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⚙️ Chief Data & AI Executive | 30+ Years of Enterprise Transformation| $3B+ Business…
Articles by Stephen (Steffin)
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Conversational & GenAI for Business
Conversational & GenAI for Business
Hello LinkedIn Audience: I'm excited to join an the Advisory Board of UBIXLabs, an innovative company with a real…
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Stephen (Steffin) Harris reposted thisStephen (Steffin) Harris reposted this𝗧𝗵𝗲 𝗮𝗰𝘁𝘂𝗮𝗹 𝗿𝗼𝗮𝗱𝗺𝗮𝗽 𝗳𝗼𝗿 𝟵𝟭% 𝗼𝗳 𝗲𝗻𝘁𝗲𝗿𝗽𝗿𝗶𝘀𝗲 𝗚𝗲𝗻𝗔𝗜 𝗽𝗿𝗼𝗷𝗲𝗰𝘁𝘀 𝗶𝘀 𝗮 𝗰𝗼𝗺𝗽𝗹𝗲𝘁𝗲 𝗺𝗲𝘀𝘀. ↓ This visualization captures why so many Proof of Concepts (PoCs) are dying before production. (I've been in this specific terminal loop many times at my day to work). The unsexy truth is that enterprise transfromation is complex and only works when people, processes, and technology are properly aligned. And getting exactly that right means, you don't get a perfect linear path. You get friction. 𝟭. 𝗧𝗵𝗲 𝘂𝗻𝘀𝗲𝘅𝘆 𝗽𝗿𝗲𝗿𝗲𝗾𝘂𝗶𝘀𝗶𝘁𝗲𝘀 → "Fixing data issues" isn't a weekend task. It's months of sanitizing the raw material for your RAG architecture. → Legal, compliance and security will question everything. You need an automated, explainable governance loop bolted on before day one. 𝟮. 𝗧𝗵𝗲 𝗺𝗼𝗱𝗲𝗹 𝗵𝗮𝗹𝗹𝘂𝗰𝗶𝗻𝗮𝘁𝗶𝗼𝗻 𝘁𝗲𝗿𝗺𝗶𝗻𝗮𝗹 → "Model works... sort of" is the builder’s common language. (A nice way of saying 'this thing just cited non-existent regulation'). You find an edge case, sand it down, then realize context rot at 100k+ tokens means stripping back the prompt engineering entirel. 𝟯. 𝗧𝗵𝗲 𝗼𝗿𝗴𝗮𝗻𝗶𝘇𝗮𝘁𝗶𝗼𝗻𝗮𝗹 𝗳𝗿𝗶𝗰𝘁𝗶𝗼𝗻 𝗽𝗶𝗽𝗲𝗹𝗶𝗻𝗲 → Security review will stop progress. It takes 3 months. (Parenthetical: because it should). → You finally launch, and user training is a hasty afterthought. Then you wonder why the business team isn't ready or why adoption is zero. I believe the only winning strategy is to embrace the tangle. You build assuming the data is imperfect, the stakeholder requirement will shift, and legal is slow. And that's why the human-in-the-loop—to debug the debugging—is essential. Anyone else currently in one of these loops? What's the point where you usually get stuck? Brilliant visual by Clare Kitching. ⇣ 𝗜 𝘀𝗵𝗮𝗿𝗲 𝗺𝗼𝗿𝗲 𝗼𝗻 𝗵𝗼𝘄 𝘁𝗼 𝗺𝗮𝗸𝗲 𝗔𝗜 𝗽𝗿𝗼𝗷𝗲𝗰𝘁𝘀 𝘀𝘂𝗰𝗰𝗲𝘀𝘀𝗳𝘂𝗹 𝗵𝗲𝗿𝗲. 𝗦𝘂𝗯𝘀𝗰𝗿𝗶𝗯𝗲 𝗳𝗼𝗿 𝗺𝗼𝗿𝗲: https://lnkd.in/dbf74Y9E
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Stephen (Steffin) Harris reposted thisStephen (Steffin) Harris reposted thisStop hiring people you can control. Start building teams that can make you think bigger. Many people see strong people around them as a threat to their own value. But here’s the truth: People who know more and think deeper do not diminish you. They can expand you. Working with people who are stronger than you in some areas isn’t a weakness. It is maturity. Because only a confident person can say: → there is something for me to learn here → being surrounded by strong people is a privilege → I do not need to be the smartest person in the room → other people’s experience can accelerate my growth Here’s what matters: If you are surrounded by smart, talented, strong people… That is not a reason to shut down, compete, or prove your worth. It is an opportunity. ↳ An opportunity to ask better questions. ↳ An opportunity to see new perspectives. ↳ An opportunity to grow faster than you ever could alone. Don´t be afraid of not being the strongest person on the team. Worry more about staying where no one helps you grow. The best environments are not the ones where you feel like “the best.” They are the ones where you become better. Because working with people who are smarter than you is a blessing, not a threat. What interaction with a strong person gave you the biggest professional growth? _ ♻️ Share this with someone who needs to hear it today. ☝️ For more valuable content, follow me: Victoria Repa | BetterMe CEO & Founder
