As Head of Global Telecom Thought Leadership for Dell, Jillian Kaplan deftly balances a technical engineering background with a creative mindset. At times, those might seem like conflicting interests, and she admits prior employers were confounded by her and unsure of how to best utilize her full range of skillsets. “They’d just have me count beans and say they’re not paying me for ideas. I just thought that’s how the corporate world worked. Then I got to Dell and they embraced my inner nerd and creativity. They give us a lot more freedom to innovate … I don’t break the rules, but I don’t necessarily follow them either. I like to do things that aren’t necessarily the norm.”
After Jillian earned her technical MBA (while working full time), she assumed her educational journey was over. (She even threw herself an “I’m never going back to school” party to mark the occasion). However, once you speak with her, it quickly becomes obvious she is not someone content to sit still and take the easy route. She is someone who is constantly looking to challenge and better themselves— and as we know, learning is a life-long process.
Back to school… again
As she worked towards her current role, she realized it might be beneficial to strengthen some skillsets for the future. She didn’t have to look far before deciding on MIT Sloan Executive Education. “I work in high-tech; my undergrad is from a technical institution; I have a technical MBA—it just made sense to go to MIT.” (Another fun fact: both her parents have master’s degrees from MIT, her mother being one of only four female students at the time.)
Jillian started with one course and was hooked. She quickly realized the time commitment was manageable and the benefits were instant. “I did one course and I didn’t feel consumed by it … It was really refreshing for me, as someone that has a career, and a child, and a husband, and a dog. It definitely helped with the skills that I wanted to develop. The courses are so concentrated you can really choose your own path.” And choose her path she did. What started as one course in 2020 quickly morphed into earning an Executive Certificate in three different tracks: Management and Leadership, Strategy and Innovation, and Technology and Operations. Earning an Advanced Certificate for Executives (ACE) is only a couple of courses away!
Forging a path
Jillian’s role requires her to not just understand the products being launched by the engineering team, but also translate their impact and market their importance to a wide-ranging consumer base. As a result, she started her journey with Marketing Innovation. Led by Catherine Tucker, she found it timely and beneficial to her current needs. It also sparked her motivation to keep going.
“I took Managing Product Platforms: Delivering Variety and Realizing Synergies, which was great and really helpful with issues we’re going through at the moment as we try to be a platform in the industry. I’ve really been able to bring information back. I took it knowing it would be applicable, but it was very applicable.”
Other impactful courses included Communication and Persuasion in the Digital Age, Maximizing Your Personal Productivity: How to Become an Efficient and Effective Executive, and Data-Driven Teams: The Art and Science of Winning. All had the common denominator of being taught by MIT Sloan faculty Ben Shields. “I’ve taken a bunch of courses taught by Ben Shields … if he had a fan club, I’d be his number one fan. I took Data-Driven Teams just because he was teaching it—and I’m not even that into sports! He’s great!”
While it’s common to take courses of interest, Jillian also found it helpful to take a course in a subject matter she wasn’t necessarily interested in. Part of her role requires project management and she often encounters suggestions to pursue a broader project management role. “I took Managing Complex Technical Projects as a way to double check and confirm if it was or wasn’t for me.” She went into the course with an open mind, not wanting to discount a possible opportunity or career path without testing the waters. In the end, her instincts were correct. “Now if someone comes up to me saying ‘Oh you’d be good at project management, are you interested in this role’ I can say ‘no’ and have an actual basis for it.” When one door closes, it can open the door wider for other opportunities to explore. Now Jillian could continue to focus her energy on other topics of interest, such as extended reality (XR).
A dose of reality
After travel restrictions lifted and the world returned to a new normal, Jillian was able to take her first in-person course, Business Implications of Extended Reality (XR): Harnessing the Value of AR, VR, Metaverse, and More taught by Paul McDonagh-Smith. “This was a fascinating class. I thought we were behind in our XR initiatives, so I was there to learn how to grow. It’s definitely something we’re in the weeds with.”
"I want so many more women at the table... The reality of being a woman, in any field, is that we’re often not the majority. If you see them; you can be them."
