WebMD Chief Technology Officer
Hofstra University B.A., Finance and Banking
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How did you get to where you are today? What is your story? What incidents and experiences shaped your career path?

Summarized By: Jeff Musk on Tue Oct 13 2020
s o. I had an interesting path for sure. So I've always been a, uh you know, I guess it's OK to say, you know, geek as a kid, but spent my life with computers, so always had computers in the house. I was coding when I was 10 years old on DSO spent a lot of my time that that wasn't spent directly in school doing school stuff. I spent a lot of time on the computer. So when I branched into my first job, which was at Goldman Sachs, um, I was actually there as a help desk. Kind of helped us support person. So I did a center here, Um, so as a help that support person, I was the person that when you know, someone's Microsoft word flared up or, you know, they needed help within Excel Equation or something like that. I was there for that kind of stuff is well, is handling emergencies and things like that. But what I would do is, um I was at the equity research division at Goldman. So these are all the people who research stocks and decide what stocks are gonna go up and down the next day, etcetera. Or that that morning. Um, so I saw an opportunity there to build software in order to automate this, uh, this process. So, um, theme the time that it used to take from when an analyst was done with their their research to the time it was actually posted for public consumption and really golden clients. Consumption was usually it would round out to be an hour, an hour and a half because it had to go through several approval chains. People were running floppy disks around the floor. So I kind of saw that as an opportunity and decided I was going to build software around that night. I was fortunate to have a boss that let me try that. So I ended up building a system that turned that hour and a half to about 10 15 minutes. And from there it was just a commitment by Goldman at that point to say, Hey, this is obviously the right path. You know this again. It's 1992 93. So at the time, we were the first bank on the street to have this type of technology. Eventually, all of them had it, obviously, but that was my Goldman Sachs time. It was really about taking advantage of an opportunity because I had the ability to the free knowledge of coding. But also, it was an organization that allowed for that. So once, Um so I did that for about nine years, so my entire time was with Goldman Was about nine years when the dot com boom started happening. Um, everybody was leaving for dot coms, right? It was that, you know, the the golden opportunity of some company you're going to join, and they're gonna go public. And, you know, all of a sudden you're going to be, um, you know, billionaire be beyond your wildest dreams. And, of course, quickly, um, that became not the reality anymore. But basically what happened was I had gone thio. Um, I left Goldman had gone to a dot com that was owned by a big media company s O. They basically wanted the online version of all their brands to be built for the media company. So we start up a separate company, basically built it as if it was a start, A real startup. Then what happened is just like everybody else at the time, it suddenly became obvious that the dot com dream was not going to happen. You know, when the when the market started to take a turn and most companies were if they had parent companies, the parent companies were bringing their dot com efforts into the parent company. We're just running it like a cost center of the business. So the parent company, which was called Advanced, are the parent company over the dot com I was that brought us in, but also at that point, maybe CTO of the entire company. Um, so that was a whole new set of challenges. Um, because there you're talking about an old style company that had, ah lot of antiquated software platforms that needed to be upgraded, so that was a good six or seven years. At that point, I then became CEO of a company that was started by all the big brokers called the Market's com. We ended up selling that and, um, travel the world for a bit. And then I started at WebMD as the head of their engineering effort. Then I became their CTO on just a you know, a year and a half ago we sold WebMD

What responsibilities and decisions did you handle in your job? What were the top three priorities? What were weekly work hours like?

