My Career Path: Interview with Jaikumar Ramanathan, CTO, Midi Health

This month, we had the pleasure of speaking with Jaikumar Ramanathan, CTO of Midi Health, about his career path and the decisions that have contributed to his success. Here at Stage 4 Solutions, we are committed to supporting professionals’ career growth, and we believe that one way to enable success is by learning from leaders.

Jaikumar is an entrepreneur and engineering leader who has worked in different domains from digital health to social media. He is passionate about building products that are simple, fast, and delightful. His expertise is in first building and then scaling successful engineering teams and products.

Recent Career Summary:

• Midi Health – Chief Technology Officer 2022 – Present
• SAIVA AI, Co-Founder and CTO – 2018 – 2022
• Cura Technologies Inc., Chief Technology Officer, Co-Founder – 2015 – 2018
• Consultant – 2013 – 2014
• Twitter, Director of Engineering, Mobile – 2011 – 2013
• LinkedIn, Senior Engineering Manager – 2008 – 2011

Feel free to: connect with Jaikumar on LinkedIn

Can you tell us about your upbringing? Who were your role models?

Jaikumar: I grew up in Bangalore, India, until the age of 17, and then I came to the US for my undergraduate degree in Computer Science. When I was a sophomore in high school in the mid-eighties, my family and I visited Malaysia and there I saw ads for a computer called the Sinclair ZX Spectrum, made by a British company. It was a small rectangular device with a keyboard that would connect to a TV, and you could write programs in BASIC on it. That device looked really interesting to me. So, I pleaded with my parents to purchase it and luckily they did! After I got the device, I went through the entire manual to learn my first programming language. That was the genesis of my love affair with writing code.

In high school, I would organize late-night programming sessions with my friends. We had a great time building games and learning from each other. I wasn’t thinking of it as a career back then.  It was just something fun. In terms of role models, it was the early days of tech and I didn’t have any particular person that I aspired to be like.

When you were at Clemson University, what were your career inspirations?

Jaikumar: I didn’t give it too much thought. All I knew was that I really loved technology. I felt really fortunate that someone would pay me for doing something that I enjoyed. I think that is about as deep as I had thought about it.  Writing software to me was a very creative experience because in essence you are creating something new from some basic raw material very akin to woodworking and pottery, but in a digital world.

What factors led you to attend Stanford University to pursue a master’s degree?

Jaikumar: When I was in my senior year at Clemson University, I applied to a few graduate schools across the country, and I got accepted into both Stanford University and the University of Illinois at Urbana-Champaign. Both institutions have really good computer science programs. The difference between the two was that Stanford gave me no scholarship, whereas UIUC did. As you can guess, it was a tough decision to make. I consulted with my parents and my brother. The overwhelming sense was that if I wanted to work with computers, being on the west coast was the better choice. Financially, it would be challenging. But my parents were generous and said, “we can support you for the first quarter, and then you need to figure something out and find an assistantship through the university.” Knowing that my parents could pay for the first quarter was comforting, but at the same time, I did not want to burden my parents with that much of a financial commitment.

So I arrived a week before the fall semester began at Stanford, and started knocking on all the professors’ doors asking if they had any scholarships open. It was a bit late to be looking for teaching assistantships because they had mostly been filled earlier in the summer.  After talking to a lot of people, I finally met one who was kind enough to offer me a research assistantship for the first quarter. I was able to extend that into other teaching and research assistantships through the rest of my time at Stanford.

How do you think studying at Stanford University vs. the University of Illinois affected your career?

Jaikumar: I think the decision to move to Stanford versus Illinois was pivotal. It helped me in spades for a few reasons. The first was the boost in self-confidence from landing an assistantship and scoring an associated scholarship. The second was the circle of peers at Stanford who became friends and subsequently helped my career. We have learned so much from each other over the years. You see what your friends are doing and where they go in their careers. There is a lot of learning by osmosis. I think the third reason, which is super important, is just being in the right place—Silicon Valley—at the right time. For anyone in tech, there has not been a better place to be than the Bay Area over the last 25 years. It has been the very center of two huge disruptions: the internet in the early 1990s and mobile starting from 2008.

How did you decide on your first job?

Jaikumar: When I graduated from Stanford, the two big companies in the Valley were Oracle and Sun Microsystems. I got offers from both. Sun Microsystems was a rising star at that point. It was newer, had just gone public, and a lot of my peers were joining it. That was the basis of my decision.

As you progress throughout your career, how did you assess new opportunities?

Jaikumar: Early on in my career, I picked roles and companies where I could focus on deepening my technical skills. And then I realized that successful companies don’t become successful because they necessarily have good tech. A lot more depends on the market that the company is in and its go-to-market strategy. So in the second phase of my career, I assessed new opportunities based on how successful I thought the new company would be. Now I’m in the third phase. I base my decision on how passionate I am about the domain and whether I feel the company can make a meaningful difference within it. That’s why I’m currently focused on the healthcare space.

You were an early employee at Healtheon, Linkedin, and Twitter, how did you know those companies would become successful?

