Fireside With Jitesh Ghai and Gene Kim

Host Intro (Gene Kim)

To motivate the next speaker, I want to tell you about one of the most astonishing things that happened to me this year.

I had the privilege of giving a talk to the Enterprise Software CEO Roundtable group. So these were CEOs of companies with revenue between $100 million and $2 billion. And at the end of the session, I made an open offer saying, "If any of you want to spend 90 minutes live coding with me, just let me know." And so I got to live code with a whole bunch of interesting people.

But without a doubt, one of the most interesting people that I got to interact with was Jitesh Ghai, the CEO of Hyland Software, one of the world's leading providers of enterprise content management, serving more than 15,000 enterprise customers worldwide, helping them manage their mission-critical documents and unstructured data. What's remarkable about him is that he started out as a software developer, and in his career he's held roles across almost every functional discipline, including marketing and sales.

So we scheduled a call, and we start working on what do you want to work on — which was building Ziggy, a chief of staff agent, working in Claude Code, working within Teams, and then ultimately Salesforce.

And it was a heady moment, but not as heady as what happened next. Because the next thing I know, I'm working with a bunch of switched-on engineers connecting MCPs and CLIs to all the important systems of record across the company. And then he asked, "Gene, I'm having a three-day offsite in Napa Valley with all eight of my L1 executives. Could you take over some of day three to help them have the same aha moment that I had?"

And it was such a fascinating day, and it was amazing to watch Jitesh model to his executives what his expectations were on how they should be integrating AI into their daily work, both in strategy and execution.

And I was so inspired that I asked him if he'd be willing to join us here at this conference to share some of the insights and teach us how to mobilize an organization from the very top. And I'm so grateful that he said yes.

Please welcome Jitesh Ghai.

Jitesh Ghai

Gene Kim: Thank you, Jitesh.

Jitesh Ghai: Thank you.

Gene Kim: And if someone could get this — Andy, if you could get that stopwatch for me, that'd be so great. So Jitesh, I'm so delighted that you're here to teach us what I think so many of us are wanting to learn. But before that, for those of you who aren't familiar with Hyland, could you educate us about Hyland and what attracted you to join the company?

Jitesh Ghai: First, thank you for having me. Pleasure to be here with all of you. Are we doing time trials? No.

And before I start, I have to make a mental note to really update my mugshot. I feel like that was from —

Gene Kim: Your hair is so good. What are you talking about?

Jitesh Ghai: — my brief flirtation with longer hair. I think it was COVID hair or something.

But before I digress any further, really excited to be here with all of you, and it's been great hearing all the other presentations today as well. Super insightful content.

To your question about Hyland and what attracted me to join — a bit about me first. I've been in the data and AI space for over two decades, and primarily in the structured data world. So think data unification, data management, data integration, data quality, data cataloging, governance — really redefining these markets from tools to a single elastic server-based AI-powered platform to build warehouses, lakehouses, drive analytics, reporting, and data science initiatives.

And through this journey over these many years, I'd always get asked by CIOs, chief data officers, chief AI officers: "Jitesh, I love what you're doing for my structured data. What can you do for my unstructured data?" And the reality was that unstructured data is very hard. It doesn't have structure. So there's very little you can do historically other than ensure governed, compliant access and use, and enable the right people to get to it and derive context from it and enable them to make decisions.

Until we all here had our collective ChatGPT moment. Large language models became a thing. They were widely available, and now you can give structure to unstructured data — at which point you can do some really radical things with your unstructured data estate, which is really 80% of an enterprise organization's data state. 20% is typically structured in your CRMs, HCMs; 80% is sitting in your content management system.

So recognizing this, and connecting these dots — fortuitously, the universe has a way of presenting opportunities. The opportunity to lead Hyland came my way a few years ago, about three years ago. And Hyland — you covered a lot of this — three decades in the making. We have the honor of serving 15,000 customers globally across the most regulated and mission-critical industries: healthcare, insurance, banking, government agencies, higher ed institutions, as well as technology organizations and other organizations. We're $1.35 billion in revenue, and we are the largest of our kind that's just focused on content management, just focused on the unstructured data problem.

