Earning a P&L role can be a key differentiator for any IT leader’s career. Here’s how the edtech CTO made the leap, what he learned, and the steps he advises CIOs take to do the same.
Jim Chilton is an award-winning CIO who serves as the chief technology officer of Cengage Group, an innovative disruptor in the edtech space. As a business and technology executive, Chilton leverages his unique experiences to drive innovation and optimize technology throughout the company.
On a recent episode of the Tech Whisperers podcast, Chilton and I explored his leadership philosophies and superpowers, including how he navigates wide ranging responsibilities, his vision for building a more robust pipeline of cyber leaders, and how he’s helping his people and the company succeed in an exceedingly complex and challenging environment. After the show, we spent some more time talking about Chilton’s experience as a P&L leader and how that has contributed to his success as a CTO. What follows is that conversation, edited for length and clarity.
Dan Roberts: How did you become a P&L leader? What have some of those experiences been like?
Jim Chilton: When I was at the enterprise software company Coda Financial in the ’90s, I was asked to be the professional services leader. I had joined as CIO, but the Americas president had asked me to step in, as we found we kept having technology consults as a larger part of the conversation. The technology, the database and all of that, was really important to the success of these implementations. Over time, I ended up with the entire consulting organization and the tech support organization as well as IT.
In this North America operations role, I was responsible for our consulting revenue, which was millions of dollars per year, because we were implementing the software for some big-name companies that had vast geographic footprints. It was an incredible opportunity to take what we do as CIOs and CTOs and put it on steroids because I was doing it for lots of companies simultaneously. Over time, the P&L part of building that consulting practice became very interesting to me, because it was a shift — one that most organizations have made now — moving away from that individual one-to-one consult to, how do you certify implementations that are done by third parties? How do you do more training and certification? Because when you have a one-to-many ratio, you get a far better P&L return and profitability.
What we were able to do for our customers, which was a big deal back then, was claim a one-to-one or less ratio [of software cost to implementation cost], and it became a huge sales approach for us. Our success allowed me and others in the sales organization to say, ‘If you spend $3 million on our software, you will not spend anything more than $3 million to implement it.’ When we had hundreds and hundreds of implementations, we could look back and say, ‘This is how we’ve been successful at doing this.’
The opportunity for me to take on P&L responsibility showed up again at Dassault Systèmes. I was asked to step into the strategy and sales role and take over the piracy business. In running strategy, sales, and operations for the SolidWorks channel, we discovered that the pirating of our software was not just a problem but a business opportunity. By having direct links in the software that would feed back to us when our software had been stolen, we could engage with the people that were stealing the software. Rather than fighting piracy, we would be able to create a new sales channel. I think today it does well over $300 or $400 million.
The most recent example here at Cengage Group would be stepping in to run Infosec Institute as the general manager. That was an incredible opportunity where we realized meaningful results when you think about our first-year acquisition.
What are some of the things you learned from that opportunity?
Post-acquisition, as happens with many M&A scenarios, we lost a number of leaders within Infosec. As a result, my first job was putting together a new leadership team that would allow us to achieve our growth goals. It would have been easy to say, ‘Let’s just give up on this year and we’ll start next year.’ The team and I agreed that we weren’t going to do that. We’re going to assemble the best team we could to deliver on the promises that we made.
During that process, I learned a lot about P&L responsibility, working with Balraj Kalsi and then Alexander Broich here at Cengage — two incredible general managers who I continue to learn from about focusing on the business and the lead management process.
Depending on your sales cycle and process, it’s inadequate these days to take on a business and just worry about the current customers and delivering great products. You have to continually grind away at getting new customers, really understanding your sales cycle, who are the personas, and what is your ideal customer profile. These were areas I focused on, and we had such a diverse customer base, with a service on one side and a software business on the other side. It was an incredible learning opportunity.
What were some of the ways you set yourself up to get the call?
I think pursuing an MBA was a real differentiator. Having an undergrad in technology and a master’s in business allowed people to see me differently, as more than a technologist. I was working on my MBA when I took on that consulting role, so I think it was clear to leadership what I was trying to do and how I was trying to be thought of differently as a business partner and executive. That willingness to be seen and wanting to be seen differently was step one.
Step two is about making sure your leadership team is developed. Part of the reason I was able to step in with Infosec was because of the strong technology leadership team and supporting members I had in place, who were already empowered to step up and take on more in their roles. Some leaders might worry that building a strong team makes them less relevant. I don’t buy into that paradigm. Making a strong team makes you incredibly relevant, and it’s part of our obligation. That’s what we should be doing, as any manager, not just a CIO or a CTO. Having a strong team enables you to thrive.
Lastly, it’s making sure the executives you report into know this is what you want to do. I’ve had conversations with Michael [Hansen, Cengage Group CEO] about my ambition around board seats, and the advisory work that I’ve done and how much I enjoy that work, and how important it is to me when I think about my future. Be vocal about the things you’re interested in beyond your current job. Now, you’ve got to earn that conversation. You have to be delivering on your promises, ask for help with your career development. When you’ve done those things, then you have earned the right to have these conversations.
Contrast your journey with those who end up getting pigeonholed. Why do some people get overlooked for new roles or opportunities without knowing why?
