55. Interview with Bill Conner: Lessons from a serial value creator

6 Aug 2025 · 57 min · 21 chapters

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In short

Bill Conner (Jitterbit CEO) discusses “serial value creation” and how to spot defensible tech category opportunities, focusing on the convergence of AI, low-code, and security. He argues AI’s real impact will come from infrastructure and “layered” approaches that reduce hallucinations and preserve privacy/security, not from silver-bullet LLM hype.

Guest backgrounds

Bill Conner is President/CEO of Jitterbit (since Feb 2024). Previously CEO of SonicWall (appointed 2016 after Dell spin-out; growth focus) and CEO of Entrust (turned declining profitability into ~20% annual growth; led sale of Entrust Tech to a top-5 PE firm, Tom O’Bravo). Earlier career: Nortel (two decades) and AT&T (roles across North America). He co-chaired DHS Corporate Governance Task Force, spoke on cybercrime before the UN, and advised UK cybersecurity; Entrust encryption used in UK digital passports.

Key claims

85% of AI projects fail (Gartner cited). Jitterbit’s approach infuses AI into a low-code platform with governance/security “underneath,” enabling business users to build faster with less hallucination risk. Public markets resist pivots; private equity can “reload” companies.

Notable examples

AT&T Super Bowl wireless campaign; Nortel data initiative buying Bay Networks for an IP stack; Entrust digital passport encryption; “Black Phone” privacy project at Silent Circle (underfunded).

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

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Bill Conner's Background

0:45 to 2:00

Exploring Bill Conner's extensive career and accomplishments.

“He achieved consistent annual growth at nearly 20%, twice the then market rate.”

Childhood and Early Influences

2:00 to 3:00

Bill discusses his childhood in Arkansas and early inspirations.

“And let's go way south and explain how a good old boy from Arkansas made his way into the nuclear fusion business.”

Journey to Princeton

3:00 to 4:50

Bill shares his experiences and challenges attending Princeton.

“That began, you know, my journey, to be honest with you.”

Interest in Nuclear Fusion

4:50 to 6:10

Bill talks about his early fascination with nuclear fusion and energy.

“I did not have the math and science to keep up with those guys.”

Pivot to Renewable Energy

6:10 to 8:10

Bill explains his shift from nuclear fusion to renewable energy studies.

“What did all this dealing with unions and negotiation with these types of stakeholders sort of teach you and maybe teach your audience?”

Career at AT&T and Union Interactions

8:10 to 10:00

Bill reflects on his time at AT&T and lessons learned from unions.

“So I actually put a proposal together with our team in engineering to build an overlay network to AT &T's network that was digital.”

Experience at Nortel

10:00 to 12:00

Bill discusses his role at Nortel and entering the European market.

“So you left AT &T after over a decade, and you arrived at the equipment manufacturer, Nortel, presumably already at that time locked in a fairly vicious competitive embrace with Cisco.”

Marketing Innovations at AT&T

12:00 to 13:50

Bill shares his innovative marketing strategies during his time at AT&T.

“They had an IP stack that could work at carrier grade and could work in the enterprise.”

Super Bowl Marketing Strategy

14:00 to 15:40

Learn how Bill Conner leveraged Super Bowl ads to promote wireless services.

“I mean, T-Mobile and Amazon now pay like$7 million a slot, but you had something way before them, right?”

Jitterbit's AI Journey and Future

15:40 to 19:20

Explore Bill Conner's vision for Jitterbit and the role of AI in business.

“If you think back, I've talked about the digital data journey and then how that led to infrastructure kind of pieces and then the web and mobile generation and then the data IP stack and then security.”
Show all 21 chapters

Public vs. Private Company Strategies

19:20 to 23:20

Understand how company ownership impacts innovation and strategy.

“Where do you see, how would you map out the future for companies that are, you know, storied and proven, like JITABIT in this market?”

Technology's Role in Cybersecurity

23:20 to 27:50

Discuss the intersection of technology leadership and national security.

“You know, I think private equity also plays a very big role, not just in that other piece with keeping you a little bit longer, you got to have deep pockets in cash to do that.”

Public-Private Partnerships and Cybersecurity

28:00 to 30:28

Explore the importance of public-private partnerships in cybersecurity and personal contributions.

“You know, from my upbringing, I believe in public-private.”

The Hype and Reality of AI

30:28 to 33:19

Discuss the current state of AI hype, its underlying realities, and its future impact.

“why it's important to give you time, why it's important to give your expertise?”

Energy Consumption and AI's Role

33:19 to 36:45

Understand how AI innovations are tied to energy needs and shifts in technology.

“the world, just like mobile did, just like data did and digital early on, just like the internet did, it's going to reshape the world we know.”

Infusing AI into Business Culture

36:45 to 42:00

Learn about integrating AI into business processes and its impact on development.

“still, whether it's electric cars or any other tools.”

The Evolution of Coding with AI

42:00 to 44:40

Learn how AI enables both novices and experts to code more efficiently.

“Then he would sit down with coders to go code it.”

Lessons from Silent Circle and Black Phone

44:40 to 47:24

Hear about Bill Conner's reflections on past tech ventures and their outcomes.

“I think it's true with our customers and partners, and I think it's true for anyone that's wanting to look at this disruptive technology or enablement.”

The Future of AI Development

47:24 to 49:26

Explore the expected advancements in AI over the next decade and their implications.

“not for the pioneers and these multi-billion play LLMs and those lucky enough to sign on, but for the rest of us in the tech industry, how do you see it all developing?”

