2016-04-29 09:04:43
Stephane Kasriel
From the May 2016 Issue
I never aspired to be a traditional engineer, but the subject suited me. I d grown up around computers, and I d started writing programs when I was 12. I read about Steve Jobs and Bill Gates in computer magazines. As I thought ahead to the work I might do as an adult, I expected to spend a lot of time writing code. In a way, I was like today s typical Silicon Valley kids, except this was in Paris in the 1980s.
I also recognized early on that I was an introvert, although I probably didn t know the word for it at the time. Some kids in high school clearly thrive on popularity and going out all the time being surrounded by lots of people. In contrast, I enjoyed being with a small number of people. I liked to read books, program computers, and do things by myself. I m not completely socially awkward I can get by in a crowd, but it doesn t come naturally.
When you think about the personality types and professional backgrounds that most often lead someone to the CEO role, you don t think about introverted tech guys like me. Until recently, even in the technology industry, the conventional wisdom was that you make the charismatic sales chief or the well-rounded chief financial officer CEO so that he or she can deal with the outside world, and you leave the brilliant engineer alone in a cubicle to focus on the product. Judging from the r sum s of company leaders today, very few have spent time as a VP of engineering or product development. Although there are certainly advantages to having a technical background when leading a technology company (and views on this have evolved in recent years), someone who aspires to be a CEO must still counter the perception that engineers don t make great leaders.
Over the past decade I have worked systematically and diligently to overcome that bias to move beyond my engineering background and gain the broad range of skills necessary to lead a business. I sought out projects and talked my way into jobs that were outside my comfort zone. I read widely to burnish my skills in strategy, leadership, and managing people. I ve spent hundreds of hours taking online courses. Since becoming CEO, in April 2015, I ve learned how someone with an engineer s problem-solving mindset must adapt to perform well in this role. As technology companies become an even bigger piece of the economy, and as boards become more open to considering people with technical backgrounds for leadership roles, my journey may be instructive to others.
From Start-Up to B-School
I always knew I wanted to be an entrepreneur. My father worked for 30 years at the same large company, which made cement products, and ultimately became CEO. I admired his career, but I wanted to work someplace smaller, where one person could more easily have an impact. This preference only increased when I left France, after engineering school, to get a master s degree in computer science at Stanford. Larry Page and Sergey Brin were in my class, and they started what became Google in the office next to mine. The department had only 100 students and a dozen professors, and in the late 1990s everyone seemed to be working on a start-up on the side. When we finished the master s program, a lot of classmates went to work with Larry and Sergey, but I didn t want to join somebody else s company. I wanted to start my own.
My first company was called Fireclick; it made software that helped companies websites load faster. (This was especially important in the dial-up era, before broadband was common.) Even though I was the founder, I functioned more like a tech guy, and I spent most of my time working on the code. Looking back, I m amazed at how naive I was we know so much more about how to run start-ups today. But we had a good run, and four years later we sold the company.
After the sale, I went to get an MBA at INSEAD. My goals weren t those of the typical business school student. I wasn t a career changer I had already worked in tech, and I wanted to stay in tech. I wasn t trying to expand my network, because I already had a good one from my time in Silicon Valley. I didn t need the MBA to get my next job. I decided to go to B-school because I d seen what mistakes entrepreneurs make (I had made plenty at my first company), and although I d learned meaningful lessons from them, I wanted to avoid repeating the mistakes that others had made. For me, that s what business school was about: Each case study represented a realistic situation I might face in the future; by studying hundreds of cases, I developed skill in pattern recognition and in matching each situation with the various options for dealing with it.
Shifting to Sales
I joined PayPal after business school, working as a product manager in France. The company had just entered the country, so we had only two people there it felt like working at a start-up. I tend to be a workaholic, and in that job and subsequent ones, I focused on doing my primary job efficiently and using any excess time to take on various challenges. For instance, if I was working an average of 60 hours a week, I d try to finish the tasks I was expected to do in 40 hours and spend the other 20 on tasks in some other part of the company. At PayPal, I used extra time to take over an orphaned project involving a money market product. I learned a lot about the banking industry, and I interacted with colleagues in finance and legal whom I might not have met otherwise. Managing your time in order to take on a second job inside the company can be a great way to broaden your skills.
