Software Without Borders

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Hiring challenges are universal—whether at big corps or startups—often stemming from outdated, one-size-fits-all processes that introduce bias and inefficiency.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. Most people can’t do all four.35:00 – Why Oshri Wants to Get FiredFractional success = team independence. But it comes with a visibility cost.43:00 – Contracts, Pricing, and Perceived ValueHow Oshri structures engagements and educates clients on invisible ROI.50:00 – The Future of Tech Talent in the AI EraHarsh truths about AI, developer value, and the mentorship vacuum.
Keywords:  fractional CTO, software leadership, startup technology strategy, CTO evolution, Oshri Cohen, CTO phases, fractional tech executive, technology consulting, software architecture, developer career path, managing dev teams, AI in tech, software without borders, Andy Hilliard podcast, CTO value, dev agency problems, startup CTO roles, scaling tech teams, open source email marketing, Mailchimp alternative, CTO business impact, getting fired as a CTO, peak infrastructure planning, event-based systems, tech leadership insights, remote tech consulting, Costa Rica digital nomad

What happens when a scientist-turned-technologist builds global teams, transforms regulated industries, and quietly reshapes how we think about innovation? In this episode of Software Without Borders, Andy Hilliard and Olivier Poulard sit down with Jig Patel, a seasoned technology and business operations executive, to explore how curiosity, connection, and clear communication drive transformation at scale. From deploying AI-enabled drones to building enterprise-wide digital cultures, Jig shares his playbook for leading with purpose in industries where tradition often outweighs change.
Guest Details:  Jig Patel is a global technology and business operations executive with over 25 years of experience leading digital transformation across Fortune 500 companies. Known for bridging the gap between technical complexity and strategic clarity, Jig has spearheaded multibillion-dollar modernization efforts in highly regulated industries—including financial services, utilities, and healthcare. His leadership has delivered measurable outcomes like a 7-point NPS lift, $50M+ in recurring revenue, and AI adoption at enterprise scale. A former scientist turned transformation architect, Jig brings a unique mix of curiosity, operational rigor, and servant leadership to every challenge. Whether he’s launching an HSA bank or integrating global teams post-merger, Jig’s approach centers on cross-functional alignment, empowered teams, and driving customer value—faster.
Key Takeaways:  Curiosity is a Core Leadership Trait Jig emphasizes that asking “why” is foundational to innovation—whether in a chemistry lab or leading a global enterprise.Business Technologists Bridge the Gap Unlike traditional tech leaders, Jig came from the business side and built his career by translating customer needs into technology solutions—an increasingly vital skill in modern organizations.AI Is a Tool for Enablement, Not Replacement Jig’s experience deploying “Mo,” an AI at Morningstar, shows how AI can enhance—not replace—human capabilities, especially when developed ethically and intentionally.Empowerment Starts with Communication High-performing global teams require deliberate, active communication and leadership that adapts to cultural and geopolitical nuances.Innovation Isn’t Always Tech-Driven Small process improvements, like reducing a 50-step process to 10, count as innovation and can be just as transformative as deploying new software.Highly Regulated Industries Still Need Change Working in finance, utilities, and other regulated sectors has taught Jig that constraints don’t mean resistance—they mean leaders must work creatively within the rules.Optionality Is the Real Superpower Leaders must offer more than a plan—they must offer multiple pre-thought-out paths in case priorities or conditions shift mid-execution.Stakeholder Influence Is Earned Through Understanding Building support from the board and ELT requires doing the homework, speaking their language, and giving them clear, actionable options.
Chapter Markers:  00:00 – Behind-the-scenes banter and setup03:53 – Guest intro: Jig Patel’s journey from science to tech leadership06:30 – The immigrant experience and early influences08:45 – Learning to listen: Sales, support, and the path into technology12:00 – Building tech through a business-first lens14:00 – Dual COO/CIO roles and why they’re on the rise18:00 – Culture of curiosity in regulated industries20:30 – Innovation in utilities vs. financial services27:00 – Morningstar’s AI initiative: The story of “Mo”31:00 – Ethical AI, planning before building, and phased deployment36:00 – Communication and cultural alignment across global teams43:00 – Leadership vs. management: Empowering vs. controlling46:00 – Working with regulatory bodies without stifling innovation51:00 – AI-enabled drones: A case study in public safety and efficiency57:00 – Stakeholder influence and communication strategy01:02:00 – Innovation through simplification and operational evolution01:07:00 – Final thoughts and closing remarks
Keywords:  Jig Patel, business technologist, technology leadership, regulated industries, digital transformation, software modernization, AI in financial services, Morningstar Mo, leadership in tech, enterprise transformation, innovation strategy, stakeholder alignment, cross-functional teams, global engineering, curiosity in leadership, AI-enabled drones, utilities innovation, agile communication, software development podcast, Software Without Borders, Accelerance, Andy Hilliard, Olivier Poulard, CIO strategy, CTO innovation, ethical AI, technology in regulated sectors