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Software Without Borders
Andy Hilliard - Accelerance
49 episodes
6 days ago
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.
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Technology
Business,
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All content for Software Without Borders is the property of Andy Hilliard - Accelerance and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.
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.
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Technology
Business,
Management
Episodes (20/49)
Software Without Borders
#39 Building High-Trust Engineering Teams in a Global World
  Episode Description: In this episode of Software Without Borders, Andy and Scott sit down with Steve Petersen, a veteran software architect and engineering leader known for building collaborative, high-trust technical teams across global environments. Steve shares the lessons he’s learned from decades of experience—coding, mentoring, scaling engineering orgs, and navigating the cultural and communication challenges that come with distributed teams.   Guest Introduction: Steve Petersen is a seasoned software architect, engineering leader, and mentor with deep experience designing scalable systems and guiding teams through growth and transformation. Known for his calm leadership style, technical clarity, and focus on people-first engineering cultures, Steve has spent his career helping developers elevate their craft while strengthening communication and trust across globally distributed organizations. Key Takeaways: Communication is the real bottleneck, not code. Highly distributed teams succeed when they over-communicate clearly and consistently. Pairing senior and junior engineers is a force multiplier, accelerating learning for both sides and strengthening team cohesion. Humility makes great engineers—those willing to ask questions, seek clarity, and challenge assumptions collaboratively. Technical leadership is not about having all the answers, but about creating a space where the best ideas surface. Avoiding unnecessary complexity leads to higher velocity and more maintainable systems. Global engineering teams thrive on structure, predictable rhythms, and clear expectations that support asynchronous work.   Chapter Markers: 0:00 Welcome to Software Without Borders 0:21 Introducing Steve Petersen 1:13 Steve’s Background & Early Career Path 2:46 Technical Leadership vs. Individual Contribution 4:05 How Engineering Teams Break Down Communication 5:32 The Power of Pairing Senior & Junior Engineers 7:01 What Makes an Engineer Truly Great 8:44 Curiosity, Humility & Asking the Right Questions 10:12 Reducing Complexity for Better Outcomes 12:09 Leading Distributed Engineering Teams 14:03 Building Predictable Rhythms & Expectations 15:58 Technical Debt vs. Necessary Complexity 17:30 Creating a Culture Where Engineers Feel Safe Speaking Up 19:03 What Steve Looks for When Hiring Developers 21:18 Why Mentorship Accelerates Team Growth 22:40 When to Step Back as a Technical Leader 24:11 Coaching Engineers Through Hard Problems 26:05 Final Thoughts & What Steve Wishes He Knew Earlier End: Closing Remarks Keywords: Software Without Borders, Andy Hilliard, Scott Pollov, Steve Petersen, engineering leadership, software architecture, distributed engineering teams, global teams, technical mentorship, engineering culture, communication in engineering, technical debt, software development leadership, scaling teams
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6 days ago
46 minutes

Software Without Borders
#39 Building High-Trust Engineering Teams in a Global World
  Episode Description: In this episode of Software Without Borders, Andy and Scott sit down with Steve Petersen, a veteran software architect and engineering leader known for building collaborative, high-trust technical teams across global environments. Steve shares the lessons he’s learned from decades of experience—coding, mentoring, scaling engineering orgs, and navigating the cultural and communication challenges that come with distributed teams.   Guest Introduction: Steve Petersen is a seasoned software architect, engineering leader, and mentor with deep experience designing scalable systems and guiding teams through growth and transformation. Known for his calm leadership style, technical clarity, and focus on people-first engineering cultures, Steve has spent his career helping developers elevate their craft while strengthening communication and trust across globally distributed organizations. Key Takeaways: Communication is the real bottleneck, not code. Highly distributed teams succeed when they over-communicate clearly and consistently. Pairing senior and junior engineers is a force multiplier, accelerating learning for both sides and strengthening team cohesion. Humility makes great engineers—those willing to ask questions, seek clarity, and challenge assumptions collaboratively. Technical leadership is not about having all the answers, but about creating a space where the best ideas surface. Avoiding unnecessary complexity leads to higher velocity and more maintainable systems. Global engineering teams thrive on structure, predictable rhythms, and clear expectations that support asynchronous work.   Chapter Markers: 0:00 Welcome to Software Without Borders 0:21 Introducing Steve Petersen 1:13 Steve’s Background & Early Career Path 2:46 Technical Leadership vs. Individual Contribution 4:05 How Engineering Teams Break Down Communication 5:32 The Power of Pairing Senior & Junior Engineers 7:01 What Makes an Engineer Truly Great 8:44 Curiosity, Humility & Asking the Right Questions 10:12 Reducing Complexity for Better Outcomes 12:09 Leading Distributed Engineering Teams 14:03 Building Predictable Rhythms & Expectations 15:58 Technical Debt vs. Necessary Complexity 17:30 Creating a Culture Where Engineers Feel Safe Speaking Up 19:03 What Steve Looks for When Hiring Developers 21:18 Why Mentorship Accelerates Team Growth 22:40 When to Step Back as a Technical Leader 24:11 Coaching Engineers Through Hard Problems 26:05 Final Thoughts & What Steve Wishes He Knew Earlier End: Closing Remarks Keywords: Software Without Borders, Andy Hilliard, Scott Pollov, Steve Petersen, engineering leadership, software architecture, distributed engineering teams, global teams, technical mentorship, engineering culture, communication in engineering, technical debt, software development leadership, scaling teams
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6 days ago
46 minutes

