HomeExecutive Career TransitionHow Your Next Executive Role Finds You With Shantanu Gupta By Gina...

    How Your Next Executive Role Finds You With Shantanu Gupta By Gina Riley

    You’ve had a successful career at the same company for many years. Exciting opportunities have kept you energized. You have been fairly rewarded. Despite the benefits and sentiment you’ve developed for some of your colleagues, however, you have many frustrations, and you can’t help thinking there is “more” out there. You’ve thought about leaving to try a new challenge, but there hasn’t been a catalyst extreme enough to force you to explore external options. You and your company have created a mutual gravitational pull that keeps you in place. You hold concurrent thoughts about the pain of leaving and the pain of staying.

    Does this sound familiar?

    Should you hit the boosters to achieve escape velocity? Or should you remain in orbit? What are the factors that force you to make a decision?

    This edition of “When the Executive Job Finds You” features an interview with Shantanu R. Gupta, Chief Executive Officer of Cascade Systems Technology, an Electronic Manufacturing Services company. Before CST, Gupta built his reputation for creating and scaling businesses and leading worldwide teams throughout a 28-year tenure at Intel Corporation. Aside from technology, his breadth of experience spans SaaS solutions for Healthcare, IoT, Communications, and Cloud and Media Processing markets. He holds nine architecture and design patents.

    My career movement seems to be based on where my curiosity has led me.

    This article brings to life Gupta’s positive, abundance mindset. It shines a light on the gravitational forces he experienced as he let go of one successful professional chapter to embrace the process of uncovering his next chapter.

    Please give me an overview of your career journey at Intel and bring me to what you do now for CST.

    I started my career at Intel in silicon design. I soon realized I wanted to work with customers and understand how the microprocessor products and silicon I had worked on were being used to create solutions. This experience led to an opportunity to run a marketing and customer enablement team for the first server group at Intel, which gave me exposure to our early server customers.

    I became intrigued about strategically designing and running a business and persuaded my manager to let me start attending strategy classes run by Stanford and Harvard.

    These turned out to be very useful and timely. I proposed a new server design idea around this time – and our senior executive said, “Hey, why don’t you go run with it?” He put me on his staff and gave me a couple of people to bring the idea to life and create a new business for Intel.

    My career movement seems to be based on where my curiosity has led me. This seemingly simple act of raising my hand to take or create new opportunities has been a bridge connecting one job to another. One of my favorite assignments was covering for a colleague who was out on sabbatical, which opened up new opportunities for me to learn and grow.

    I hit my stride when I convinced my management internally to fund a global lab solution. It was an organization I ran like an autonomous group, much like a startup. I had to hire my own team and scrap for resources. There were lots of ups and downs with the business and a lot of learning. I realized I enjoy creating, producing, and launching products. Intel taught me how to turn challenges into positive outcomes.

    Fast-forward, and I was in my last position for nine years and feeling burned out doing the same thing. I knew I had to make a change and go back to creating and launching products. I moved back to run server boards and systems marketing and created a new product idea that launched into a business. After the business got off the ground, I felt I was not getting the next-level challenging assignments, the culture was not suiting me, and I was not feeling valued. Those were the main drivers for why I decided to make a change.

    I didn’t want to spend any more of my life feeling frustrated. I was 52, and I thought, what if I took the jump and started something new? The worst that could happen is I won’t work again. I knew deep down that I would be OK.

    I knew if I did not make a change while Intel offered a lucrative retirement package, I would end up working on similar jobs for years and eventually be hauled out in a

    wheelbarrow. I had to ask myself if I wanted to do something different. Did I mean it? Was I worried about leaving the security of Intel?

    What was the last thing going through your mind when you thought to yourself, “I am going to say yes. I’m taking a retirement package.”?

    My wonderful wife, Jacqueline, came to the office and said, “I want to watch you say yes. You are waffling too much. You know what needs to be done, and you need to do it.”

    I was there for 28 years. I was raised at Intel. I grew up there. I had a great run at an amazing company. I kept trying to talk myself into staying by thinking I could make one more change and I’d be OK. I had to be honest with myself – it was time to leave.

    Also, my career coach had been listening to me say I wanted to run a small or medium-sized company and exercise all of my business muscles. I would never know what it would be like unless I left Intel. I had to listen to my heart, my gut, my coach, and my wife.

    It was not easy.

