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

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

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

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

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

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

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

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

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

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

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

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

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