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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.