    Two months in, you knew retirement would not stick. What led you to the startup world? What was the driver?

    When I look back at my time at Intel, I asked myself when I was having the most fun and realized it was when I was doing internal startups.

    It utilized all of my skills – not just running one functional area, like marketing. I liked running strategy, planning, creating the roadmap, and overseeing product and design teams. I loved the creativity of taking a product through to launch and the challenge of running a business. I wanted to exercise all of those capabilities.

    I wanted to pitch, tell the story, create the messaging, positioning, and strategy. I wanted to be immersed in the business, margins, revenue, and details of the business itself.

    Working with four startups after leaving allowed me to do all of this. I learned so much about the challenges of a startup outside of Intel. I enjoyed diving into all aspects of the business. And now, running a manufacturing company, I enjoy going on the factory floor and finding the root cause for what is going on, analyzing our financial indicators, making decisions, driving sales, engaging customers, all of which allows me to exercise many of my different capabilities and “muscles.”

    When you started networking, you quickly found your skillset was not translating. You knew you had the capability, but your initial approach with investors wasn’t resonating.

    When I had conversations with VCs, they assumed coming from a big company, I was used to resources and would have false expectations of support I would not get. My transferrable skills were not obvious, and I learned how to express them to decision-makers. I also learned that what VCs cared about was not what I initially thought.

    I started to realize I had to reinvent myself outside the context of Intel, and my Portland network was extremely weak. My new reality was such that opportunities would not present themselves unless I dramatically increased my engagement with people.

    Over the next three years, I dove into learning about many different industries through my active work with four different startups – that had little to do with my high-tech experiences. They ranged from a patient-care management app, cleantech, nonprofit, and business-intelligence app for physician practices. Engagements with these startups kept me active and learning. I was constantly taking coffee meetings to understand what other people were doing and generating new conversations.

    So, you went through a deep dive, spending time working across a lot of different sectors. It was a bit of an awakening process, right?

    Yes! The awakening happened while I was consulting and working with these startups. I developed the good habit of writing things down. I would spend 6-10 hours researching, organizing, and preparing for say, a one-hour consulting call. I was always prepared to tell stories to show I understood their problems.

    My approach was well received, and I started getting repeat calls from people who wanted to follow up again and again. I wasn’t just responding to their questions – I had predicted what they wanted to know. I always wrote it down. I would connect and communicate through storytelling, not just strategy-speak.

    I used my internal startup experience and applied it to the businesses I was serving. It helped me refine my storytelling and connect with different companies.

    You invested time to understand your target audience’s needs and values so you could tell the right stories within the context of what they cared about. At the same time, you showcased your thought leadership, expertise, and transferable skills.

    Spot on, Gina! Do you know when I first learned that skill? When I first left engineering and entered the world of marketing. I realized I did much more effective presentations to customers when I gave them a chance to present first and listened to their problems. Listening first resulted in better positioning of the material on hand that resonated with the customer.

    I made it a rule for my team way back in the mid-’90s to let the customer present first when possible. It was a simple change, and it taught me to listen more!

    What led you to your first CEO job with CST?

    I had been looking for a CEO job, but I never saw one advertised – never once. I saw lots of VP jobs. So, I applied for a VP of Sales job. After talking with the chairman/owner, I realized the company might be ready for a change in leadership. I was persistent and stayed in touch. Sure enough, when the opportunity came up to hire a new CEO, I landed the role in a matter of three weeks. It was because I’d stayed engaged and interested.

    The job found me when the timing was right – following all the conversations that laid the groundwork for the opportunity to present itself. You have to keep your network up, even if you don’t know if it will bear fruit.

    Sometimes people feel desperate if it’s taking them a while to land a job. Sometimes they talk too much and oversell themselves. Your story highlights the importance of finding out what your target audience needs and cares about, so you can answer the right questions.

    I absolutely agree with you. There is another lesson I learned over the years, which is – don’t become too attached to the outcome. When you want an outcome badly – you start to oversell.

    The trick is wanting it and yet not being attached to that outcome. It is a mental thing that is difficult, but it needs to be learned by jobseekers. You need to be completely OK if this particular situation does not work out. It will be OK because you are OK with or without the job that you are seeking. Know that and believe it.

    When it doesn’t work out, know it’s not about you. It’s about something else. Have confidence, and don’t be too attached to an outcome. If it doesn’t work, it’s fine.

    You must have either faith or a deep sense in your bones everything will work out.