Jaikumar: When I joined LinkedIn and Twitter, it was really easy because they were in hyper-growth mode in their user base. I think at that point any reasonable person would see that those companies would get a lot of users. Then the next question is “They will get a lot of users, but will they be a successful company?  Will they keep growing revenue at the same rapid rate? Will they be profitable?” I think that’s where you have to take a leap of faith. I trusted what the market was saying at that point: Eyeballs will translate into ad dollars, which proved to be true on the revenue side.

What has surprised you the most in your career?

Jaikumar: I think one of the important things that a lot of people discount is being in the right place at the right time. The rising tide lifts all ships. So, if you were in Silicon Valley in the 1990s and 2000s in the tech industry, you are now doing just fine because you have been through two great disruptions that have propelled the industry. Living in the Bay Area also gave me a lot of connections not just in my company but in my industry. You learn from your peers at your company and at other companies, and that’s what ends up driving your career. So, if you are working in a domain and are not at the center of gravity of that domain, I would recommend that you physically move to where that is (Southern California for entertainment, New York for finance, Bay Area for tech, etc.)

How do you think location plays into careers now in this “post-Covid” world?

Jaikumar: Maybe I am old-fashioned, but I still think location makes a difference. I don’t think you have to go to the office every day, but I have noticed that the best ideas come out when you are brainstorming in person. A lot of great ideas get generated serendipitously when you are talking to the person who is sitting next to you or when you get coffee in the break room. These interactions are very hard to mimic over technologies like Zoom. 

So, I do think that location still matters. And I think early on in your career, it is even more important that you try to work physically in the office.

Now, companies are trying hybrid and other models. I think it is nice if you have a hybrid model where there are certain fixed days for people to go in.  A hybrid model where everyone can go in whenever they want is really not that useful as people aren’t guaranteed to meet as a team.

Can you tell us about an important career risk you took?

Jaikumar: Early in my career I was at Sun Microsystems for more than five years and things were fairly comfortable for me. Netscape had just come out with its browser and there were many startups building companies that delivered goods and services over the internet. All kinds of new business models were happening in the Valley. I could have just stayed at Sun and it would probably have been fine for me. But I decided to leave the steady employer and join a company that was booking online airline tickets. That job isn’t even on my resume, because I only stayed there for a couple of months before joining BroadVision. But it was important because it taught me to guard against complacency. Leaving Sun to join the madness that was ha​​ppening on the internet made me comfortable taking other risks, including leaving larger companies to start something on my own. I think when you feel yourself going on autopilot, it is fine to continue for a little bit, but not for too long.

How do you balance your professional and personal goals?

Jaikumar: I try to stay fairly well-rounded. I have a lot of different interests from tech to medicine to business to psychology. I have attended courses at Stanford about psychology of user behavior and persuasion, social media, and healthcare.

What I have noticed counterintuitively is that the best ideas come to me when I am not working. In fact, working too much can be a detriment to generating new ideas. When people learn, they use two modes of thinking, the focused and the diffused mode. Focused work is when you are “in the zone” and time flies by. This happens for example when you are writing code to solve a problem, writing an article, etc. But, then sometimes you find yourself trying to solve a really hard problem and you don’t know how to proceed and you find yourself just banging your head against the wall. This is when it is best just to stop working and do something else—take a walk, work out, play tennis, whatever. Haven’t you noticed that sometimes the best ideas come to you when you are in the shower? This is the diffused mode of learning. Your brain is still processing stuff in the background and connecting the dots. Just noticing those kinds of things has helped me realize that you don’t want to be working all the time.

What advice would you give to your younger self? Younger professionals?

Jaikumar: There are three pieces of advice I would give. The first is to become a self-learner. You are responsible for your own career and there is no company that is going to take care of you. You need to do that yourself. And I’ve found that the best way to learn is by reading, and in particular long-form as opposed to reading articles on the Internet. I think the Internet has taught us to consume information in bite-sized chunks and there is a bunch of noise and chaos that happens in the short term. You want to try to distill the signal from the noise and books generally have the advantage of giving the author a longer period of time to see the common patterns over time. Try to read far and wide to broaden your horizons into areas that interest you.

The second piece of advice is to try to find a group of like-minded peers who can support each other. I am a member of a group of friends and we meet every two months or so in a fairly structured format. What is really important about our meetings is that we share our goals, our progress, challenges, and difficulties and learn from each other. You realize that what you are going through is nothing unique. All your friends and peers are going through similar challenges, and you see the ups and downs. As the Buddha said, “Nothing is permanent. Everything changes.” So whether you are going through your greatest wins or really difficult times, everything changes. It is really helpful for me to have this formal meeting structure to discuss things and get advice from a trusted group. We also have a follow-up once a week where we pair up and just call each other to help keep us on track.

The third piece of advice is to discover what makes you happy and identify a role where you find that happiness. I was very fortunate as I discovered what makes me happy—technology and programming—at a very young age. Even to this day, I still code about 30 percent of my time, because that’s my happy place.  At the same time, I like going broad because I enjoy working on all aspects that make a business succeed.  For me to be able to go both deep and broad, I realized I need to work at an early stage company because that is where I can wear many hats.