Summarized By: Jeff Musk on Tue Oct 13 2020
So, as a chief technology officer, you're responsible for several facets of how technology interacts with the business. Now there's a special carve out for if your business is based on technology, so I'll talk about that in a second. But just as a chief technology officer of any company, your chief goal is to make sure that technology and the things that you're working on, where you're spending your money, is aligned with what the business goals are, right, just as a general textbook type definition. What that means, though, is you somewhat have to do you use your technical background, but at a certain point you have tow, let go of some of it, and the higher up the chain you get, the more the higher percentage of a business orientation you kind of have to have. So, um, I'm just really in question here, So as far as that goes within a dot com type or a a company whose product is technology now, all of a sudden you're also responsible for the customer facing portion of that. And that brings on a whole new set of challenges when something can go wrong and revenue is impacted in a big way because of it. It changes how you approach things like that on. Do you become less of a concerned about just cost and you suddenly become more concerned about? Or do you see the value in heavy innovation because that can actually lead Thio more revenue?not. So this is I would even call a side priority. But stability, of course, stability of the environment is the basis of the whole thing. Um, then you come Thio You want to have a team in place that could respond to needs as flexibly as possible. So, um, you don't wanna have thio? Ideally, of course, this never happens. But ideally, you have a person for every project that someone could dream up. Of course, that never happens. Like I said, so all of a sudden, you responsible for prioritizing And that that would be the next level of responsibility is figuring out where toe where your engineering efforts, for example, should be spent where their best spent and making sure that everybody understands the cost profile on the benefit profile I remind were all over the place. I'm I'm late, worker. So I mean, going back to even my Goldman Sachs days. I would you know, there was my twenties, so I was able to do things like work till three in the morning and then come in at eight. But, you know, I I'm probably a little more hands on than most chief technology officer. So I probably spend more time in the office with my people. In that sense, um, but it's I would say that my average leaving time was probably eight or nine PM on figure. I'm getting in at nine, so that's that's an average call it eight o'clock average.

What were major challenges and pain points in your job? What approaches were effective in overcoming them? Discussing examples will help students learn better.

Summarized By: Jeff Musk on Tue Oct 13 2020
so I'm gonna leave aside. It is technology. Depending on what technology you're dealing with, you can that technology can introduce risk and challenges. Or it could be something that's pretty straightforward. And you know you're following a well tread path that doesn't really require too much heavy lifting. So technology aside, because that has its own nuances, that probably the biggest challenge is where people intersect with technology. Now, if you are anywhere within the technology organization, you have to worry about that. To me. I always say I've done many of the jobs within technology. The hardest job to me is the help desk because and I've been engineer for huge products and I've run. I've done network conversions and done operation type stuff, and those are the categories and technology. But help desk what you If you are developing an application and you have a bug, you can fix it. You have control over that. If you're on the operational side, you you forge your your existence on just making sure that the stability is there and you have lots of contacts of companies, etcetera. The help desk. You are the face of the entire technology group really, But you are the person that gets called when someone's mad. By the same token, you're also the person that has no control over. You know, how likely are you to get Microsoft to help you with a problem that the user has on our desktop? Not too likely. So it makes for a very difficult job. So again, that's where people intersect with technology. So on the engineering side, probably the biggest year. If you're writing software, the biggest problem you have is you're executing your writing, your building based on someone's opinion, right? Someone, whether it's a formal process of the hand you expect whether you're doing an actual development where they sit down with you in a stand up on bond. Explain some bit of functionality. However it is someone's communicated their vision. The problem is that you don't you're limited by how much information they actually put in there, and you can't expect anybody to put every detail they expect. So now you brush up against what's your experience with applications? How do you What do you think? I would say there's probably 20 micro decisions a developer mix every week. Eso those are decisions that they're never gonna ask about because they're too small and they probably have their own assumptions and built in ways they think this button should look or this text box should ask act. So, uh, in general, my approach with that stuff is, um not to be cliche about it, but to be is communicative and transparent as possible. So the mawr just taking engineering again as a as a as an example, the mawr, an engineer knows about what the goal of the project is, the better decisions they're going to make. And like I said, there's some decisions they're not gonna ask about because it's just not, You know, you wouldn't think you'd even need thio. But if they understand that for this particular application, you're actually not looking to maximize users you want and you don't wanna attract a lot of traffic, so you might approach it a little differently. As long as the person who's actually doing the coding understands that, then you're ahead ahead of the game. So that's probably the biggest thing is make sure that people are informed, um, and also that they're appreciated, right, so that when the work is done, everyone who is involved in a project should should understand the impact that they had

What tools (software programs, frameworks, models, algorithms, languages) were typically used in a role like yours?