Navigating the Tech Investment Landscape

49:26 to 55:00

Understand the current trends and risks associated with tech investments.

“If you think your company is going to be able to keep up with the AI technology and speed and lifecycle, you're not.”

Building Unique Leadership Positions

56:00 to 56:15

Learn the importance of differentiating in the tech startup landscape.

“We think it's because so few tech startups are able to build and lead their own categories.”
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Transcript

Automatic transcript. May contain errors.

0:00Welcome to The Difference Engine, the show for tech founders, investors, and innovators.

0:13Our very special guest today on The Difference Engine is President and CEO of Jitterbit, Bill Conner. Bill's a seasoned technology executive known for driving transformative growth across cybersecurity, cloud, and software. As a proven value creator and four-time CEO, his skills are more in demand than ever. He's been at Jitterbit since February 2024. Previously, in 2016, he was appointed president and CEO of SonicWall, following its spin-out from Dell under Francisco Partners and Elliott Management. Earlier, he joined Entrust as president and CEO during a period of declining profitability and transformed the company.

0:47He achieved consistent annual growth at nearly 20%, twice the then market rate. During that time, as well as advising the UK on its atrocious national cybersecurity and putting Entrest Tech in every single British digital passport, he orchestrated Entrest's sale to one of the world's top five private equity firms, Tom O 'Bravo. He spent the first two decades of his career at Nortel Networks, where we did have the pleasure of working with him, and at AT &T, where he fulfilled roles right across North America. Serving on many company boards, he's also co-chaired the US Department of Homeland Security's Corporate Governance Task Force, has spoken before the UN on cybercrime, and was even named as one of CRN's 25 most influential executives.

1:30Bill Conner:Bill Connor, welcome to The Difference Engine.

1:37Bill, it's been a while coming. Thank you so much for agreeing to be on our pod. We are very honored. And I'm going to start, actually, strangely, with a chap called Frank W. Connor. Oh, you remember him? That is Bill, for those of you who don't know. And it's been a long journey for Frank W. Connor to get to AI. And we're going to get to all of that. We've got a lot to go through. But let's start. Let's go south. And let's go way south and explain how a good old boy from Arkansas made his way into the nuclear fusion business. Now, not sure many of us would equate Bill Quinton's home state with the latest state of the art in energy production.

2:14So hot, it's still being perfected today. Bill, as they say, tell me about your childhood.

2:20Bill Conner:Well, it was a great childhood. Loved to think about it growing up. As they say, Arkansas is the land of opportunity. It certainly gave me an opportunity. Loved growing up in a place called West Helena, Arkansas. Great family. My mom was a teacher, my father proprietary in retail, brother and a sister. So great school, really terrific school back in those days. And love sports, had a great sports. Arkansas obviously had good sports in high school and got some notoriety, personal enjoyment out of that and some recognition. Loved math and science, had some of the math and science teacher, really enjoyed that.

3:01Bill Conner:That began, you know, my journey, to be honest with you. Got some recognition out of that with a National Youth Science Camp, which is the top two math and science students in every state get together once a year as seniors. And you still do that, right? You're still involved. Yeah, I'm still involved in that, actually. Just got the alumni award a few years, a couple of years ago, actually. And a great program that is spanned now into all the Americas. And then I also got some recognition for the civic work I did as well. So got a teenager recognition, kind of over all the South. And somehow that got me recognized by Princeton as someone that should be looking to go there.

3:43Bill Conner:Of course, there weren't a lot of people from where I grew up, Arkansas, heading to Princeton. And certainly I was not one that could afford it, but fortunately, somehow they found it in their way to get me in and some scholarship money and some alumni help. And then I worked 20 hours a week when I was there and as a teamster in the summers to put me through. So it was a great place to be in and grow up. And it was a great place to leave and go to the East Coast to begin my new journey. So you ended up at Princeton at the Ivy League studying nuclear fusion. So just talk us through the sudden desire to do nuclear fusion.

4:22Bill Conner:Well, you know, in high school, I just found it fascinating. I thought it was kind of the leading edge of where energy would go to because of the ability of it to create unique energy without residuals. And of course, Princeton had the Tokamak reactor. And so I went there, but it was a short journey. Is there going to be a famous kind of pivot coming up here? Oh boy, that was my first quick pivot. I did not have the math and science to keep up with those guys. And I mean, it's just, there is math and science, and then there's math, science, and physics. And that certainly that plasma research facility, you know, you quickly realize that was, that was too big a pivot for me and my skills.

5:09Bill Conner:So I did make a different pivot, though, to an undergrad renewable energy. So I ended up running the renewables energy lab and doing a lot of consulting that helped pay my way and do a lot of consulting and alternative energy with solar and biogas ahead of the curve as usual it's nothing like doing experiments all night with a box of sludge with beer underneath it there you go so all of this of course is before we get you as the category defining tech leader that you are today um but you did make your way you've finangled your way to at &t where there's another twist in the journey of our serial ceo here and oddly, this was where your humble upbringing gave you a competitive advantage.

5:54And we're talking about interfacing with unions in manufacturing. And it's hard to remember that once upon a time, because we're all in tech, unions were really influential in tech because stuff had to be made. You dealt with some pretty interesting characters. I think you call one of them Charlie Brian, Charlie Big Big. How could that possibly be so? What did all this dealing with unions and negotiation with these types of stakeholders sort of teach you and maybe teach your audience?