And so, as the trusted custodians of this mission-critical unstructured data, as I joined Hyland a few years ago — three years ago — we formulated our AI-native vision, strategy, and roadmap for where we're taking Hyland next and where we're going to take our 15,000 and growing customers next, to unlock the value out of their enterprise content, their unstructured data. And with it, critically important was not just building AI-native products, but also becoming AI-native ourselves. Not just building it, but also living it. AI-first, AI-native Hyland in its own operations — and that's the journey we've been on over the last few years.

Gene Kim: Yeah, fantastic. And I still remember, we got on a Zoom call, Teams call.

Jitesh Ghai: Yeah.

Gene Kim: And we installed Claude Code. And you had to articulate, "You want to build a chief of staff agent." We connected Teams, connected Salesforce, and we clearly had some sort of aha moment building Ziggy. Can you describe for all of us what was that specific aha moment, and why did you think it was relevant to you in the role as a company CEO?

Jitesh Ghai: Yeah. By the way, I highly recommend — there's only one Gene, so it's tough to scale him. But if you want to inspire your leaders, I highly recommend you set something similar up.

For me, it's: if I'm going to ask my 4,000 Hylanders globally to be AI-native, then I myself need to be AI-native. Not just simply intellectually understand it, but live it and transform my own operations through the power of GenAI, through the power — in my case — of Claude, which we used to build Ziggy.

And through the process, I had multiple aha moments immediately. One of the aha moments was, well, connecting to Salesforce is not enough. I need to connect to every system of record within the organization that I care about — my ERP, my CRM, my HCM. I need to connect to Confluence so that I can have Ziggy give me some perspectives on the existing architecture for our context engine. I need to connect to Gainsight, so I have an appreciation of customer experience. And so it really gave me empathy and real appreciation that to truly enable AI, it needs to have a meaningful amount of context, and that's going to come from the respective systems.

Gene Kim: And if we may just drill down for a second — Salesforce is easier, right? Because there was either an MCP or a CLI, a command-line interface, to it. But the others were hard.

Jitesh Ghai: Yeah.

Gene Kim: Right? And so next thing we know, we're joined by one, two, then three different engineers.

Jitesh Ghai: Yeah.

Gene Kim: Basically, you're like, "I heard you're trying to do XYZ," and some of it took days, weeks to actually wire up. Is that —

Jitesh Ghai: It is. That was also part of that deep appreciation of: well, if you need to get your agent access to important information that's fragmented across multiple structured and unstructured data sources — how can we make that as seamless, as easy as possible so that we can get to the outcomes, versus "I need to get this cert for this system, need to provision this MCP server for that." And so that was an interesting insight for sure.

Gene Kim: And actually, I also have this memory of this specific look of glee that you had on your face as you were starting to have this very quick, this incredible discussion with Salesforce.

Jitesh Ghai: Yeah.

Gene Kim: Can you describe what it is you were trying to do and what made it so joyful? Not that interacting with Salesforce was joyful, but the expression on your face was joyful.

Jitesh Ghai: Well, the interaction was with Ziggy. Ziggy was interacting with various systems in the backend — Salesforce and others by that time. And what Ziggy does for me, in the most rudimentary but very meaningful way, is it's looking at my calendar, it's looking at conflicts, it's identifying important meetings, it's assembling meeting briefings for customer meetings or keynotes, or for whenever I have my board meeting as part of my exec session.

Ziggy's also a strategy partner. So I asked Ziggy to go off and formulate an international expansion strategy. Which countries are we going to invest in? Which customers are we going to target? Who are our prospects? What does investment look like in terms of how many sales executives do we need in which country, in which industries, et cetera.

Because in parallel, I'd asked my strategy and sales and marketing team to come up with a similar plan of how are we going to rapidly grow our international presence. And then we compared notes. Ziggy gave me its output and its work. I worked with my leaders, and they reviewed their proposal, and the result was a robust discussion and a better outcome. I'm not saying Ziggy was always right, but it was a great way to really pressure-test the existing output.