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Stephen (Steffin) Harris shared thisOften we don’t realize it when we are in a growth cycle —-because our focus is often overwhelmed by the challenge we are in or are facing,! Looking back, Looking forward, and realizing in this very moment… My greatest periods of growth, have been when facing challenges for which the solution wasn’t in my back pocket, nor could I miraculously do it alone! ….I had to build new relationships, gain buy-in with existing, and forge partnerships with the opposition, laying the foundation for “win-win” outcomes for all parties! This forced me to get out of my comfort zone, learn something new, reimagine what I already knew, but in the context of the current challenge at hand! Finally, I limited the distractions around me to remain focused on landing the win! It’s not about just Facing Challenges It’s “OVERCOMING CHALLENGES” that yield meaningful growth!Stephen (Steffin) Harris shared thisWe often pray for smooth seas and clear skies. We look for the path of least resistance, believing that comfort is the ultimate reward for our hard work. But if you are currently facing a mountain that feels too steep to climb, I want to offer you a different perspective. We don’t grow when things are easy; we grow when we face challenges. Comfort is a beautiful place, but nothing ever grows there. It is in the "stretch," the tension, and the moments where we feel tested to our absolute limit that our true leadership capacity is forged. Strength is built in the resistance; Just as a muscle requires tension to grow, your character requires a challenge to strengthen. Easy times rarely teach us anything new. It is the difficult seasons that force us to innovate, adapt, and discover who we really are. You cannot appreciate the summit without the grit of the climb. If you are struggling today, do not see it as a sign of failure. See it as a sign of expansion. You are being prepared for the next level of your purpose. Stay the course. The challenge isn't there to stop you; it’s there to move you toward the person you were meant to become. Keep growing, keep leading, and keep the faith. Our Leadership First family is standing with you. - Our new Amazon Bestseller, Inspirational Leadership Quotes, Finding The Courage To Lead, is more than just a collection of quotes; it serves as a heartfelt guide for transformation. Each page inspires you to embrace new perspectives, strengthen determination, and ignite action. Learn more by clicking the link below. https://lnkd.in/eT5HKFnV.
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Stephen (Steffin) Harris reposted thisI perfectly 👌 agreeStephen (Steffin) Harris reposted thisMost leadership relationships have an expiration date. People change roles. Teams reorganize. Careers move on. What’s less common is what happens after. Some leaders disappear the moment the reporting line ends. Others remain a quiet presence—offering encouragement, perspective, or a word of support when it matters. Years later, people rarely remember the meetings or the org charts. But they remember the leader who kept cheering them on even when there was nothing left to gain from it. Because that’s when leadership stops being a role and starts becoming an influence. Thank you Leadership First for sharing this insight.
