Q&A With Harvard Alumnus, Jack Plotkin

September 12, 2019 - By 
Jack Plotkin

With an appetite for knowledge and a drive for success, Jack Plotkin has continuously found himself at the forefront of emerging technologies and industry change. Jack, a graduate of Harvard University, has spent nearly 20 years working with healthcare companies and almost seven years in the cauldron of healthcare’s technological advancements. In that time, he has become a recognized industry thought leader and a driving force behind cutting edge healthcare technologies.

We had the pleasure of sitting down with Jack for an exclusive interview to discuss his life and work:


Where did you go to college?

Harvard, or as some of my fellow alumni refer to it: that little school in Boston.

What was your favorite course? Why?

My favorite course outside of my major was a class called Art and Architecture. It opened new horizons for me and gave me a newfound appreciation for culture, aesthetics, and history.

Who was your most influential educator? 

Even though I went to public schools in California, which was ranked near the bottom in quality of public education at the time, I was blessed to have several exceptional teachers. My sixth-grade teacher recognized talents in me that I didn’t know I had. She nurtured and supported them, taking a shy kid and building up his self-confidence. My ninth-grade teacher kindled and directed my love for writing. In high school, my physics and English teachers pushed me to dream big, work hard, and reach for the stars. I am eternally grateful to all of them.

Do you feel that your education adequately prepared you for your career?

I believe that the purpose of a liberal arts education is to prepare a person for life, not a career. In that sense, I’m grateful for everything I learned at Harvard, both in and out of the lecture hall. I left with a wonderful foundation upon which to build a career.

And how did you choose the career path you’re on?

I have always been interested in both business and technology. At Harvard, I pursued a minor in computer science. On Wall Street, I built complex models using a variety of programming languages and analytic tools. Technology is reshaping humanity’s future in unimaginable ways, but to be truly transformative, it has to be tied to a solid business strategy and coupled with effective execution.

What do you think brought you to your current position?

I graduated in 2000 and, like a number of my classmates, joined a leading investment bank. While there, I had the opportunity to advise Fortune 500 firms on billion-dollar financial strategies and transactions. Some years and title changes later, I decided to pursue an entrepreneurial career at the nexus of business and technology. I built a successful online publishing and digital advertising business, then opened my own advisory and investment company to develop start-ups and consult established companies. It’s hard to believe that I have now been CEO of my own company for more than seven years. I am most proud of our impact and opportunities to make a tangible difference.

What are some of the professional challenges you have faced, and how did you overcome them?

In the early stages of my career, key professional challenges had to do with solving large-scale problems in the context of hyper-aggressive investment banking timeframes. A typical example: I was asked to build a model for a multi-billion dollar insurance portfolio for one of the largest financial companies in the world. I was handed reams of data and four weeks to do it even though at the time I knew next to nothing about the insurance industry. As you can imagine, work/life balance was a challenge, as I worked 80 plus hour weeks and was routinely in the office on weekends and holidays, including Christmas and Thanksgiving. But I persevered because I believed in the value of what I was doing and enjoyed the intellectual rigor of the work.

Later in my career, the professional challenges took a more strategic tint. I had to advise companies on difficult decisions, including large-scale resource commitments, product pivots, high-stakes contract negotiations, and personnel rightsizing. The key to overcoming these types of challenges was problem-solving in terms of the big picture and ensuring all tactical decisions were consistent with an overarching plan.

What would you consider the most significant accomplishment in your career?

Being an original member of the team that built VirtualHealth from a two-desk start-up to one of the 40 fastest-growing companies in North America according to the Deloitte Fast 500. Not only did the company revolutionize healthcare technology, but it profoundly improved how healthcare is delivered to millions of the most vulnerable patients across the country.

Getting more into the day-to-day, what is a typical workday for you? How do you start your day?

I may be in my home office, at a client, or on the road but the routine is generally similar. I start by going through my emails and messages. After that, I get to work on the critical items on my to-do list, which include research, analysis, document reviews, and meetings.

And the rest of the day?

A crucial part of my focus is solving strategic issues across my portfolio of projects. This may involve formulating a business strategy or product design, engaging in contract negotiations or document reviews, building teams or mentoring leaders, or simply reading and writing things that hopefully have some lasting value.

Do you have any productivity tips that keep you motivated and grounded?

In my opinion, the key to productivity is the ability to maintain a single-minded focus on the task at hand. I like to say that I’m not a multi-tasker, but just an efficient serial tasker.

Tell us a bit about your workplace.

