Software Without Borders

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...

Digital transformation succeeds not by managing distance, but by mastering smart architecture. In this episode Andy Hilliard and Olivier Poulard talk with Bob Grogan, an experienced enterprise architect and technology leader. Bob dives into the critical role of design in driving digital transformation, the impact of AI on enterprise architecture, and how to align tech strategies with business goals. Discover how thoughtful architec...

What if AI and robotics could make law enforcement not only safer but smarter and more ethical? In this episode Andy Hilliard and Olivier Poulard dive deep into this game-changing topic with Roman Grigorii, a software engineer at Axos and researcher with a PhD in Mechanical Engineering. Roman shares how innovations like computer vision and AI-powered transcription are currently transforming public safety in remarkable ways. Don’t m...

What happens when global teams break down cultural barriers and work as one? In this episode, we talk with Hema Ramaswamy, a seasoned tech leader and founder of Sunlit Live. Hema shares her multicultural journey from software engineer to a leadership role, explaining how she turned the challenges of managing multinational teams into strengths. She highlights the importance of a "one team" mindset, clear communication, and documenti...

If you think building the perfect product means waiting until it’s flawless, think again. Today, Glenn Bachmann—CTO of Field Squared and mentor at the Charleston Harbor Entrepreneur Center—reveals how the ‘Build, Measure, Learn’ Lean methodology can be the key to unlocking startup success. With over 30 years of experience, Glenn has guided countless founders through the process of testing assumptions, rapidly iterating, and getting...

What happens when you fail to understand the client's perspective when choosing a software development partner? Misaligned expectations leading to wasted time and costly miscommunications; things we all want to avoid. In today's episode, we tackle this crucial topic with the person who's responsible for delivery to the client. Jeff Scott, the Chief Delivery Officer at KMS Technology. With over 30 years of bridging the gap between b...

What does it take to transform your software team from mere order-takers to proactive problem-solvers? Today we're joined by Michael Marmor, a seasoned Venture Partner and Fractional CTO with over 30 years of experience in building and scaling global software teams. Michael shares his unique insights on how modern product development has evolved, emphasizing the importance of empowering teams to own both the problems and the soluti...

What happens when you don’t prioritize culture or hire the right partner for your global team? In this episode, we explore the serious pitfalls of neglecting cultural integration in digital transformations with our guest, Troy Hiltbrand. Troy is a seasoned leader in global team dynamics with over two decades of experience. Troy shares his journey from software development to becoming a Chief Digital Officer, highlighting how overlo...

Today we're exploring a topic that's reshaping the very definition of software partnership across the globe; hyper -specialization. How can partnering with niche experts reduce risk and foster a culture of accountability? To shed light on this critical issue we've brought on Jim Marascio, CEO of Equals 11. With his extensive experience in Salesforce consulting and post implementation optimization, Jim is uniquely positioned to disc...

How do you foster a collaborative culture when your developer team is remote? Today we explore this question with Patrick Mee, a veteran software development leader with extensive experience at companies like Apple and Sourceforge. Hear Patrick's journey from engineering to management and discover what he learned about creating a culture with remote software teams. This episode is a must-listen for both developers and leaders.

Transformational leaders inspire and drive their teams toward a shared vision of the future. But in the ever-changing tech industry, how is this done? In today's episode, Andy and Jarret uncover these very secrets with Pete Panagakis, a seasoned expert with three decades of hands-on experience in software development and global team leadership. Prepare to be inspired and equipped to lead your global teams in a new way with advi...