Software Without Borders
#38 Creating Alignment in Times of Chaos
In this episode of Software Without Borders, we sit down with Joe Forgét—founder of Igniting Momentum and a leader who has lived through mergers, global team integrations, and the uncomfortable-but-necessary transitions that define high-growth companies. Joe breaks down what really happens when organizations hit those inflection points: culture drift, misalignment, operational chaos, and the quiet pressure founders and leaders carry while trying to scale. Guest Introduction: Joe Forgét is the founder of Igniting Momentum, a leadership and operations coach who helps growing companies rebuild clarity, alignment, and execution discipline. With deep experience leading global teams through mergers, restructures, and rapid scale, Joe blends operating system rigor with human-centered leadership. His work centers on creating momentum through intentional rhythms, strategic alignment, and practical accountability structures. Key Takeaways: Companies often realize they need help when they hit the moment Joe calls: “The business owns me now.” Momentum comes from structured operating rhythms — not heroic effort. Frameworks like EOS, Pinnacle, and System & Soul provide scaffolding, but must be tailored to each organization. Early-stage founders may not need full frameworks yet, but scale-ups absolutely do. Mergers & acquisitions create cultural collisions; alignment must come before acceleration. Empowerment only works when role clarity and accountability structures are in place. Progress must be viewed through “the gap and the gain,” recognizing wins instead of only missing pieces. Chapter Markers: 0:00 Welcome back to Software Without Borders 0:23 Introducing guest Joe Forgét 2:17 Joe’s discovery of coaching 4:11 The Ignition Framework (Align → Activate → Accelerate) 6:22 EOS, Pinnacle, System & Soul explained 8:04 Coaching in fast-growth organizations 9:47 The moment leaders realize the business owns them 11:35 Measuring early momentum 15:51 The Gap and the Gain mindset 17:02 People-first additions in newer operating frameworks 20:03 Why implementation must be customized 23:35 Cultural blending in mergers 26:58 Choosing between scale, exit, or reinvention 30:25 Post-inflection indicators that help is needed 33:12 Role clarity as empowerment 35:05 Why coaches need their own coaches End: Closing insights and wrap-up Keywords: Software Without Borders, Andy Hilliard, Scott Pollov, Joe Forget, Igniting Momentum, leadership coaching, operating rhythms, EOS, System and Soul, business scaling, mergers and acquisitions, organizational alignment, executive coaching, leadership frameworks, global team leadership
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2 weeks ago
52 minutes

Software Without Borders
#38 Creating Alignment in Times of Chaos
In this episode of Software Without Borders, we sit down with Joe Forgét—founder of Igniting Momentum and a leader who has lived through mergers, global team integrations, and the uncomfortable-but-necessary transitions that define high-growth companies. Joe breaks down what really happens when organizations hit those inflection points: culture drift, misalignment, operational chaos, and the quiet pressure founders and leaders carry while trying to scale. Guest Introduction: Joe Forgét is the founder of Igniting Momentum, a leadership and operations coach who helps growing companies rebuild clarity, alignment, and execution discipline. With deep experience leading global teams through mergers, restructures, and rapid scale, Joe blends operating system rigor with human-centered leadership. His work centers on creating momentum through intentional rhythms, strategic alignment, and practical accountability structures. Key Takeaways: Companies often realize they need help when they hit the moment Joe calls: “The business owns me now.” Momentum comes from structured operating rhythms — not heroic effort. Frameworks like EOS, Pinnacle, and System & Soul provide scaffolding, but must be tailored to each organization. Early-stage founders may not need full frameworks yet, but scale-ups absolutely do. Mergers & acquisitions create cultural collisions; alignment must come before acceleration. Empowerment only works when role clarity and accountability structures are in place. Progress must be viewed through “the gap and the gain,” recognizing wins instead of only missing pieces. Chapter Markers: 0:00 Welcome back to Software Without Borders 0:23 Introducing guest Joe Forgét 2:17 Joe’s discovery of coaching 4:11 The Ignition Framework (Align → Activate → Accelerate) 6:22 EOS, Pinnacle, System & Soul explained 8:04 Coaching in fast-growth organizations 9:47 The moment leaders realize the business owns them 11:35 Measuring early momentum 15:51 The Gap and the Gain mindset 17:02 People-first additions in newer operating frameworks 20:03 Why implementation must be customized 23:35 Cultural blending in mergers 26:58 Choosing between scale, exit, or reinvention 30:25 Post-inflection indicators that help is needed 33:12 Role clarity as empowerment 35:05 Why coaches need their own coaches End: Closing insights and wrap-up Keywords: Software Without Borders, Andy Hilliard, Scott Pollov, Joe Forget, Igniting Momentum, leadership coaching, operating rhythms, EOS, System and Soul, business scaling, mergers and acquisitions, organizational alignment, executive coaching, leadership frameworks, global team leadership
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2 weeks ago
52 minutes