Gene Kim: Yeah. By the way, I have a memory — I'm not sure if it was there or at the offsite — but it's like when you're doing activities like that, you might want to make sure you're using the biggest model for that.

Jitesh Ghai: Yeah.

Gene Kim: Use the right model, not a tiny model.

Jitesh Ghai: Yes.

Gene Kim: So, I had mentioned that one of the highlights of my year was being asked to take part in your exec offsite, and I know how valuable that time is. That was a multi-day offsite. You're taking leaders away from their daily work, and it's very valuable time, how you use that time. So what was important for you — for your executives to have their own aha moments, and what were your desired outcomes out of that offsite?

Jitesh Ghai: Yeah. The moment I had my session with Gene, it was clear that — same principle — I need to be AI-native. I need to not just intellectually understand it, but live it. So do my leaders. I need them to not just intellectually understand it, but also live it. I need them to have their aha moments as well. And so I asked Gene to join me.

We brought some proctors to help him because there were about nine or ten of us, and we went through various exercises, whether it was my chief revenue officer, my chief marketing officer — and actually that's a photo of us jamming. That's us vibe coding, and the person at the desk there is my chief revenue officer, Steve Baird, former OSU alum, football player, and he's generating code as we speak in that photo.

There were many aha moments — for my chief revenue officer, my CLO, as well as my chief customer officer, my CFO, even for my CTO and CPO, who've been living this for a few years.

That was one dimension of it. The other dimension was something that we figured out in my session, but I wanted them to experience it — which is what really makes such a session productive: three pillars. You need to have the functional business expert. You need to have the AI expert that understands the art of the possible with the technology. And then you need technologists that can help you take what you're trying to do to solve a business problem and facilitate the implementation of it within the existing systems, integrate with the appropriate systems, with the appropriate technologies in your tech stack.

And that was another big aha moment for them — appreciating those three pillars to enable their respective functions.

Gene Kim: Oh, by the way, where did I learn that from? It was from Joe Beutler, from his talk they asked him to give in April, right? Where he was talking about that magical trio that works with OpenAI, especially with Sarah Fryer, the CFO, and her finance department. So that was one aha moment — super powerful.

And those were the two aha moments that I was looking for, and mission accomplished.

Jitesh Ghai: Yeah. And actually, by the way, if I can share two things that I found amazing. One is, I think there were some bets about who would actually not be able to finish a vibe coding exercise. And I think you had mentioned Steve —

Jitesh Ghai: Yeah.

Gene Kim: — the chief revenue officer. They're like, "Yeah, he's an ex-football player. I doubt everyone's going to finish except for him." I heard one person say that. And a lot of us were worried about the CFO, because he was on a Windows laptop. And one of the things I loved hearing was Jitesh say, "I will never trust a CFO who's not on Windows," which I'd never heard before.

Jitesh Ghai: There's just some things that just can't be done without being on a Windows laptop. Yes.

Gene Kim: But I am proud to say that every one of the executives finished.

Jitesh Ghai: Yes. Everybody across the board.

Gene Kim: Yeah. So that was amazing. So actually, one interaction I just found really interesting — we had a specific exercise: all right, you've all created code in this session. It was really three portions. One was a briefing. Two is, with everyone, we had a similar "let's build something together."

Jitesh Ghai: Right.

Gene Kim: And the third portion was a role-play. Let's imagine a fictitious exercise where we're going to do something cross-functional — how would you create the team?

Jitesh Ghai: Yeah.

Gene Kim: With that trio that you talked about — the functional expert, the developer, and the AI expert. And one thing that was interesting: it was Steve and the chief customer success officer. The instinct was that they thought it was their job to do the data analysis, as opposed to some of the other staff. Do you remember that moment?

Jitesh Ghai: Yeah. There were a lot of interesting ahas. First was: okay, well, you did this mini transformation for yourself — how are you going to now deploy this for your function in sales and marketing, or cross-functionally? And how are you going to build that team?

That was one question. So everybody started thinking, "This person will be my AI expert because they are, and then I will pair them up with that person from IT, and I will pair them up with my VP of revenue operations, who's the business expert on the sales side."

