The tech industry is ever-changing. What’s hot one day is outdated the next. Keeping up with the latest skills and technologies can be all-consuming if you let it be. It is a balancing act: how much time should you spend learning new things vs. doing your current job? How should you think through whether to make a jump onto a new industry trend, either by moving to a new role in your current company or by switching companies?
These are questions we think through on behalf of administrators who use our VMware infrastructure products on a day-to-day basis. For example, many vSphere admins came from Windows server admin backgrounds. The jump from Windows server admin to vSphere admin was straightforward, as many of the concepts and tooling were similar and vSphere was critical for improving the Windows server admin’s job. The current industry shifts are driving the advent of DevOps and platform engineering, both of which require much more coding and automation. This is a much bigger transition for these admins, as they must step out of their comfort zones.
I’ve been fortunate to be a part of a number of industry shifts during my career. While I’ve worked at VMware for close to 18 years now, I’ve moved around quite a bit within the company and have changed roles a few times. A quick summary of my path at VMware:
- Summer 2002: Intern working on the vmkernel in ESX
- 2003 – 2005: Full time as part of UserWorld’s team in ESX
- 2005 – 2009: vMotion owner; created Storage vMotion
- 2009 – 2013: Started a performance-management product that eventually would become vRealize Operations
- 2013 – 2015: End User Computing (EUC) CTO
- 2015 – 2016: Created Cloud Native Apps BU (CNABU) and was its General Manager
- 2016 – 2020: Cloud Platform BU CTO
- 2020 – 2021: VMware Cloud CTO
- 2021 – present: VMware CTO
My career trajectory was never a straight path. I took advantage of what was presented to me. There were a few key things that helped me.
Watch for opportunities, make the jump.
After I had spent about four years on the vMotion team, having become well-known in the company for this critical technology and creating Storage vMotion, I had the opportunity to join the early team working on a performance-management project that would eventually become vRealize Operations. While the opportunity was certainly interesting, the project was early and unproven, and vMotion (and Storage vMotion) was very successful and highly visible. Why should I move? After thinking about it and doing some research, I decided to make the switch because of the business opportunity the performance-management project presented for VMware and my ability to contribute meaningfully to the company here.
While that transition took me a while to evaluate, since then, when an opportunity does arise, I evaluate it based on the following criteria:
- Fit: Does this role match your interest and skillset? If you have a desired career path, does it help you progress on that path?
- Learn something new: Does the role enable you to learn something new? This could be a different role than you’ve done in the past or a similar type of role but in a new space. Pushing yourself out of your comfort zone means you’ll be in constant learning mode, which is great for your growth.
- Growing market: What is the broader market opportunity with this role? Is it on the “right side of history,” so to speak? While you can move into a role in a shrinking market, the dynamics are very different from a growing market, so you want to be clear about what you’re getting into.
Another question I ask myself is: in five years from now, what will the right move have been? Even though there’s always some degree of uncertainty to these decisions, taking that broader perspective often helps clarify things for me.
While the switch from vMotion to what would become vRealize Operations was a tough decision, my switch from EUC CTO to Cloud Native Applications Business Unit (CNABU) GM was an easy one. Why? Because I had been actively monitoring the space and the strategic opportunity was very clearly massive.
In general, because we work in the tech industry and it’s changing so rapidly, we must always have our ear to the ground to learn about new happenings. I subscribe to a few tech newsletters, follow many tech folks on Twitter, and read blogs to stay on top of the latest tech developments. If I see something interesting, I take a note to research it and I set aside time weekly just for new research. Even blocking out 30 mins can be super helpful in understanding the trending topics of the day and determining whether they’re worth spending more time on.
I started just naturally spending more and more time on the cloud-native and container spaces, trying to understand the rise of Docker, how customers and other vendors were reacting, and more. It became clear that this space was super important, so I quickly took the plunge, created CNABU, and started as its general manager.
Industry shifts take longer than you think. You’re not too late.
I learned a lot as CNABU GM, not just about the cloud-native space, but the nature of industry change. With the rise of Docker, many industry pundits were predicting the death of VMware. I saw this as an existential threat. Luckily, I was able to convince our CEO Pat Gelsinger and others about the importance of this effort. He gave us a ton of resources to go and tackle the problem, so we raced like crazy right out of the gate, making a lot of announcements and creating many new projects.
That was 2015, and we’re still seeing the cloud-native space maturing. Yes, most companies are running containers in production today, but it’s often still a small percentage of their total application estate. While cloud-native is absolutely the future, there is still much work to be done. Admins still struggle to operationalize it. Developers struggle to build on top of it. Given this, in retrospect, I should have taken it slower and taken the time to properly build up a more solid foundation on top of which to build our new cloud-native products.