Software Without Borders
#37 How Leaders Can Harness AI Without Breaking Their Business (Video)
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. From building a “culture of curiosity” to using proven software-industry frameworks for prioritization, Kristina brings a grounded, practical perspective on how leaders can move fast and smart.   Guest Introduction: Kristina Crane is a transformational executive and fractional COO/CSO with deep expertise in AI adoption, organizational change, and strategic operations. As CEO of The Canyons Group, she helps government agencies, enterprises, and growth-stage companies navigate complex transitions with a framework centered on “Navigate to Elevate.” Kristina spent 12+ years at STC Health leading a major shift from a dev-shop model to a scaled SaaS organization, driving 10x revenue and 60% efficiency gains through AI. Key Takeaways: AI transformation is a people problem first—tech only works when teams understand the “why” and feel empowered. episode-37 Companies must balance curiosity with prioritization to avoid shiny-object chaos. The software industry provides proven frameworks (like RICE) that non-tech organizations can use to evaluate AI opportunities. Old-school executive teams need a business-first, tech-translated approach to adopt AI successfully. Strategic planning cycles must speed up—leaders should revisit their business model, ICP, and value proposition every 12–36 months. Consultants accelerate outcomes not because of frameworks, but because of pattern recognition and objective accountability. Chapter Markers: 0:00 Intro 1:07 Welcome to Software Without Borders 1:12 Introducing Guest — Kristina Crane 1:56 Kristina’s Background in Strategy, SaaS & GovTech 3:41 Teaching Roots → Consulting → SaaS Incubation 5:58 Transition to STC Health & Leading SaaS Transformation 6:34 Difference Between Kale Crane & The Canyons Group 8:08 AI FOMO, Human Intelligence & Organizational Change 9:03 Navigating Noise & Extremes Around AI 10:26 What AI Forces Every Organization to Learn 12:30 How Old-School Exec Teams Can Embrace AI 14:14 Culture of Curiosity & Empowering Teams 15:34 Guardrails, Governance & Safe Experimentation 16:57 When to Bring in Technologists 17:12 Prioritization Frameworks (RICE & ICE) 18:54 Governance Policies & Early-Stage Experimentation 19:29 Curiosity Champion Groups & Brown-Bag Cycles 22:22 Training Teams to Think Like Product Organizations 23:19 Overcoming Fear & Starting Small 23:46 Strategy vs. Operations — Big Picture Impacts 24:58 Business Model Iteration in the AI Era 26:51 The SaaS Business Model Shift as an Analogy 28:12 Professional Services & White-Collar AI Disruption 29:37 Innovating Without Breaking the Core Business 30:01 Leading Large-Scale Change Inside Mature Organizations 32:21 Why Consultants Matter in AI Transformation 33:15 Seeing Blind Spots & Reading Culture 34:10 Accountability, Execution & “Skinned Knees” 35:13 The Hardest Transformation Leaders Will Face End Closing Thoughts Keywords: Software Without Borders, Andy Hilliard, Scott Pollov, Kristina Crane, The Canyons Group, AI transformation, organizational change, SaaS transformation, leadership, culture of curiosity, AI adoption, operational strategy, RICE prioritization, business model evolution, enterprise AI, government tech
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1 month ago
51 minutes

Software Without Borders
#37 How Leaders Can Harness AI Without Breaking Their Business (Audio)
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. From building a “culture of curiosity” to using proven software-industry frameworks for prioritization, Kristina brings a grounded, practical perspective on how leaders can move fast and smart.   Guest Introduction: Kristina Crane is a transformational executive and fractional COO/CSO with deep expertise in AI adoption, organizational change, and strategic operations. As CEO of The Canyons Group, she helps government agencies, enterprises, and growth-stage companies navigate complex transitions with a framework centered on “Navigate to Elevate.” Kristina spent 12+ years at STC Health leading a major shift from a dev-shop model to a scaled SaaS organization, driving 10x revenue and 60% efficiency gains through AI. Key Takeaways: AI transformation is a people problem first—tech only works when teams understand the “why” and feel empowered. episode-37 Companies must balance curiosity with prioritization to avoid shiny-object chaos. The software industry provides proven frameworks (like RICE) that non-tech organizations can use to evaluate AI opportunities. Old-school executive teams need a business-first, tech-translated approach to adopt AI successfully. Strategic planning cycles must speed up—leaders should revisit their business model, ICP, and value proposition every 12–36 months. Consultants accelerate outcomes not because of frameworks, but because of pattern recognition and objective accountability. Chapter Markers: 0:00 Intro 1:07 Welcome to Software Without Borders 1:12 Introducing Guest — Kristina Crane 1:56 Kristina’s Background in Strategy, SaaS & GovTech 3:41 Teaching Roots → Consulting → SaaS Incubation 5:58 Transition to STC Health & Leading SaaS Transformation 6:34 Difference Between Kale Crane & The Canyons Group 8:08 AI FOMO, Human Intelligence & Organizational Change 9:03 Navigating Noise & Extremes Around AI 10:26 What AI Forces Every Organization to Learn 12:30 How Old-School Exec Teams Can Embrace AI 14:14 Culture of Curiosity & Empowering Teams 15:34 Guardrails, Governance & Safe Experimentation 16:57 When to Bring in Technologists 17:12 Prioritization Frameworks (RICE & ICE) 18:54 Governance Policies & Early-Stage Experimentation 19:29 Curiosity Champion Groups & Brown-Bag Cycles 22:22 Training Teams to Think Like Product Organizations 23:19 Overcoming Fear & Starting Small 23:46 Strategy vs. Operations — Big Picture Impacts 24:58 Business Model Iteration in the AI Era 26:51 The SaaS Business Model Shift as an Analogy 28:12 Professional Services & White-Collar AI Disruption 29:37 Innovating Without Breaking the Core Business 30:01 Leading Large-Scale Change Inside Mature Organizations 32:21 Why Consultants Matter in AI Transformation 33:15 Seeing Blind Spots & Reading Culture 34:10 Accountability, Execution & “Skinned Knees” 35:13 The Hardest Transformation Leaders Will Face End Closing Thoughts Keywords: Software Without Borders, Andy Hilliard, Scott Pollov, Kristina Crane, The Canyons Group, AI transformation, organizational change, SaaS transformation, leadership, culture of curiosity, AI adoption, operational strategy, RICE prioritization, business model evolution, enterprise AI, government tech
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1 month ago
51 minutes

