All Episodes

Believe in YOURSELF w/ Trevor Colhoun | Episode 193

Become Intimately Familiar With Your Business Models w/ Bobby Tahir | Episode 192

Keep Doing More, Don't Delay, Do It Now w/ Shimon Ben-David | Episode 191

Learn from your failures, Fail FAST, Move QUICK w/ Cary Gahm and Ed Thomas | Episode 190

Finding the right balance of trusting AI Tools w/ Stephen Chen | Episode 189

When To Use Pure AI Or Human Empathy w/ Nathan Strum | Episode 188

More Collaboration, More Success w/ John Grunas | Episode 187

Adopt New Tooling Before It's Too Late, Be Bold, Take Chances w/ Aron England | Episode 186

How AI is TRANSFORMING Incident Management w/ Sylvain Kalache | Episode 185

Engineering Growth Starts with Bi-Directional TRUST w/ Joseph Solomon | Episode 184

Teams That PLAY Together, STAY Together w/ Abe Jarrett | Episode 183

Building REAL, Genuine HUMAN Connection w/ Nick Gattuso | Episode 182

Leverage AI and Stay AHEAD of the Curve w/ Wendy Dole | Episode 181

Lean Into Risk Or Get Left Behind w/ Bradley Friemel | Episode 180

Your Team Knows What to Do. Let Them Experiment With AI w/ Jonathan LaCour | Episode 179

You've Got To ACT. Do NOT Ruminate On Decisions w/ Martin Mrugal | Episode 178

Trust, AI, and Scaling Smart: Valuable Leadership Lessons w/ Guyte McCord | Episode 177

Product and Engineering Can Be Separate, but NEVER Disconnected w/ Todd Persen | Episode 176

How to Use Tech Debt WITHOUT Going Bankrupt w/ Maha Virudhagiri | Episode 175

AI Helps, But Fundamentals WIN In Strong Product Development w/ Michael Cieri | Episode 174

Vibe Coding Is NOT Enough, An Engineer MUST Review Our Code FIRST w/ Eric Poff | Episode 173

Save Countless Hours With AI, Master Prompts & Vibe Coding w/ Brian Bauer | Episode 172

Why Aligning Your Product & Engineering Teams Earlier WORKS w/ Jeff Prince, CTO of XOi | Episode 171

The Secret Is Quality Meetings w/ Ben Ede, Engineering Director of Envoy | Episode 170

Ajay Chankramath on Platformetrics Engineering, AI Tools & Reducing Developer Friction

Michael Terry on Building Regulated Software, AI Reality & Engineering Talent

William Steenbergen, CTO of Federato, on AI-Native Insurance & Engineering at Scale

Matt Ryan, CTO at Kythera Labs, on Healthcare AI, Data Strategy & Real Execution

Nathan Miller, CEO of Rentec Direct, on Real Estate Tech, AI Automation & Scaling SaaS

Matt DeBergalis, CEO at Apollo GraphQL on AI Readiness, API Explosion and Enterprise Scale

Herb Hogue, CTO of Myriad360, on AI Infrastructure, Talent, Quantum & The Future of Compute

Michael Campbell, CEO of Fusion Risk Management on Operational Resilience and AI’s New Reality

Ken Johnson, CTO & Co-Founder of Dry Run Security on AI Risks, AppSec Scale and Developer Velocity

Edward Calvesbert VP of Product for IBM WatsonX on Enterprise AI, Data Strategy and Real-World Scale

Peter Horadan, CEO of Vouched on Digital Identity, AI Agents and Building Billion-Dollar Platforms

Behnam Bastani, CEO of OpenInfer on Edge AI, Mementos Memory Tech and High-Performance Teams

Jimi Li, CTO of ALM on AI, Digital Transformation and Leading High-Performance Teams

Tanner Hackett, CEO of Counterpart on Agentic Insurance, AI Adoption and Building World-Class Teams

Mathias Herzog, CEO of Korn Ferry Digital Business on AI, Talent Transformation and Scaling SaaS

Jim Sullivan, Founder & CEO of eDiscovery AI on Legal Tech, Automation & the Future of Attorneys

Corey Ercanbrack, CPTO at Vasion on Scaling Engineering, AI Agents & Building Product That Works

Jose D. Perez-Diaz, VP of Engineering at Vetspire on AI-Native EMRs,UX Innovation & Remote Team Leadership

Justin Farris, VP of Product of Read.ai, Product Leadership & Building AI From the Ground Up

Jameel Al-Aziz, Bastion CTO on Crypto Security, Stablecoins & Building Trust in Web3

Chris Dean, Treasury Prime CEO on AI, Fintech Innovation & Building Banks That Talk to Startups

Andy James, Stead Impact Ventures CTO on AI, Product Leadership & Building Tech That Truly Matters

