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Upwork s CEO on How an Introverted Engineer Learned to Lead

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:

R1605A_KASRIEL_A.jpg

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

R1605A_KASRIEL_B.jpg

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

R1605A_KASRIEL_C.jpg

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.