6:21Bill Conner:Well, you know what's interesting? You know, I went from Princeton, I got selected to be on something called a management development program. They had four kind of top talent of MBA schools. There were two of us from undergrad schools that were actually engineering students, the rest were MBAs. And it was a high risk, high reward program. They started you with, you know, very good managerial roles with, but every year you had a project, you were in a role and, you know, a third of you would be let go every year. And, but it was a really fundamental to my, my growth. I mean, AT &T, fortunately I was competitive enough to be able to do multiple assignments, but I started out in headquarters doing long range planning, then went to Chicago to do implementation of technology.

7:10Bill Conner:And both those assignments were on digital and data. That was my first pivot at AT &T, trying to take them away from voice and away from analog. And so we put in, we planned the first fibers, we planned the first digital radios, and we put them in. And then I got to go run a service group for the largest 24 accounts that AT &T had to put in their first private data networks. and then take on the FCC and a bunch. But along that journey, I worked for Crazy Joe Nascio, and I was running an$8.6 billion income statement at probably about 32. And I realized that I was competing with MCI that was using different technology.

7:54Bill Conner:And the technology they were using came from not our vertically integrated company called Western Electric, but from Nortel or Northern Electric. And that's when I realized, you know, I've got a network bigger than MCIs, but I don't have the technology that's underpinning. So I actually put a proposal together with our team in engineering to build an overlay network to AT &T's network that was digital. And that's what led me to that infamous union group in Columbus, Ohio, because the board decided I didn't understand the value of vertical integration. So they took their service guy, which was me at the time, and I needed to go learn about vertical integration and our factories and that technology.

8:42Bill Conner:And then they took a factory guy and put him over in the communication side. And I met, took me to one of the largest factories that had, you know, we have our core switching, our data switching and wireless, all kind of the new technology coupled with all the old technology. Right. They were trying to school you, Bill. Oh, they did. Because I'll tell you, the first time I met Charlie Bigrig, I mean, they had five unions. He was on the national bargaining team. So that's, you know, a pretty important role for all unions. And I remember when they introduced me, he spit his tea across the table and looked at me and said, damn, this one's young enough to be my son.

9:23Bill Conner:And I looked back and said, that's right, dad, you better up your allowance. And you know what? It became a true partnership. And that had not been done there. But they needed respect and they got it. And I learned that from my Chicago operating days. And I was the first guy to actually speak at their union meetings. And he and I did a pig roast the night before I left to go back to headquarters or actually to leave to go to Nortel. So he was one of those guys that was revered and hated. See, they normally say you can't have both, but maybe you can. Yeah, absolutely. So you left AT &T after over a decade, and you arrived at the equipment manufacturer, Nortel, presumably already at that time locked in a fairly vicious competitive embrace with Cisco.

10:15and this was I think your first direct experience of the European tech market. So Bill Conner, powering his way up corporate America, finds himself with a European responsibility. Can you remember your first impressions of this new horizon? Did they change over time and was there anything you had to move quickly to make us Europeans get on the program so to speak?

10:44Bill Conner:Well, you know, it's interesting, Jonathan. That was part of the reason after I left AT &T, I went to Nortel because while they were ahead and they were way ahead, I felt like an international. I felt like AT &T always had a foot planted in the U.S. and maybe an arm or a toe. I mean, of course, AT &T is global. It's got connections everywhere. But operating wise, Nortel was much more international in nature. I mean, UK seems like home away from home now. I spent so much time. Part of what I did at Nortel was, you know, really go in. And while they hired me, Paul Stern hired me and then Jean Monty promoted me after he came in to be CEO, was to really drive the data initiative.

11:28Bill Conner:So I and that I did. I was the first president of data, about a billion dollar business. We went out and bought Bay Networks, which, as you know, in the technology world, at that time, there was Frame Relay, there was ATM, there was X25, there was all these different computing standards. And then there was IP with Cisco. The only other IP stack was with Bay Networks. We bought Bay for$9 billion because we needed an IP stack. And I remember going to the board, just like I did at AT &T, saying we needed data switching from Nortel. we needed data and they had it. They had an IP stack that could work at carrier grade and could work in the enterprise.

12:11Bill Conner:So we bought it. And then I became the first chief marketing officer to do all kinds of fun campaigns around Europe. But the big other piece after we got the data piece going was security. And that began the kind of next part of my revolution and evolution because we incubated a company that I spun out that worked for me called InTrust that was really around PKI, public key infrastructure. And if you really go behind that, it's encryption, it's digital signature, and it's authentication, all of which exist today in pieces. But that's where I became really, really close. I've been close on the voice and data side with UK, obviously, through Nortel.

13:00Bill Conner:But the security piece of that and carving that out, I took it out of Nortel, made it public, ultimately became the CEO of it for 13 plus years. They took it public, took it private with Tomo Bravo. But in that journey, that's when I became really close with UK government and the big agencies and customers, because literally every passport in the UK uses Entrust technology encryption. Over half the digital passports in the world actually do. And then we built the first web portal for the government with Andrew Pender, who's no longer with us, and Tony Blair. So really did a lot of work on the digital encryption side and the digital authentication side there.

13:50Jumping back to your time with the big spending companies you worked with before you went into the exciting fast growth. So don't you have a distinction in terms of your marketing roles about Super Bowl ad slots? I mean, T-Mobile and Amazon now pay like$7 million a slot, but you had something way before them, right?

14:10Bill Conner:That was part of when I mentioned I was running the outbound services at AT &T, that$8 billion income statement. And MCI was running ads and meters against us showing how much cheaper they were running. And, you know, at that time we were FCC controlled. So I took them on and promotions and won some battles in Washington against them. And, of course, being a little bit of a smart asset or smart person, wanted to do some marketing around it. So I got a great agency and we ran counter meters. I did it with a 57 Corvette and we were going to put it on the Super Bowl and it went all the way up to the board.