Simplify, Focus, and Scale: Lessons in Software Leadership from David Funck

Gajus Kuizinas on Building Contra, Loom-Driven Development & Staying True to Vision in Tech

Todd Albert on CYPHER Learning, Building AI-Powered LMS & Why Failure Builds Better Leaders

Vernon O’Donnell on Voxel, Applied AI for Safety & Leading with Mission Over Metrics

Tom Cook on LegitScript, AI Confusion & The Challenge of Being a CPTO in 2025

Michel Floyd on Fractional CTO Life, Building AI Products Fast & Staying Curious in Tech

Ihab Rimawi on My-Fi.AI, Values-Based Investing & Personalizing Finance with AI

Marlon Misra on Assembly, YC Lessons & Building the Client Portal of the Future

Michael Smith on Fortium Partners, Fractional CIO Leadership & Why Business First Beats Tech First

Raj Bakhru on Datasite, M&A Deal Intelligence & The Future of Agentic Diligence

Claire Fang on Fullstory, CPTO Leadership & Falling in Love with the Problem

Sam Clemens on Reprise, Demo Engineering & Scaling Product with AI

Tobe Sullivan on PFF, AI in Game Strategy & Engineering at the Speed of Sports

Ryan Debenham on GRIN, Building “Living” Software & Why Engineers Make Great CEOs

Steve Marshall on Aidentified, AI Prospecting & Why Focus Beats Features

Dan Zimmerman on TreviPay, B2B Payments AI & Leading as a CPTO

Frank LaSota on Zyter|TruCare, Agentic AI & Solving Healthcare’s Hardest Problems

Bill Rokos on Parsec Automation, Manufacturing Software & Building a Career of Loyalty

Olly Downs on Curinos, AI in Banking & Turning Data into Decision Intelligence

Alex Pape on Assetmark, WealthTech Innovation & Leading as a CPTO

William Benner, CEO and CTO of Pangolin, on Laser Show Tech & Turning Passion into a Global Business

Matt Peters on CAI, AI in Government & Leading with Extreme Ownership

Jared Shepard on Hypori, Veteran Leadership & Building Secure Tech from the Battlefield

Jared Crapo on Carta Healthcare, Why Great Products Are Built by Iteration, Not Big Bangs

Steven Miller on Steelcase, AI in Design & How to Build Tech That Serves 50 Quadrillion Products

Sean O’Neil on Dasion, Voice Biomarkers & Building Global Tech Teams from Africa to Latin America

Tom Doyle on Medidata, AI in Clinical Trials & Building Tech That Improves Patient Outcomes

Tanuja Korlepra on Bonterra, AI for Social Good & Building Outcome-as-a-Service

Charity Majors on Honeycomb, Observability & Why Normal Engineers Build World-Class Teams

Maria Colacurcio on Syndio, Pay Equity AI & Building Careers with Conviction

Diamond Bishop on Datadog, AI Agents & Lessons from Building Alexa, Cortana & Beyond

Priya Vijayarajendran, CEO of ASAPP, on AI-Powered Contact Centers & Scaling from Engineer to CEO

Akash Nigam on Genies, AI Avatars & Building the Visual Layer for All LLMs

Samar Abbas, CEO of Temporal IO, on Durable Execution & Building Infrastructure for the AI Era

Bryan Mishkin on Code Climate, Engineering Productivity & the Future of AI-Driven Dev Work

Allan Leinwand on Webflow, AI-Optimized Websites & Building Engineering Teams that Scale

Todd Greenbaum on Input1, Modernizing Insurance Payments & Building a Remote-First Culture

Evan Shy, CEO of HTD Talent, on AI-Ready Engineering & Lessons from Startups to Private Equity

Chris Sullens on Scaling CentralReach, AI for Autism Care & Lessons from Multiple Exits

Raj Mallempati on BlueFlag Security, AI-First SDLC Protection & Lessons from Adobe to Microsoft

Mark Sundt, CTO of Stax Payments, AI-First Engineering & Lessons from Microsoft to Fintech

Jack Kearney on Turnkey, Crypto Key Security & Building Verifiable Blockchain Infrastructure

Oliver Tavakoli on Vectra AI, Signal-First Cybersecurity & Lessons from 20 Years in the Trenches

Jon Nordmark, CEO of Iterate.ai, on Compressing Large Language Models for Edge Devices

Michelle Tinsley, CEO of Sciata, on AI Strategy, 25X Growth & Lessons from Intel to Startups

Jason Truppi, ForceMetrics, on Cybersecurity, AI in Public Safety & Building Force Metrics

Tom Aulet on how Ergatta Combines AAA Gaming and Cardio to Hook Hundreds of Thousands of Users

