C-suite career advice: Summer Weisberg, Testlio – IDG Connect

By IDG Connect
IDG Connect |
What tips would you give to someone aiming for a c-level position? “Embracing a broad vision of the…
Looking back with 20:20 hindsight, what would you have done differently? “Early on in my career, I…
What conferences are on your must-attend list? “I love the spirit and content of Security BSides…
What type of CTO are you? “As CTO, the most important thing for me is to make sure I’m creating a…
Name: Summer Weisberg
Company: Testlio
Job Title: Chief Client Officer
Location: Florida
Summer Weisberg has over 20 years of experience in IT ranging from enterprise software development and testing to professional services and customer success. Her current role as Chief Client Officer at Testlio has allowed her to return to her greatest passion: software testing. She has a passion for problem-solving and fully believes that technology enablers must be combined with business value outcomes to support successful customer adoption. 
What was the most valuable piece of career advice that you received? “You can be brilliant but if people don’t like working with you then you’ll never hit your goals.” I can’t remember the exact quote but it was something along those lines from my first FedEx manager, Cathy Pugh. She hired me right out of college and was a great mentor in many ways — but this was likely what I needed to hear at that time. And she was 100% right.
What was the worst piece of business advice that you received? When I was considering leaving fedex after 11 years someone told me not to do it. They had the best intentions of course. FedEx is an amazing company; I had a great career there and was highly valued. So it made no sense to them why I would leave for a startup they had never heard of.
Thankfully I moved past that advice and made the leap, and I’m glad I did. Moral of the story: seek advice from those you trust. But at the end of the day you have to trust your gut.
What advice would you give to someone starting their career in IT/tech? Create their own definition of success and follow it. Many people will try to tell you what success looks like — but it really doesn’t matter what anyone else thinks. What do you think qualifies as success?
For some that’s going into management, for others that is becoming an expert in a certain area. The point is, unless you know what success looks like for you then you won’t know whether or not you are on the right path.
Did you always want to work in IT/tech? Absolutely not. I didn’t even know what IT/Tech was until I was two years into college. Growing up, there was no computer in my home. I didn’t own a cell phone until my first job out of college.
The only thing I knew was that I was good at math & science. And then I participated in a few STEM programs, including a scholarship between the University of Central Florida and Kennedy Space Center that encouraged women & minorities to pursue STEM careers. That program steered me toward computer engineering in college.
What was your first job in IT/tech? FedEx was my first pure IT/tech job. I started working in the Requirement, Analysis & Design group as a programmer analyst. This was when software was developed with the Waterfall methodology. I took end user business requirements and translated them into system requirements. It was a great link between understanding business impact and technology.
What are some common misconceptions about working in IT/tech? It isn’t all men. 😀
Seriously, the stereotypes are overplayed. Not everyone is a hoodie-wearing, hard-core developer, dialed in and programming all day. There are a variety of career paths in technology — I’ve done everything from business analysis, to development and testing, to project management, to customer success. Sometimes people take too narrow a view of working in IT and assume it isn’t for them. There is actually a lot of variety, both in roles and increasingly, in terms of people.
What tips would you give to someone aiming for a c-level position? Be Patient. Seek and find the right opportunities. Taking any position simply because it’s one step closer to the c-suite can be fraught with challenges. Instead, carefully work to gain a level of experience and competence that will allow you to seek, find and evaluate the right c-level position, at the right company, at the right time. It will be worth the time and effort.
What are your career ambitions and have you reached them yet? Is it ok to say “I don’t have ‘career ambitions?’”
I prefer to concentrate on life ambitions — and those have honestly changed over the years, and encompass a lot more than just work. I think there are some people that can aim for the c-suite from the start, often because they’ve had exposure from mentors, family and others to high-level management and understand what these roles entail.
That wasn’t the case for me. I have figured out what I want as opportunities presented themselves, and the corresponding ambition grew over time. For me the process has been a series of stops along the way:
I started in my 20s, just trying to figure out what careers were available in IT. Then, I deliberately changed roles at FedEx every few years to learn different skills and figure out what I liked.
In my early 30s, my goal was to find and maintain reasonable work-life balance. I had young children, but was also ready for the challenge of stepping into management.