14:50Bill Conner:And the board said, oh, no, you can't do it. I said, well, you're going to pay a million bucks. And that's not the production. That's the cost for the ad. And by the way, on Super Bowls, you got to put them in the can, they say, on Friday. So it runs on Sunday. So you got to make a decision in the next hour. And by the way, I don't have any other ads to run at or quality to go on the Super Bowl. So do it. Lo and behold, it went on. And what was the funniest story out of that one, Paul, was because it was a Corvette with someone sitting in it using a wireless phone. AT &T had AT &T Bell Labs had the patent on wireless, but we had never put it to use.

15:30Bill Conner:And so out of that, the biggest interest was in the wireless service. service not even my service but we quickly turned that one on too so anyway yeah long story short from Super Bowl ads.

15:48So here you are you find yourself yet again recreating a company it's actually been around for for 20 years so you want to tell us a little bit about Jitterbit and its AI journey and where you see the company evolving in the next, say, three to five years?

16:04Bill Conner:Interesting insight, Jonathan. If you think back, I've talked about the digital data journey and then how that led to infrastructure kind of pieces and then the web and mobile generation and then the data IP stack and then security. You know, I was in security for 30 years. Well, after I came out of SonicWall on the last one, I had the year sabbatical and I I looked at what next was big. It's kind of like every once in a while you get to look over the sunset and kind of ponder what's the next big wave coming. Now, you've got to pick the right one as a surfer. But as I saw it, like I looked and just based on my own history, you know, security is never going to go away.

16:45Bill Conner:But and low code has done an incredible amount of making coding simpler and more democratic. So fewer skills are required to do it, but you still have to have skill because this is an industry that is completely skill restrained globally, everywhere. And that's the big promise of AI, right? And just like we learned with Internet, it starts with platforming. As I looked around and saw what NVIDIA was doing in the chip space, breaking Moore's Law and the comp speed, energy, cost, and performance, and doing it not just with hardware but with an operating system, it reminded me of the internet days and the mobile days as those started forming.

17:32Bill Conner:And, of course, I've been around machine learning for a while, which is kind of the father of AI, right? It's because machine learning is learning from data and trying to build models. Well, that's really what AI is. It's just using voice processing and more power and more compute. So when I looked at that, I saw a confluence of security, AI, and low code coming together to build kind of the next government transition from sovereignty as well as capability around GDP, as well as business transformation. and and you know it's kind of been interesting because 18 months ago paul we got to start this journey yet again you did you didn't believe me at the time where's bill going with this yeah well you know one of my great advisors out of the university of pisa said the same thing that you know it's a black belt obviously in security and and what's in ai it's like bill i i hear you usually have a point of view but i don't see it yet it took about six months but here we are right Now you see Informatica and Salesforce coming together, and the promise of AI is here and growing, as you can see, in infrastructure first.

18:50Bill Conner:Next will be applications and software, and Eugenic AI is all about that. But now, you know, the UK has always been at the forefront in privacy and security, at least in thought and action, whereas the U.S. is more the wild, wild west. The UK is more measured. Yeah, so we're early on, right? I mean, like we see the low code and vibe coding and all of this stuff coming out, offering some proven, some not proven technologies, right, yet to be proven. Where do you see, how would you map out the future for companies that are, you know, storied and proven, like JITABIT in this market? Like, give us like a vision three to five years out.

19:30It's real. Let's start with that.

19:32Bill Conner:So, a lot of, you know, there's this big debate. Do you jump on it? Because a lot of the people that jumped early had, you know, use the energy analogy, dry holes, right? I mean, if you look at what Gartner said last year, about 85 % of those projects failed. And they failed. I mean, we're all technologists, at least on this call. I mean, they failed because they were a silver bullet. They were a technology looking for a project or a project looking for technology as opposed to a solution to a business or opportunity to solve a business. And that's why what we did was when I came was take the focus of how do I evolve it, meaning put AI with low code and security so you can travel at your own pace and you can go back and forth.

20:23Bill Conner:So now whether you're a line of business or you're ISIT, you've got the platform underneath it that brings all the security, governance, scalability, trustworthiness underneath. But on top, you can use low code or you can use AI. So you don't have to be a coder. If you need it, you can go back and forth. And now you don't have to have all those resources. I mean, today, if you're a business person, I mean, it's interesting. IDC thinks there's going to be 500 million apps developed in the next two years. I mean, the average enterprise today has a thousand apps and only 28 % of them are integrated.

21:01Bill Conner:I mean, those apps are going to be web apps, are going to be mobile apps, are going to be what I call system apps. You know, customers are getting tired of going to the big monolithic, big bundles because it's costing a lot of money. It's costing a lot of money and they don't want to be tied up just with one vendor. So I think there's a world for the jitterbits that are kind of leading this next generation that can put all that together from the applications to the integrations to the exposures through APIM using AI and low code, and it's transparent, and it evolves with you. You know, you've led both public and private businesses, and you've taken public businesses private, and then you sold them on again.

21:47You know, what's your view on the impact that a public listing has on a company's ability to innovate or even pivot? Should companies actively seek different ownership at different stages of their growth? Should that be a strategy rather than a reaction to what's going on?