Software Without Borders
#36 You Can’t Scale Chaos (VIDEO)
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 chaos.” Together, they dive into recurring SDLC pitfalls, hidden costs, and proven frameworks to turn fragmented delivery into a cohesive, measurable system. If you lead distributed teams or manage offshore partners, this conversation delivers a playbook for building sustainable, high-quality software outcomes.   Guest Introduction: Olivier Poulard leads Global Software Engineering Strategies at Accelerance, bringing decades of experience on both sides of the delivery equation—as a global client managing teams of over 1,000 engineers and as a strategic partner architecting offshore and nearshore delivery systems. His practical, systems-level insights help clients design efficient, scalable, and high-performing software operations built on clarity and alignment rather than chaos.   Key Takeaways: You can’t scale chaos—adding people only multiplies inefficiency without fixing underlying issues. True delivery success requires alignment across people, process, technology, and data. Clear, complete requirements (including transition and information requirements) prevent rework and estimation failures. “Definition of Done” is critical for predictability—teams need shared clarity on what completion means. Leaders must control scope and observe team dynamics to restore stability before scaling again. Context switching, unclear requirements, and unmanaged change requests are among the costliest hidden inefficiencies. Chapter Markers: 0:00 Intro 0:09 Guest Introduction: Olivier Poulard 1:16 Evolution of Accelerance’s Consulting Arm 3:03 The Myth of “Adding More People” 5:09 Aligning Clients and Partners for Real Outcomes 8:18 Why You Can’t Scale Chaos 10:46 The Two-to-Tango Rule in Global Delivery 12:28 Top SDLC Bottlenecks: Ambiguous Requirements & Bad Estimation 18:42 Building Predictable Estimation Models 21:19 The Power of a Strong Definition of Done 22:24 Using Checklists to Stabilize Teams 24:00 The Hidden Costs of Context Switching 27:13 Controlling Change Before It Controls You 29:11 Restoring Predictability Without Stalling Delivery 32:37 Measuring Team Health and Stress Indicators 34:03 Final Thoughts on Effective Partner Collaboration   Keywords: Software Without Borders, Andy Hilliard, Olivier Poulard, Accelerance, software delivery, global engineering, software development lifecycle, SDLC bottlenecks, outsourcing strategy, agile transformation, software estimation, offshore teams, nearshore delivery, global software operations, leadership in tech
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1 month ago
52 minutes

Software Without Borders
#36 You Can’t Scale Chaos (AUDIO)
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 chaos.” Together, they dive into recurring SDLC pitfalls, hidden costs, and proven frameworks to turn fragmented delivery into a cohesive, measurable system. If you lead distributed teams or manage offshore partners, this conversation delivers a playbook for building sustainable, high-quality software outcomes. Guest Introduction: Olivier Poulard leads Global Software Engineering Strategies at Accelerance, bringing decades of experience on both sides of the delivery equation—as a global client managing teams of over 1,000 engineers and as a strategic partner architecting offshore and nearshore delivery systems. His practical, systems-level insights help clients design efficient, scalable, and high-performing software operations built on clarity and alignment rather than chaos.   Key Takeaways: You can’t scale chaos—adding people only multiplies inefficiency without fixing underlying issues. True delivery success requires alignment across people, process, technology, and data. Clear, complete requirements (including transition and information requirements) prevent rework and estimation failures. “Definition of Done” is critical for predictability—teams need shared clarity on what completion means. Leaders must control scope and observe team dynamics to restore stability before scaling again. Context switching, unclear requirements, and unmanaged change requests are among the costliest hidden inefficiencies. Chapter Markers: 0:00 Intro 0:09 Guest Introduction: Olivier Poulard 1:16 Evolution of Accelerance’s Consulting Arm 3:03 The Myth of “Adding More People” 5:09 Aligning Clients and Partners for Real Outcomes 8:18 Why You Can’t Scale Chaos 10:46 The Two-to-Tango Rule in Global Delivery 12:28 Top SDLC Bottlenecks: Ambiguous Requirements & Bad Estimation 18:42 Building Predictable Estimation Models 21:19 The Power of a Strong Definition of Done 22:24 Using Checklists to Stabilize Teams 24:00 The Hidden Costs of Context Switching 27:13 Controlling Change Before It Controls You 29:11 Restoring Predictability Without Stalling Delivery 32:37 Measuring Team Health and Stress Indicators 34:03 Final Thoughts on Effective Partner Collaboration   Keywords: Software Without Borders, Andy Hilliard, Olivier Poulard, Accelerance, software delivery, global engineering, software development lifecycle, SDLC bottlenecks, outsourcing strategy, agile transformation, software estimation, offshore teams, nearshore delivery, global software operations, leadership in tech
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1 month ago
52 minutes

Software Without Borders
#35 AI, Talent, and the Future of Product Development with Raja Musunuru (VIDEO)
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 innovation, Raja brings a wealth of insight into what it means to lead in today’s era of rapid disruption. If you’re a leader looking to understand how AI impacts product development, talent strategies, and business growth, this conversation is one you won’t want to miss.   Guest Introduction: Raja Musunuru is the Chief Product Officer at Tiffin, with an impressive background spanning 25 years at organizations like Sony, AAA, Amicus, and Gaylord Entertainment. Today, Raja is at the forefront of AI-powered product innovation, blending technical depth with visionary leadership. He’s passionate about building lean teams that deliver with speed, excellence, and purpose—shaping the future of wealth management, investment intelligence, and beyond. Key Takeaways: True leadership shines in crisis: Raja’s experience during the 2010 Nashville flood taught him radical prioritization that still guides his approach. AI isn’t just hype—it’s slashing product development cycles from months to days, enabling faster feedback and clarity between product and engineering teams. Small, focused teams deliver better results than bloated headcount—especially when empowered by modern AI tools. Senior engineers who adapt thrive with AI, while new grads must become “AI natives” to succeed in today’s market. Success doesn’t come from selling AI—it comes from solving real problems better than anyone else. The global outsourcing model is shifting from “more people” to “more excellence.”   Chapter Markers: 0:00 Intro 0:15 Guest Introduction – Raja Musunuru’s career highlights 3:00 Defining moments in leadership: lessons from the Nashville flood 7:00 Radical prioritization and the “tour of duty” mindset at Tiffin 10:00 Building lean product teams and rapid MVP cycles 12:00 Where AI creates true disruption in product development 17:30 Aligning stakeholders in a fast-moving AI environment 19:00 How AI is reshaping engineering talent and global delivery models 23:00 Senior vs. junior engineers in the age of AI 26:00 Lowering barriers: from AWS to AI-powered MVPs 29:00 Redefining donor-advised funds with AI and automation 31:00 Global teams: from volume outsourcing to excellence-driven delivery 35:00 What AI means for hiring and talent pipelines 40:00 Closing thoughts and key advice for leaders Keywords: Raja Musunuru, Rich Wanden, Tomas Hilliard, It Comes Down To This podcast, AI disruption, product development, lean teams, MVP cycles, global talent model, outsourcing, engineering productivity, donor-advised funds, wealth management innovation, Tiffin, product leadership
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2 months ago
39 minutes