That was one important aha moment, but another really important aha moment in this exercise was: okay, now let's pick a problem to solve — and how are you going to solve it?

And the instinct immediately was, "Well, we'll assemble this team of three, this holy trinity, and then we're going to go and spend a few weeks figuring it out and then come back and report back." And I said, "No. 24 hours, 48 hours max." You've got machines doing all this data analysis and work for you. And I'll make myself available so that as you're going through the next 48 hours trying to figure out what would otherwise take weeks, you're going to need decisions and actions — and that's what I will be there for. I'll be available to help facilitate those decisions and actions.

And that was another interesting aha moment: if we're going to do this, we don't have to operate at the same speed. We can operate — certainly from an analysis and design perspective — at much faster speeds.

Gene Kim: Yeah. In fact, one of the things that I marveled at was one of the commitments that each one of those executives had: if we create this switched-on team, given this very tough problem, the expectation is within 48 hours we're going to have something to show. But each one of those executives — yourself included — would be essentially on call. If people got stuck, if there was something that needed to be adjudicated or a prioritization decision made, everyone would be available, say, within 15 minutes. Did I remember that correctly?

Jitesh Ghai: That's exactly right. Which is then what enables the pace in getting to the answer, versus creating a Gantt chart and project managing something that can operate at machine speed.

Gene Kim: Yeah. There was something else — something that you had said after the thing — as people were sharing their aha moments across the L1 exec group, you had said it's not like your executives were ignorant of AI, right? They were routinely briefing your board on it, but there was something different that happened that was very important to you. Can you share what that was?

Jitesh Ghai: Yeah. I was alluding to it earlier. We all intellectually get it, and we all think that I just need to enable and empower my respective individual contributors. But the real aha moment of appreciation was: what it can do for me, what it can do for each one of my leaders.

And then the ask was: now go and repeat this with your staff. And when you're done with that, go and repeat it with their staff, and so on and so forth — which was the ask and the action that every one of my leaders took. And to scale it out, we pulled in learning and development in HR to now programmatically go through every layer of our management hierarchy and ensure a facilitating of these aha moments.

And I'm not worried whether it's in product and engineering, where they're much further along in this AI journey — because even my CTO had his own aha moment. He spent the vibe coding session creating digital twins of his staff, so that if any of them were traveling, he could just ask his questions of these digital twins — which I thought was pretty cool.

Gene Kim: Yeah, and in fact, I have to mention this: the thing I did not expect was your call to action at the end, essentially stating your expectation that they cascade all the way down. So could you just — for, I'm thinking about people here, leaders who might not have someone as enlightened as you — can you sort of speak to their CEOs? What specifically was your expectation, and why was it important to you that that was the next step?

Jitesh Ghai: Yeah. And first, you're very kind — thank you.

We're in a once-in-a-generation, multi-generation technology wave that's hugely transformative to how we work, live, play — personally and professionally. And what an incredible opportunity as technologists to really maximize what we can do for our organizations, our respective missions, to really deliver incredible outcomes for our organizations, for our organizations' respective stakeholders, our customers.

And really, what was important in doing so — and what I would advise all of you to do as you're scaling out your ideas and your transformations — is start with being super intentional about it. This is a transformation. It is change management. And so step one is: declare it. Declare that you, your function, is going to be AI-first, AI-native. Declare it to your management, declare it to your CEO, declare it to your stakeholders — those that you depend on, those that depend on you.

And communicate it. Communicate it deeply, intentionally. Share the benefits of it, and then get going. Start embarking on it.

And it's not about blowing things up. There's a lot of noise out in the industry of, "Oh, you need to blow up your entire enterprise, and you need to blow up your entire tech stack, and you need to move everything to the cloud, otherwise you won't be able to do it." No. There is an immense amount of value you can deliver with your existing tech stack. Half of it is probably hybrid. Your entire architecture is probably hybrid — probably sitting, some of it in one cloud, probably in another cloud. No, you don't have to blow any of it up. You simply have to meet your infrastructure where it is, and then AI-enable it. AI-enable your processes and operations from it.

