Welcome to The Deep Dive, where we unpack huge
amounts of research and distill it all down to
the essentials you need to know. And today, we
are really digging into a big one. We are. We're
tracing the 25 -year evolution of a major tech
company, Akamai Technologies. It's really a story
about change, about how leadership has to mature.
And, you know, how a startup culture survives
that transition to becoming a, what, nearly $4
billion? global leader. So our guide on this
journey is Kate Prouty. She's the current CIO
of Akamai. Right, and she's the perfect person
to track this because she joined the company
way back in 1999, right at the beginning. She's
been in leadership there for over two decades.
And we need to set the scale here. Akamai is,
for many, basically the backbone of the internet.
They're handling content, security, cloud computing.
billions of times a day. So this isn't just about,
you know, changing the snacks in the break room.
No. This is a fundamental shift in the company's
DNA, all while managing this insane technical
complexity. So our mission for this deep dive
is to unpack the sources from Prouty's experience.
How did they actually drive that change from
the top down? And I think more importantly, what
parts of that that sort of wild 1999 culture,
did they have to leave behind to survive? Because
the big takeaway here is that change, well, it's
not really optional. OK, so let's jump in that
time capsule. Let's go back to 1999. What was
that startup environment really like? The sources,
they paint a very specific picture. It's that
high octane, late dot com era. Right. It's exhilarating.
You know, frenetic energy, food deliveries, and
my favorite detail. people literally on rollerblades
in the office. Rollerblades? I mean, that detail
says so much, but that pace, it wasn't just for
show, was it? There was a real technical need
for that speed. Oh, absolutely. They were building
a global content delivery network from scratch.
They had to be faster and louder than everyone.
And that desperation, it translated directly
into their culture. So how did they define that?
Their motto, and this was literally printed on
their walls, was the word obstreperous. Obstreperous.
I love that word. It's so... Noisy, defiant.
That was the whole point. It meant you were a
disrupter. You were making noise, demanding change.
The lines between jobs were, you know, intentionally
blurry. If you saw a problem, you just jumped
in. But this idea of healthy debate, it sounds
like it often tipped over into something, well,
less healthy. It did. The sources are pretty
clear that this culture was full of young, very
academic people. And it created this environment
of constant, intense confrontation. So the goal
wasn't collaboration? Not really. The goal was
often to be the smartest person in the room.
To actively search for the mistakes in your colleague's
work. Wow, that sounds incredibly stressful.
A real pressure cooker. It was. And they had
a mantra for it, you were behind. Jeez. Yeah.
And the way they recognized success just solidified
this whole individualistic, heroic thing. They
had something called the Titans Award. OK, the
Titans Award. Let me guess. It wasn't for the
best team player? Not at all. It was explicitly
for the superstar Titan individual contributor.
The one brilliant person whose Herculean solo
effort saved the day. So management, teamwork,
that was all secondary to just these heroic solo
acts. Totally. And the expectation was complete
and utter dedication. 15 plus hours a day in
the office was normal. It was a badge of honor
to sacrifice your personal life. People rarely
even talked about their lives outside of work.
So that culture, as exciting as it sounds, it
really had a shelf life. It was a ticking time
bomb. It was completely unsustainable. And that
connects to the bigger picture, right? The mandate
to evolve wasn't just about technology. It was
about, well... about scaling their humanity.
Akamai and Prouty basically grew up together.
And the sources show that the pressure for change
often came from very personal places. Yes, exactly.
Prouty mentions that she was one of the very
first people at Akamai to get pregnant back in
those early days. And if you look at how the
company handled that then versus now, I mean,
it just perfectly shows the massive gap they
had to cross. The contrast is it's really dramatic.
Back then, she was one of maybe five people in
the mother's group. Just five. Maternity leave
was rigid. 12 weeks just following the law and
zero paternity leave. It was seen as a concession
You know not a benefit and now you fast forward
the company has over 12 ,000 employees You just
can't ask thousands of adults with kids and mortgages
and real lives To operate like those 22 year
old rollerbladers the leadership finally realized
it The old culture was actively hurting their
ability to keep the senior people they needed
So their most precious asset, their people, was
being worn down. Exactly. The mindset had to
shift from, how much time can we get out of them,
to something more like, how do we support their
whole lives so they do better work? It's that
old saying, right? What got you here won't get
you there. It's so true. The heroic, chaotic
stuff that built the company in the first place
was never going to get them to that next stage
as a mature, multi -billion dollar organization.