Software Without Borders
#35 AI, Talent, and the Future of Product Development with Raja Musunuru (AUDIO)
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 innovation, Raja brings a wealth of insight into what it means to lead in today’s era of rapid disruption. If you’re a leader looking to understand how AI impacts product development, talent strategies, and business growth, this conversation is one you won’t want to miss.   Guest Introduction: Raja Musunuru is the Chief Product Officer at Tiffin, with an impressive background spanning 25 years at organizations like Sony, AAA, Amicus, and Gaylord Entertainment. Today, Raja is at the forefront of AI-powered product innovation, blending technical depth with visionary leadership. He’s passionate about building lean teams that deliver with speed, excellence, and purpose—shaping the future of wealth management, investment intelligence, and beyond. Key Takeaways: True leadership shines in crisis: Raja’s experience during the 2010 Nashville flood taught him radical prioritization that still guides his approach. AI isn’t just hype—it’s slashing product development cycles from months to days, enabling faster feedback and clarity between product and engineering teams. Small, focused teams deliver better results than bloated headcount—especially when empowered by modern AI tools. Senior engineers who adapt thrive with AI, while new grads must become “AI natives” to succeed in today’s market. Success doesn’t come from selling AI—it comes from solving real problems better than anyone else. The global outsourcing model is shifting from “more people” to “more excellence.”   Chapter Markers: 0:00 Intro 0:15 Guest Introduction – Raja Musunuru’s career highlights 3:00 Defining moments in leadership: lessons from the Nashville flood 7:00 Radical prioritization and the “tour of duty” mindset at Tiffin 10:00 Building lean product teams and rapid MVP cycles 12:00 Where AI creates true disruption in product development 17:30 Aligning stakeholders in a fast-moving AI environment 19:00 How AI is reshaping engineering talent and global delivery models 23:00 Senior vs. junior engineers in the age of AI 26:00 Lowering barriers: from AWS to AI-powered MVPs 29:00 Redefining donor-advised funds with AI and automation 31:00 Global teams: from volume outsourcing to excellence-driven delivery 35:00 What AI means for hiring and talent pipelines 40:00 Closing thoughts and key advice for leaders Keywords: Raja Musunuru, Rich Wanden, Tomas Hilliard, It Comes Down To This podcast, AI disruption, product development, lean teams, MVP cycles, global talent model, outsourcing, engineering productivity, donor-advised funds, wealth management innovation, Tiffin, product leadership
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2 months ago
39 minutes

Software Without Borders
#34 (VIDEO) Revolutionizing Hiring: John Collins on AI, Challenges, and Yogan's Vision
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 explore how hiring has evolved over the last decade, the pitfalls of outsourcing and over-relying on AI, and Yogan's game-changing approach to faster, fairer, more cost-effective talent acquisition. John shares his vision for empowering recruiters, boosting offer acceptance rates, and using AI thoughtfully to transform hiring forever. If you're a business leader navigating global software teams and talent challenges, this episode is packed with actionable insights—subscribe now and join the conversation!   Guest Introduction: I'm excited to have John Collins with us—a proven leader with over two decades at powerhouses like Microsoft and Apple, plus scale-ups such as Snapchat, Vinted, and Flixbus. Now, as founder of Yogan, John's on a mission to overhaul hiring, making it faster, fairer, and more strategic for growth. His global experience brings fresh perspectives on talent acquisition in today's evolving tech landscape.   Key Takeaways: Hiring challenges are universal—whether at big corps or startups—often stemming from outdated, one-size-fits-all processes that introduce bias and inefficiency. The last decade's shifts, like AI in resumes and interviews, can amplify biases if not handled right; human oversight remains key to fair evaluations. Outsourcing recruitment might cut costs short-term, but it risks disconnects—internal recruiters as strategic partners yield better long-term results. Yogan disrupts by auditing processes for free, quantifying risks like added stages costing $3,000 or dropping acceptance rates, and training interviewers for better experiences. Focus on candidate experience boosts acceptance rates and retention; gamified AI training in Yogan makes interviewers prepared and engaging. Communicating ROI to C-levels is tough but vital—highlight hidden costs in delays, turnover, and lost opportunities to show hiring's business impact.   Chapter Markers: 0:00 Intro 0:04 Welcome and Host Introductions 0:21 Guest Welcome and Background 1:06 Universal Hiring Challenges 3:38 Changes in Hiring Over the Decade 7:36 Yogan's Disruption and Vision 10:02 Risk Assessment in Hiring Processes 10:46 Interviewer Training and Preparation 15:45 Impact on Candidate Experience 19:20 Global Hiring and Cultural Alignment 26:28 AI's Role in Yogan 41:22 Gamified Training with AI 43:10 Communicating ROI to C-Level 48:55 Wrapping Up and Final Insights 51:43 Closing and Call to Action     Keywords: Andy Hilliard, John Collins, Software Without Borders, hiring challenges, AI in hiring, talent acquisition, Yogan startup, global software teams, recruiter empowerment, interview processes, hiring ROI, candidate experience, tech hiring evolution, outsourcing recruitment, bias in AI
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4 months ago
52 minutes