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Stephen (Steffin) Harris shared thisPriya Raman - Thank You!!!!such a great call-out and POV- likely being missed in all the “AI-Noise”, let’s mark this post and revisit it in 2 years while we “Sip our tea with a slight smirk”! Two points I want to reinforce and call out from your message….for all enterprise leaders, board members! 1) AI is eating Softwares Lunch - aka FDE and Agentic-AI, the answer is much more complex than headcount reduction to realize ROI, your talent will be critical to manage continuously evolving business models and change! 2) The point on the the failed AI deployments to date at the intersection of “Data”…,, Delayed Data Investments are Today’s AI Tech Debt, activated and realized in all the failed AI Initiatives not meeting expectations of outcomes - Action: Prioritize AI Ready Data Investments! Why this matters! Can you imagine having to explain to the board why the forecasted ROI on AI is not meeting expectations given the Billions in Infrastructure investments! And the answer being “Our Data wasn’t Ready”? This is why Chief Data Officers, are best positioned to become AI Officers and in the future all Forward Deployed Engineering, Data and AI in Production will become the responsibility of yet another role to be introduced to the market - The Chief AI Operating Officer equivalent to today’s COO! #aiperspectives Action! Prioritize your Data Investmets Today to Avoid AI Failires Tomorrow to minimize “AITechDebt!Stephen (Steffin) Harris shared thisA job title you’ve probably never heard of is quietly threatening a $4 trillion industry. It doesn’t involve building AI models. It doesn’t involve working in a research lab. And most engineers don’t even want the job. Yet some of the smartest companies in AI like Palantir, OpenAI, Anthropic (among others) are betting their enterprise strategy on it. The role: Forward Deployment Engineer. And what it represents is much bigger than a job title. Enterprise AI has a dirty secret. The models work, the technology is ready, the demos are dazzling. But inside real companies - Most AI deployments are failing quietly. Not because of the technology. Because of the LAST MILE - The part where AI meets: → data that hasn’t been touched in a decade → systems that were never designed to talk to each other → workflows that exist only in someone’s head → stakeholders who can’t agree on what success looks like This is the gap nobody talks about at AI conferences. But the signals are getting louder. • Job postings for Forward Deployment Engineers grew 10x in 2025 • Earnings call mentions jumped from 8 to 50 in a single year • Compensation is pushing well past $500K Something structural is happening. And here’s the part that should make consulting firms nervous. For 30 years, enterprise technology ran on a simple model: 1. Vendors built it. 2. Consultants implemented it. 3. Enterprises operated it. Three layers. Trillions in fees. An entire industry built around the gap between technology and execution. The Forward Deployment Engineer collapses all three into one role. One operator who is: - Engineer - Architect - Product manager - Field strategist Embedded directly inside the customer’s business. No SOW. No evalutation and handoff. Just someone who understands both the model and the mess..and closes the gap. I’ve spent 30 years leading enterprise transformations across product and services companies. I’ve seen delivery models shift before. And one pattern is consistent: When a faster, closer-to-the-customer model emerges - value migrates. Every time! The question isn’t whether Forward Deployment Engineers matter. The real question is: What happens to the traditional services layer when AI companies start sending their own engineers into the field? The biggest disruption in AI may not be the algorithm. It may be who delivers it. What’s your read? Is Forward Deployment Engineering just a hiring trend? Or the early signal of a fundamental restructuring of enterprise AI delivery?
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Stephen (Steffin) Harris reposted thisStephen (Steffin) Harris reposted thisIn a world obsessed with curated perfection, we often forget the power of our own humanity. Nobody’s perfect. We are all a work in progress—weaving a story through the mistakes we make and the lessons we harvest. We fall, we stumble, and yes, we fail. But the magic isn't in the fall; it's in the rising. When we allow ourselves the grace to learn and the courage to move on, we aren't just surviving—we are truly living. Embrace your imperfections today. They are the soil in which your growth is rooted. Keep growing, keep learning, and keep moving forward. - Our new Amazon Bestseller, Inspirational Leadership Quotes, Finding The Courage To Lead, is more than just a collection of quotes; it serves as a heartfelt guide for transformation. Each page inspires you to embrace new perspectives, strengthen determination, and ignite action. Learn more by clicking the link below. https://lnkd.in/eT5HKFnV.