22:04Bill Conner:Yeah, I think you're seeing it more as a strategy now for the smart ones. Look, if you're really in the hot zone and growing 20 to 40 percent and you can see that for, you know, that continuing two, three, four years, you know, you got one of two choices. You can IPO and tap that capital market and list. And that is built for that today. but increasingly you see also people staying private a little bit longer because they want they believe that even though they're growing at that speed they want to incubate it longer to get it bigger so it's got battle strength and you can do m &a if you need to or pivot because the market still pivots so i think you've got to really decide on that for if you're in that kind a growth rate, especially if you're tech, whether you're already in the space like NVIDIA, where you know you can do it, or others, or you need to stay private a little bit longer to get that battle strength and warrior strength, because you want to do some M &A, and you don't want to get confused with it.

23:20Bill Conner:You know, I think private equity also plays a very big role, not just in that other piece with keeping you a little bit longer, you got to have deep pockets in cash to do that. But it also serves for those that need to either get out of the market or go retune themselves. That's what PE is great for, because you can kind of bring that ship back into the harbor. That is not what you want to do in public. I've tried that, and I tried that within trust, right? We were making the pivot, and we were public, and half the business is government. So it's already lumpy. Great technology, great growth. But just, you know, the public markets don't want to deal with change.

24:05Bill Conner:So we brought it back into the harbor with Tomo Bravo. And, you know, rebuilt it for five and a half years. And guess what? It didn't go back public, it got sold to Datacom, which is now called in trust. The European owner, actually, but that it served its purpose to rebuild and reload and restructure it. And of course, on top of all of this business architecture and funding stuff, what's really interesting about you, Bill, is the technology savvy, right? So you're a technology innovator. There's no question about it. If I think about what you've told us, you know, the IP stack you needed to go and find early on, you need to persuade the board to go after that.

24:47The move to figure out that PKI was important. There was another technology in sight, which drove a market motion to go after that. And of course, you talked about AI and machine learning now at your current birth at Jitterbit. But your track record says that you looked at these new categories and you see pretty early the promise. What is it about your approach, the way that you view tech that enables you to do this? We have a lot of people listening to or pod who are interested in building categories. How can tomorrow's category designers spot these defensible opportunities with moats faster than the rest of the field?

Read the full transcript

25:26What do they need to do?

25:27Bill Conner:Easiest analogy I've got is kind of like surfing. I guess I'm on the water analogies this day. At least for this hour. But, you know, I talked about looking over the sunset, right? If you're a surfer, you're out there and, you know, they're always looking for that perfect wave, right? Right. And you can tell the good surfers and bad ones by the ones that know how to pick the wave. And there are a lot of waves that come in, but not all of them are the good ones. And so part of that is experience, right? Because the more you do it, the more you get to see it. But I also think you've got to just have a wide angle perspective.

26:07Bill Conner:And I do believe having, you know, looking at wider views than the swim lane you're in or the lane on the track that you're running in, you got to look at all nine lanes. Because at least in technology, it's a lot of specialty. But discontinuity comes when one hits another. Think of the wave theory again. the biggest disruptions when you know that wake of the boat gets bisected by another one it amplifies that wave even bigger so i've had some good ones i've had some bad ones but clearly more right than wrong as a track record and i think it's you know you got to be open-minded you got to be willing to look you got to trust your instincts but then you've got to have the depth to go really deep to try to understand the why i love that yes it's like breadth of vision but also the ability to go deep i mean it's it's it's not it's clearly not an easy skill to master well we're talking about why and the who and the what i mean uh thinking about your career more recently with with you know these leading firms in cyber security like entrust and sonic wall you know technology is taking you around the table with with the very highest echelons of Western societies.

27:28And what I mean by that, listeners, is, you know, Bill's been around the table with the Joint Chiefs of Staff, the UK's National Cybersecurity Centre, GCHQ, you know, and several others in the international intelligence community. And I think Bill legendary told NATO a decade ago that the next battlefront will be cyber. So I think the thing here is, you know, as software eats the world, Bill, is there a clear line between those who lead our societies and those who lead in tech? And are those two areas converging and who should be scanning the horizon?

28:01Bill Conner:You know, from my upbringing, I believe in public-private. I was fortunate out of that National Youth Science Camp. The governor of Arkansas was a Rockefeller. The governor of West Virginia, where the National Youth Science Camp was a Rockefeller, was Jay Rockefeller, who ultimately then became Senator Rockefeller. So he and I used to host the National Youth Science Camp every summer on the Hill. So, you know, what did I do? I helped him, right? I helped him with science camp, because I cared about it. I cared about the kids in science. And that became a relationship that, you know, he and I wrote the FCC stuff in his office that's now in place in the SEC and in our laws.

28:48Bill Conner:You know, after 9-11 and, you know, that night Bush spoke to the joint sessions, I was briefing joint sessions the next morning on cyber and the implications of that. And you mentioned NATO, and yeah, that was pre-9-11. I was on the Joint Forces Advisory Board here in the U.S. and as a private citizen with expertise in data and digital and security, which is why I was there. And, you know, I was younger, and certainly a lot of those generals, I can tell you, did not exactly like me. And that was fine. I wasn't there to be liked. I was there to for cause and for a reason. And and I that's why I did the joint work for the, you know, Homeland Security on public private partnership on cybersecurity.

29:42Bill Conner:I just I believe you got to give back. And, you know, that's why I did so much work with Tony Blair and Andrew Pinn in the UK, because you governments need to take this stuff seriously. Because it does have national impact for the businesses and the government and the citizens at the end of the day. That has definitely been a feature. I mean, you've even talked to the Vatican at various points, which for most people would be a fantastic thing. I mean, this has clearly proved important for you personally and for your business. And are there some sort of hints you can give the younger generation who are coming up and trying to understand how to influence the world and help make the world work and, you know, why it's important to give you time, why it's important to give your expertise?