I work with a variety of clients, so I have exposure to different work environments. The diversity appeals to me – I have the opportunity to learn from different perspectives, and then apply those lessons.

How do you end your workday?

Jack PlotkinI’m not a punch-in, punch-out kind of guy, so my workday doesn’t have well-defined start and end times. I can be checking email first thing in the morning or jumping on a call after midnight.  I’m fortunate to love my work, so I don’t mind taking it home with me. Away from work, I try to spend quality time with family and friends, stay fit, travel, enjoy the arts, and do a bit of lighter reading and writing. Believe it or not, I am a published author of two fiction novels and am currently finishing a third.

What about weekend activities?

When my calendar and the weather cooperate, I like to leave Manhattan and get outdoors.

I want to talk a little about your industry as a whole. Could you describe the industry you work in?

As I like to say, I work at the intersection of business and technology. I get involved with companies that are either building new technologies or that have a reliance on specific technologies. I have had the good fortune to work with clients in a lot of different industries, including e-commerce, retail, consumer goods, finance, insurance, transportation, media, gaming, telecommunications, manufacturing, and energy, among others. However, the industry I have worked in the most is healthcare.

What is your background? What makes you an authority in this industry?

I first became aware of healthcare through advising life sciences companies, such as Merck and Pfizer, while on Wall Street. I became far more involved in the industry in 2012 when I had the good fortune to partner with VirtualHealth. Having spent nearly two decades working with healthcare companies, and seven years exploring the next generation of technology within healthcare, I have had the opportunity to make a real, lasting contribution to the industry. I don’t know if that makes me an authority – that’s probably a question for my colleagues.

What excites you about this industry?

Healthcare is the most significant sector of the U.S. economy and the single biggest contributor to a person’s quality of life. With technology, I believe we can make healthcare far more proactive – we can catch issues before they turn into chronic conditions or acute episodes. The social impact of working in healthcare is tremendous. I am privileged to see that technologies and products that I spearheaded are changing how care is delivered for millions of people

What’s the current state of your industry?

Healthcare is a highly regulated and, by its nature, a somewhat conservative industry. As a result, it tends to be slower to embrace new technologies. It is also highly fragmented, meaning that the rate of adoption is not uniform. This nature of healthcare makes it challenging to drive positive change, but it also makes the change that much more valuable. The good news is that right now a lot of technology players are trying to disrupt healthcare, and there is more forward movement than ever before. It’s an exciting time.

Who are some of the largest service providers in your corner of the healthcare industry?

The healthcare technology landscape is vast. Every year I go to HIMSS, which is the primary healthcare IT (“HIT”) conference. HIMSS is massive – it occupies the largest conference centers in the country, with thousands of vendors and a sea of visitors. Within HIT there are several exceptionally large vendor categories, such as electronic medical records, data management, population health, medical devices, and analytics, among many others.

How have things in your industry changed over the past 5, 10, 20 years?

Some of the most significant evolution in healthcare over the last couple of decades has arisen as a result of regulatory and technological changes. The Affordable Care Act expanded Medicaid programs and pushed both Medicare and Medicaid to embrace value-based care. This put additional accountability on health insurance companies to focus on health outcomes. In turn, this has driven an explosion in technologies seeking to help both payers and providers to better manage patients and improve care delivery.

What are some of the biggest challenges your industry faces? How do you see it overcoming these challenges?

Healthcare is an industry where change is difficult because the cost of every wrong decision carries such a profound impact. People put their trust in the healthcare system: in the knowledge of doctors, in the operation of hospitals and other facilities, in the financial stability of insurers, and in the accuracy of clinical data systems. As a result, healthcare decision-makers tend to be conservative when it comes to introducing new technologies or approaches. They require credibility and validation. This makes it challenging for new companies to break into the industry and can have a dampening effect on existing companies’ willingness to innovate.

I believe the key to course-correcting healthcare’s understandable inertia is through a combination of regulatory change and thought leadership. The good news is this is starting to happen in many parts of healthcare.

What does the future of healthcare look like to you?

The future of healthcare has never been brighter. There is more knowledge and more technology to support the optimal delivery of care. Value-based models are forcing both insurers and providers to focus on being increasingly proactive in how they think about the patient journey. New healthcare technology start-ups are appearing more and more to challenge the status quo and usher in new ways of thinking.

In the coming years, healthcare is going to become increasingly personalized and digitized. People are used to having end-to-end digital journeys for everything from banking to fitness. Why not for healthcare? There is an increasing focus on the concept of patient engagement in healthcare resulting in everything from patient portals for viewing prescriptions and labs to automated text messages for appointments to connected devices for tracking vitals.