Software Without Borders
#34 (AUDIO) Revolutionizing Hiring: John Collins on AI, Challenges, and Yogan's Vision
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 explore how hiring has evolved over the last decade, the pitfalls of outsourcing and over-relying on AI, and Yogan's game-changing approach to faster, fairer, more cost-effective talent acquisition. John shares his vision for empowering recruiters, boosting offer acceptance rates, and using AI thoughtfully to transform hiring forever. If you're a business leader navigating global software teams and talent challenges, this episode is packed with actionable insights—subscribe now and join the conversation!   Guest Introduction: I'm excited to have John Collins with us—a proven leader with over two decades at powerhouses like Microsoft and Apple, plus scale-ups such as Snapchat, Vinted, and Flixbus. Now, as founder of Yogan, John's on a mission to overhaul hiring, making it faster, fairer, and more strategic for growth. His global experience brings fresh perspectives on talent acquisition in today's evolving tech landscape.   Key Takeaways: Hiring challenges are universal—whether at big corps or startups—often stemming from outdated, one-size-fits-all processes that introduce bias and inefficiency. The last decade's shifts, like AI in resumes and interviews, can amplify biases if not handled right; human oversight remains key to fair evaluations. Outsourcing recruitment might cut costs short-term, but it risks disconnects—internal recruiters as strategic partners yield better long-term results. Yogan disrupts by auditing processes for free, quantifying risks like added stages costing $3,000 or dropping acceptance rates, and training interviewers for better experiences. Focus on candidate experience boosts acceptance rates and retention; gamified AI training in Yogan makes interviewers prepared and engaging. Communicating ROI to C-levels is tough but vital—highlight hidden costs in delays, turnover, and lost opportunities to show hiring's business impact.   Chapter Markers: 0:00 Intro 0:04 Welcome and Host Introductions 0:21 Guest Welcome and Background 1:06 Universal Hiring Challenges 3:38 Changes in Hiring Over the Decade 7:36 Yogan's Disruption and Vision 10:02 Risk Assessment in Hiring Processes 10:46 Interviewer Training and Preparation 15:45 Impact on Candidate Experience 19:20 Global Hiring and Cultural Alignment 26:28 AI's Role in Yogan 41:22 Gamified Training with AI 43:10 Communicating ROI to C-Level 48:55 Wrapping Up and Final Insights 51:43 Closing and Call to Action     Keywords: Andy Hilliard, John Collins, Software Without Borders, hiring challenges, AI in hiring, talent acquisition, Yogan startup, global software teams, recruiter empowerment, interview processes, hiring ROI, candidate experience, tech hiring evolution, outsourcing recruitment, bias in AI
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4 months ago
52 minutes

Software Without Borders
#33 (VIDEO) Leading Teams and Transformations with Mike Hostetler
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 role, and leading high-performing distributed teams. From tools like AMP and Cursor to avoiding intelligence hyperinflation, Mike’s wisdom is a must-hear for tech leaders. If you’re ready to unlock AI’s potential and build global software teams that thrive, hit play and subscribe for more episodes that dive deep into software’s impact worldwide!   Guest Introduction: I’m thrilled to welcome Mike Hostetler, a seasoned AI/ML specialist and entrepreneur who’s all about building. From his early days with open source projects like jQuery to leading AI-driven change at ServiceCore, Mike’s got a knack for blending C-suite strategy with hands-on coding. His insights on AI agents and global teams make him the perfect guide for navigating today’s tech landscape.   Key Takeaways: Mike’s story—from QBasic to AI leadership—shows how a builder’s curiosity can spark decades of innovation. AI in enterprises isn’t just tech; it’s about people, processes, and a new Chief Agent Officer to connect the dots across departments. Leading remote teams means prioritizing clarity, human connection, and leadership over mere management to unlock their full potential. Tools like AMP and Cursor are transforming coding, but human skills like taste and long-term planning are still the secret sauce. To stay ahead, focus on learning velocity—train teams to adapt fast and outpace competitors in the AI era. Rewriting software isn’t taboo anymore; AI’s cost-cutting power makes upgrading brownfield projects a smart move.   Chapter Markers: 0:00 Intro 0:04 Host Welcome and Show Intro 0:23 Guest Welcome and Career Kickoff 1:44 Mike’s Early Days as a Builder 2:48 QBasic, Modems, and the Internet’s Dawn 5:32 Diving into AI and Machine Learning 9:39 Bots, Agents, and Classical AI Foundations 10:39 AI’s Role in Enterprises and the Chief Agent Officer 19:20 Tackling Intelligence Hyperinflation 26:28 Secrets to Leading Distributed Teams 39:23 Measuring Remote Team Success 45:00 AI Tools: Capabilities and Limits in Engineering 53:28 AI’s Impact on Productivity and Quality 57:41 Defining ROI and Value in AI Initiatives 1:05:28 Closing Remarks and Thanks   Keywords: Andy Hilliard, Mike Hostetler, Software Without Borders, AI transformation, global software development, distributed teams, Chief Agent Officer, AI agents, software innovation, remote work leadership, coding tools, intelligence hyperinflation, open source software, enterprise AI, software engineering
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4 months ago
1 hour 6 minutes