30:33Bill Conner:You know, I think it's a personal choice, Jonathan. You know, I grew up in a poor home. It wasn't poor. I mean, it wasn't poor, but it was poor, relatively. and people helped along the way. I didn't get here without so many mentors financially, mentally, professionally and I talked about Senator Rock. I've got so many people, Andrew Pender who was your e-envoy that was trying to bring digital to the UK before digital was even cool. So to me, it's just something that's been about it. So what I would tell the people listening that are younger, you all have some passions. And I'm not talking about the ones just for you.

31:26Bill Conner:What are you passionate about in the society you live in? And if you can find a way to connect what you do, and I don't care if it's tech or non-tech, honestly, because we all bring some kind of value to this world. It's a lot of fun to get more scale and leverage out of it. and meet other people that have similar passions.

31:52Let's go away from the social and the public-minded a little bit to the more venal side of the fence here. We're looking over here in Europe, we're aghast at how much, frankly, American companies are giving to people to sign up. you know individuals are commanding a couple of billion in seed funding as we've just seen with with one of the founders raising that recently and the transfer fee packages the sign-on bonuses for some of these ai scientists the guys who are publishing papers would make certainly english soccer clubs but even like american basketball clubs even a little bit where are we with the ai hype is it too much and and obviously you're in the ai game you've got your your fingers on the on the on the thrust controller jitter bit how are you finding holding on to this rocket ship and you know is it got a little bit too hypey for you what's your thoughts on that

32:49Bill Conner:it's way hyped for sure but underneath all that smoke and hype is a real fire um uh as you and i've talked paul when i started this journey um uh it's real uh as i've said when I came into this job, my next 20 years will be at this intersection of AI, coding, and security. It is the next generational technology transition that's going to reshape the world, just like mobile did, just like data did and digital early on, just like the internet did, it's going to reshape the world we know. And I think you can really see that by what I'm calling this sovereign behavior now that has broken out across the world.

33:47Bill Conner:Because I just think 18 months ago when we started this journey together, Paul, at Jitterbit, and when we said US was clearly in the lead and it's the wild, wild west and lots of money and lots of capability being built, right? If we went to the UK, a little more standoffish and not quite so sure, got to think about this, let's wait and measure it, size it up, study it, and then be a little more, a little cautious. And then you go to Brazil, right? Where, you know, we have a large facility and customer base and, you know, they were trying to spell AI. So to, you know, this last round now, And you see, even with all the global leaders, it's a it's a sovereign race from the Middle East to China, to the UK, to the US.

34:42Bill Conner:It is now and, you know, it's interesting. One of the ex Federal Reserve individuals that's now at an investment bank and I were having a discussion. And it's kind of interesting because he put it in perspective. If you look at all of our GDPs, they're all down, right? The economy globally is not in a good space. And he said, if you look around, there are a lot of things you can't control right now. Wars, politics in some cases, a lot of cases. There's just a lot of things impacting businesses and governments. and you can't influence. And so if you're government and you're going to bet on how to get GDP up and if your business is going to bet on how do I get my cost down and business up, enter AI.

35:39Bill Conner:And so while I think the hype is there, I think there's a deep hell belief and I think you're now seeing coming out of that hype, the real fire underneath that the transforming infrastructure of AI, supply the chips the processing the energy supply the the tools the llms the rack it's kind of like quality in the early days right people are getting the lexicon they're starting to see how it can transform and if you look around what else is going to transform you i would offer that's the leading engine in the train what's it going to do it's going to pull energy back to our earlier discussion on nuclear, nuclear is back.

36:25Bill Conner:Why is nuclear back? Because you know what? I did my undergrad around solar. Solar is a topping system. It's not variable. It can't scale in the same way that gas, coal, or nuclear can. They all have different. So I think there's That AI revolution and innovation is driving then a consumption of energy, not just for the tools, but for society that's energy craving still, whether it's electric cars or any other tools. I mean, no one said that electric cars are going to take less energy. Super interesting. I like the way you drew the whole thing together there, because when you see the scope of the change going all the way back to energy, and obviously you say back to the start of your career, it really does tie it together about how big this could be and maybe puts the hype into perspective.

37:27Bill Conner:Well, and I think that's why you see even the Middle East right there. They've got an energy dependent society that can take advantage of that today, but take a lead on powering the capacity and the capability and take it in a transformative mode to transform a whole culture and an industry. That's why I think, to your point, Jonathan, there is a lot of hype. But I can tell you it is overhyped. But if you pull back the PowerPoints, you pull back the BS, there is a fundamental truth underneath those that is a very strong, compelling assumption that is, I think, going to be revolutionary for the next 20 years.

38:15Bill Conner:As we embrace that, it's going to be like cyber, right? Everybody was like, oh, cyber is great. But then it was cybersecurity. Then it was cyber arms race. Paul and I talk, you know, when we're not on podcasts like this, but when we're over a glass of wine or together, we talk about what is an AI race. And we're kind of in that now. But in that AI race, we've got to remember the security. It's going to be good and bad. So you've got to be prepared. And that's what I think we're trying to do at Jitterbit is make sure you understand the privacy security and build in those checks and balances along the way.

39:01You know, we are entering an absolutely a new age, but we're still really pioneering it. And you are as well in moving a company forward. Building AI infused technologies is super hard. And the reason I think it is is because others may not yet see its relevance, but you're leading a whole team. And you've got a development team, you've got a sales team, and you've got the customers to convince. How do you lead under these circumstances?