Mahdi Hussein on Supersonic POS, AI-Driven Retail & Lessons from Scaling Fast

Brian Soby, co-founder & CTO of App Omni, on SaaS Security, Zero Trust Gaps & Building AI-Ready Apps

Eric Anderson, CTO of Synmax, on Disrupting Energy & Maritime Intelligence with AI and Satellites

Justin Reock, DX Deputy CTO on Developer Productivity, AI Hype & Building Better Engineering Systems

Justin Stouder, FireMon GM, on Cybersecurity, Acquisitions & Leadership Retreats in the Rockies

Dr. Sergio E Sanchez, Coleman Health CIO on AI in Healthcare, Cybersecurity & Career Lessons

Matt Wampler, ClearCOGS CEO, on Restaurant AI, Demand Forecasting & Startup Lessons

Aron Semle, HighByte CTO on Industrial DataOps, AI Agents & Lessons in Manufacturing Tech

Traackr CEO, Pierre-Loïc Assayag, on Managing Global Remote Teams & Multicultural Talent

Charles Yeomans, AtomBeam CEO on AI, PCM & the Command Center of the Future

Transact CTO, Taran Lent, on IDX, Cloud Native Platforms & Continuous Delivery

WellSaid Labs CEO, Benjamin Dorr, on AI Voice, Responsible Tech & Scaling Enterprise Adoption

Serenity Forge CEO on Storytelling, Team Culture & Longevity ft. Zhenghua (Z) Yang

Outschool CEO on EdTech, AI Volatility & Building Resilient Teams ft. Amir Nathoo

Emburse CTO on AI Expense Tools, Acquisitions & Leading Global Engineering Teams ft. Ken Ringdahl

Lucidworks CEO on AI Valuations, Hype Cycles & Business Reality ft. Mike Sinoway

Steve Valero on AI Trends, Organizational Psychology & Engineering Culture

Neubloc CEO on Nearshore Talent, AI Projects & Scaling Global Teams ft. Armando Viteri

Rater8 CEO on Reinventing Healthcare Reviews with AI & GEO ft. Evan Steele

Aditya Jami on Building Enterprise-Grade AI Systems That Scale

Weave Bio CTO on SpaceX Lessons, AI in Drug Filings & Startup Leadership ft. Levi Malott

Structure’s CTO on Navigating Supply Chain Risks & Technical Breakthroughs

EnFi Co-Founder on Angel Investing, Agentic AI & 10x-ing Teams Without Hiring ft. Joshua Summers

Charity Navigator CPTO on Tech Debt, AI Use & Scaling Nonprofit Impact

Landbase Co-Founder on AI-Driven GTM, Vibe AI & Building Category Leaders ft. Daniel Saks

Chris Chapman on Patented Tech, Hybrid Teams & Turning Macs into Enterprise Cloud

CTO on Building Software That Actually Touches the Real World | Kumar Srivastava

Noemiq CTO on Semantic Search, Defense Projects & Team Chemistry ft. Chris Davis

Anthony Presley on Surviving the FTC, Building Remote Teams, and Listening to Users

Sketch Development CEO on AI, Identity Crises & Product Truth ft. John Krewson

Building at the Speed of Trust: The Engineering Culture Behind Petfolk

Sheldon Arora on AI Matching, Offshore Devs & Speed to Market

Building Remote Teams That Scale | Jim Olsen’s Leadership Playbook

Ken Pickering on Failing Forward, Leading Remotely & Building With Purpose

Engineering at DoorDash: Behind the Tech That Powers Millions of Orders

Building ARR Without Disruption: Gary Guseinov's Smart Scan Tech Explained

AI, Cybersecurity & Scale: The CTO Playbook from Broadridge’s Jason Birmingham

CIO Chris Ortega Gets Real: AI, Agile & the Human Side of Tech

Reid Lentz on AI, Process-First Tech & Vibe Coding Done Right

Dan Sloan on Fixing Broken ERP Systems, SaaS Overload & Why Process Comes First

Bob Provencher on Building Health Platforms & Scaling with Microservices

Alan DeKok on Building FreeRADIUS, InkBridge Networks & the Truth About AI in Networking

Rick Schott on AI CRM, Route-O-Mise & Brutal Startup Lessons for Tech Leaders

Dymaptic CTO Christopher Moravec on AI, Maps & Why Tech Alone Won’t Save You

Sonatafy CTO Christopher Horvat on AI-Driven Prototyping, Modern CTO Challenges & Resilient Teams

Kusari CTO Michael Lieberman on Securing the Software Supply Chain & Fighting AI Slop Squatting

Nick Woodhead on Building a Custom ERP, Translate Tech & Bridging the CTO-Business Gap

CIO Rob Zelinka on AI, Resilient Leadership & Building a Legacy That Outlasts You

