An interview between Pivot > Managing Directors Jair Clarke and Chelsea Grayson
As AI dominates every boardroom conversation and companies race to have a defensible “AI story,” few leaders can speak to what actually separates transformation that works from technology bets that leave a company exposed.
Jair Clarke, Managing Director of AI and Technology at Pivot >, brings a rare vantage point to this question, shaped by roles as a Fortune 15 CTO, CEO, Chief AI Officer, and board member, along with senior leadership positions at Microsoft, Disney, IBM, and Lockheed Martin. Here, he talks with Chelsea Grayson about the technology mistakes he sees most often in distressed companies, why disaster recovery testing deserves far more attention than it gets, and what he looks for in a technologist before ever putting them in the boardroom.
Chelsea Grayson: You’ve been in the CTO seat, you’ve been in the CEO and founder seat, we’ve been in the boardroom together, you sit on a whole bunch of boards, and you also advise CEOs privately at the highest level. From all those perspectives, what is the most common technology mistake that you see in a distressed company?
Jair Clarke: I think the most complex problems that companies have are people, and the solutions to those complex problems are also people. When you think about C-level leadership and understanding what they’re attempting to do, it’s really the lineage — you have roadmaps, you have execution, you have the ability to really understand what’s happening at the lowest level, and how that lineage traverses on the way up. Unfortunately, leaders don’t always go through that whole process. It stops at middle management, it stops at upper management, or it skips a couple of levels.
To really understand how technology, digital transformation, and AI can truly make an impact, you have to understand where your north star is as a company and what’s truly happening day to day, so you can identify that gap and fill it. The people are the ones who can provide you that as-is versus to-be gap analysis.
Chelsea Grayson: I think every company right now is feeling the pressure to have an AI story. What do you actually see when you look under the hood of how distressed companies are approaching AI? How are they getting it right, how are they getting it wrong? Do you see situations where AI just wasn’t the answer, and they misinterpreted the problem?
Jair Clarke: It’s a very impactful question, and one I get asked quite a bit. There are some companies that see the current wave of AI products and say, “We have to fit this into what we do.” They see a product and they reverse-engineer and force-fit it into their culture and organization. Other companies look at it and say, “This is the next thing, so we’re going to bet all of our chips on this particular technology,” but they don’t necessarily understand that a competitor may be catching up fast. Then two or three years later, a different solution becomes the more prominent one, and now they’re stuck.
What I advise is this: understand who you are as a company, understand what you need to do, understand when and where and why you need to do it. The how will then be the final and very important answer. Understand what you’re doing and where you’re going before you figure out which AI product or technology will help you get there, because there are plenty of them. Sometimes it’s an ecosystem of products. You may have 100 different software solutions and rationalize it down to a few, but it won’t be just one. When you start asking companies those foundational questions about who they are and what they’re really attempting to do, they start to realize, “Wait, I don’t just need this one tool. I may need this and this. Or actually, these two are comparable. Let me run both for a couple of quarters to figure out which one is more impactful.”
Chelsea Grayson: In addition to being a technologist, you’re a go-to-market specialist. Can you talk about how you help organizations pull back and say, “We need to put process in place and answer these questions before we dive in”?
Jair Clarke: Let’s use a current example. If you saw certain capabilities out there and jumped at the chance to use them, and for whatever reason there’s now governance over that particular company that says they can no longer provide that capability or service, you’re at the mercy of that product. And that company themselves may not have the ability to deliver on what you partnered with them to do. Regulations, law, and governance will dictate certain things outside our control. So, from a go-to-market perspective, you really want to make sure you’re not completely tethered to something external to your business such that if something upsets that external business, it upsets yours.
There have been other situations where you can put your market and audience on a sheet of paper and map it all out, but the real-world dictates something else entirely. The signals from your audience will tell you where the market and the industry are going. You need to lean in and listen to that. And it’s not just what the signals tell you; it’s also what they don’t say. Understanding what the signals aren’t saying can reveal the void or gap that you can actually capture.
Chelsea Grayson: When I was running one of my apparel companies, we were still servicing the original total addressable market the company had set out to reach, but that audience was no longer really interested in our product. A whole other audience had come in, with the expendable income we wanted, and our marketing department hadn’t caught up. They were still doing outdated marketing for the original audience and hadn’t even realized this new audience existed. When your TAM evolves, how do you catch up with that?
Jair Clarke: Imagine being in the room with multiple presidents, each running tens of billions of dollars in business, each doing what they need to do to run their individual companies, while the whole ecosystem is saying, “We need to shift and move forward together. We need integration between businesses. We need to show up as one cohesive solution.” Imagine having those conversations and convincing leaders running tens of billions of dollars that the best go-to-market move is to do it together. That’s something I experienced. It was a great learning experience. The company eventually did it, it’s extremely profitable, and it’s now part of their DNA. But before that work was done, it was far from their DNA.
