My first day as CEO taught me I had prepared for the role my entire life

Josh Leslie; Business Insider

  • Josh Leslie is the CEO of Cumulus
  • When Leslie was 30, he told his manager that he wanted
    to be a CEO by the
    time he was 40.
  • By his late 30s, CEO was nowhere in sight and his
    career seemed to be on a distinct sideways trajectory.
  • Leslie changed his perspective, stopped thinking
    about his next job, about the size of his team, or about the
    perception of his accomplishments — and ten months
    later, he
    became the CEO.
  • On his first day, he realized he had been preparing for
    the role for years.

I joined Cumulus Networks in June
of 2015 as the vice president of sales, which was a role I had
been in for several years before, and I was comfortable with. Our
founder, JR Rivers, was CEO when I joined. But as time went on,
JR transitioned to the CTO role, and gave me the opportunity to
lead as Cumulus’ chief executive.  

So, ten months after I joined the
company, I walked into the office for day one of a completely new
role: CEO.

It was an exciting, thrilling
opportunity; Something I had perhaps been unknowingly preparing
for since childhood, and something I had definitely put at the
top of my goal list.

Thinking back to my first day as
CEO, I realize it wasn’t that much different than my experience
in the previous ten months as VP of sales — I knew my team, I
knew my way around the office, and I knew a bit more of what I
was getting myself into versus starting a new role at a
completely new company.

But it was this ten month
introduction to Cumulus, along with an entire lifetime preparing
for the CEO role, that showed me I was more than ready to take on
this new chapter. I was 100% ready to be CEO on my very first

Preparing for CEO since childhood

My earliest memories of the
software business were as a young child. My dad had converted one
of our bedrooms to a home office and on the weekends, he’d be in
there, on the phone, talking shop. It was the first time I heard
my dad swear: “That’s a bunch of bullshit!” he would say.
 Followed shortly by, “screw those guys.”

It was kind of shock to hear, but
after that shock wore off, I was simply fascinated by the grit
and the pace of business and watching my dad ‘doing

My dad is Mark Leslie. He was the
CEO of Veritas Software and built the company nearly from
inception. At its height, Veritas was a Fortune 1000 Company with
annual revenue exceeding $1.5B.

My dad was revered by Veritas
employees and widely respected in Silicon Valley. He left the
company in 2001, to advise startups, invest, and teach at
Stanford. In short, he knows pretty much everyone in tech and he
casts a pretty long shadow.

When I was nine, I didn’t think
about what it would be like to follow in his footsteps. I wasn’t
one of those kids who started some amazing business at a young
age, and I wasn’t writing code. But I did know that I had an
intense interest in the business world.

As I grew older, I still listened
in on those phone calls, perused my dad’s open emails when he
wasn’t around, and had dinner table conversations about OEM
licensing deals, stock options, and UNIX file systems.

I didn’t realize it then, but
looking back now I realize I was training to be a CEO. Sort of.
It wasn’t like I was waking up at 6 a.m. to work on spreadsheets
and cap tables. But I was surrounded by my dad’s work.

Eventually I grew up, went to
college, and started my career in sales. This was my dad’s
influence again. Salespeople, he said, are the ones that know
what’s really going on in a company. Salespeople know how to
solve problems. Build the product or sell the product, he told

It only took my one semester in
college to learn I wasn’t smart enough to build the product, so I
began my sales career.

When I was 30, I told my manager
at VMware that I wanted to be a CEO by the time I was 40. He
laughed and said fifty was a more reasonable goal, if

Eventually I left VMware and I
became a VP of Sales at a small Series A startup. I worked harder
than I ever had but the company and the job did not turn out the
way I hoped. I took another VP Sales job at another early stage

After a few years at startup
number two and I was approaching 40. CEO was nowhere in sight and
my career seemed to be on a distinct sideways trajectory.

I had a great family, by most
measures a very good career, but when I measured myself against
my dad, or against my peers, and I measured my ‘wins’ (or lack
thereof) and I was unhappy with the score.

But then I had an epiphany. I
remember as a young parent, seeing one of my children display
some startling ability (or at least, I was impressed!). I
thought, perhaps I will be most remembered as the parent of one
of my children and not for any of my own accomplishments.

It was a big change in
perspective for me. For the first time, I realized: Perhaps I
won’t be a CEO. Perhaps I won’t be a ‘serial entrepreneur with
multiple successful exists.’ 

And maybe I don’t care that

It was about the journey, not the destination

For the first time in my career,
I started to focus on the journey, not the destination. I will
simply be the best VP of Sales I can be. I will treat customers
with care and employees with respect. I will spend my time on the
things I know I’m good at (building trust with customers) and get
help where I’m weak (process).

So that was it. I was going to be
a great VP of Sales and let the chips fall where they may. I left
start up number two and joined Cumulus Networks.  For the
first time in my career, I did not seriously negotiate my
compensation, my title or organization.

VP of Sales? Sure, I thought,
that works for me. There were many questions of organizational
ownership, but I had come to understand that all of those things
would eventually get sorted out correctly if we focused on the
right priorities and built trust with the team.

I had truly stopped thinking
about the next job, about the size of my team, or about
perception of my accomplishments. It was the first time I was
leading. Ten months later I became the CEO.

Josh is a seasoned technology executive and currently serves
as CEO of Cumulus Networks. Prior to Cumulus, Josh spent time at
Instart Logic, VMware, and CommValut Systems, holding various
leadership roles in both sales and business development.

A Bay Area native, Josh received a BA from the University of
California, Berkeley and an MBA from Columbia Business School.
When he’s not in the office, Josh enjoys spending time with his
wife, two kids, and his poodle, Peggy.

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