Summarized By: Jeff Musk on Tue Oct 13 2020
um, As a chief technology officer, really? You're using email and using your browser. You know, in any type of internal communication tools you know, chat or you know, whatever chat program your company might use. Um, there's not a lot of specialized tools at that level now, going a level below. That depends on what development language you're using and what angle of technology you're working with. But, I mean, there's a long list of tools. Uh, if you are, if you are in the engineering side, you know what those programming tools are, but generally, uh, within a company you're probably looking at somewhere in the technology organization you're looking at using tools to manage a budget. You lose them tools to control spending or understand what spending is. And, um, beyond that, it's just kind of standard email and browser stuff.

What were the job titles of people you routinely worked with, within and outside of the organization? What approaches were effective in working with them?

Summarized By: Jeff Musk on Tue Oct 13 2020
Yeah, so on the team, just a generic technology team would be set up. You have. You know, the two typical camps would be operations and engineering. So there are branches and subsets of those. But basically, operations are the people who, uh who a ensure that what you have existing in the environment is stable and also making sure that as you update that that that's also stable. So engineers, of course, their mantra is they're changing stuff. They're building stuff all day, so you can immediately see like those two are in conflict because an operation person, their goal is to never get called at night. And an engineering goal is to change stuff. And changing stuff is what makes an operations person get called at night. So there's a natural kind of tension there. Um, but aside from that project managers or an essential part of the organization, I've always found it funny, and I'm sure this is different now. But project management is such an essential piece of the, you know, technology pie. Andi. It's such an essential part of success. I was always surprised starting out that it wasn't a bigger function in school at school didn't focus. Now that could be totally different now. But I remember, as I realized the importance of project management being surprised that I had to learn it in the work world. It wasn't even. It wasn't really something that was taught in school world.

How would you describe your management style? How has it evolved over the years? Can you tell about experiences or books that influenced your management style?

Summarized By: Jeff Musk on Tue Oct 13 2020
Yeah. So, uh, probably my biggest tenant. And my biggest, you know, core value, if you will, is transparency. So and I definitely extends to my management installed. Becomes a big part of imagine style, actually. So I believe that, um the more your technology people know about what's going on the company a the better off. Of course, they're like I described before the better product they're gonna build, but also, the better they're gonna feel about being there, and that's important in the technology world. You're talking about a world where the I've never had a time where I wasn't looking for engineers, for example. Um, the demand is so high, and the demand for true skill is so high that you really do get a, um, do you learn to be very, uh, uh, defensive about making sure people are happy and making sure that you're doing the right thing? So that's that's, like, now cost for entry for anyone. Managing technology team is making sure that the team is functioning right? Functioning Well, um, now, beyond that, transparency is a Z. I mentioned a big thing Also pushing people to communicate, so communication and being customer focused. So these are the things that I probably preach on an hourly basis and it za thread in most of my conversations. But it's really about making sure that people understand that their role is not just is not just to do a job if you want to think about getting ahead. And um, yeah, listen, if you're happy coming in at nine and leaving it five and you just wanna you know you're happy with your little slice of the pie. As long as that slice of the pie will always be there, it's all good. But, you know, I think there's enough ambitious people in this in this world to say, um, if you're looking to get ahead, it's really about learning communication. I always say, Learn two things, learned psychology and learned marketing. And when I say that it's not textbook psychology and marketing it s'more, take examples from movies and see how I was it. The hardest thing to do is to change someone's mind. So if you're sitting there and you're watching a movie or a TV show where someone didn't especially effective job, of course it's scripted, but you can evaluate what would work in real life and what wouldn't? Obviously. So if you see great examples, you take him down like you, you know, on a you know, memo and you're on your phone or whatever it is you you take examples of. Here's something. There was a tense situation between two people, whatever it waas, um, taking those examples, understanding them and learning from them and really understanding the connection to people. Um is something that I preach in my management style constantly. Um, so experiences are books, So I am always recommending how to win friends and influence people, and it's an old but I've had people come back and said, This is an old book, but I feel like the ideas. I read it early in my career and found like it did change my way of thinking about and handling relationships within the workplace. And I think the biggest thing is, uh, some people look at it and say, Well, you're being fake. Your you know, this is telling you how to say something to make someone happy. And I would say the main mantra is you're not lying, right. You you'd never express something that you didn't believe, and that's the key point to start with in all this. But, um, if you take that a step further, you really just understanding you have a goal. Someone you're dealing with has a goal. And how do you align those? And how do you make sure that the person enjoys working with you? I had one CEO one Say to me that the you know, your biggest goal should be whenever you're in a meeting. Whenever you're interacting with someone, your biggest goal should be. If I ever leave, that person will wonder how they'll get along without me, you know? And it's really about that. It's about pushing that extra, um, three extra giving that extra effort, showing that you care about a project. Um, those are the things. So as far as you know, I've had experiences that have taught me that. But I do feel like how to win friends and influence people is just a baseline like that will give you the good foundation