Chelsea Grayson: This idea that when the water rises, all boats float. But I think a lot of people trying to do it all alone these days is impossible, especially those of us who came up white-knuckling it through our careers. What do you think about this idea that you have to build a professional community, that you have to work as a team, and you can’t just do it alone anymore?
Jair Clarke: That’s been my philosophy. Think about the military; it’s entirely a team concept. The highest, most elite commands and forces are centered on doing things together and solving things together. The team concept works in every aspect of people’s lives. Why wouldn’t it work in corporate America?
Chelsea Grayson: Can you walk us through a moment where technology either became a genuine catalyst for recovery, or quietly derailed a turnaround? An epic failure, or something they just didn’t catch quickly enough?
Jair Clarke: There are some divisions that impact the world where technology was brought to its knees because of a squirrel — literally. The impacts were severe because of a lack of business continuity planning, disaster recovery planning, and technology that can automate and quickly restore operations when the most unexpected situations bring things down.
When you look at technology from a disaster recovery standpoint, it’s cool to see a shiny car with shiny objects, but does that car actually run when it needs to? And are you continuing to check that it runs? Think about some of the airline outages; being able to replicate your production environment and simulate what happens when you add or remove technology, so that when that situation occurs, you can get back up faster. How often do you actually test your disaster recovery plan? How often are you sure that new technology you’ve added is backwards compatible with the legacy systems you haven’t tested it against?
Chelsea Grayson: Is that almost a full-time job for part of the CTO’s division, the constant testing, the compliance checks, the fail safes?
Jair Clarke: It’s critically important, and it’s just as important to other stakeholders within the company. Hypothetical situation: business is booming, everything’s going well, but a few people clicked an email link they weren’t supposed to click. How do you isolate that? How do you reduce the exponential impact across the company? That’s not something you go to a conference and give a paid speaking engagement about. You’ve got to look at it from an SMTP perspective, anything you can do to isolate it, and then ask: How do you audit it? How do you understand how it happened in the first place? What training do you need to provide? What tools can you give people so they can do their jobs without feeling like they have to click through four things just to send an email? That’s the stuff nobody really talks about, but it gets everyone’s attention from the top down when something like that happens.
Chelsea Grayson: In the boardroom, the only time we hear about it is when something bad has already happened. Do you think boards should be asking about this stuff more proactively?
Jair Clarke: I think it’s a mix. Operators need to operate, but I really believe it’s important that from an audit committee or governance standpoint, those big building blocks, cybersecurity, disaster recovery, ecosystem rationalization, are present and visible. Even if it’s just a dashboard, it’s important that someone in the boardroom with that expertise can ask one question, get a solid answer, and either move on or say, “That was a fuzzy answer, let’s dive deeper in an offline session.” Just having someone in the room to ask the right questions, so you can move through it quickly when everything’s good or drill down when needed, that’s important in the boardroom.
Chelsea Grayson: When you’re thinking about bringing in a technologist board member, especially in a distressed environment, what attributes would you want them to have? Is it general technology expertise? AI-focused? Disaster-focused? Are all technologists interchangeable, or are there specialties that matter?
Jair Clarke: This is a really good question, and unintentionally a loaded one. There are so many titles out there now: Chief Digital Officer, Chief Digital Transformation Officer, Chief AI Officer. And CIO may mean both Information Officer and Innovation Officer. There’s constant debate about the difference between a CTO and a CIO, and people don’t really understand the back-end side of keeping the lights on.
To me, it really boils down to this: have you ever done it before? Have you been on a keyboard and written lines of code? Have you been in a situation where everything was down and you had to bring it back up sequentially, not just point to a strategy, not just get on a whiteboard, not just tell somebody else to do it, but actually be on the bridge asking the fundamental questions about configuration settings, business rules, architecture, what layers are truly involved, and made the calls yourself? If the answer is yes, great, let’s go through some of those situations and make sure you went deep enough. If the answer is no, no worries if you’re an amazing talent, but let’s find the right role for you. A CTO, in my eyes, is someone who has truly been there before, because you earn your experience from actually being responsible for fixing something when you can’t look left or right for someone else to do it.
Chelsea Grayson: Not many people have those kinds of skills, and that is incredibly meat-and-potatoes advice I’m going to take back to my boardrooms. I can’t thank you enough for your time today, Jair. It’s always really good to reconnect with you. Thank you so much.
Jair Clarke: Thanks for the time, I appreciate it.
