Honestly, I lean more on our
investors—we used to have two
or three, and now as a public
company, we have thousands.
So it’s much easier to gather
thoughts and feedback about
what we’re doing, and what we
could be doing better.
Can that feel like an overwhelm-
ing amount of advice?
It’s both a gift and a challenge
to have lots of ideas—think
about doing a brainstorm-
ing session and then all of a
sudden you have 50 ideas to
execute instead of three. But
I’ve learned to prioritize the
ideas that bring the most value,
and that’s given me the tools
to explain those decisions to
investors: “This direct-buy
initiative will have a huge ROI,
and this idea around X or Y
might be interesting someday,
but we’re focusing first on
higher- value opportunities.”
People love to talk about Stitch
Fix’s habit of hiring actual rocket
scientists to the data team to
improve intelligence used to
personalize customers’ offer-
ings. At this point, how much
room for improvement is there?
There’s never going to be
a sense of Oh, we solved it!
There’s a constant evolution
in people’s personal style—you
might love something today but
not next year. That’s the chal-
lenge. Our predictive models
are very strong, but they’re
not 100 percent. And I don’t
expect that they ever will
be. Our success rates have
improved dramatically since
2014, and we have the data to
show that. The more we get
to know people, the more we
understand people.
What do you do when a
customer isn’t happy?
Eighty-five percent of the time,
customers choose to share
feedback: I didn’t like this; I
just had a sweater in a similar
color; these pants are too long.
I’ve never once filled out a
survey to let a company know
what I did and did not like
about an item of clothing, but
our clients do that regularly.
That helps us add the human
element and serve them better.
Sometimes things will be great,
sometimes they may not be
great, but we’re here to listen
and help.You get a lot of attention for
being a young female founder
in tech. Do those monikers ever
get tough to embrace or feel
like a burden, or is it something
you’re happy to lean into?
No matter how I feel about it
at any given moment, it is very
important for somebody like
me to be in a role like I am, and
to be visible and show possibil-ity. I know that from my own
upbringing: I never thought
entrepreneurship was for me,
and nobody ever told me as a
kindergartner that someday
I’d be a CEO. And yes, for a
long time I was reluctant to be
categorized as a great female
CEO—can’t I just be a great
CEO? But I hope there will be
many, many more. When I took
the company public, I was the
youngest female founder ever
to do so, and I hope that title
doesn’t last long.What was your experience
like in the earliest days, as
a woman building a brand that
would primarily serve women?
Fundraising was reallyOver the past nine years, how
have you changed as a leader?
The IPO was, of course, a mile-
stone, but what are some other
moments that really affected
your leadership style?
Teams are built in hard
times, and lucky for us, we’ve
had a lot of those. In the early
days of the company, there
was a time when we were eight
weeks away from not making
payroll, and I was so stressed-
out thinking about the two
people on my management
team who had mortgages and
kids. And I thought, Should
I bring them along and tell
them what’s going on, or is it
too scary for them to know? But
ultimately, I told them, and
because they were financially
responsible adults—which
I wasn’t at the time—they were
more concerned about thecompany than how they
would personally be impacted.
That was a pivotal moment
for me.How has that lesson stuck
with you?
It’s really helped me bring the
team together. I’m not sure if
this is the right analogy, but it’s
like when you only see someone
post pretty pictures on Insta-
gram, you kind of know that
their life isn’t really like that all
the time, right? It’s the same
thing as a leader—if you only
stand up and talk to your team
about the good things happen-
ing at the business, it’s just not
authentic. And the people in the
room know better.challenging for all kinds of rea-
sons, but mostly because there
just aren’t enough female inves-
tors out there. VCs are the ones
who decide what gets funded.
They decide which people will
become leaders. They decide
who our children are going to
work for. Those are really, really
important decisions being made
by a relatively homogeneous
group of people. But the good
news is, success ignites the
capitalist part of a VC—and
there are 50 VCs out there who
passed on Stitch Fix. So they’re
now looking at the market and
trying to not make that kind of
miss again.Now that you are in a position
of power, what are you doing
to support founders who might
not be getting the attention
they’re seeking?I’m generally only able to
take one or two non–Stitch Fix
meetings a week—I just can’t
do more given the demands
of my day job. But I do this
thing on Instagram called
Mentoring Mondays, where
I post a Q&A and throughout
the course of my day find
time here and there to answer
questions from people who
write in. If I have a sit-down
meeting with Susie, there’s no
scale to that, even though we
might have talked about some-
thing that would be helpful
to thousands of people. So
doing these sessions on Insta-
gram, it’s very scalable, and the
info is captured and available
to everyone.IT IS VERY IMPORTANT FOR SOMEBODY LIKE ME TO BE
IN A ROLE LIKE I AM, TO BE VISIBLE AND SHOW POSSIBILITY.
I KNOW THAT FROM MY OWN UPBRINGING: NOBODY EVER
TOLD ME AS A KINDERGARTNER THAT SOMEDAY I’D BE A CEO.”March 2020 / ENTREPRENEUR.COM / 15