The big takeaway is that these massive industry shifts take time — often much more time than we initially think. I learned that it’s not necessary to immediately jump on the newest thing. It’s important to keep your ear to the ground, as we discussed above, but you should take the time to create a proper plan, rather than rushing headlong into it without such a plan.
This also applies to taking a role in an emerging space. Some people see the evolving situation and feel they’re too late, that they’ve missed the boat. But the reality is that there is usually much more time than you think. That doesn’t mean you shouldn’t jump on a good opportunity if you see one. You should be proactive and research new things you see people talking about. But you also don’t need to over-rotate and go in blindly. Take the time to figure it out.
Specifically, now is a great time to get involved with the cloud-native and, specifically, the Kubernetes space. It’s not too late!
Play to your strengths.
When I took the role as general manager of CNABU, it was my first time being a GM and managing a team greater than five people. It actually took me by surprise how different the GM role is compared to CTO and all the learning I had to do to go from managing ~5 people to ~150 people. Looking back, it should have been obvious, but those were the heady early days of CNABU! I wasn’t prepared for this very different type of role and didn’t know what I should be focusing on or how to navigate various aspects of the role. As I thought about it, I have strengths in areas like technology, architecture, strategy, evangelism, and the like — all classic CTO focus areas. Moreover, my natural skills are a great fit for a CTO: I prefer to work through influence, can boil down complex technical topics, bring people together to align on issues, and have a knack for public speaking.
I eventually made the decision to switch out of the GM role and took a role as CTO for the Cloud Platform BU. This role benefited me, as it allowed me to play to my strengths while also allowing me to contribute even more to our cloud-native effort. I was able to more effectively drive cloud-native strategy both for the CNABU and for Cloud Platform (e.g. vSphere). The upside is that I was both able to broaden my focus and increase my impact. This helped us get to cool stuff like Project Pacific, Monterey, and many more cool things we have yet to announce!
The takeaway is that you shouldn’t be afraid to try new things, even if they are a bit outside your comfort zone. My time as CNABU GM was one of the biggest learning experiences I’ve had in my professional career. I was able to better appreciate my strengths and it helped me better understand the right career trajectory. For VI admins thinking about moving into more of a Site Reliability Engineer (SRE) or platform ops role, I highly recommend that you push yourself and take the plunge. Yes, there is more coding in these roles, and for many folks that is intimidating, but there are many ways to contribute to these teams. You owe it to yourself to explore those opportunities.
One final point here — while my stint as a GM didn’t go well, I did learn a tremendous amount in that short time. I’m leveraging many of those learnings as I enter into the new role of VMware CTO, where I now oversee a large engineering organization. There’s always opportunity in a crisis and in this case, my previous experience, even though it didn’t go well, prepared me for bigger challenges in the future.
In the end, it’s all about leaning into the ever-changing landscape:
- Know your natural skillsets. Find the role that best leverages them.
- Look for areas where you might see yourself expanding your skills or using them in a new way.
- Keep an open perspective and willingness to explore new areas.
- Don’t be afraid to ride the waves of technology trends.
Saying yes as part of embracing change is crucial. The quote from Noah Emmerich, the actor/director of hits like The Truman Show, is so fitting here: “It seems like the more I live, the more I realize that saying ‘yes’ is almost never a mistake.”
6 comments have been added so far
This is an awesome & honest self assessment which also gives a ton to think for others in their own careers. Thanks for this Kit. Wish you continued successes
Great perspective and very helpful!. I also include “What’s the worse that can happen?” in my considerations. This, for me, has always helped me in taking the leap.
Thanks a lot for taking the time and writing this Kit, as a young engineer it’s always very interesting to read about other people’s career journey and how the dots connect looking backwards. It seems to me that it’s much harder to make the decisions at those critical points.
I have to say I really like your mindset and wish you the best in your new role!
Thanks for sharing the experiences, personal journey and insights! Especially the specific examples (Windows to vSphere Admin and vSphere Admin to Site Reliability Engineer, Cloud Native Strategy, Market Monitoring). A thought-provoking article that I’m sure I’ll be sharing often in my circle!
THANK you for sharing your personal journey and your takeaways.
I sincerely agree with you, though I always found it extremely hard to setting 5yrs goals (or even 3yr!) especially in our fast-moving industry, which often swifts us off our feet (planning-wise) !
But daring is usually winning!
Worth the time spent reading it, with food for thought on how some of these learnings could apply to one’s own career. Thanks for sharing.