A Would-Be CEO s Reading List
Stephane Kasriel read widely to prepare for a leadership role. He cites the following as the most influential titles:
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Anticipate. The Architecture of Small Team Innovation and Product Success
by Ronald Brown
The Charisma Myth: How Anyone Can Master the Art and Science of Personal Magnetism
by Olivia Fox Cabane
Continuous Delivery: Reliable Software Releases Through Build, Test, and Deployment Automation
by Jez Humble and David Farley
CustomerCentric Selling
by Michael T. Bosworth and John R. Holland
The Four Steps to the Epiphany: Successful Strategies for Products That Win
by Steve Blank
Getting Things Done: The Art of Stress-Free Productivity
by David Allen
The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers
by Ben Horowitz
Hooked: How to Build Habit-Forming Products
by Nir Eyal with Ryan Hoover
How Google Works
by Eric Schmidt and Jonathan Rosenberg
Inspired: How to Create Products Customers Love
by Marty Cagan
Jack: Straight from the Gut
by Jack Welch with John A. Byrne
Lean Enterprise: How High Performance Organizations Innovate at Scale
by Jez Humble, Joanne Molesky, and Barry O Reilly
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Made to Stick: Why Some Ideas Survive and Others Die
by Chip Heath and Dan Heath
The New Strategic Selling: The Unique Sales System Proven Successful by the World s Best Companies
by Robert B. Miller and Stephen E. Heiman with Tad Tuleja
Predictable Revenue: Turn Your Business into a Sales Machine with the $100 Million Best Practices of Salesforce.com
by Aaron Ross and Marylou Tyler
Rework
by Jason Fried and David Heinemeier Hansson
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Steve Jobs
by Walter Isaacson
Super Crunchers: Why Thinking-by-Numbers Is the New Way to Be Smart
by Ian Ayres
Thinking Strategically: The Competitive Edge in Business, Politics, and Everyday Life
by Avinash K. Dixit and Barry J. Nalebuff
Zero to One: Notes on Startups, or How to Build the Future
by Peter Thiel with Blake Masters
When I left PayPal, I joined another company as head of sales. As an engineer, I wasn t an obvious candidate for that job, but I argued that my time at PayPal had involved a lot of business development and sales-related work. And I tried to be honest. I ve never been a VP of sales before, and I m not pretending I ll be the best one you ve ever had, I said. But you have a very technical product, and I really understand how it works. That may help us close more business.
Shifting into sales was a major fork in the road for my career. At some point you need to decide between two paths. One is to stay in your area of functional expertise, which probably increases the odds that you ll be consistently successful but that approach may well limit your overall trajectory. The other is to take a leap, such as moving into an entirely different function. That will definitely increase your risk of failure, but it will give you a greater breadth of experience if you succeed. Historically, engineers have been risk-averse and have tended to follow the first path. You see a lot of people who are the head of engineering first at a company with 10 engineers, then at a company with 100, and then at a really large company. There s a limit to how much impact you can have in those roles you re still doing what someone else tells you to do. Google and Facebook are among the exceptions: Their ubergeek engineers are the heroes, because that s the culture that Larry, Sergey, and Mark Zuckerberg have
worked to create. As I ve moved into leadership roles, I ve tried to do the same to create a corporate culture in which it s cool to be an engineer, where technical people are empowered to influence the strategy of the company.
The Challenge of Being Introverted
At some point in the midst of these job changes, I took the Myers-Briggs test for the first time. The results confirmed what I d always suspected: that I m very strongly introverted. There s no question that an introvert who aspires to be a CEO will face challenges. When you re a leader, it s useful if not necessary to be cheerful, smiling, and outgoing. That s not easy for everyone, but it is achievable. One way to get better at it is to make concrete goals. A particularly difficult task for someone like me is to go to a big networking event or conference where there s a large room filled with hundreds of people I don t know and mingle. To make that manageable, I set goals: I m going to talk to at least 30 people, get 10 business cards, and arrange five follow-up meetings. Because I m competitive and results-oriented, those goals counterbalance the anxiety I feel about inserting myself into a random conversation and introducing myself. I ve worked on the skill of starting a conversation. I ve also worked on
finding ways to say good-bye gracefully, because not every interaction at these events needs to be a long one.
