Ep 3: Taking Risks to Become Failure Proof at Princeton University with CIO Jay Dominick

Evan: Hi there and welcome to Enterprise Software Innovators, a show where top tech executives share how they innovate at scale. Each episode covers unique insights and stories that will help you succeed as a technology leader. I’m Evan Reiser, the CEO and Founder of Abnormal Security.

Saam: And I’m Saam Motamedi, a general partner at Greylock Partners.

Evan: Today on the show, we’re bringing you a conversation with Jay Dominick, Chief Information Officer at Princeton University, where he’s worked for almost a decade. Jay has been a technology leader in higher education for almost 30 years, and was previously CIO at Wake Forest University, and Vice Chancellor of IT at UNC Charlotte.

Saam: Princeton has about 8,000 students and over 7,000 employees, and is recognized around the world for its cutting edge research. In this conversation, Jay shares how he navigated the sudden shift to online education at the beginning of the pandemic, learnings from innovating at a 275 year old organization, and why avoiding risk can lead to failure. 

Evan: Jay, thank you so much for joining us.

Jay: Delighted to be here, Evan, and thank you, Saam, for the invitation.

Evan: You know, you've had a long career, you've seen a lot of things, right? What would you say is kind of the biggest lesson from your career that’s kind of most informed your leadership today?

Jay: It does seem like a long career at this point, it's nearly three decades starting before the internet really became the dominant technology in our lives. And I think the thing that I've learned most from this is really to be flexible, to be nimble and to think about the possibilities the technology is bringing us. What's happened over my career is I've gone from being a tremendous technology optimist in my youth where technology could do everything to really becoming more of a technology realist, recognizing that there's upside. And there's downside.

Saam: Jay, I want to double-click on going from technology optimist to technology realist. And I think one of the things that's so interesting about the journeys you've run is the perspective of looking at technology and IT from the university side or from the education side. What do you think is similar? And what's different about how universities approach technology and IT versus other organizations or enterprises?

Jay: Universities are a really interesting special model. We run a business. Our business is to teach and to do research, but in the residential model, we are also the home for 8,000 people or so who live here, who work here, we have a power plant, we have a police force. We feed people, we have sporting events. So universities are an institution that's also a community. And we have many different concerns and constituencies to optimize around, which makes really being a CIO in higher education very complicated because the business is complicated. 

Saam: How do you organize your team? You're solving for these different constituents, as you said, that have different requirements around technology. How do you organize yourselves and how do you think about serving these different constituents effectively?

Jay: We are largely a centralized organization, so we run core infrastructure, right? This is like kind of every CIO’s bread and butter. We run everything from the network to our enterprise systems, but then we also have  constituencies or parts of the department that focus on the delivery of specific services for specific customers. And one of those, most obvious, would be research computing. So we have a pretty large research computing team. Their job is to enable the faculty to do the work that they need to do to advance the frontiers of discovery. And then we have teams who work with students who have very different sets of needs. And we really want to have kind of a consumerish experience. They want to learn, they want to be part of the community, but they want their X Boxes and their PlayStations to work, too. So we're central, but then we try to have teams that are really kind of focused on the individual customer sets. 

Evan: It's a really interesting environment where like you said, people live, right, in the environment that you support. Where you are trying to drive innovation, but there's also kind of other things to worry about, you know. Many of your peers outside of higher education probably don't quite understand like some of the challenges. Like what are maybe a couple of things that are surprising about kind of what your job entails that maybe other CIOs might not fully understand?

Jay: I think there are kind of two parts. One is that the faculty themselves are independent actors. They are employees of the university, but their intellectual property is their work. They own it, and they're responsible for it. It's not owned by the university in any way. So our job is to help them create their own IP, which they then publish. 

On the student side, you know, we live in a world where I've got 7 or 8,000 people here who are all innovating. They're innovating for me, with me, and against me, right? So we want to support that. Particularly amongst our students, we want them to be innovative. We want them to create new apps. We want them to leverage our platforms to the extent that they can.

And if you're a CIO at a bank or at a financial services firm of any kind, you're not expecting your employees to constantly being hacking you, or trying to figure out how to create the next big app on your information infrastructure. So, we don't wanna stop that stuff because that's kind of the creativity in the space. 

Evan: In that experience, are there things that you've learned about how to kind of foster innovation inside the community that you think should maybe be more applied outside of higher education?

Jay: You know, what we're trying to do is to make our infrastructure, whether that's the network itself or our information infrastructure as available to our budding entrepreneurs as possible. So what we're trying to do is figure out how we can leverage our assets to help them actually accomplish what they want to do. And I think that most firms really want to encourage creativity from their own staff as well to innovate. But the standard model that we have is to lock everything down and to squelch that sort of innovation, because it's a risk.