Dell was supposed to open a new physical lab in 2021, but due to COVID supply chain issues, it didn’t open until earlier this year. At the end of 2021, already six months behind schedule, Jillian proposed building the lab in VR as way to bring people in. Aligned with her talented colleague to get the idea off the ground, her bosses gave them the freedom and the budget to innovate and implement. It proved so successful that even though the physical lab is now open, customers from all over the world still visit the VR lab. They hosted an extremely popular webinar about it and even brought it as a demo to tradeshows.
Knowledge at MIT is a two-way street. Paul asked her to present her case study to the rest of the class. “I gave a thirty-minute presentation on what we built and how. It went so well that Paul asked me to come back and be a guest speaker for the next session of his course this fall. I’m really excited! So, if anyone wants to take the course in September, you’ll get to see what we’ve built!”
Rise by lifting others
Let’s be honest, being a woman in tech is not always easy, and often you’re the sole female representation in the room. “I was struggling with my leadership capabilities.” Jillian mentioned she’s never actually had a woman as a boss. However, she’s quick to note she works for an extremely supportive group of men who give her space to find (and exercise) her voice. That allyship is equally important and meaningful.
When she discovered the new Women’s Leadership Program being offered, she realized she had to apply. When she was accepted, her bosses immediately approved the expense. The week-long course is an intense experience compared to the prior two-day courses Jillian had taken. Since she opted to commute daily from home, days were often twelve-hours long. There was also a good deal of pre-reading and homework required prior to attendance to help set the stage for what to expect in the classroom.
Once she got to campus, Jillian was impressed. “I don’t remember the last time I was in a room with 37 women. It was powerful to be with all these accomplished, supportive professional women. The professors were amazing. I was inspired. Everything was really positive, and I still have a lot of thinking to do.”
Prior to Dell, Jillian mentioned she would do great work, but not talk about it. That humility didn’t get her anywhere. When she got to Dell, she decided she’d be more transparent about her work and her goals, and opportunities flourished. Nothing had really changed regarding her capabilities; people were just aware of them now. It led her to co-develop a workshop—The Art of the Subtle Brag—aimed at helping women share their accomplishments.
Jillian (L) stands with Elsbeth Johnson (R) - MIT Sloan faculty and co-director of the Women's Leadership Program
“Part of the reason I enrolled in the Women’s Leadership Program was to become more of a leader and exemplify my skills, but also to bring other women with me. I feel a lot of times that I’m the female face of what we’re doing, and I want so many more women at the table. Attending was partly for selfish reasons, but also a bit of ‘How do I continue to pay it forward? How do we bring people with us so that maybe someday the world will be more inclusive?’ The reality of being a woman, in any field, is that we’re often not the majority. If you see them; you can be them.”
Jillian and the other participants left with homework. They were told to make a promise to themselves, on video, to accomplish a stretch goal by June 2024. Jillian’s commitment is to file a patent. (Now that it’s in this blog post, it’s an even bigger certainty.)
“Two things that I say a lot are 1) great things never come from comfort zones and 2) we rise by lifting others. I’m a big believer in that.”
What’s next?
Jillian hopes to take Digital Learning Strategy, another course taught by Paul McDonagh-Smith. She’s also managed to convince a co-worker to take the course with her because her role, focused on sales enablement and education, would benefit from the content. “I’ve been looking at others’ roles, seeing what might be applicable to them, and encouraging them to take courses. It’s all part of bringing people up with you. It’s just a part of who I am.”
By 2024, Jillian hopes to earn her ACE. “I never planned on doing this. And after the ACE? I don’t know. Maybe Ben Shields will inspire me to get a PhD! The more I learn, the more I want to learn. I’m super grateful—the programs have been fantastic.”
Advice for others
Jillian wishes she had started sooner. If you’re unsure of where to start, just take a course on a topic that piques your curiosity. You can take a course and be sated with one—there’s no pressure to continue, but the flexibility is there to craft something more robust. “Realize that it’s not all-consuming. You can still have a life, a job, a family, and take a course. I’ve gone very slow—just two classes a year. That’s comfortable for me financially and for my schedule.”
Lastly, whatever path you take for yourself, Jillian encourages you to share the experience with others. “Be proud of yourself for taking a class! Celebrate it! Brag! Invite a friend to join you. To me, there’s no downside to continuing your education.”
Learn more about Executive Certificates.
Contributed by Elaine Santoyo Goldman