39:31Bill Conner:Well, you lead with it being part of the business and the culture and the change, right? So it's a really important question, Jonathan. And we talked about it earlier, Paul. 85 % failing, you know, let's give benefit of doubt, maybe it's 50 % right now. Our whole framework that my CTO and I took when I came in was how do I evolve and revolutionize at the same time? So we have a local platform, as I kind of mentioned. It does integrations, it does APIM, it does EDI, and it builds apps, mobile web and system apps. What we decided to do was infuse AI into that low-code platform. What do I mean by infuse?

40:21Bill Conner:Today, instead of just coding, we're now giving you a UI UX that is AI. because at its technical underpinning, AI is a voice or prompt instead of a code. So it's still coding behind it. So what we chose to do for our customers is infuse the AI into the products with how the customers use it today. So that same UI, UX, and that's important because AI is a non-deterministic system. And if I infuse it into the existing products, UI, UX, and use cases, guess what? I'm now applying UI and AI at the lowest level of the data and use case. That means it's got more accountability and less hallucinations.

41:16Bill Conner:Really, really, really important. No one in our space is doing that. What it means for the user, though, is now they can code in low code or they can use AI interchangeably. It's just a click, go back and forth. Now, if you're a line of business, what's been most interesting about building applications with it is, you know, you still needed 90 days of training and probably 90 days to code an application. It could be less. It could be more. Guess what? AI reduces that by orders of magnitude. But how did you used to build an app? You used to build an app by someone in the business that knew what the hell they were doing would go sit down with ISIT, tell them what they want.

42:03Bill Conner:He would write it down. Then he would sit down with coders to go code it. You got to have people. You got to have resources. You got to have time and you got to be able to get picked in that priority against resources of money and people to do that. Now, they don't have to do that at all. What we found in all the betas working with our customers is because you can do it as a novice or an expert in our system, that most of those people were truly experts. That's why they were telling others what to go code. And instead of telling the person, they're just typing it in a prompt or saying it in natural language to the AI.

42:45Bill Conner:And it's coding it for them. And now they can build a prototype. And guess what? Because it records all that stuff. IS and IT can look at it and go, oh, I've got all the security, the privacy, it's timestamped, it's digitally signed. So all the documentation, all the stuff that used to be a burden, it bridges the world. So that's the difference that we're approaching it. And then we're trying to take, because I'm from Arkansas and we were cobbler's kids, you know, we're trying to use that technology in. So, you know, we just were in London announcing our Genic technology about a month and a half ago, I think, Paul, keep me honest.

43:25Bill Conner:And, you know, we were putting those agents in our company to do for us what they're going to do that we're now putting on our marketplace to do to others or for others. So it's really how you think through the disruption and the enablement. What's so cool about that, it doesn't change what they do today. It just changes how they can do it. So you can go at your own speed. If you want to go faster, lean in, go. And by the way, if you get stuck, you can go back to what you were doing before and get around it. So I just I think it's really to the tech people listening to this, think through how you introduce it on the business side.

44:12Bill Conner:If you're pondering AI, think of what AI is going to do for you. What do you want it to do for you? Think through that, because that's why projects are founded. If you think of it as just an LLM and efficiency to cut resource out, that's what business outcomes do you think it can help you solve? Is it a resource issue? Is it a speed issue? Is it a money issue? Is it a process issue? That's how we tend to apply it. And I think that's true at Jitterbit. I think it's true with our customers and partners, and I think it's true for anyone that's wanting to look at this disruptive technology or enablement.

44:55Bill Conner:You've got to think through it before you just throw it out. You mentioned earlier on that you haven't done everything right in your career. There's been the odd failure. Looking back, is there anything that sort of stands out to you that you might have done differently in your tech journey so far? There's always a beta in your video repertoire, right? That VHS took it over. Beta was better technology, but didn't make it right. That was kind of my silent circle experience. After Entrust, I took my year off. Really loved what silent circle was doing. It had ephemeral certificates that, you know, around encryption.

45:34Bill Conner:So ephemeral certificates are a fancy word per se, and taking ambient noise and a bunch of random stuff and creating encryption out of that. And they use the current technology use it's most known for now is WhatsApp. This science circle came out with that capability about when WhatsApp did, but we were trying to move, I thought we would move that from a consumer WhatsApp piece to an enterprise grade. So business could use encrypted texts and we had something called a black phone. It was the first encrypted phone because it basically took the Android system, operating system, and we rewrote it for privacy.

46:24Bill Conner:So if you're on an Android or an Apple today, your privacy settings are frankly junior compared to it. Most people don't use them, and if they do, they don't know what they're using, and they're really not fine-grained control. So the Black Phone was the first phone that was built with security and privacy in mind on a modified Android platform. It's in the Smithsonian today. I can go see my mistake. So anyway, I'll just leave it there. The problem was it was a great idea. It was great capability. It just didn't have enough money. It was underfunded and hard enough, unique enough, that it just didn't make it.

47:24What does the future hold? Let's look into our crystal ball. Where do you think AI is headed? not for the pioneers and these multi-billion play LLMs and those lucky enough to sign on, but for the rest of us in the tech industry, how do you see it all developing?

47:40Bill Conner:I think for the next five years, it's going to be pioneering. And I think the ones that are going to succeed are either on the edge, pushing the frontier on the tools and the capabilities and embedding it into their current products. And then I think five to 10 years is a different life cycle. This is, I mean, we talked about Moore's Law earlier, right? I just, the life cycle, and you've heard me talk about it all, But, you know, when we built our first app builder AI integration, right, with our low code and introduced it in London, by the time we'd come back to London six, five months later, it had already been ripped out and replaced again.

