Software Without Borders

What happens when a hacker-turned-CTO ditches convention and builds a career out of saving struggling tech teams across industries? In this episode of Software Without Borders, I sit down with Oshri Cohen, a fearless, no-nonsense fractional CTO who thrives at the intersection of chaos and clarity. From coding viruses as a teenager to leading global teams, Oshri brings unmatched energy and insight into what it really means to guide a company through technical transformation. We cover everything—from the absurdity of inflated CTO titles to why his goal is to work himself out of a job. It’s candid. It’s unfiltered. It’s a deep dive into the mindset of a CTO who sees through the noise and fixes what’s broken—fast. Whether you’re a founder wondering if you need a CTO, or a technologist eyeing the fractional path, this one is packed with perspective. Don’t miss this bold, raw conversation about the future of tech leadership.
Guest Details:  Oshri Cohen – Fractional CTO, RedCorner.ioOshri 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 his blunt honesty, chameleon-like adaptability, and mission to “get fired” by making tech teams self-sufficient, he’s the guy founders call when everything’s on fire—and he thrives in the heat.
Key Takeaways:  Not All CTO Roles Are Created EqualThe title "CTO" means wildly different things depending on a company’s stage. Oshri breaks it down into four phases—from hands-on dev to visionary leader—and argues most companies confuse the role entirely.Fractional CTOs Are the FixersOshri often steps into companies already on life support. His approach is simple: stabilize, train, and work himself out of the job. His real value lies in preventing problems before code is even touched.The CTO as a ChameleonA fractional CTO must wear many hats—therapist, strategist, tech lead, even babysitter. Oshri thrives in this fluidity, adapting based on what's most broken today.You’re Not Building for Average—You’re Building for the SpikeOne of Oshri’s clients had peak traffic needs that their infrastructure wasn’t ready for. He reframed the problem: design systems around time as a resource—not just users or throughput.AI is Not the Savior—It’s the DistractionDespite the buzz, Oshri warns that AI is promoting keyboard-driven busywork over deep, strategic thinking. The industry is undervaluing senior talent in favor of junior devs who can prompt a bot.Saving Money Isn’t Always the WinOshri shares how he saved a client $10K/month by proposing an open-source Mailchimp alternative. But fractional leaders often struggle to prove their value because great work becomes invisible when things run smoothly.The Ultimate Goal Is to Get FiredIronically, Oshri’s metric for success is simple: the company runs so well, they no longer need him. That means training teams to be independent, not reliant on heroics.
Chapter Markers:  00:00 – Costa Rica Life & Connectivity WoesOshri shares life off-the-grid and how it reflects his flexible work style.04:00 – From Teenage Hacker to Dev ProdigyA wild origin story involving C++, viruses, and early coding ethics.08:00 – Hustling Through the Dot-Com BustHow Oshri landed developer roles during an economic drought.13:00 – Building a Consulting EmpireSelling Microsoft CRM and implementing early automation before it was trendy.16:00 – Creating Twilio Before TwilioHow a campus shooting in Montreal sparked an SMS idea a decade early.20:00 – Why Most Startups Don’t Need a CTOOshri’s breakdown of fractional work and why strategy trumps headcount.25:00 – The 4 CTO ArchetypesDeveloper → Manager → Leader → Visionary. Most people can’t do all four.35:00 – Why Oshri Wants to Get FiredFractional success = team independence. But it comes with a visibility cost.43:00 – Contracts, Pricing, and Perceived ValueHow Oshri structures engagements and educates clients on invisible ROI.50:00 – The Future of Tech Talent in the AI EraHarsh truths about AI, developer value, and the mentorship vacuum.
Keywords:  fractional CTO, software leadership, startup technology strategy, CTO evolution, Oshri Cohen, CTO phases, fractional tech executive, technology consulting, software architecture, developer career path, managing dev teams, AI in tech, software without borders, Andy Hilliard podcast, CTO value, dev agency problems, startup CTO roles, scaling tech teams, open source email marketing, Mailchimp alternative, CTO business impact, getting fired as a CTO, peak infrastructure planning, event-based systems, tech leadership insights, remote tech consulting, Costa Rica digital nomad