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Stephen (Steffin) Harris reposted thisGood breakdown. One thing I would add from the ontology side of the world. What most people call a semantic layer today is really a metric governance layer. It standardizes definitions, calculations, and reporting logic so everyone gets the same numbers. That is extremely useful, but it is not the same thing as semantics. Semantics requires a formal model of the domain. Entities, relationships, roles, constraints, and how those things interact. That is what ontologies provide. Without that structure underneath, a semantic layer can keep metrics consistent, but it cannot explain how the business actually works or allow systems to reason over the data. Our view at Interstellar Semantics is that a true semantic layer ultimately has to sit on top of formal ontologies. Otherwise you are managing definitions, not modeling meaning. As AI starts interacting directly with enterprise data, that distinction becomes increasingly important.Stephen (Steffin) Harris reposted thisI'll be honest—I didn't fully understand the difference between a semantic layer and an ontology until recently. And I don't think I'm alone. These terms get tossed around like they mean the same thing. They don't. The way I think about it now: A semantic layer is about consistency. It makes sure everyone's working with the same numbers and definitions. Super useful for reporting. An ontology is about connection. It maps how things relate—the "why" behind the data, not just the "what." That distinction used to be academic. Now it's practical. Because when AI starts working with your data, it doesn't just need accurate metrics. It needs to understand how your business actually thinks. And that's a different problem entirely. Jessica Talisman wrote a really clear breakdown of this in Metadata Weekly. The line I keep coming back to: "𝗠𝗲𝗮𝗻𝗶𝗻𝗴 𝗶𝘀𝗻'𝘁 𝘁𝗵𝗲 𝘀𝗮𝗺𝗲 𝗮𝘀 𝗺𝗲𝗮𝘀𝘂𝗿𝗲𝗺𝗲𝗻𝘁." Worth a read if you're trying to make sense of where context graphs fit into all of this.
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Stephen (Steffin) Harris shared thisImani Dunbar - This is amazing, thank you for sharing, what a class act production, it was just the "pick-me-up", I needed on a Thursday afternoon! What a great commercial - I've cc'd former VMware colleagues now President of Product & Engineering @Zoom Velchamy Sankarlingam, and Awinash Sinha Chief Digital Information Officer @Zoom.Stephen (Steffin) Harris shared thisFinally ready to share this w/ the LinkedIn universe. A lil something I wrote and performed several years ago! ❤️ Shout out to my: 🎹 music producer - Thomas Newton Correll 📽️ video producer - Christopher Eldridge 📋 associate product - Ben Maloy and all-star video cast - Ben Maloy, Jackie Davenport, Kirk Sims Jr., Linda Walubengo, Liza Smyth, Meg Garlinghouse, Megan Ketchum, Melissa Selcher, Michelle S., Nicole Cloonan, Nicole Leverich, Stephen McCumiskey, Tanya Staples ⚡ Enjoy! 😅
Stephen (Steffin) Harris commented on a post
18h
Congratulations Lindsay-Rae McIntyre - It's so great to see you land this opportunity. I hear great things about Alaska's culture and people, and I know you will be a major value add to the company!
Stephen (Steffin) Harris commented on a post
21h
Victoria Mensch... This is another validation of the role of data in AI, scoping AI for outcomes not just experimentation, there is no AI success without governed data, pre-established outcomes, and a path to production.
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Stephen (Steffin) Harris liked thisRecovering Chief Data Officer... this was once my life: CTO: Build us an AI-driven future Country GMs: Well we fund your function… so keep building us dashboards. I reported to one, the other(s) paid my team’s bills and it got awkward. My solution was to brute force a new op model where I ringfenced my team’s capacity between AI innovation, platform modernisation and BAU. Dashboards and ad-hoc analytics support got a strict % of capacity only. It was a bloodbath. The business no longer had an analytics team at their beck and call 24/7. Removing the business’ expensive dependency on us was an exhausting, highly political exercise and the collateral damage was material. Would I do it again? No. I’d make the business truly self-serve so they could answer first-line queries without raising a jira ticket, sending a Slack or approaching our desks with the ‘this’ll just take five minutes’ face. I'd love to hear anyone else's thought on this rock + hard place.
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Stephen (Steffin) Harris liked thisStephen (Steffin) Harris liked thisIntroducing Critique, a new multi-model deep research system in M365 Copilot. You can use multiple models together to generate optimal responses and reports. Available today in Frontier: https://lnkd.in/g3mzcpk6
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Stephen (Steffin) Harris liked thisStephen (Steffin) Harris liked thisTrust is not a leadership style. It’s a decision with consequences. Micromanagement signals control. Empowerment signals belief. But neither guarantees results. Because trust without structure breaks. You don’t get outcomes just because you say “I trust you.” You get outcomes when: • Expectations are clear • Standards are non-negotiable • Ownership is defined • Accountability is enforced That’s when trust works. Without that, “empowerment” turns into confusion. And confusion always kills performance. Trust is not given. It’s built through clarity and enforced through standards.