48:37Bill Conner:So, you know, I'm used to pretty fast life cycles in software where, you know, it's 12 to 24 months. Microsoft is, you know, Satya is saying it's six months. I will tell you it might be six months at Microsoft scale. I'll tell you it's a three month operating scale on some of these AI capabilities. And we're in the early piece of that innovation. So I just, I, you know, I think the next five years are going to be innovating heavily. And the people that take those innovations and embed them, knowing it might not be for a very long time because the capability is changing, you've got to be built for that.

49:25Bill Conner:But I think that's a value proposition, too, because I tell customers and partners this. If you think your company is going to be able to keep up with the AI technology and speed and lifecycle, you're not. Unless you're a very big company. You're going to have to rely on your vendors to embed that. And you then to add AI to your process or tools to work with it. So think of layered AI as the way, as a business should be thinking of it, not that you're going to control the whole AI stack, because if you try to build it all the way, you'll never get there. That's so interesting because for several years now, and you see it hard in cyber especially, the mantra is lose the vendors, consolidate, simplify your tech stack.

50:21And what you're saying is forget it, pipe dream.

50:24Bill Conner:I do think you will not rely on just one. I mean, we introduced layered AI. The first layer is our infused AI. The second layer is the agenda that rides on top of it, right? And then the third is what other AI you build into it, whether you use Copilot or other things in your enterprise that are part of the other pieces. I think that part layered is going to be similar to security because the further AI gets away from the source data, the more the hallucinations, because it's got to make assumptions. That's why this approach we took at Jitterbick is so important. Because we built it off the 20 years of machine learning and data and use cases, that AI is picking that up right from the source and the data and the use cases we built over time and adding to it.

51:21Bill Conner:And then I can look across those different products and data silos that we've now integrated into our platform and do another layer that is more accountable because it's closer to it. So the next layer AI is much more effective and trustworthy and accountable for its outcome. So by the time I get to Eugenic, it's really effective. It's really accountable. And you're not worried about the privacy and security because it's nested, it's layered, and it's linked. But if you just go build AI at the top of that stack and think it's going to go down and touch 30 different data silos, you're going to have some wild hallucinations in your dreams.

52:08Within that very, very grounded view of how AI can develop in its layers and so on, is there anything that particularly excites you about this journey that you think, wow, we are going to be able to do that if we get this right moving forward?

52:24Bill Conner:You know, that's an interesting question, John. To me, it reminds me of two big changes. The IP stack, because data is just, you know, it's going to change the world because you're going to have interconnectivity where we didn't. So it's going to just power. And then the security piece. I think AI is equal to both of those plus then some. And to me, that's why, you know, being aware of it is one thing, understanding it's even more important. And I think just like we learned with dimming with quality, you know, you got to learn the lexicon. You got to you've got to spend time with it because, you know, I can tell you we've done the surveys.

53:12Bill Conner:The next generation expects it. They're using it. They're playing with it. They're using it in their life. They're going to expect it in the world. And, you know, I'm not the young guy, but I'm a technologist at heart and a marketeer, I guess, too, clearly. But you have got to spend the time in your business figuring out how to incorporate and where to incorporate it and why.

53:45You know what? This really grinds my gears. I just think, is there anything in particular that frustrates you about the current tech scene?

53:56Bill Conner:I mean, the numbers are staggering being thrown around right now. I mean, money abounds, unlimited. But I think that's also because of what we talked about around sovereignty. A few people get it. They really get it deeply at country state level, our nation state level, and at business levels. And even in private equity, right? So I think the stakes are extremely high. Are they overflated and hyped? Probably, ultimately, yes. But it's the fear of missing out. It's hard to say. History will judge the bets. I was with a company that no longer exists, that spent$9 billion on IP. That was a good bet.

54:55Bill Conner:But there were a lot of other bets they made that didn't pan out, right? That cost them stuff. So there will be bets that are made and cashed in, and there's going to be a lot of bets that are not cashed in. As I used to say, in the VC world, one in 10 is all you're looking for. Now they're like three in 10. But there are a lot of big checks and there's a lot of people with the knowledge making a lot of money. But just because they have it right in one environment doesn't mean it's going to work in yet another environment. Everything's not portable, even in AI.

55:34Thank you for listening. If you want to learn more about category design, head to becategorical.com. If you need help designing and dominating your category, then get in touch. Contact details are in the show notes.

55:56Think there are too many lookalike tech companies chasing the same markets? We do. We think it's because so few tech startups are able to build and lead their own categories. What matters most is to be different. Stop following and start building your own unassailable leadership position today. Working with the category design gurus at Categorical brings decades of differentiation expertise to your team. Book a consultation from our website today and we will send you our one pager detailing how to start designing your own highly differentiated category. Thank you.

From the publisher

A seasoned technology executive with an extraordinary career spanning more than four decades, Bill Conner is the real deal. 

From leading companies through high-stakes turnarounds to creating category-defining tech products, Bill has done it all. He’s been a four-time CEO, a trusted partner to Private Equity and Venture Capital, and a go-to expert for driving both top and bottom line growth in complex technology businesses.

In this episode, we sit down with Bill to trace his remarkable journey from early engineering roles at AT&T to reshaping the future of cybersecurity at SonicWall and now leading innovation at Jitterbit, where he’s leading their AI-infused low-code platform. We dive deep into AI’s inflection point, his time advising global cybersecurity policy, and the leadership principles that have powered decades of success.

Bill's story is a masterclass in resilience, strategic vision, and value creation. If you're building, investing in, or leading a tech company, this episode is not to be missed.

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