    Yeah, I guess you’re right. I believe or hope. I’m an optimist. No matter how bad it gets, I truly believe it’ll work out.

    I was lucky to work with a career coach who helped me face my fears by using a simple four-step process that I still use today. If I tell you there’s a grizzly bear outside – should you be afraid and run for your life? No? First, see if it is a bear that will eat you up. Is it true or your imagination?

    So, check your assumptions?

    Ninety percent of the time, it is your perspective and assumptions. If there is indeed a grizzly bear, ask yourself what you can do about it. Then, make a game plan.

    If I can’t do anything about it right now, I think, “What is the worst that can happen? If the worst came true, would I be OK?” No matter how bad it gets, at the end of the day, you’ll be OK. You can look at so many life stories of people who’ve gone through so much in their lives, and they are OK. The human spirit is incredible. We all have it inside of us. We have to trust it.

    How did mentors or sponsors play a role in your career progression?

    I had a hard time seeking help. Perhaps I wanted to be successful on my own merit. I didn’t overtly seek mentorship, but there were clearly leaders who I looked up to as mentors and observed how they conducted themselves, how they led, what they did or didn’t do. There were people I respected, like Pat Gelsinger (Intel CEO). I think of him as a mentor and a role model who taught me a lot.

    As I progressed through my career, I learned to look for “micro-mentors” or people who had deep expertise in specific functional areas. If they were very good at marketing, I would see what I could learn about marketing. If another person was exceptional at presenting, I would focus on learning that aspect of their expertise.

    I had mentors and advisors along the way, but sponsors played a bigger role in my career.

    These people identified what I could bring to the table – people who gave me exposure to senior leaders. I got an inside look at how they think and operate. I learned about boldness and risk-taking. When some of my sponsors started to leave Intel, it made moving into new roles more difficult.

    What would you recommend to leadership-level job seekers to be seen and heard in a crowded market?

    The first thing I recommend is network, network, network – and listen. Seek out alignments. Check your assumptions and adjust, because these conversations are dynamic.

    Second, offer help without any expectations. Don’t expect the outcome of your helping will result in a job offer. Have conversations. Offer your wisdom, your guidance, and your brain. Ask them, “Hey, you can think about it this way or that way?” or “Would you like me to spend time writing something up for you because I just enjoy doing it?”

    Prune your messaging and positioning because you don’t want to be an oversized or under-sized shoe. You want to fit “just right.”

    Coming out of Intel, sometimes I was over- or undersized. For example, I needed to learn how to raise money from a VC perspective. On the other hand, I’d done many other things. I had to figure out what size shoe I was positioning myself for and customize my messaging to fit. I learned not to go into conversations as an oversized shoe.

    I had to learn to position myself properly. I had to get people talking and listen to their pain points. Once I understood those, I could sprinkle in some of my relatable experiences to help anchor our thoughts together.

    I landed the job I have now by having conversations with the company chairman/owner and listening to what the company needed. While talking with me about taking on a VP of Sales role, I could hear the company needed to consider refreshing the leadership down the road.

    The third thing is not to become too attached to any particular outcome and test your fears. Don’t believe everything you think is true. If ten conversations don’t result in anything, it’s OK. Keep going. Keep staying busy. Keep networking. Keep exercising your brain and thinking about the things that excite you in your work. Keep producing.

    What do you recommend people do to be seen and heard in a crowded job market?

    Concentrate on adding value versus selling – we are measured on adding value. Make your intentions clear to the universe. Offer genuine help. You will get pulled in when the time is right. Don’t get hung up on the outcome because it takes you off the path you have to build. Create a pull strategy and hone your storytelling ability.

    Finally, grow your network, get engaged, offer help, and stay positive!

    I find your positivity, persistence, ability to listen, and the customization of your messaging based on diligent research extraordinarily inspiring. You learned how to shape your narrative around your target audience’s pain points, which causes them to lean in and hear what you have to say. I know this is an honest message many aspiring leaders need to hear. 

    Thank you so much for sharing your career story, Shantanu.

    Gina Riley
    Gina Riley
    Gina Riley is an authority in career transition at the powerful convergence of career coaching, executive search, and interview skills training. She created the Career Velocity™ system to help leaders and executives effectively manage career transitions. Inspirational writer and speaker, Riley is a certified YouMap® coach who also consults for Talence Group Executive Search.


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