I think it has a lot to do with the willingness to be vulnerable about what you’re looking for while also being clear about what you expect for the work that goes into it. I’ve seen some people will do a few things and think they’ve earned the right. You have to be very clear about the expectations of your role, and demonstrate how you have fulfilled those multiple times. Saying you had one good year, one good project, one good implementation is not enough. It’s not enough for the types of conversations where you say, trust me with your $200 million acquisition. You have to earn that.
It’s also about patience and being comfortable and vulnerable enough to ask for additional things to do. The risk in saying, ‘I want something more to do,’ is that the receiver of that information, your CEO, may be like, ‘You don’t like your job?’ ‘No, I love my job. I do my job well. I’ve done all these things. I’ve talked about my successes and the things that the team and I have done. I want to do more.’
It’s also saying: ‘I want to do more on my time. I’m happy to take this on and do this. I’m going to go from a 40-hour work week to an 80-hour work week because I want to do this and I can be someone who can help make a difference both for the company and for this organization and this acquisition that we made.’
Too often I see people that want more, and before the more even starts, they want to know how much more they’re going to get. They lead with, ‘I want more and you should pay me more or give me more equity or do this or do that.’ It’s my belief that when you work hard and do these things, good things will happen, and you will be rewarded and recognized. That’s why you’ve got to believe at your core that you want to do this and that the value of these experiences will extend beyond the current role. Make sure that you’re doing it because you care, you want to learn, and you want to develop.
I’ve never liked that expression ‘fake it ’til you make it’ because I think it sends the wrong message. I think a better message might be ‘grit it ’til you get it.’
I’ve seen disastrous things happen for people that fake it ’til they make it. At Dassault Systèmes, I watched some incredible people come in as interns from great universities, super bright, they pushed and clawed for more money, more titles, got all the things they wanted, got frustrated when they finally couldn’t get more money or more titles and they left the company. Then they discovered that they couldn’t do that job at that level, and they lost that job — and then they discovered, again, that they couldn’t do that job at that level. And now they’ve got two or three back-to-back blemishes on their resume. No one wants to hire them at that level; no one wants to hire them below that level. They have painted themselves into a corner.
I’ve watched those people claw their way back decades later, finally earning their stripes to that actual title, and what a painful process that is. The managers of those people failed them by promoting them and giving them a title way too soon. That’s a responsibility I’ve taken seriously, and I know some people on my team love me for it, and some probably hate me for it. But I think you owe it to people to set them up for success.
For those who are coming up in the IT ranks today, why should they seek out a role in the business?
It’s a great opportunity to do two things: First, to differentiate yourself. To show you are diversified and broad enough in your thinking that you can do more than the track you’re on. Diversification and differentiating yourself as a candidate is super important and you’re going to learn a ton of things.
Second, you will be far better at your job as a result. When I was the general manager of Infosec, we were having challenges around lead generation, and there was great technology that we could put in place that would allow us to generate leads more rapidly. When I put my CTO hat on, those were rules that would break my policies about how we would generate leads. The general manager of me is like, ‘I absolutely want to use this technology because it will allow me to accomplish my business objectives.’ As the CTO I’m like, ‘You can’t use that technology. It’s against our values and principles as a company.’
It allows you to get in the other seat so when you’re going back to that CTO job and you’ve got a business unit leader standing in front of you telling you they desperately need to be able to do something, you have a completely different understanding about the pain that they are feeling and the understanding that you have to give them because you’ve lived the experience now.
Finally, this experience is becoming ever more critical to being a good CTO or CIO. The expectations for executive-level technologists today are very different than when I took on my first leadership role. Now, if you sit at the table, you represent the whole business, no longer just your function. The company, the CEO, and your fellow leaders are depending on your guidance on technology, cybersecurity, and risk. Today’s CIO/CTO must bring the technology expertise to the table, while also demonstrating strong business and leadership skills.
This has become a multidimensional job. Being a great technologist who created a great product or solved a problem for company X is no longer adequate. You must be able to create a vision, inspire teams, show relevance to their work and business outcomes. This can be a fascinating role where you can participate in nearly every dimension of the business to truly leverage technology as a differentiator.
Would you say that’s one of the ways you’re a better CTO today, because of this P&L experience?
The level of appreciation and understanding I have for the business and the leaders in those businesses — I mentioned Alexander Broich, who’s one of our general managers — I have an incredible amount of respect for him after working with him on Cengage Work and Infosec, a whole other level of understanding from watching these folks who have been doing this type of work their whole life. The same with Balraj Kalsi and Michael Hansen. Just incredible intellects in the work that they do, and learning from them is a humbling experience. My blind spots were things that they saw right away.
As I go back into the CTO role, it allows me to have a ton more respect for the people that are running those businesses and the challenges they are faced with, but it also gives me more context for what the team and I can be doing to help us be successful in those endeavors, with a whole different perspective on what challenges exist for these business leaders. When we’re talking about standards and compliance and governance and all of these things, to understand that just complying and responding to our requests may be a burden against their very existence of trying to grow that business, grow the revenue, grow the EBITDA, really improve that business. We’re sitting there pestering them about something that they may see as far less relevant. So our job is really helping them understand why it is relevant, why this can help you, and how this could be an unlock for the business.
For more insights from Jim Chilton’s leadership playbook, tune into the Tech Whisperers podcast.
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