Some of the most meaningful careers aren’t built by staying the course, but by knowing when to pivot.
For Milo Speranzo, that fork in the road appeared more than once. Before becoming the North America chief marketing officer for the global tech giant Lenovo, he’d already lived several professional lives, like joining the military and going to school for electrical engineering.
“You start by just listening and studying, asking questions and engaging, and then your confidence slowly builds.”
Milo Speranzo, chief marketing officer at Lenovo
“At 40, I figured out what I wanted to be when I grew up,” Speranzo told Technical.ly.
His earlier experiences shaped his mindset, though they didn’t feel like the perfect fit.
After serving 13 years in the Air Force, Speranzo transitioned into procurement for the formerly known Department of Defense, then founded a consulting firm specializing in government-focused IT. He built that company for over a decade before selling it. From there, he entered the marketing world at Dell Technologies. That move ultimately led him to Lenovo.
Now, the 47-year-old Pittsburgh native is at the helm of a new partnership between Lenovo and the Pittsburgh Penguins. The collaboration is putting Lenovo tech in the hands of coaches, scouts and staff to review game footage, analyze player data and make key draft-day decisions that are shaping this year’s season.
With Lenovo’s emphasis on diversity and sustainability, Speranzo said the role has reignited his sense of purpose.
“Typically, after a year or two of working somewhere, you get the feeling of whether this is long-term,” Speranzo said. “This is probably the first company I’ve been at where I haven’t had one minute of doubt that this is the place I should be.”
In this edition of Technical.ly’s How I Got Here series, Speranzo reflects on the career pivots that shaped his path and the lessons he’s carried from each turn.
This Q&A has been edited for length and clarity.
What experiences or lessons from the Air Force continue to guide you in your career?
We could do 10 interviews on what I learned in the military.
One of the big ones that you hear a lot, though, which is also very, very true: attention to detail. In the military, you really rewire your brain to see things sometimes from the bottom up, instead of top down. That attention to detail really lent itself not only to my current career, but also to relationship building. It’s really something that’s touched every aspect of my life and career.
Also, the military is hard. There were a lot of times, especially post 9/11, when my friends and I were put in extremely stressful circumstances.
Vets have been tested in some difficult situations, and they’re able to handle tense situations in the private sector that might take the typical business executive a lot longer to feel comfortable with.
You learn how to make decisions, who is a detractor and who is enabling your talk track. Having that experience in high-stress situations makes the transition to the corporate world easier.
What factors helped you build a successful consulting firm that was eventually acquired?
Being an entrepreneur is different for everybody, but I do think there are a couple of common attributes to building a successful business and one is that it cannot be a hobby.
It can’t be something you’re doing on the side. Some people thrive at that, but they’re outliers. I had no other choice. No backup plan. For me, there was a lot of anxiety, but also a lot of energy knowing that I had to make this work.
It was night and day, calling every contact I had, talking to other entrepreneurs and looking for mentors. Once you get the first couple of contracts, that first year under your belt, you might not be making a lot of money, but you feel that little bit of success. Then you see the areas that you can double down on versus where you can cut in the future.
I see a lot of entrepreneurs who get good at a piece of their business, and they get really excited, so they try to do everything. I’m not a master of prioritization, but I had an epiphany that I needed to prioritize. When I did, that really helped the business not only gain revenue, but also gain network, and network ended up being the key to the exit plan. It’s important to continue to nurture the soft side of the business, like the network.
What challenges did you face transitioning into the corporate world?
There were growing pains. One is imposter syndrome, and when I came over, I had it bad.
I was in my early 30s, and I had done a lot in the military, maybe even for the country, but I didn’t know if I really belonged at the table with the people around me. They were speaking in a completely different tongue than I had ever heard, with all the new acronyms. But, I thought to myself many times during the transition, “Somehow I talked my way into this meeting.”
It takes a couple of concrete examples that you deserve to be there and it takes a lot of listening. You start by just listening and studying, asking questions and engaging, and then your confidence slowly builds.
What do you wish you’d known at the beginning of your career journey?
When I look at the multiple pivots in my career journey – from the military, the Department of Defense, to civilian life, the IT sector, entrepreneurship, sales and marketing – all required self-confidence and the understanding that I didn’t know everything right away.
I was very hard on myself in the early days of all of those pivots. That anxiety leaked into my personal life. Those pivots are extremely stressful times. This is cliché, but you’ve got to take time for self-care. Don’t forget about yourself during those times.
Even in this most recent pivot to this role as the North America CMO at Lenovo, allow yourself space and a little bit of grace. Take time to go fishing, too. That’s my quiet spot.