Software Without Borders
#33 (AUDIO) Leading Teams and Transformations with Mike Hostetler
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 role, and leading high-performing distributed teams. From tools like AMP and Cursor to avoiding intelligence hyperinflation, Mike’s wisdom is a must-hear for tech leaders. If you’re ready to unlock AI’s potential and build global software teams that thrive, hit play and subscribe for more episodes that dive deep into software’s impact worldwide!   Guest Introduction: I’m thrilled to welcome Mike Hostetler, a seasoned AI/ML specialist and entrepreneur who’s all about building. From his early days with open source projects like jQuery to leading AI-driven change at ServiceCore, Mike’s got a knack for blending C-suite strategy with hands-on coding. His insights on AI agents and global teams make him the perfect guide for navigating today’s tech landscape.   Key Takeaways: Mike’s story—from QBasic to AI leadership—shows how a builder’s curiosity can spark decades of innovation. AI in enterprises isn’t just tech; it’s about people, processes, and a new Chief Agent Officer to connect the dots across departments. Leading remote teams means prioritizing clarity, human connection, and leadership over mere management to unlock their full potential. Tools like AMP and Cursor are transforming coding, but human skills like taste and long-term planning are still the secret sauce. To stay ahead, focus on learning velocity—train teams to adapt fast and outpace competitors in the AI era. Rewriting software isn’t taboo anymore; AI’s cost-cutting power makes upgrading brownfield projects a smart move.   Chapter Markers: 0:00 Intro 0:04 Host Welcome and Show Intro 0:23 Guest Welcome and Career Kickoff 1:44 Mike’s Early Days as a Builder 2:48 QBasic, Modems, and the Internet’s Dawn 5:32 Diving into AI and Machine Learning 9:39 Bots, Agents, and Classical AI Foundations 10:39 AI’s Role in Enterprises and the Chief Agent Officer 19:20 Tackling Intelligence Hyperinflation 26:28 Secrets to Leading Distributed Teams 39:23 Measuring Remote Team Success 45:00 AI Tools: Capabilities and Limits in Engineering 53:28 AI’s Impact on Productivity and Quality 57:41 Defining ROI and Value in AI Initiatives 1:05:28 Closing Remarks and Thanks   Keywords: Andy Hilliard, Mike Hostetler, Software Without Borders, AI transformation, global software development, distributed teams, Chief Agent Officer, AI agents, software innovation, remote work leadership, coding tools, intelligence hyperinflation, open source software, enterprise AI, software engineering
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4 months ago
1 hour 6 minutes

Software Without Borders
#32 - Driving Product Success in a Data-Driven World (VIDEO)
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 leveraging data analytics to stay ahead. Want to know how to build products that dominate markets? This episode’s packed with insights! Subscribe, drop a five-star review, and let’s keep the innovation flowing! Guest Introduction:Say hello to Andrew Hosman, a product genius who’s mastered the art of building winning SaaS solutions. As VP and Head of Product at EigenRisk, Andrew’s expertise spans insurance, risk management, and IoT. His knack for blending tech know-how with customer empathy makes him a powerhouse. Tune in for his secrets to driving innovation and nailing product strategy! Key Takeaways:• Andrew’s coder-to-leader path shows how understanding tech and customers creates unstoppable SaaS products.• AI’s your sidekick, not your boss—use it to cut busywork and focus on game-changing ideas.• Visuals like flowcharts and mockups are your secret weapon for uniting global teams across cultures.• Data’s your superpower: descriptive, predictive, and prescriptive analytics drive smarter product choices.• Roadmaps are living tools—use them to spark conversations, not lock in rigid plans.• Ditch outdated features to keep your product lean, cost-effective, and ready for market shifts. Chapter Markers:0:00 Intro0:12 Guest Introduction1:41 Andrew’s Journey to Product Management5:34 AI’s Role in Product Management10:31 Enhancing Products with Machine Learning14:53 Fostering Innovation in Teams17:02 Prioritizing Customer Needs19:04 Crafting Effective Roadmaps20:54 Managing Global Teams23:28 Vertical-Agnostic Best Practices26:22 Andrew’s Teaching Aspirations28:27 Data-Driven Product Strategies31:31 Predictive Analytics Challenges33:44 Future Trends in Product Development38:14 Building Successful Product Portfolios39:32 Sustainable Product Growth42:26 Closing Keywords:Andy Hilliard, Andrew Hosman, Olivier Poulard, Software Without Borders, product management, SaaS products, AI in product development, data analytics, customer-centric design, global team management, product roadmaps, innovation strategies, predictive analytics, risk management, IoT solutions
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5 months ago
43 minutes 23 seconds

Software Without Borders
#32 - Driving Product Success in a Data-Driven World (AUDIO)
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 leveraging data analytics to stay ahead. Want to know how to build products that dominate markets? This episode’s packed with insights! Subscribe, drop a five-star review, and let’s keep the innovation flowing! Guest Introduction:Say hello to Andrew Hosman, a product genius who’s mastered the art of building winning SaaS solutions. As VP and Head of Product at EigenRisk, Andrew’s expertise spans insurance, risk management, and IoT. His knack for blending tech know-how with customer empathy makes him a powerhouse. Tune in for his secrets to driving innovation and nailing product strategy! Key Takeaways:• Andrew’s coder-to-leader path shows how understanding tech and customers creates unstoppable SaaS products.• AI’s your sidekick, not your boss—use it to cut busywork and focus on game-changing ideas.• Visuals like flowcharts and mockups are your secret weapon for uniting global teams across cultures.• Data’s your superpower: descriptive, predictive, and prescriptive analytics drive smarter product choices.• Roadmaps are living tools—use them to spark conversations, not lock in rigid plans.• Ditch outdated features to keep your product lean, cost-effective, and ready for market shifts. Chapter Markers:0:00 Intro0:12 Guest Introduction1:41 Andrew’s Journey to Product Management5:34 AI’s Role in Product Management10:31 Enhancing Products with Machine Learning14:53 Fostering Innovation in Teams17:02 Prioritizing Customer Needs19:04 Crafting Effective Roadmaps20:54 Managing Global Teams23:28 Vertical-Agnostic Best Practices26:22 Andrew’s Teaching Aspirations28:27 Data-Driven Product Strategies31:31 Predictive Analytics Challenges33:44 Future Trends in Product Development38:14 Building Successful Product Portfolios39:32 Sustainable Product Growth42:26 Closing Keywords:Andy Hilliard, Andrew Hosman, Olivier Poulard, Software Without Borders, product management, SaaS products, AI in product development, data analytics, customer-centric design, global team management, product roadmaps, innovation strategies, predictive analytics, risk management, IoT solutions
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5 months ago
43 minutes 23 seconds