Citadel CIO Leonard Niebo on AI in Higher Ed, Cybersecurity & Building Future Leaders

Brett McLaughlin on Architecting Cloud, Writing O’Reilly Books & Getting Hired as a CTO

Disney Alum Cydni Tetro on AI, Vibe Coding & Getting More Women Into Tech

Brad Buscher on AI Hype, M&A Tech Strategy & Leading with People

Engineering Trust: Rob Riggs on Scaling Teams, AI Hype & Digital Strategy in 2025

Andy Elmhorst on Scaling Tech, AI Strategy & Leading with Code

From Self-Taught Coder to Taco Bell CIO: Haeden Kolb on Custom ERP, Franchises & Tech Grit

CIO Heidi Anderson on Breaking Barriers, Building Bots & Leading with Purpose

Hello Alice CTO Kelsey Ruger on AI, UX at Scale & Redefining the Future of SaaS

Kevin Surace on AI-First Testing, Digital Twins & Surviving 30 Years in Tech

Paragon Films CIO Kenny Mullican on AI Agents, ERP Strategy & Staying Hands-On in Tech

Atom Tickets CTO Archith Sharma on AI, Scaling Teams & Building Culture After Acquisition

CallRevu CTO Jeff DePascale on AI-Powered Sales Training, Tech Culture & Letting Go of Code

CSK Legal CIO Jason Thomas on AI Agents, IT Modernization & Leading Tech in Law

Mahaska Health CIO Bob Berbeco on Data Governance, AI in Healthcare & Leadership That Listens

High Ground Founder John Price on GovTech, AI Legislation & Cracking the Government Sales Code

Moda Operandi CIO Don Allen on AI Risk, E-Commerce Tech & Building Calm in Chaos

Source Advisors CTO Jason Wilcox on Generative AI, Engineering Leadership & Fixing Data Chaos

UMCU CTO Sherry Wu on AI Chatbots, FinTech Partnerships & Leading in a Male-Dominated Industry

Neurodyne CEO Mark Myers on Seizure Tech, AI in Healthcare & Building Medical Devices from Scratch

Zest Dental CTO Fawad Rashid on AI in Dentistry, Revenue Ownership & Leading Beyond Tech

From Burnout to Breakthrough: Fernando Higuera on Mental Health, AI & CTO Leadership

From DOM Standards to Data Fabric: Gavin Nicol on AI, Web History & Building at Context Labs

SBIR CTO Bryan Guinn on $750M in Non-Dilutive Capital, AI-Driven Defense Tech & Startup Funding

From CTO to President: Ryan Ruscett on Scaling Startups, Fixing Teams & Leading with Grit

AstrumU CTO Kaj Pedersen on Trusted Data, Resilient Teams & The Real Future of AI

Fractional CTO Chris Bee on DevPlan, Startup Clarity & AI's Real Impact on Product Teams

From Grant Money to CTO: Bazyl Horsey on Scaling Arvist, AI for Warehouses & Tech Leadership

Trinity Logistics CTO Russ Felker on AI Hype, Data Strategy & Reinventing Supply Chains

Navigating the Tech Landscape with Ken Stott

Transforming Tech Leadership with John Mann

AV Meets AI: Why Gesture-Controlled Conferencing Is Just the Beginning | ft. Doug Schaefer

The Importance of SCADA in Modern Industry featuring Rich Wagner

Revolutionizing Mortgage Tech: Amir Kundalik on Speed, Scale & Fintech That Actually Works

Global CTO Srikanth Victory on Building AI That Works, Scaling Teams & Leading with Empathy

From Law to $230M Tech Success | Joe Emison on Disrupting Insurance & Serverless Engineering

From Operations to CIO: Scott Bendle on ERP Success, AI Adoption & Global Tech Challenges

Revolutionizing Hospice Care with AI: CTO John Crighton Shares All

Lena Skliarova-Mordvinova: Ethical AI in Beauty Tech & the Future of Product Innovation

4-Time CTO Nick Hnatiw on Cybersecurity, Zero Trust, & Leading with Purpose

Inside HP Enterprise: Chad Smykay on AI Agents, Private Models & The Future of Enterprise Tech

From Code to CTO: Jason Gilmore on SaaS, No-Code, and Private Equity Leadership

Cameo’s CTO on AI, Coding Culture & Building the Future of Fan Engagement | Dom Scandinaro

Leading Through Change: Mark Losey on Innovation, People & Software Strategy

Return of the CTO: Inside Conor Sibley’s AI-Driven Comeback

Leading with People, Not Just Code: Matthew Mixan on Scaling What Matters

Jason Tesser on Startup Scaling, Data Challenges & Job Hunt Lessons | Software Leaders Uncensored