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Stephen (Steffin) Harris liked thisBack in December, I dropped some 2026 predictions. My boldest take was that AI wouldn't kill jobs but create them. Yeah, I know, shocking! I even spelled it all out in 'The Coming AI Hiring Boom: And why it will sort winners from Window dressers' (link below). Turns out, I'm not alone; the smart folks at Gartner agree. Who knew? Jevon's paradox? Yeah, it's as real as ever. History's greatest hits of General Purpose Technologies have proven it time and time again. Get ready for a wild ride—jobs and careers are about to get messy, but the whole 'jobs apocalypse' is just good old-fashioned hype. Hold on tight. https://lnkd.in/gxfdg4DYStephen (Steffin) Harris liked thisGartner forecasts a net increase in jobs from AI beginning in 2028. Yes, you read that correctly. It’s time to move the AI productivity conversation away from headcount reduction and toward real productivity gains—for teams that use AI effectively. Discover how: https://gtnr.it/4oLPefj #ArtificialIntelligence #Jobs #Productivity #Layoffs #AI
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Stephen (Steffin) Harris liked thisStephen (Steffin) Harris liked thisCongratulations to Lindsay-Rae McIntyre on her appointment as Chief People Officer at Alaska Airlines. With over 28 years of leadership experience, including senior roles at Microsoft and IBM, Lindsay-Rae brings deep expertise in global talent strategy, culture transformation, and leadership development at scale. Her appointment comes at a pivotal time as Alaska Airlines strengthens its global footprint and advances its integration with Hawaiian Airlines, making people strategy central to delivering a seamless and high-quality customer experience. As organizations navigate scale, integration, and workforce transformation, leaders like Lindsay-Rae play a critical role in shaping engaged, high-performing, and purpose-driven cultures. Commenting on the appointment, Ben Minicucci, CEO of Alaska Airlines, said, “Lindsay-Rae is an accomplished people leader with deep experience strengthening culture and leading complex global organizations… we’re excited to welcome her as we continue to grow and integrate our operations.” Wishing Lindsay-Rae McIntyre great success in driving Alaska Airlines’ people agenda forward. 𝗥𝗲𝗮𝗱 𝘁𝗵𝗲 𝗙𝘂𝗹𝗹 𝗦𝘁𝗼𝗿𝘆 𝗛𝗲𝗿𝗲 : https://lnkd.in/gmQ-EfWm 𝐒𝐮𝐛𝐬𝐜𝐫𝐢𝐛𝐞 𝐭𝐨 HR TODAY : https://lnkd.in/dxKmqXqn #AlaskaAirlines #Leadership #HRLeadership #PeopleStrategy #Culture #Transformation #HRTODAY
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Stephen (Steffin) Harris liked thisStill recovering from the laughs last night at SFJAZZ! 😂 The Bond Fund is all about making real connections, and sometimes the best way to do that is getting 20 of us together to watch our own industry get brutally roasted. If you haven't seen Austin Nasso, Jesse Warren, Nikita Oster and the team from Socially Inept live, you're missing out. Strongly recommended. #TheBondFund #SFJazz #ComedyRoast #SociallyInept #SFTechStephen (Steffin) Harris liked thisLast night, The Bond Fund took over SFJAZZ for a much needed reality check! Our group stepped away from the screens and slide decks for an absolutely hilarious (and ruthlessly accurate) evening at the Comedians Roast San Francisco: Tech Roast Show. A massive shoutout to Austin Nasso, Jesse Warren, Nikita Oster and the brilliant team at Tech Roast Show for putting on a phenomenal performance. There is nothing quite like bonding over our shared industry quirks and watching pitches get roasted live on stage. 😂 We believe that the best professional connections are built when we can get together, unplug, and not take ourselves too seriously. Seeing our community show up and share so many laughs together was the absolute highlight of our week. Who is ready for the next one? #TheBondFund #TechRoastShow #SFTech #SanFrancisco #VentureCapital #Startups #FounderLife #CommunityBuilding #TechHumor #SFJazz #NetworkingEvent
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Stephen (Steffin) Harris liked thisStephen (Steffin) Harris liked thisTwo weeks ago: I left insightsoftware. This week: I’m building the future of data infrastructure. Some of you already know I’ve been working on a startup. Here is the unveiling. I'm that guy who formats his brand new laptop just to build it from scratch (iykyk). Working on a startup is where I do my best thinking, my best work, and feel the most alive. AI does not have a model problem. The models are already pretty amazing. But AI has a data problem. Data pipelines that deliver data to AI models are more critical than they've ever been. Data pipelines are critical to whether your AI works … or ends up as part of that famous 88% of PoCs which never "graduate" to production. But for the first time, machines - not humans - are the primary consumers of data. Yet the data pipelines weren't designed for agents, rag, or systems that adapt. That’s why we’re building Dagen - Dagen.ai (short for data + agent). We believe data pipelines themselves need to become agentic; autonomous, self-healing, and able to orchestrate themselves. Not just faster pipelines. Smarter ones. Because in the AI era, the pipeline isn’t plumbing. It’s the system that decides whether your AI works or not. Let’s build!!! (You may wonder why this picture? I’m in Los Angeles -probably my 100th time- but my first Warner Bros studio tour. One of the few photos I took was Jack Warner’s phone book. Under “D” you see names like Disney (Walt), Davis (Bette), Dali (Salvador). And at the very top: the Drugstore. That’s what made me think of data pipelines. The unsung hero that quietly makes everything else work.)