How do you manage conflicts within and across teams? How do you promote trust, openness and a healthy work culture? Sharing stories will greatly help.

Summarized By: Jeff Musk on Tue Oct 13 2020
I think, um, if you take you know, hopefully, um, anyone listening to this will get the chance to take over a team, and that's probably the hardest scenario where you have Thio create trust where you don't know what the relationship was with their former bus. You don't know how how they feel about their current, uh, their current environment. So, um, and I'm trying to not be cliche and saying listening and showing an actual response and then finding little tricks. So listening eso Whenever I've taken over Team, I've sat down with every single person in that team, took notes on what they said and understood that they have their concerns, that you do have to distill that into what's reasonable. And you know, everyone you know, you don't want to get hopped up into someone's strong opinion about something if it's not, uh, not a realistic thing, Um, but it's important to show that you are George listening and like I said with action, so I would always start these off with. Here are some things I'm thinking, and that's a good scenario where, where it starts off, probably not the trust level, Andi. Then you that's what you really have to break down a wall. If you show that you're being transparent, here's what I'm thinking and you stick to that and don't surprise people without unless they're scenarios where of course, you can't help it. But as long as this information that could be shared and needed to be shared a certain moment, if you make sure or take responsibility for sharing it and taking responsibility means not do it not just doing it. But if you don't get a chance to do it, then you say, I'm sorry I meant to do that and at least that would you know that would keep that. But But also there's little tricks like, um, so I've had employees come to me and say, uh, have issues with their team and I was trying toe give guidance for how this person would bond with their team. So here's a good example. So, um, if you're in a conference, you're in a meeting. A lot of people are talking. If you say, um, say someone is trying to talk and they just can't get their point out and you stop, and especially if you're the manager, you stop and say, Hold on. I want to see what that person you know. I want to know what that person thinks. That person's gonna love you forever, right? Because that person now knows that you're looking out for You want to hear what they say But there's little tricks like that that you can you can learn again. You can watch movies and learn them, but ways Thio connect. Oftentimes it just takes time, though. And it takes experiences. So you should go in not expecting that the press is going to be there and that you have to earn it. Andi Overtime Ugo.

How can one get better recognition of work from one's boss and higher management? What mistakes should one avoid? Stories or examples will be quite helpful.

Summarized By: Jeff Musk on Tue Oct 13 2020
Yeah, The biggest thing there is reporting. So, um, and again, you know, not Thio like beat the Transparency drum again. But if you're I've been in so many situations where there have been reports available, information is sent to a manager and the manager is fine just knowing that information is there. So if you are open about what you're doing, you offer to do a weekly report. Um, things like that that will always go a long way in helping you with your peers and your management. Um, yeah, I would say it's just like the the media world. If you make a mistake, you own up to it immediately. Um, it's okay. Like it's not There are. There are rare situations. I guess we're a mistake. Could get someone fired. But the much more common scenario is that if you say oh, well, you know, listen, we made this mistake happens all the time in technology, right? It's a you know, someone didn't test something. Whatever it was, you own up to it, um, you fix it and that's the important thing is when a problem happens and problems happen when a problem happens, How do you handle it. You handle it. You take responsibility. You make sure the right resource is on something, and you take it seriously. Especially if you have someone complaining to you about it. You know, take out a pen and paper. You're taking notes like this is important to you. Um, so that is, um, probably a mistake or that it's, ah, way to avoid the mistake of ignoring something you should take responsibility for.

What indicators were used to track performance in a job like yours? Think of the indicators such as key performance indicators (KPIs), objectives & key results (OKRs), or so on.