Evan: Jay, that makes total sense in abstract, but maybe more practically, what advice would you give a CIO that’s from a different world about how they can implement that and get an easy win there?

Jay: You know, I think easy wins are really aligned to how do you align your incentives with the incentives of innovators? You know, for us, our incentives are aligned pretty well. We want students to be able to be successful. And I think for CIOs, if you're encouraging innovation from within, you have to figure out how to align your own success and interests with the innovator's success and interests. So whether that's shared responsibility for the security of the innovations or whether that's shared credit. I think you have to find a way that, how you get rewarded is aligned with doing the right thing, or having your innovators do the right thing for the institution.

Saam: Jay, I want to double-click on earlier you mentioned these two sets of constituencies, one being the internal network or students and the folks on the education side, and then the other being on the research side. Let's start with the first. And I'm really curious, like take us back to March 2020. The start of COVID-19 pandemic and figuring out how to transition that first constituency into the digital world. How did that happen? And what was the role that you and technology played in that transition?

Jay: We sent our students home with virtually no notice, we transitioned the campus to being all online. We moved from our most sophisticated technology being chalk to being completely dependent on some cloud technologies that, you know, people had seen before, but not really kind of invested in. And I would say over that first period, the first month or so, our task was to do a couple of things. One is to communicate and that's to communicate what the options were, to communicate how the business could run with this technology, but then to communicate to our own teams that things were going to be okay. We had to face the dual challenge of getting campus ready for online. And then we had to move ourselves online. So we had a complicated department, it’s critical to the university's operation, and we had completely discommoded our own ways of working. So really there was the external constituency, getting them ready, and then it was getting us ready, keeping people safe and letting them know that, you know, in the middle of a financial crisis, no less, that things were going to be okay, that they were needed, and that we were going to get through this.

Evan: Jay, in that moment of kind of uncertainty, right? How do you strike the right balance between speed and innovation versus risk mitigation and quality? How do you guide the team about where to be there?

Jay: Normally we balanced the sort of risk opportunity equation focused on risk mitigation, right? So we were very concerned that we not take too much risk too quickly. What we were facing was an existential crisis, more or less, right. 

And so the risk mitigation switched into failure mitigation, right? So we had to take risk to avoid failure. And I think that's an important distinction for people. People tend to be risk averse, but really they should focus on being failure averse. And for us, we had to change a lot of rules, you know, our policies and our practices around work at home or around what students could be considered to do with respect to technology in their studies. 

So suddenly we had to let students take their exams online. So we had to rethink, how do you actually assess student learning, you know, if you can't really do it the way that you've always done with a pencil in class. 

Saam: So, I’m fascinated by the following tension - on the one hand, there’s a culture and set of behaviors that have been embedded over hundreds of years, with some aversion to risk-taking, and on the other hand, on the research side, it’s all about risk-taking. How do you enable the team to serve both of these constituencies that have such different cultures?

Jay: Yeah, it’s crazy. And I'll get back to the failure versus risk. You know, in the science, failure's a part of the equation. You know, the faculty who are - they’re taking risks all the time, they know how to deal with failure. Experiment doesn't work, you pick yourself up, you think about what didn't work and you do it again. 

On the rest of our business. That's different, right? The university in general is set up to continue to exist over time. Our job isn't to fail or to fail creatively as an institution. Our job is to continue to be here, to sustain our way of being over time. And for 274 years, two hundred and actually seventy five now, I think, this institution and a number of them have been extraordinarily successful at being failure proof. Went through a revolution, we've been through two or three wars, pandemics, plagues, depression. Our campus was occupied by the British for, you know, a year or so, but we've continued to function and we've continued to stay, you know, true to our values through all that, because we're pretty much failure proof to a certain extent.

Evan: Wow, Jay, that is - that’s some really interesting history. I guess I’d have to ask you - like, what advice would you give other technology leaders that are navigating this tension between risk-mitigation vs. driving change and innovation?

Jay: Organizations like mine, like IT organizations, fail when they become so far out of the norm of what the efficiency and effectiveness curve gives you that they become legacy. Right? And so my job is - and I think a lot of CIOs, their job is to make sure their organizations don't become legacy because, you know, once you become legacy, you're no longer relevant and you get disintermediated in some sort of way.

Evan: So Jay, how do you think about working with startups to drive that type of innovation, in order to make sure that you’re not failing because you're innovating too slowly?

Jay: So one of the reasons we do work with startups is to give the department, give our own staff, give our organization, the opportunity to see when people are just thinking differently. So people who have taken some risk, and have come up with solutions that are quantitatively different than what we do. It gives us a sense into the innovator's mind, but it also challenges us, quite frankly, to think about, okay, if those guys are doing that, where does that fit with what we're doing? 