Software Without Borders
#31 - AI Revolution Unveiled: Jack Teitel on Transforming Business with Machine Learning (VIDEO)
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 scalable solutions, this episode is packed with actionable strategies for business leaders. If you’re ready to unlock AI’s true potential for your organization, hit play now! Subscribe, leave a five-star review, and join us for more tech innovation talks. Guest Introduction:Folks, we’re thrilled to have Jack Teitel on the show! Jack’s a trailblazing AI/ML specialist and founder of Tidal AI, with a stellar career spanning healthcare, computer vision, and large language models. From leading data science teams in hospital networks to revolutionizing software development, Jack’s all about delivering real business value. His insights are a goldmine for anyone looking to harness AI’s power—let’s dive in! Key Takeaways: AI shines brightest when it’s targeted: Jack emphasizes building AI for specific tasks to assist humans, not replace them, for maximum impact.Data privacy is non-negotiable: Lessons from healthcare, like HIPAA compliance, show how to secure data while unlocking AI’s potential.Code faster, but stay sharp: AI coding tools can boost speed 3-5x, but developers must understand every line to avoid tech debt.Monitor and adapt: Regular model and data drift checks are crucial to keep AI tools effective in dynamic environments.Start now or fall behind: AI adoption is becoming a business requirement—act within 3-5 years to stay competitive.Train your team: Proper training ensures employees embrace AI tools, driving measurable ROI. Chapter Markers:0:00 Intro0:04 Guest Introduction0:50 Jack’s Journey into AI4:06 AI in Healthcare: Impact and Insights7:44 Data Privacy Lessons from Healthcare11:04 Gaps in AI Adoption: Avoiding the Hype14:21 Turning AI Concepts into Business Value17:07 AI’s Role in Software Development29:57 Garbage In, Garbage Out: Ensuring Quality32:28 Scaling AI for Small and Mid-Sized Companies35:09 Monitoring AI for Efficiency39:03 Tackling Model and Data Drift43:33 Signals for Reevaluating AI Strategy46:23 Closing Keywords:Tomas Hilliard, Olivier Poulard, Jack Teitel, Software Without Borders, AI, machine learning, Tidal AI, healthcare AI, data privacy, HIPAA, AI coding tools, software development, business value, model drift, data drift, AI strategy
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5 months ago
47 minutes 44 seconds

Software Without Borders
#31 - AI Revolution Unveiled: Jack Teitel on Transforming Business with Machine Learning (AUDIO)
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 scalable solutions, this episode is packed with actionable strategies for business leaders. If you’re ready to unlock AI’s true potential for your organization, hit play now! Subscribe, leave a five-star review, and join us for more tech innovation talks. Guest Introduction:Folks, we’re thrilled to have Jack Teitel on the show! Jack’s a trailblazing AI/ML specialist and founder of Tidal AI, with a stellar career spanning healthcare, computer vision, and large language models. From leading data science teams in hospital networks to revolutionizing software development, Jack’s all about delivering real business value. His insights are a goldmine for anyone looking to harness AI’s power—let’s dive in! Key Takeaways: AI shines brightest when it’s targeted: Jack emphasizes building AI for specific tasks to assist humans, not replace them, for maximum impact.Data privacy is non-negotiable: Lessons from healthcare, like HIPAA compliance, show how to secure data while unlocking AI’s potential.Code faster, but stay sharp: AI coding tools can boost speed 3-5x, but developers must understand every line to avoid tech debt.Monitor and adapt: Regular model and data drift checks are crucial to keep AI tools effective in dynamic environments.Start now or fall behind: AI adoption is becoming a business requirement—act within 3-5 years to stay competitive.Train your team: Proper training ensures employees embrace AI tools, driving measurable ROI. Chapter Markers:0:00 Intro0:04 Guest Introduction0:50 Jack’s Journey into AI4:06 AI in Healthcare: Impact and Insights7:44 Data Privacy Lessons from Healthcare11:04 Gaps in AI Adoption: Avoiding the Hype14:21 Turning AI Concepts into Business Value17:07 AI’s Role in Software Development29:57 Garbage In, Garbage Out: Ensuring Quality32:28 Scaling AI for Small and Mid-Sized Companies35:09 Monitoring AI for Efficiency39:03 Tackling Model and Data Drift43:33 Signals for Reevaluating AI Strategy46:23 Closing Keywords:Tomas Hilliard, Olivier Poulard, Jack Teitel, Software Without Borders, AI, machine learning, Tidal AI, healthcare AI, data privacy, HIPAA, AI coding tools, software development, business value, model drift, data drift, AI strategy
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5 months ago
47 minutes 44 seconds

Software Without Borders
#30 - Why Most Startups Don’t Need a CTO with Oshri Cohen
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. Mos
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7 months ago
1 hour 47 seconds

Software Without Borders
#29 – Leading Transformation in Regulated Industries with Jig Patel
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
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7 months ago
59 minutes 15 seconds

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.