Summarized By: Jeff Musk on Tue Oct 13 2020
Yeah. So, um, at the level at a CTO level, I always considered my, um, uh, my religion or my team's relationship. So if I think of internal and external my team's relationship with other internal entities, um, and it's a little, um, non scientific in a way. But you can definitely tell if your team is doing a good job. If you're in meetings and you're hearing that such and such helped out in a great way in this project or, you know, we were hoping to have we were hoping to have someone, um uh, trying to think of, ah, recent example or a more recent example of something like that. Um, so when I one of the jobs I started at there was a terrible relationship between, Actually, it's a typical story te relationship between technology and the rest of the business, and, you know, they were vilified in the whole bit. Um, by the time my job was five or six years in, I went from sitting in meetings and hearing about complaints. And you know how everyone how this person was doing something wrong, etcetera Thio. Um, now we have, uh, scenarios where people on the business side are actually championing people in technology, and they're happy that this tool was built for them and, you know, they realize it's a partnership. So, um, that partnership existing is probably a good kind of anecdotal, Um, were of a qualitative measure. I mean, at that level, you know, things like stock price in revenue, I would still consider measurable to the CTO, especially if your business is digital where the product is technology, so they're obviously that's, ah, that's a measure as well.

What skills and qualities did you look for while hiring? What kind of questions did you typically ask from candidates?

Summarized By: Jeff Musk on Tue Oct 13 2020
So generally I look for so cost of entry is the skills there, right? So you know, obviously you want some level of depending on the role. But in general, let's just say there's some level of skill that you know needs to be achieved beforehand or if it's an entry level position, some level of experience before that, the good news and a lot of the technology stuff is that while you know, 2030 years ago, it took so much work Thio to be an experienced developer, for example, or to three experienced in any side of technology and security, etcetera. Now, these things are so easy to spin up, and, you know, you can spend open environment very easily. Building an app on your own is totally so you have that skill level, um, to validate you have those, you know, those elements that could validate someone coming in. So, um, main point, with that being, we look for experience, Yes, but also, if it's not a role where experiences is possible, um, someone doing something proactively they proactively built a nap. That is a quality that that I would say it's pretty important, that kind of self starter need to be innovative. Um, that kind of that kind of thing

Can you discuss career accomplishment(s) that you felt good about? Please discuss the problem context, your solution, and the impact you made.

Summarized By: Jeff Musk on Tue Oct 13 2020
so I'll go back. Thio When I waas cto of that dot com, which was It was a dot com that was owned by a big media company, and when this dot com got started, it was an Internet company that was the Internet version of all the brands and the parent company. So there was, I'd say, outright animosity over people who were in the company and built these brands and Randy's brands for 30 plus years. Now, the Internet guys were coming in and deciding that they're, you know, they can figure out what's right for the brand's. There was a lot of animosity between three the people building the technology and the people who owned the brands. So when we got scooped into the into the parent company, um, that really needed to be changed. That need to be changed anyway. But even more so at this point, So what? What we did was instead of sitting there and crossing arms and saying, with the Internet people, we know what this should be. We actually built tools which allowed the brands to manage their own lives. So instead of saying we got this, we said we're building you tools, you do anything you want. Most people didn't want to get into that level of detail, but they they were happy to know that they could if they wanted Thio. Um, so with that one move of building, like a tool, set a factory instead of, you know, deciding what their branch should look like. Um, it changed the aspect of the relationship of these these groups forever. I mean, way then embarked on several years off incredibly productive building products for, um, for the, uh for the the core business. So building products for them revenue exploding right? Because now all of a sudden, they can manage their own content. We gave them lots of, uh, tools like classified sites and Thea Bility to really customize the look and feel things like that that they could and even things that they could monetize. So all of a sudden, we were all in this game of let's make this into something that generates revenue. Eso I'm pretty proud of that

What responsibilities and decisions did you handle? What were the top three priorities and pain points? What strategies were effective in dealing with challenges?