Maybe we're being challenged, maybe we are being - are falling behind. So it almost doesn't matter what the product is. It's the think keeps us healthy. It keeps us young, and keeps us connected to where the industry is going, quite frankly.

Saam: Jay, we have a number of startup founders and builders who listen to the podcast. Do you have any advice for how they should navigate working with someone like Princeton? And I've always respected that you've been early to partner with some of the most innovative companies. What have those companies done well in approaching those partnerships with you and what are mistakes that they've commonly made?

Jay: I think that one of the challenges with working with higher ed is sort of the cycle time. We're slow, right? The sales cycle with Evan was probably a year, with Abnormal. And we're a great example for an entrepreneur of how you deal with a big organization that has process, that has procedures, that has lawyers, and is worried about reputation and risk. Universities in general, probably big companies in many cases, aren't the places that you go as an innovator to get a quick win and be done. If you can sustain engagement over time as an innovator and need a mature partner, universities are great places to go to do that because we will take risks. We will try things, but we're not for the faint of heart. And we're not for innovators who can't be patient, which is, I know, is a hard thing to do for an entrepreneur and an innovator.

Evan: So Jay, what are some of the common mistakes you see startups making when they try to engage with higher education or universities like Princeton?

Jay: I think there are two of them. One is don't tell us our business. Companies from time to time, they come and say, you know, we're going to revolut - revolutionize your business. We know your business better than you do. Just let us do it. No, you know, that's just not what we're going to do. You know, we've been in this space a long time, probably gonna be here longer than most of you. You know, don't tell us our business. 

And thing two is when you're pivoting tell us early. Don't let us be surprised when the idea that you pitched us to begin with doesn't work out and you find a new opportunity. So, businesses pivot all the time and we're happy to see that pivot, particularly if it lines up. But don't leave us surprised.

Evan: That's probably good advice for entrepreneurs, investors and enterprise innovators, right? No surprises.

Jay: No surprises. 

Saam: Jay, we like to end every podcast with our lightning round. So we've got a set of questions for you. What should a new CIO focus on getting done in the first four quarters? How do you get a huge win on the board right away?

Jay: You figure out what the organization wants and deliver on it.

Evan: So Jay, on the other side of that, what is the biggest mistake a CIO can make?

Jay: Thinks he or she knows better. CIOs that come in with their own agenda and say, you know, this has worked for me in the past, I'm going to do A, B and C, and we're going to be fine without recognizing the institutional culture that they bring their experience into, don’t do well.

Saam: Maybe related to this, how do you measure the performance of a technology executive?

Jay: It's different in every organization. In higher ed, technology leaders are measured by the trust that they build amongst their peers, they're measured by are they able to deliver projects on time, on budget, just like everybody else. And they're also measured on did you get hacked?

Evan: I know you spent a few years in the Air Force. Do you mind sharing a little bit about how that influenced your leadership?

Jay: What I learned in the Air Force is really a good leader doesn't make anybody else do anything that he or she is not willing to do. Right? A good leader takes accountability for their mistakes. A good leader gives credit for their successes to others, to the team. And I learned that really being authentic, that being honest and being transparent, good or bad, was really the essential quality of a leader.

Evan: Any other advice you'd give to aspiring leaders?

Jay: One of the pieces of advice that I like to give to aspiring leaders is really to do hard things and to be able to do things that you could reasonably fail at. But to try. Too many people are afraid to try to do hard things. I mean, this is your life, right? You're entrepreneurs, you're doing hard things every day and at great personal cost. And that's what I encourage people who want to be leaders, who want to be transformational leaders, to do is to do hard things.

Saam: What’s the best book you’ve read recently and why?

Jay: I've been reading a lot lately about the Second World War in the Solomon Islands. But the other book I would, I think has made a huge impact on me recently is the book Caste. If I had prepared for this, I would remember the author's name, but it's really about the role of caste in race relations in the United States over the past 400 years. That's probably been the most transformational book that I've read in the past six months.

Saam: Well, Jay, I want to thank you so much for joining us on the podcast. Evan and I have both been really excited to have you on given the vantage point you have, your approach to risk, innovation, failure proofing, and I'm thrilled our listeners are going to get to hear from you. Thanks for joining us. 

Jay: Saam, Evan. Thank you very much. This has been just a delight. Thank you for the invitation. 

Evan: Thank you, Jay.

Saam: That was Jay Dominick, Chief Information Officer at Princeton University. Thanks for listening to the Enterprise Software Innovators podcast. I’m Saam Motamedi, a general partner at Greylock Partners.

Evan: And I’m Evan Reiser, the Founder and CEO of Abnormal Security. Please be sure to subscribe, so you never miss an episode! You can find more great lessons from technology leaders and other enterprise software experts at enterprisesoftware.blog.

Saam: This show is produced by Luke Reiser and Emily Shaw, and mixed by Veronica Simonetti. See you next time!