What happens when a scientist-turned-technologist builds global teams, transforms regulated industries, and quietly reshapes how we think about innovation? In this episode of Software Without Borders, Andy Hilliard and Olivier Poulard sit down with Jig Patel, a seasoned technology and business operations executive, to explore how curiosity, connection, and clear communication drive transformation at scale. From deploying AI-enabled drones to building enterprise-wide digital cultures, Jig shares his playbook for leading with purpose in industries where tradition often outweighs change.
Guest Details:  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 outcomes like a 7-point NPS lift, $50M+ in recurring revenue, and AI adoption at enterprise scale. A former scientist turned transformation architect, Jig brings a unique mix of curiosity, operational rigor, and servant leadership to every challenge. Whether he’s launching an HSA bank or integrating global teams post-merger, Jig’s approach centers on cross-functional alignment, empowered teams, and driving customer value—faster.
Key Takeaways:  Curiosity is a Core Leadership Trait Jig emphasizes that asking “why” is foundational to innovation—whether in a chemistry lab or leading a global enterprise.Business Technologists Bridge the Gap Unlike traditional tech leaders, Jig came from the business side and built his career by translating customer needs into technology solutions—an increasingly vital skill in modern organizations.AI Is a Tool for Enablement, Not Replacement Jig’s experience deploying “Mo,” an AI at Morningstar, shows how AI can enhance—not replace—human capabilities, especially when developed ethically and intentionally.Empowerment Starts with Communication High-performing global teams require deliberate, active communication and leadership that adapts to cultural and geopolitical nuances.Innovation Isn’t Always Tech-Driven Small process improvements, like reducing a 50-step process to 10, count as innovation and can be just as transformative as deploying new software.Highly Regulated Industries Still Need Change Working in finance, utilities, and other regulated sectors has taught Jig that constraints don’t mean resistance—they mean leaders must work creatively within the rules.Optionality Is the Real Superpower Leaders must offer more than a plan—they must offer multiple pre-thought-out paths in case priorities or conditions shift mid-execution.Stakeholder Influence Is Earned Through Understanding Building support from the board and ELT requires doing the homework, speaking their language, and giving them clear, actionable options.
Chapter Markers:  00:00 – Behind-the-scenes banter and setup03:53 – Guest intro: Jig Patel’s journey from science to tech leadership06:30 – The immigrant experience and early influences08:45 – Learning to listen: Sales, support, and the path into technology12:00 – Building tech through a business-first lens14:00 – Dual COO/CIO roles and why they’re on the rise18:00 – Culture of curiosity in regulated industries20:30 – Innovation in utilities vs. financial services27:00 – Morningstar’s AI initiative: The story of “Mo”31:00 – Ethical AI, planning before building, and phased deployment36:00 – Communication and cultural alignment across global teams43:00 – Leadership vs. management: Empowering vs. controlling46:00 – Working with regulatory bodies without stifling innovation51:00 – AI-enabled drones: A case study in public safety and efficiency57:00 – Stakeholder influence and communication strategy01:02:00 – Innovation through simplification and operational evolution01:07:00 – Final thoughts and closing remarks
Keywords:  Jig Patel, business technologist, technology leadership, regulated industries, digital transformation, software modernization, AI in financial services, Morningstar Mo, leadership in tech, enterprise transformation, innovation strategy, stakeholder alignment, cross-functional teams, global engineering, curiosity in leadership, AI-enabled drones, utilities innovation, agile communication, software development podcast, Software Without Borders, Accelerance, Andy Hilliard, Olivier Poulard, CIO strategy, CTO innovation, ethical AI, technology in regulated sectors

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 leaders ready to elevate their impact by aligning teams, simplifying processes, and staying relentlessly focused on the customer.
 