Pick the highest-ROI initiatives, solve those, knock them down, move to the next one. And if there are bottlenecks, surface them up, discuss them, and then agree and decide. If you can't get to an agreement, escalate.

Gene Kim: And one thing I've noticed in talking with Jitesh is he's very deliberate with the word "AI-native," right? That's a signal.

Jitesh Ghai: Yeah.

Gene Kim: When broadcast up to the CEO, it's immediately recognized — as we heard from Calvin at Morgan Stanley, right? Often, unlike so many technology movements, it's driven from the business, and they're looking for things like "AI-native."

So I had mentioned that the people in this audience and the presenters are really at the vanguard of bringing AI into technology's daily work. And we've already heard from Dustin from NRC Health that often their technology used to be the bottleneck.

Jitesh Ghai: Yeah.

Gene Kim: And now, because things are done two orders of magnitude faster, they're putting immense pressure on the rest of the organization. We heard from Dustin that it actually required this new SVP, David, to come in and get people to actually use — and get off of — the legacy platform that might be going away, to actually get it transitioned.

So, imagine you're talking to a director of engineering in your own organization, and you hear similar complaints where, "We are no longer the bottleneck. We now need to escalate things to get basic things that we need to get from here to there." What advice would you give to that person who's looking for someone to help rewire the organization so they can actually move the needle on things that everyone knows is important?

Jitesh Ghai: Yeah. That's the change management part — being really intentional about declaring it, communicating it to your leadership so they know what you're up to and why you're up to it, to your team so that they understand this is the mandate and charter of how you're going to operate. And then, like I said, to your stakeholders — both who you depend on and who depends on your specific function — that this is what you're doing, and these are the benefits. That's super important. And then get going.

And then there will be issues. Things will bubble up, and now you can discuss them because you've declared this is what we're doing. You've driven that alignment, and as those bottlenecks bubble up, you have those conversations within your organization as well as cross-functionally, and start knocking down the decisions, knocking down those bottlenecks. And if you can't, escalate.

Some of my Hylanders are here in the room, and you can ask them. I've told all 4,000 of them: "If at any point you feel that you're bottlenecked from accomplishing what you need to, escalate. And if you're not getting what you need, send me a message."

It's really about — it's transformative, but it's one step at a time. It's one problem at a time, one initiative at a time. And before you know it, you'll be a radically different organization.

Gene Kim: And specifically — I'm the director of engineering, you're the CEO. I say, "Jitesh, I don't expect you to do my work for me, right? You have other things to do. But I'd love to be able to meet with you every two weeks, because I know it's important to you. What homework would you assign me to get done in the next few weeks, specifically?"

Jitesh Ghai: So who's the director of engineering?

Gene Kim: I'm the director of engineering.

Jitesh Ghai: Okay.

Gene Kim: And the homework you gave me was something like: find out who all your stakeholders are, get them together, do something, and then —

Jitesh Ghai: Exactly right. That's the intentional part. Take a step back, understand who you depend on and who depends on you, communicate your plan and the benefits of it to your stakeholders, why they should care, and then some of what they should expect — and then get going.

Gene Kim: Yeah. That's it.

Jitesh Ghai: And specifically, you said, "And if you can't get alignment, bring it back to me."

Gene Kim: Yes. "And then I'll show up in the next meeting."

Jitesh Ghai: Yeah. As technology leaders, as leaders, we set the direction, we set the agenda, we set the incentives — and then we become chief unblocking officers. And as you become the chief unblocking officer, you are mediating these types of things to drive progress. And that's not just as the CEO. Every leader should be a chief unblocking officer for their respective teams. It's about removing the friction so that they can make progress.

And in doing so, you automate the mundane, and you bring joy back to the job — for yourselves, for your teams, for your stakeholders, your customers, your partners, and your people.

Gene Kim: Very good. Well, Jitesh, again, I'm so grateful that you were willing to come here, present, and share some of your teachings to this technology leadership community that's facing problems that you find so familiar. So thank you so much. Jitesh will be around during the break to answer any of your questions — you'll find him in the reception area. And again, Jitesh, thank you so much.

Jitesh Ghai: My pleasure.