What advice would you give to those looking to enter this field?

You are ultimately working to help patients, so be patient. Do not be discouraged by setbacks and take advantage of every opportunity, no matter how small, to evangelize and showcase the impact of your innovations. The mantra of doctors is to “do no harm,” which means they, and the industry, are going to be hesitant to adopt a new technology or approach until it is proven and validated. The key is to find ways to show the benefits of the innovation within the context of an industry that is literally in the business of making life and death decisions daily.

The other major piece of advice I would give is to take the time to understand the regulatory rules and operational approaches of the industry. Before you can improve upon the landscape, you must understand the landscape.

What makes your company a leader in its field, and why would your services be a benefit for someone looking for help?

My experience and proven track record in building technologies, optimizing processes, and delivering results across multiple industries provides unique positioning for solving the full range of business problems, ultimately resulting in increased revenues, reduced costs, and, most importantly, positive social impact. I’d like to think that there are many organizations I have yet to meet who could benefit from my experience and expertise.

What are some resources or books you think someone entering this industry absolutely must-read?

I have always told folks – only partly in jest – that everything they might need to know about the business and operation of healthcare is on the Center for Medicare and Medicaid Services (CMS) website. In all seriousness, it is a massive but truly invaluable resource. The sheer amount of information represented there can be overwhelming. Anyone willing to put in the time and effort to read and understand the key concepts presented on the CMS website would learn a tremendous amount of information about the field.

Of course, merely reading is not enough. The other part is direct experience with how operations are structured in specific sectors of the industry. Consulting can be an effective on-ramp in gaining this knowledge. Consultants are exposed to a broad range of companies and operational challenges and get first-hand exposure to how organizations go about delivering healthcare services.

Let’s shift gears a bit away from work. Where do you live and how long have you lived there?

I live in New York City. I moved here for work after graduating from college and ended up falling in love with the vibrancy, diversity, and endless possibilities of the city. I just never left.

How have you seen the city change since you got here?

Jack PlotkinManhattan, in particular, was more socioeconomically diverse when I first came there for my summer internship in 1999. The city has seen a lot of new development and the continued rise of young professionals and upper-middle-class families, which have profoundly altered the look and feel of many neighborhoods. And then, of course, there was 9/11. I was working a few blocks from the World Trade Center and the events of that day were a profound turning point for the city and for all of us who lived through it. It brought New Yorkers together and made us realize that, as a city, we could overcome the unimaginable.

What makes NYC special?

There are so many things that make New York City special. As the largest metro in the world’s largest economy, it represents an unbelievable melting pot of cultures, ideas, and possibilities. There is so much to see and do, from world-class museums to Broadway shows to new restaurant concepts – the list is truly endless. The people are known for moving fast, talking fast, and being hyper-focused to the point of rudeness. Once you get to know them, though, you realize how open-minded, compassionate, and personable most New Yorkers really are. For me, many personal firsts are linked to New York. My first job. My first apartment. My first Broadway show. My first view from the top of a high-rise. My first ride on a ferry. And, of course, the really important personal stuff, but we’ll save that for the next interview.

Moving to New York City, starting a successful company, working on changing the healthcare industry; you’ve done a lot over the course of your life. What is something that you struggled to overcome professionally or personally in that time?

I have always believed that people should be measured by objective standards rather than personal preferences. It was difficult for me to see people being promoted or held back because of their relationships with managers and executives, rather than based on the quality of their work. I struggled to fit into a corporate structure where politics and bureaucracy were the norm.

How did you overcome it?

First, I began to pursue more entrepreneurial opportunities, where I had the chance to build something on my own. Second, I tried to design processes and cultures that would support innovative thinking and result-oriented incentives. Third, in working with clients, I tried to empower individuals and inspire them to change the status quo.

What was the best advice you received during that challenging time?

The best advice I received is that you can either complain about how things work, or you can do something to change it. There is a well-known quote: “you can get busy living, or you can get busy dying.” In the context of bureaucratic structures, difficult bosses, unfair practices, and so forth, I say it like this: “you can get busy complaining, or you can get busy changing.”

Is this still something you are battling or has the issue dissipated?

The ever-growing collection of business books are proof positive that the issue of politics and bureaucracy in business is not dissipating any time soon. The books on history, sociology, and anthropology make it clear that these things are a natural outgrowth of human social structures. So, I try to find ways to nudge my clients to a healthier way of managing processes and supporting teams while understanding that it’s a long-term process.