Experience & Education
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AI Perspectives
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Advisory Board Member
Waters Technology
- Present 8 years 10 months
Science and Technology
Representing the intersection of Technology, Financial Services and Regulatory requirements
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Advisory Board Member
Modal
- Present 3 years 11 months
Science and Technology
Helping to reimagine and illuminate the e-learning journey Buikding courses targeting data science, data engineering, data analytics, and data program management professionals to best serve the business and technology teams in which they serve.
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Patents
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Heuristic Weighted Autoencoder: A Deep Learning framework for Anomaly Detection in Batch Context: A service on top of Cloud
Filed US FIP ID 2647045 G767.ID
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SYSTEM AND METHOD FOR RECOMMENDING DEMAND-SUPPLY AGENT COMBINATION PAIRS FOR TRANSACTIONS USING MACHINE LEARNING
Issued US F689.ID
SYSTEM AND METHOD FOR RECOMMENDING DEMAND-SUPPLY AGENT COMBINATION PAIRS FOR TRANSACTIONS USING MACHINE LEARNING
Honors & Awards
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Dale Carnegie| Certificate of Achievement
Dale Carnegie & Associates, Inc
Certificate of Achievement having met the standards for completion of the Influencing Without Authority
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NASA Group Achievement Award
National Aeronautics and Space Administration
Process Based Mission Assurance (PBMA) Columbia Accident Investigation Board Support Team, for the outstanding achievement of rapidly implementing a highly secure, web based capability for documentation, file exchange and electronic communication in support of the Columbia Accident Investigation Board (CAIB)
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English
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IA Forum
Advisory Board Founding Member
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American Association of Big Data Professionals:
Board Member
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Judah Phillips
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I build AI from 0→1—and take it from demo to sale to exit.<br><br>Today I’m Chief AI & Product Officer at Market Holdings, where I lead AI platform strategy, product, engineering, and GTM across a portfolio of brands. I work directly with the CEO and board on AI investment, commercialization, and governance—turning predictive and generative AI into production systems that drive real outcomes.<br><br>Before that, I founded and led Squark, a no-code AI platform for prediction, forecasting, and decision intelligence. I built the company end-to-end—product, engineering, sales, partnerships, and go-to-market—and led it through enterprise adoption and acquisition in 2024.<br><br>We sold to enterprise customers including IBM, DHL, Nielsen, UPMC, Innovairre, HubSpot, Dynata, and Mass General Brigham, and built partnerships with Snowflake, NVIDIA, and McKinsey.<br><br>Earlier, I built and led analytics organizations at scale (60M+ users, 300K+ customers), managed multimillion-dollar budgets, and contributed to M&A. Through SmartCurrent, I advised companies including Ford, Best Buy, Helen of Troy, The Nature Conservancy, and the U.S. Holocaust Memorial Museum.<br><br>I also invest in and advise early-stage companies across AI, data, and digital platforms, and founded Boston AI Week and the Boston Generative AI Meetup.<br><br>Author of three books on analytics and AI (Pearson/FT Press), with a fourth forthcoming.<br><br>Most people focus on models. I focus on outcomes—how AI gets deployed, adopted, and trusted when real decisions depend on it.
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