Yeah. OK, this is where it gets really fascinating
to me. How does a company that literally rewarded
people for being at their desks for 15 hours,
how do they suddenly pivot to celebrating the
idea that you might never need to be in the office?
It was a massive, massive undertaking. They went
from that culture of mandatory face time to something
they call flex space, which lets employees choose
where they work best. And it's not just a policy
on paper. No, it's real. Over 80 % of their employees
now work four or more days a week from home.
So my question is, the one every manager listening
is probably thinking, how do you keep collaboration,
productivity, all of it going when 80 % of your
team is remote, especially coming from where
they came from? Well, it's a huge investment,
both technical and managerial. Technically, their
systems had to be flawless and cloud -ready.
But the managerial shift was the big one. You
had to stop managing by sight. Exactly. The focus
had to move from inputs, you know, did I see
you sitting there, to outcomes. Trust had to
become the default. Managers are trained to assess
results, not your proximity to the office. And
you mentioned that Titan Awards still exists,
but it means something different. That must have
required a total overhaul of how they review
performance. It did. The Titan is no longer the
solo superstar. So what is it now? The new definition
is all about collaborative impact, cross -functional
success, mentorship. The performance metrics
now explicitly reward you for sharing knowledge
for making the whole team succeed. So being a
brilliant jerk is no longer a viable career path
there. Not if you want to be a titan, no. It's
about channeling that old intellectual fire in
a way that's... you know, sustainable and positive.
They didn't ask people to stop being disruptive.
They just asked them to be constructively disruptive.
Yes. They institutionalized that obstreperous
spirit. They realized you can't rely on chaotic
arguments for innovation when you're a giant
global company. So they build formal structures
like their annual innovation challenge. Tell
me more about that. How does a formal structure
like that create safety? It gives a clear, safe
path for anyone, no matter their role, to pitch
an idea all the way up to the CEO for funding.
It empowers people to challenge the status quo
without the fear of, you know, personal backlash
if the idea doesn't work out. So it's structured
risk taking. It creates room to fail. That whole
idea of letting people burn down the couch, not
the house. Exactly. They made innovation a system,
not something dependent on a random confrontation.
The core values are still there. Disruption,
innovation. But now they're channeled through
a system built on trust. So let's bring this
home for the listener. What does all this mean
for someone who's in an organization right now
that feels stuck in its own 1999 mindset? Okay,
key takeaway number one. You don't have to wait
for the CEO to have an epiphany. Proudi is really
clear on this. You can be responsible for your
own culture. You can be the catalyst. You can
be the catalyst. If you see something that needs
to evolve, speak up. Even if it's just in your
small corner of the company. And that leads right
into the second big idea. Control your immediate
environment. Even if you can't change a whole
company, you can change your team. That micro
level change is so powerful. You can build trust,
respect, and safety right where you are. Set
clear expectations for teamwork. Hold your team
accountable for eliminating those little microaggressions.
Make your bubble a safe place for people to bring
their whole self to work wherever they're working
from. Right. And for anyone in a leadership role,
this all demands a huge shift in style. It's
about being authentic, not just copying the old
titans. Which brings us to the third takeaway.
This is about leading by example, but also learning
from, well, from bad examples. Yes. Prouty talks
about the power of the anti -mentor. The anti
-mentor. I think that's a brilliant concept.
What does that actually look like? It's about
deliberate observation. You watch the leader
who is technically great but relationally terrible,
the one who micromanages their remote team or
engages in that destructive personal kind of
debate. And you just take notes on what not to
do? You observe their actions and you consciously
vow, that is a behavior I will never ever repeat.
You're not copying their success, you're learning
from their failures. It's such a powerful way
to build your own authentic leadership style
instead of just mimicking the people who came
before you. Exactly. The end goal is authenticity.
Don't pretend you're a 1999 Titan in today's
world. It just won't work. Because the world
is constantly changing. The moment you get comfortable
is the moment you fall behind. And that is the
final warning. If you like how things are now,
great. But you have to constantly be challenging
yourself and adapting. Because, as the old Ikemae
saying goes, if you're standing still... You're
gonna be behind. You're gonna be behind. What
a journey. From a frenetic rollerblading startup
to this flexible, team -focused global company,
the lesson from Kate Prouty's 25 years is just
so clear. Evolution is not optional. It is absolutely
necessary for survival. And if you're feeling
challenged by change right now in your own work
or life, we should leave you with Prouty's favorite
quote on this. It really sums it all up. What
is it? If it doesn't challenge you, then it won't
change you. Powerful. So don't just wait for
change. Be the catalyst for it. Thank you for
joining us for the deep dive. We'll see you next
time.