Vivek Kartha’s Path to CEO and Why He Never Stops Learning

Vivek Kartha is a CEO-in-Residence (CIR) at Alpine Investors where he’ll soon be leading an Alpine portfolio company with the backing of Alpine’s proven playbook. Previously, Kartha was CEO at WorkSpace, a cloud-based software platform for commercial real estate, which is backed by Alpine Software Group (ASG), Alpine Investor’s software platform. He was placed in his first CEO role through Alpine’s CEO-in-Training (CIT) program which brought him the executive experience that will serve him as a CIR. In sharing his story, Kartha reflects on his career path by sharing the traits, experiences, and learnings that got him to where he is today.

I was never sure about what I’d do with my career. There was a time when I thought I was going to be a physicist, then the next great American author, and later a chef. But one thing that has been with me since childhood is my obsession with “why”. I can’t help my desire to know why things are the way they are, and I’ve certainly never been satisfied with explanations that came short, much to the terror of my teachers and parents. That obsession drove me to study philosophy in college where I could ask “why” all I wanted. I also studied economics, where I looked at how trade, commerce and markets were formed throughout the world. Combining these two subjects laid the groundwork for looking at business with deep curiosity.

I started my career as a product manager at Progressive Insurance. There, my natural predisposition to ask “why” served me well. Why did this product do better than that one? Why did this price increase work when others failed? Why does this team perform better than that one? I was lucky to be called on to help with several pricing, product, and distribution challenges, culminating with helping our sales team sell trucking insurance in Oklahoma. I got a rush from building my reputation as the guy to work on tough, ambiguous, and thorny problems, so strategy consulting became a natural next career destination. After a brief, but intense, stint with Deloitte Consulting, one of my clients offered me a unique opportunity to join an M&A team at AIG. I jumped at the chance.

At AIG, I was lucky to be in the right place at the right time and follow my curiosity. I overheard our CEO in an elevator bank questioning the company’s presence in the tiny country of Papua New Guinea. Over the next several months, my team diagnosed our massive global footprint to help rationalize and streamline our international presence. That work turned into leading corporate development efforts in Latin America, which in many ways was my dream job.

Finding My Fit with the CEO-in-Training Program

Even after a wide range of experiences, I wasn’t sure what to do next with my career, so I enrolled at Harvard Business School (HBS) to help narrow things down. I knew I’d enjoyed leading a team and business unit, but I wasn’t sure if that would manifest into a role as a GM, in running my own startup, or something completely different. After trying out my hand at a Colombian venture capital fund and a coffee startup, I spoke to a career counselor at HBS and expressed my frustration after exploring what felt like every avenue. He suggested that I look at all the companies recruiting on campus and pick some that I’d never think about applying to– and then apply anyway. The idea was to lean on my curiosity and give something new a shot, which always had a way of working out for me in the past.

I never considered private equity before, so I decided to apply to Alpine Investors’ CIT program. My first discussion was with Matt Moore, a partner at Alpine. Matt was interested in learning about me beyond what was listed on my resume. He asked me questions about my upbringing, my friends, and family. When he did ask about my career, the questions were different from those in traditional interviews. Matt wanted to know what I uniquely brought to the table. He wasn’t looking for people who were part of a fast-moving river or who were products of wildly successful environments. Instead, he wanted to know who I was and how I uniquely created value. It was clear that Alpine was looking for confident people who could drive outcomes instead of focusing on accomplishments listed on a resume. I was hooked.

It was clear that Alpine was looking for confident people who could drive outcomes instead of focusing on accomplishments listed on a resume.

I decided to go through the interview process with Alpine, and soon after spoke to several partners at the firm. It stood out to me that each of Alpine’s leaders brought the same unique combination of humility and intensity. Not only was Alpine’s team generous with their time, but there was consistency in everyone’s approach.

While interviewing, I was invited to explain what I was looking for. First, I wanted a role where I had the burden of responsibility. I didn’t want the option to pass the buck to someone further up the chain of command. Second, after being close to the ebbs and flows of a public board at AIG, I wanted to learn the art of successfully managing a board. And third, I wanted to manage people when I had no idea how to do their job. For me, that meant managing engineering staff having never been a software developer myself. The Alpine team assured me that the CIT program could uniquely give me all three things immediately after I wrapped up at HBS. That made the decision to join an easy one.

How the CIT Program Helped me Help WorkSpace

The CIT program delivered exactly what I asked of it. The Alpine team never promised me anything overly specific, such as the revenue of the company I’d run, the number of people I’d manage, or the volume of acquisitions I’d do. Instead, they committed to help me develop those three skills I asked for during my interview, and all three happened during my early years as CEO of WorkSpace.

Alpine offers a Playbook to its portfolio leaders with best practices on how to run a business and access to Playbook experts who can help create and establish processes. I approached the Playbook with some skepticism, thinking that I’d be best off with trial and error. But, in many cases, I eventually realized that the Playbook could have saved me valuable time and energy.

The Playbook areas I used the most were around hiring and people management. One critical discovery was the exponential effect the first few hires can have on company performance. Early in my tenure at WorkSpace we were hiring about 10 open roles on a small team of 20. At first, I was the main person covering hiring, relying on selling myself to win new talent. Once we filled our first few roles with great people, the change was staggering. Through the interview process, our candidates were energized by meeting a series of like-minded, high-energy, optimistic people. Every additional hire we got right was a powerful, positive influence on the next. Soon, I was removed from most of the hiring process and realized the roster of talent we’d added was our biggest selling point to new candidates. Using Alpine’s hiring playbook taught me the incredible importance of getting the first few hires right, and to never let up on standards for the sake of expediency. I’m proud that we’ve set up an environment and brought in people who can do what they do and be incredibly successful when we give them the space to do it.

Lessons like these are easy to consume from afar, but impossible to internalize until lived through experience. Getting into a hands-on operating seat right after business school allowed me to practice MBA theory in the real world, quickly. Successfully leading a company, top to bottom, is a far cry from producing slides and Excel models. It’s much more about respecting, understanding, and motivating people of different ages, experiences, and educational backgrounds. Testing your values, patience, and consistency is best done in practice, and while I’m far from perfect, I’d be much farther behind the curve without getting into a CEO seat as early as possible. To my knowledge, there aren’t many firms willing to give a 30-something-year-old that chance.

It’s much more about respecting, understanding, and motivating people of different ages, experiences, and educational backgrounds. Testing your values, patience, and consistency is best done in practice, and while I’m far from perfect, I’d be much farther behind the curve without getting into a CEO seat as early as possible.

Making the Move from CIT to CIR

The way I’ve found joy and wonder in life follows a similar refrain: throw myself into the deep end, learn as much as possible, and always remain open-minded. Returning to Alpine as a CEO-in-residence to lead a business in a new industry, facing new challenges, with new people continues that pattern. It’s made even sweeter that I get to work with investors I respect and trust. More than anything, I can’t wait to leverage all the hard-earned lessons from mistakes I’ve made in the past to be better the next time around.

Alpine’s executive leadership programs are a unique experience. To go through it successfully, you must understand the opportunity that’s being given, invest your energy, and lean into it. It’s not perfect for everybody, but for those who take the plunge, you get the opportunity to be the executive of a company right out of business school. That’s not exactly common. But it’s made possible because you’ll be backed by a team of exceptional individuals that truly care about the people they work with.