Introducing Gigster’s New CEO Phil Fasano: Hall-of-Fame Tech Leader and Remote Work Convert – Part 1

Someone who knows Phil Fasano well once told him there are two types of people in the world: the type who run away from fire and the type who run into burning buildings. Fasano counts himself among the latter.

Long before the term “digital transformation” became part of business lexicon, Fasano was demonstrating what that meant in practice, helping companies large and small in different sectors of the economy tap technology to revive – and in some cases even rescue – their operations.

Over the course of four decades, the roster of companies where Fasano left his imprint as a top executive includes AIG, Kaiser Permanente, Capital One, J. P. Morgan Chase, Deutsche Financial Services, and Bankers Trust. After a career harnessing technology to make products and services more affordable, convenient, and accessible for customers, Fasano was inducted into the CIO Hall of Fame in 2017.

Now Fasano is thrilled to take on his latest challenge as the new chief executive officer at Gigster. We caught up with him last week to talk about his plans as well as his views on the future of distributed work, the evolution of startup cultures, and the special sauce that Gigster brings to help companies manage software talent in this extraordinary time. 

Q: You’re a New York guy. Where’d you grow up – the city or the boroughs?

Long Island but I spent most of my time in the city. So, I guess I can claim the title of man about town, as they say.

Q: Yankees or Mets?


Q: When you were younger, did you give much thought about what you’d like to do professionally?

Technology seemed like a good path. There were a lot of indicators back then, or enough that I got interested. 

Q: And it later led to you getting a degree in computer science from the New York Institute of Technology.

Just so you know, I didn’t go to college intending to get a computer science degree. I was in my first math class and found it to be a waste of time. It was way too easy, so I asked to speak to the head of the math department. The professor in charge of the department had me take an aptitude test and when she got back the results, she looked at me and said, “You’re a computer science major.”   

Q: When you began studying computers in the mid-1970s, they looked a lot different than they do nowadays.

Punch cards and Xerox computers. I programmed on Sperrys and on IBMs with Fortran and COBOL as the primary languages.

Q: There’s a story that one of your college statistics professors inspired you to explore fields beyond technology to broaden your knowledge. Can you share that anecdote?

Based on his recommendation, I ended up going to Wall Street and worked in the financial industry, programming again. After being there a brief while, it became very evident that getting a graduate education in finance was a good idea. So, I ended up getting my MBA at Long Island University, commuting back and forth in the evenings for night school. Both degrees served me quite well over the years, everything from what I did on Wall Street, to what I’ve done since as a business executive.

Q: Let’s talk about that. You’ve done a lot of work in financial services and then parachuted in for a tour of duty at Kaiser to fix their problems. As you look back on those experiences, what can you apply to your new role at Gigster?

I’ve always dealt with very complex organizational technology and company challenges. Part of company leadership is thinking about the strategy of the organization, driving outcomes, sales, marketing – all the disciplines – and I’ve been involved in every one of them.

So, at any point in my career, I have had P&L responsibilities for hundreds of millions of dollars of business. I’ve had very big decisions that have changed the directions of companies – including one that’s today an $80 billion company. You make decisions and try to be as thoughtful as you can about each of the challenges. At this point in my career, there’s very little that I haven’t seen and there are very few decisions I haven’t had to make. I’ve been one of the top three or four people at major companies where you’re in the room all the time and your opinion counts and has to be heard – and you have to have one. So, from that perspective, I think all of those skill sets come to bear here, for sure.

Q: Do you consider yourself to be a disruptor? You were once described as the Steve Jobs of healthcare.

I think they said that because when I joined Kaiser, the early headlines were brutal. The view was that there was no way someone without healthcare experience could be the CIO at Kaiser Permanente. 

Kaiser was an organization filled with challenges and they needed a steady hand, someone who in a crisis wouldn’t tip over. They had a CEO who knew he wasn’t getting the outcomes that Kaiser needed from technology. He and I became great partners. And after a year and a half, when we’d solved the biggest issues going on with the company’s medical record systems, I had confidence that we were beyond those issues. The larger opportunity was to transform healthcare. From that point on, that’s why I was there. It wasn’t just about Kaiser. It was more important for me to show what healthcare could be.

And I happened to have a CEO and a board who were extremely supportive. If I said we should spend $500 million on “X” because we would get great incremental value for the company and it would matter to our members and our patients, there was a lot of credibility behind that statement. So, we did it. And we managed to do something that completely changed people’s perception of how healthcare could be. People can call it disruptive. I actually would say that it’s really about building a great business and a great outcome for everyone involved.

Q: What are the challenges and opportunities before you at Gigster?

There are challenges, no question. But they’re mostly financial and those can be dealt with. We have great opportunities. When I look at this company and the assets created by its business model, Gigster’s time has come. Consider our technology and how it helps achieve the outcomes we get. I’ve had conversations with some of the greatest management consulting companies in the world and some of the biggest recruiting companies in the world and others and each one can see a fit for what we’re doing. The future of work is now in front of us. We’re living it. 

Q: What will organizations need to learn in order navigate their way toward distributed work environments?

There was the historic view that if you couldn’t see or touch something, you couldn’t lead or manage it. I grew up in that time and personally prefer to be in an office where I can walk down the hall and engage with my colleagues. But video has now become that way of doing it. And it works. It’s efficient. It lets us deal with geography, and frankly, we can be anywhere. As long as we’re awake, we can manage to work together. Now, building that relationship has become a little different. You’re talking to screens and not to the physical person. But the person is still on the other end and the psychology of dealing with people is still what it was. At the end of the day, the challenge is how to manage a remote work force and feel comfortable that you’re achieving the levels of performance that you should. And also figuring out how to motivate that workforce to do things that they never thought possible.

Q: You were once asked in an interview which tech vendor you most respected. You selected John Chambers who then ran Cisco. What about today?

There are some terrific companies and tons of great people in tech, but I would say Tim Cook. He’s managed Apple to a really great position, and I don’t think that’s repeatable. He also faced an extraordinarily difficult and leadership challenge in the face of a lot of public skepticism that he would never be able to be Steve (Jobs). Instead, he’s been Tim and Tim has been really good for Apple, and really good for those who buy their products. In the end, that’s all he had to be. And he’s done it in a very unique way that you can respect.

Q: In that same interview, you were asked if you weren’t a CIO, what would you be. You said the CEO of a midsize company. It strikes me that this is your first opportunity in a startup. So how do you view that challenge as well as the opportunity?

It almost doesn’t matter what size the company is. It’s really about the opportunity the company has. And when it comes to the opportunity with this company, the sky’s the limit. People have asked me, is it services or is it now the product or a platform? And I keep saying, it’s both. I really don’t understand how you could sell this platform without an immense amount of time and energy put in to help people understand it if you didn’t do the services.

Click here for part two of our interview with Phil.

Gigster Corporate Communication

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