Based on experience at: CTO, TheMarkets.com
Summarized By: Jeff Musk on Tue Oct 13 2020
um, so, I mean, the responsibilities were pretty much the same. They were so at the at the abstract. Right? So if you just extracted Thio, you're worried about stability. You worry about innovation. You worry about relationships. You worry about supporting the business. Um, that's kind of the you know. That's the mantra in both of those jobs. Now, how that manifested itself was different between the two jobs. Andi, even the CEO job before that. But, you know, those were always the priorities, though.

What college programs did you attend and what were their best parts? How did each of your college programs prepare you for your career?

Summarized By: Jeff Musk on Tue Oct 13 2020
So I was a computer guy from when I was a kid, so I kind of already had that part worked out. Um, I was a finance major, and it's funny when I was picking a major. I've also been a musician, by the way, since I was a kid. So I was had up until, like, middle of college, I was gonna be, you know, big musician, right? So but one thing that was important to me was to not just sit there and say I'm a technology guy and I'm gonna major in computer science or something. I actually thought this was on the advice of a friend of mine. Um, So, um, combining the technology with another skill set your 10 times more valuable than just the technology person or were just the business person. So, um, finance was the thing of the eighties when I started college, and, um, I majored in finance, and, you know, what do you know? I ended up the Goldman Sachs and got to use that combination pretty well. But really, the point was to not, um, route myself into one skill set and to be the combination of those

What three life lessons have you learned over your career? If any, please also discuss your experiences facing adversity, or trying something unusual.

Summarized By: Jeff Musk on Tue Oct 13 2020
so I would say the I'll tell it in two stories. I always I always tell people on my team's about e described the bread guy and a nail woman, right? So I'll explain that. So I was once getting lunch and the, you know, they had a salad made. He chopped it up and, you know, would you like some bread? Yes, I would. And he had Ebola bread in front of him, and he picks up a piece of bread and then looks at it and puts it back and takes another one and put it in my salad. So the fact that he looked at something and said, now the spread isn't good enough for that guy. It's just I actually felt like, Wow, this guy's looking out for me. I think that's a lesson of people want to know that you're on their side and you're looking out for them. So be the bread guy, I say on then. You know, if you ever seen someone get their nails done, there's always like the manicure. There's always the moment at the end when the person stares at the nails in order, I guess I don't know if it happens every time. But, yeah, they'll stare at the nails and we'll make sure it's you know it meets their approval. And that's another lesson I say. That amount of caring it makes you that person cares, at least give. The impression gives a good impression that they care what they are doing. Um, that they want to make sure that the result is good enough for you. Um, and they show some pride in their work and, you know, it's it's back to this. This other thing of I would say, treat a project as if it's your own. So we all have our own projects. Everyone has their own goals. But when you get involved in someone else's project, um, if you have the attitude that I'm going to do exactly what I would do if this was my own project, that person will feel it, and it will be all the difference in the world. So there's just a few of a few of the questions

What starting job (after internship) would you recommend to students who hope to grow professionally like you? What other parting advice, dos, and don'ts would you give?

Summarized By: Jeff Musk on Tue Oct 13 2020
I would say, if you are looking to go up a technology path, definitely no. The technology. So I mean, there's a pretty well tread like if you know, a couple of programming languages. Like I said, if you could build a nap, then you are golden. Um, you know, this is a riel. Ah, it's a really candidates market, right? Actually, always is. So if you do that basic stuff, if you know your stuff and you can prove it, then you're not gonna have a problem finding a job for sure. Even in the worst of times, that's been the case again. If you are. If you know your stuff and you can prove it, that's the That's the key thing there. Um, but I would recommend, um if you want to move ahead professionally and you have to then drop some of the technology bravado. So, um, I often get into conversations about technology perfection. Right. So if you took a computer computer, if you have a computer science degree, you learned a lot about what things should be. But you have to understand when you hit the business world all of a sudden, um, perfection is hard Thio. Allow yourself to take the time to dio so often times you have to be okay compromising some of those ideals. So once you show that you could do that, um, you could grow a lot faster to show that you're not gonna be the, you know, the staunch technical person who must do it this way. No, you could understand I actually do this a little faster so I can find a shortcut, and it's uncomfortable, but this is gonna get us out the door faster. Those are the kinds of people who make it up up the ladder pretty quickly.