Key Takeaways:
Agile Is a Mindset, Not a Framework
Rose and Olivier agree: following an Agile playbook isn’t enough. Success comes from adopting Agile values—feedback, iteration, simplicity, and ownership—regardless of process.
Customer Centricity Begins With Empathy
Rose emphasizes the importance of understanding the customer journey. Engineers should “eat their own dog food,” sit with support teams, and interact with products like real users.
Decentralize Decision-Making, Centralize Vision
Global teams thrive when each region has accountability and autonomy, but shares a unified direction. This alignment empowers faster, better decisions across time zones.
Value Over Code Elegance
Rose challenges teams to prioritize customer outcomes over technical purity. The best software isn't the most elegant—it’s the most useful and adopted.
AI is a Tool, Not a Silver Bullet
Generative AI is powerful but overhyped. Rose warns leaders not to chase tools without understanding the real problems they’re solving.
Cross-Functional Metrics Create Accountability
Shared KPIs between product, marketing, and engineering—like customer adoption and satisfaction—drive aligned execution and true collaboration.
Modernization Requires Contextual Strategy
Migrating to the cloud looks different for every product. Rose shares how both monolithic and microservices-based strategies can succeed—if aligned with customer needs.
Leadership Means Going to the People
Rose and Olivier agree that leaders must proactively engage teams, not wait to be approached. It's about listening deeply, enabling growth, and leading from the front.
 
Chapter Markers:
00:00 – Introductions and Wine Club Jokes
06:00 – From Pro Volleyball to Product Leadership
13:30 – Motivations Behind Leading Digital Transformation
15:45 – Rose’s Product Development Philosophy
20:00 – Why Engineers Must Understand the 'Why'
22:00 – Real-World Cloud Modernization Stories
25:00 – What It Means to Be Truly Customer-Centric
30:00 – Customer Journey Empathy and Field Feedback
35:00 – Empowering Engineers to Be Co-Creators
40:00 – Aligning Global Teams with Clear Vision
42:30 – CI/CD and Cloud Strategy for Efficiency
47:00 – Connecting Customer Satisfaction to ROI
53:00 – OKRs, Cross-Functional Metrics, and Alignment
55:00 – Rose’s Take on the AI Hype and Future Trends
58:30 – Final Reflections and Thank You
 
Keywords:
software leadership, customer-centric development, agile mindset, agile software, digital transformation, product management, Rose Schamberger, Olivier Poulard, Andy Hilliard, global engineering teams, software modernization, software strategy, CI/CD automation, cloud transformation, feedback loops, engineering culture, software ROI, product innovation, agile team alignment, empathy in software development, Software Without Borders podcast, Accelerance podcast, technology executive interview, product owner mindset, user experience in software, tech podcast for leaders

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 between IT and business strategy, why stakeholder alignment is the key to impact, and how companies can move from theoretical data science to real-world execution.
 
To support our show please visit our sponsor:
Software Without Borders is delivered to you by Accelerance. Powering future-forward software outsourcing and project delivery solutions. https://www.accelerance.com

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 insights on bringing products to market, scaling software teams, the future of AI-driven efficiency, and why trust drives business success.
 
To support our show please visit our sponsor:
Software Without Borders is delivered to you by Accelerance. Powering future-forward software outsourcing and project delivery solutions. https://www.accelerance.com

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 rules of data strategy, and why businesses that don’t adapt risk getting left behind.
 
To support our show please visit our sponsor:
Software Without Borders is delivered to you by Accelerance. Powering future-forward software outsourcing and project delivery solutions. https://www.accelerance.com

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 faster decision-making, smarter scaling, and a culture of continuous improvement. He also breaks down the risks of ignoring agility in your own business, from leadership bottlenecks to stalled innovation.
 
To support our show please visit our sponsor:
Software Without Borders is delivered to you by Accelerance. Powering future-forward software outsourcing and project delivery solutions. https://www.accelerance.com

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, inspire developers to take ownership of their products, and get your team to obsess over solving customer problems.
 
To support our show please visit our sponsor:
Software Without Borders is delivered to you by Accelerance. Powering future-forward software outsourcing and project delivery solutions. https://www.accelerance.com

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 to maximize valuation. Whether you're scaling a startup or preparing for an acquisition, this episode is packed with real-world advice on turning tech investments into business growth.
 
To support our show please visit our sponsor:
Software Without Borders is delivered to you by Accelerance. Powering future-forward software outsourcing and project delivery solutions. https://www.accelerance.com

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 customer feedback into the development process. If you're ready to turn vision into action and lead with clarity, tune in and subscribe for an episode packed with actionable strategies.
 
To support our show please visit our sponsor:
Software Without Borders is delivered to you by Accelerance. Powering future-forward software outsourcing and project delivery solutions. https://www.accelerance.com