In 2012 I joined oDesk. The company had been founded by two Greek immigrants in 2003. They saw that Silicon Valley was desperate for technical freelancers whose jobs could be performed from anywhere, but the companies had no good way to find the right people. So oDesk was like a professional matchmaking site. I started out as the head of product but ended up doing the head of engineering job as well when the person filling that role departed. We interviewed a lot of potential head engineers, but nobody clicked, so I agreed to fill the need temporarily. After a time, the CEO asked if I d do both jobs permanently, and I said yes. In 2014 oDesk merged with Elance, the other big player in the space. Elance s CEO became the CEO of Elance-oDesk, which later changed its name to Upwork, and he asked me to continue serving both functions.
Upwork Facts
Founded
In 2014, when Elance and oDesk merged. Renamed Upwork in 2015.
Freelancers
10 million+
Countries
180+
Clients
4 Million+
Value of Work Done
$1 billion+ a year
Top Five Project Categories
Web, mobile, and software development
Graphic design and content production
Advertising, sales, and digital marketing
Translation, localization, and writing
Administrative and customer support data entry, content writing, and internet research
At that time the CEO had been in charge for 13 years, and a few months later he decided to step down. The board considered external candidates to succeed him, but I made it clear I wanted the job. The board s biggest concern was that I d never served as a CEO before, and some of the directors felt it would make more sense to hire an outsider with previous CEO experience. That feeling is common in Silicon Valley. While I was head of engineering, I got lots of calls from other companies looking for a head of engineering, but nobody would call me about a CEO job because I hadn t been a CEO. It s a chicken-and-egg issue. Ultimately, I had to convince the board that I understood the range of skills I d need to succeed in the job.
Engaging Employees
Since then I ve learned that the tasks and decisions facing CEOs are often much more complicated than the technical problems that an engineer encounters. A lot of a CEO s job comes down to emotional intelligence and understanding what other people need and want. Some days I feel like the company s chief psychologist, and I have to be emotionally prepared for that. My natural impulse when I hear about a problem is to go to a whiteboard and start to diagram how to fix it, the way an engineer would. But for a CEO that s often not the right response. A lot of the people who bring problems to the CEO aren t looking for a solution they just want to feel that they ve been heard. That isn t always the easiest part of my job, but it is a part, so I m learning to listen first and not see every situation as a problem that needs a solution.
I ve also learned a lot about time management and what kind of direction I should be giving employees about day-to-day tasks. I m now out of the office more, because speaking with customers and investors and attending conferences is really important to our business. So when I m in the office, I need to be there for team members, to provide guidance and hear details about what they re doing. But I haven t taken this need as an invitation to micro manage; I still let employees do what they do best. Most CEOs should not be like Steve Jobs. My role is to help people feel excited about their work, empower them, and give them the resources they require to do their jobs well. One of Upwork s big advantages is that our employees agree with our mission, which is to create economic opportunities for millions of people around the world by matching freelancers with clients. We don t offer the same perks that some of Silicon Valley s sexiest companies do, but the mission helps keep our employees engaged.
Until fairly recently, people like me, who shifted from engineering into a chief executive role, were unusual. Bill Gates, Larry Page, and Mark Zuckerberg are well-known examples, but I think more people will make this jump in the future. The venture capitalist Marc Andreessen now says frequently that founders (many of whom have technical backgrounds) should stay on as CEOs. People are starting to realize that employees who understand in great detail how the product works may well be the best people to decide on the future of the company and to sell that story to investors and customers even when they find that communicating with people comes less naturally to them than interacting with technology.
A version of this article appeared in the May 2016 issue (pp.35 38) of Harvard Business Review.
Stephane Kasriel is the CEO of Upwork, formerly Elance-oDesk.