What advice would you give to others in the same situation?

The best advice I can give is to understand yourself. Understand your purpose in the context of a professional career. Then, proceed backward from that to figure out the type of organization and the sort of work that will empower you to self-actualize. There will always be aspects of work that will be tedious or unpleasant. If that represents the whole of your professional life, then you know you have to make a change. But to make sure it’s the right change, you have to understand what gives you that all-important sense of meaning and accomplishment.

What was the best piece of advice you’ve received?

I have been fortunate to receive advice and help from many different people from many different backgrounds. The most important lesson I learned is that you should always keep an open mind. Never assume that someone is not qualified to give you advice just because of their age or job title. Some of the best advice I have received was from people who were younger, or less experienced, or from a different profession or walk of life. Rather than judge the messenger, be thoughtful about the message.

There is a lot of growing throughout life, and a lot of advice to help us grow in uncertain times. Some people find their “calling” early out of college, while some don’t discover theirs until decades later. What was your most influential decade? 

My most influential decade to date was my 30s. I feel that I had matured to a point where I knew how to extract the most value from the lessons I had learned. It was also a decade during which I built several successful businesses with the help of those same lessons.

What lessons did you learn? Was there a role model you modeled your career after? Did you have a mentor that would give you frequent advice?

The most important lessons I learned professionally all had to do with how to start, build, and grow a business. Strategically, I learned how to develop and execute a business model, how to develop and lead a high-performing team, and how to get from capital to revenue. Tactically, I learned how the business should run; from product or service development to delivery to sales/marketing to account management to operations. I also learned a lot about the people, processes, and products that are likely to succeed.

Are there any lessons you learned that affected your life as a whole?

Because my professional life is such a significant part of my life as a whole, I feel that every lesson had profound impacts beyond work. By finding ways to work smarter and achieve better results, I was able to find a healthier work/life balance. Also, many professional lessons positively affected my personal life. Perhaps the most important of these was the ability to act tactically but think strategically. It’s easy to get caught up in the minutiae of daily life. I find that maintaining a long-term perspective enabled me to make better decisions, have greater patience, and respond to events in a more thoughtful manner.

What advice would you give to someone else in their 30’s trying to find their way?

I would advise someone embarking on their 30s to remain open to ideas and thoughtful about possibilities. I would encourage them to take the lessons they learned in their 20s to heart. To build a long-term plan, and then to make sure their actions are consistent with it and the kind of person they aspire to be.

It seems like you’ve really become the person you want to be, which brings with it a recognition of who you are and what you like to do. Along those lines, what is your favorite hobby?

I probably have too many hobbies, but two of my favorites are traveling and writing. I have self-published a handful of books via the Amazon and B&N distribution platforms, including two successful novels under the pen name of “Michael May.” Their titles are “Blindside” and “Sonora Sunrise.” I was pleasantly surprised to discover that, at one point, “Blindside” was ranked among the 50 most popular financial thrillers on the entire Amazon Kindle store.

How did you discover a love for writing?

I’ve always enjoyed writing, but I really fell in love with it in high school. I had a lucky streak of incredible and inspirational English teachers who stoked and nurtured my passion for writing.

I try to spend several hours each week writing, and several hours each day when I have the opportunity to get away for a few weeks. If I had unlimited free time, I would probably write for an hour or two most days.

I’ve been kind of shocked that thousands of copies of my books have sold, despite me investing exactly zero dollars into marketing or publicity. Some readers even left five-star reviews – my guess is that they’re either awfully kind or didn’t read the book.

You also said traveling was one of your favorite hobbies. How many countries have you been to? Do you have a favorite?

Jack PlotkinI have been fortunate to visit many amazing countries, including places in the Americas, Europe, and Asia – from Aruba to Austria, from Israel to Italy, and from Panama to Poland, just to throw a few alliterations your way. I absolutely don’t have a single favorite country, but I have a great appreciation for the beautiful cultures, characters, and cuisines in each of the countries I have visited. I try to stay away from the touristy places and get a real sense for the local way of life. It definitely gives you a new perspective.

Do you travel mostly for business, or are you able to get out for personal enjoyment, too?

I travel both for business and personal enjoyment, but even when I travel for business, I try to spend a little time exploring.

Do you typically travel alone or in groups? Do you prefer one over the other?

I enjoy both traveling with people and on my own, but they’re very different experiences. Traveling with others is a beautiful way to share the process of discovery and to grow closer. On the other hand, traveling alone offers an intoxicating feeling of freedom and limitless possibility.


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