25 years across Fortune 500 companies and innovative startups. Raja shares how AI is transforming the way products are built—shortening cycles from months to days, empowering small but mighty teams, and reshaping the global talent model. From crisis leadership lessons at Gaylord Hotels to redefining donor-advised funds with AI-driven i...
Welcome back to Software Without Borders! I'm Andy Hilliard, and today I'm thrilled to dive into the world of hiring with John Collins, a leader who's shaped talent strategies at Microsoft, Apple, and scale-ups like Snapchat and Flixbus. As the founder of Yogan, John's tackling universal hiring headaches—like one-size-fits-all processes, AI biases, and lengthy interviews—that slow down growth and inflate costs. We e...
Hey folks, Andy Hilliard here with another episode of Software Without Borders! I’m pumped to sit down with Mike Hostetler, an AI/ML guru and software builder who’s reshaping enterprises at ServiceCore. We trace Mike’s journey from coding QBasic games as a kid to pioneering open source like jQuery and now driving AI transformations. He shares game-changing insights on orchestrating AI agents, the rise of the Chief Agent Officer rol...
Hey, folks! Andy Hilliard here, your host of Software Without Borders, bringing you a game-changing chat with Andrew Hosman, VP and Head of Product at EigenRisk. We’re diving deep into how AI is revolutionizing product management, from slashing grunt work to sparking customer-focused innovation. Andrew shares his journey from coder to product leader, revealing tips on crafting killer SaaS products, leading global teams, and leverag...
Hey, Software Without Borders fans! Tomas Hilliard here, joined by Olivier Poulard, diving into the AI revolution with Jack Teitel, founder of Tidal AI and an AI/ML maestro with over a decade of experience. Jack shares game-changing insights on leveraging AI in healthcare, software development, and beyond, emphasizing data privacy, human-AI collaboration, and avoiding overhyped pitfalls. From speeding up coding 3-5x to ensuring sca...
Oshri Cohen is a battle-tested Fractional CTO who’s led global dev teams, built multi-million-dollar payment systems, and rescued more than 30 companies from the brink of technical collapse. With a career that began in teenage hacking and evolved into executive leadership across industries like health tech, fintech, and e-commerce, Oshri brings a rare blend of hands-on engineering expertise and strategic business acumen. Known for ...
Jig Patel is a global technology and business operations executive with over 25 years of experience leading digital transformation across Fortune 500 companies. Known for bridging the gap between technical complexity and strategic clarity, Jig has spearheaded multibillion-dollar modernization efforts in highly regulated industries—including financial services, utilities, and healthcare. His leadership has delivered measurable outco...
From athlete to architect of transformation, Rose Schamberger shares her journey from professional volleyball to leading global tech teams in this powerful episode of Software Without Borders. Hosted by Andy Hilliard and Olivier Poulard, the conversation explores agile leadership, customer-centric development, and what it really takes to modernize software in today’s fast-changing world. Rose offers a playbook for growth-minded lea...
Manish Limaye doesn’t believe in data science for the sake of knowledge - he believes in applied data science that drives real business results. As Chief Data Officer at Revenate and a veteran of Equifax, Travelport, and CITA, he’s built a career transforming data from a back-office function into a revenue-driving force. In this episode, Manish joins Andy Hilliard and Olivier Poulard to discuss how data teams can bridge the gap bet...
Kenneth Lopez has built his career at the crossroads of software development and entrepreneurship, scaling various companies with relentless tenacity. As a software executive and investor, he’s mastered the art of bootstrapping, leveraging AI for smarter development, and navigating the delicate balance between technology and human connection. In this episode, Kenneth joins Andy Hilliard and Ryan Schauer to share his hard-earned ins...
Adam Rhuberg has spent his career at the intersection of data science and product development at companies like Upwork, eBay, and Jawbone. His secret to success? Turning raw data into real results with clear roadmaps that connect analytics to smarter business decisions. In this episode, Adam joins Andy Hilliard and Ryan Schauer to unpack the powerful connection between data science and software development, how AI is rewriting the ...
Mark Orttung has pulled off what many software companies fail to do - apply agile principles beyond software development. And the results are profound. With a career leading digital transformation at scale, Mark brings deep expertise in operational agility, leadership alignment, and business growth. In this episode, he joins Andy Hilliard and Rich Wanden to discuss how embracing agile thinking across an entire organization leads to...
Jesse Demmel, CTO of Uplight, is helping energy companies tackle grid challenges with smart devices and customer behavior. With a career spanning giants like Intuit and Under Armour, and as a contributor to Andy Hilliard's upcoming book Total Cost of Delivery, Jesse brings unique insight to today's conversation. In this episode, he joins Andy and Ryan to break down how to access specialized skills in distributed teams, insp...
Where you invest in technology today determines your company’s value tomorrow. In this episode, Andy Hilliard and Rich Wanden sit down with Pete Panagakis, a veteran technology leader with deep experience in software outsourcing, business transformation, and scaling global teams. Pete shares practical insights on how to make smart technology investments, avoid crippling technical debt, and strategically align IT with business goals...
How can leaders navigate the balance between agility, innovation, and accountability in modern software development? In this episode, Andy Hilliard and Olivier Poulard are joined by Darrell Swope, a seasoned technology leader with a track record in scaling high-performance teams and implementing agile methodologies. Darrell shares real-world insights on creating strong product roadmaps, fostering team alignment, and integrating cus...
Great software teams aren’t built by accident—they thrive under leaders who prioritize trust, simplicity, and agility. But how do you accomplish that in today's fast-paced global market? In this episode, Andy Hilliard and Olivier Poulard sit down with Jeff Andrews, a seasoned technology executive with over 30 years of experience in cloud, SaaS, and enterprise systems. Jeff shares practical lessons from his career with real exam...
What sets successful tech startups apart in today’s competitive landscape? In this episode, Andy Hilliard and Ryan Schauer sit down with Howie Altman, a seasoned executive, tech entrepreneur, and Fractional CTO. Howie reveals the core principles behind thriving startups, from aligning technical strategies with business goals to building strong relationships and cultivating self-aware leadership. Learn how to navigate the challenges...
Technical skills will only get you so far in modern software leadership. Trust, communication, and leadership are the real keys to success. In this episode Andy Hilliard and Olivier Poulard sit down with Tom Holt, a seasoned software executive and agile transformation expert. Tom explores the soft skills that truly define effective software leaders: fostering psychological safety, streamlining lines of communication, and leading di...
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