In my mid-30s, I was fortunate to have a husband that agreed to put his career on hold and stay at home with our children so that I could lean into my career. That’s when my ambition to be in executive management really took hold. I could devote more energy into work because I had very few other responsibilities thanks to my husband’s focus on our family.
Then in my early 40’s, Chief Client Officer (CCO) started to be a more common title. I knew that was where I wanted to be — a sweet spot that made perfect sense given my experience and interests. In fact, when I interviewed at Testlio, I told our CEO Steve that I wasn’t really looking to become CEO — but really wanted to grow into CCO. And here I am (but still growing).
Again, what has always been most important to me is life ambitions. My first priority has been to have a happy, healthy family that spends time together, that values and gives back to our community, and puts kindness and compassion above all else. Career ambitions have always been second to that and always will be. In a way, the two have come together; my family values align pretty well with Testlio values.
Do you have a good work life balance in your current role? Arguably more than I’ve ever had at any point in my career. Testlio practices something called “distributed by design.” We all work remotely, but just being “remote” is not enough. The way that a company empowers and connects its remote workforce matters. We all commit to being engaged and responsive, especially during standard business hours, but we also have a high degree of flexibility in terms of when and where we get our work done. We each design our own workdays and work environments.
For example, everyone is free to work from anywhere within a few time zones of their home region — which is tremendously popular for those who like to travel. For others, the concept of porosity is important. Days at Testlio are naturally porous — people exercise, practice an instrument, visit friends and family, take care of medical needs, and do other things during “normal” work hours without a lot of over communicating and overthinking. We just trust each other to do the right thing. This provides a huge advantage for people with families in particular.
My calendar, for instance, lists every one of my children’s activities (generally softball and baseball games). That time is blocked. I “leave the office” regularly at 4:30 to make sure I’m present for them. It’s important that this be a ‘top down’ part of the culture. If I do it, my large team can feel empowered to do it too.
What, if anything, would you change about the route your career path has taken? Honestly, I don’t think I would change anything. As I look back at every portion of my journey, each stage has provided invaluable insight, experience, and connections with people.
Which would you recommend: A coding bootcamp or a computer science degree? This is hard, and probably depends more on the individual and how they learn. For me it would be a computer science degree. The way I absorb and understand information requires me to have a solid grasp on fundamentals and big-picture thinking. I feel like computer science gives you all of that — and then picking up the coding skills is easier because you have all the context.
How important are specific certifications? That will always depend on the role and the responsibilities. I do look at this on resumes for specific roles that benefit from credentialing, but more often than not, I consider certifications because they can help me understand where a person’s interests and skills might lie.
What are the three skills or abilities you look for in prospective candidates? Curiosity — above all, tech is always changing. What you learn in college will be irrelevant in a few years, so you have to stay curious and keep learning
Grit / Determination — if you’re going to brand yourself well, think about what stories, activities in life show can stick with something when its hard and find thoughtful solutions to problems that don’t have predetermined answers
Sharing Your Journey — Can you tell a story about your journey that paints a picture of the full person? What have you learned; why it has unfolded as it has; what is important to you. Good managers, the ones worth working for and with, usually hire the full person, not just their skillset.
What would put you off a candidate? Any sense of entitlement or arrogance. Being humble and kind (while also being confident) speaks a lot to how someone will interact with a team. I dig deeply for those character traits in an interview. This ties back to that initial point of being brilliant, and also someone that people like working with.
What are the most common mistakes made by candidates in an interview? How can those mistakes be avoided? People often aren’t able to articulate their journey as a coherent story. It comes off more like a series of “victory vignettes” instead of a narrative.
It doesn’t matter if your career journey is a straight line or full of winding curves — there is still a reason behind it, and a candidate should be able to articulate that. And, as we practice telling our story, that provides space to reflect on where you’ve been and where you want to go next.
Do you think it is better to have technical or business skills – or a mix of both? Both, 100%. I’ve found the most valuable team members are those that have a technical understanding tied to keen business acumen. It is rare to find those two things tightly paired together, but it’s a powerful combination.
Copyright © 2023 IDG Communications, Inc.

source