SAL: I'm here with Jessica.
What do you do here, Jessica?
JESSICA: Great question, Sal.
My title here is the chief of staff,
but I like to think of it as a catch-all for any position
that we haven't hired full-time for, I pick up.
So it's a lot on the business strategy and operations
side of the house and covers everything
from recruiting and prepping our documentation for our board
meetings to going to Costco and picking up
the toilet paper if we need it.
SAL: When necessary.
JESSICA: When necessary.
SAL: From very high level tasks to somewhat low level--
but sometimes has to get done.
And how did you end up here?
Where did you start your career?
What did you think you're going to end up being?
JESSICA: I am a native of California,
so I went through the UC system, went to UC San Diego,
and started studying electrical engineering.
SAL: And you went on some type of super scholarship.
JESSICA: I was a Jacobs scholar while I was there.
It is a full merit scholarship.
SAL: Named for Irwin Jacobs.
JESSICA: Yes.
Dr. Irwin Jacobs and his wife, Joan, very generous supporters
of UC San Diego and had started the scholarship program
in hopes of attracting talent on the caliber of the Ivy Leagues.
He had been at MIT before that and had
wanted to create that culture [INAUDIBLE].
SAL: And this was a full ride.
JESSICA: It was a full ride.
SAL: And how many students got this at UCSD every year?
JESSICA: So I was the inaugural class,
and we were a class of 10.
SAL: A class of 10.
JESSICA: A class of 10.
SAL: Probably not too easy to get.
JESSICA: I figure I was just really, really lucky.
My parents were very happy, too.
SAL: And a lot less.
They could go buy a car or something.
JESSICA: They were able to retire a little earlier.
SAL: Retire a little bit earlier.
And so you majored in electrical engineering,
and so you thought you were going
to be an electrical engineer?
JESSICA: I did.
So I did all of my internships in electrical engineering,
had worked at a number of defense companies,
worked at Qualcomm.
And then I ended up going to Stanford
for a PhD in electrical engineering.
And then my first quarter, I actually
got sidetracked when a friend took me
to a management consulting info session that was actually
geared towards engineers.
And I had no idea what this field was.
I'd never heard of it.
SAL: Few people do.
JESSICA: But they had talked about,
you can have all this impact.
You get to work with amazing companies and learn a lot
and travel the world while you're at it.
And I just thought, what could be a better education,
while getting paid a little bit at the same time.
SAL: And staying in nice hotels--
JESSICA: Exactly.
SAL: Nice dinners.
JESSICA: It's amazing how quickly you become obsessed
with travel points.
SAL: And how long did you do that for?
JESSICA: I did that for three and a half years
following my master's, so I went directly
from Stanford into McKinsey.
SAL: So you are now in your early 20s?
JESSICA: Mid-20s.
SAL: Mid-20s, now.
And what kind of work-- how was McKinsey what you expected,
or how was it different than you expected?
And what kind of stuff did you end up doing?
JESSICA: So I ended up focusing on consultancy jargon
of operational and organizational transformation,
which looks at the operational piece goes into organizations--
oftentimes it's technology organizations in my case--
and looking at how people did things,
and thinking of ways they could do it more effectively or more
efficiently.
So I worked with engineers, data centers, executives,
and the like.
On the organizational side, it was actually looking more at
how company culture was, and how you
could make that thrive in an organization
and think about development for people.
SAL: Which sounds eerily similar to some of what you do here.
JESSICA: Yes, very eerily similar.
And then a third piece of what I did at McKinsey, I
had this awesome stint in their internal learning group--
so developing the training of how
to make a consultant a consultant
and looking at how to allow people to learn how to problem
solve and become better with client relationships
and interpersonal skills.
So I really loved the learning piece of it.
SAL: And then, while you were at McKinsey, that's
where you first met Shantanu who is our president.
JESSICA: Yes, we worked on several projects together.
SAL: And despite that, you still wanted to work with him.
JESSICA: Despite that.
For some reason, rose colored glasses [INAUDIBLE]
were really good memories out of it.
Yeah, consulting was interesting.
It was a lot of long hours, a lot of travel.
People think it's glamorous when you're
traveling to other places.
Oftentimes it was like, typing up my PowerPoint
slides as I was on the go and on my phone.
SAL: It's probably a little bit of both.
It was a little bit glamorous.
JESSICA: The traveling was amazing.
I don't think I ever would have had an opportunity
to [INAUDIBLE] otherwise.
SAL: And you were interfacing at a very high level
with a lot of these organizations,
the senior executives.
JESSICA: Best learning experience
I could have ever hope for coming out of school.
SAL: Especially at that age, to be
able to interface with senior people
at some major organizations, I could
imagine would be very great learning.
JESSICA: Absolutely.
It was and incredible training ground.
SAL: And then after that-- what was it,
three and a half years-- and then you decided to leave for--
JESSICA: Yeah, so after three and a half years,
the lifestyle was tough.
I found whenever I was at home, I
was just sleeping to make up for the work week.
And so I decided to leave, and I went to Yahoo!
Given my background in transformations,
this was a company that was in the midst of a huge one.
And I thought I could help.
So I went there-- also was a great actual learning
ground for me.
I was able to interface with everybody
from the engineers to marketing, finance, legal, and just
learned about the entire organization
and how things worked both on the search side of the house
as well as on the advertising side of the house.
SAL: And you worked with a whole-- you ended up at Search.
You were--
JESSICA: I did end up in Search.
SAL: --a product manager there.
JESSICA: Yes.
So I ended up in Search as a senior project manager
by the time I left.
SAL: And so that sounded pretty good.
So how did you end up here?
JESSICA: Yeah.
SAL: Which now, in hindsight, is the worst decision you ever
made.
JESSICA: Best decision ever.
You can pay me $5 after.
SAL: Yes, yes.
JESSICA: Just kidding.
SAL: I would have edited out any negative remarks anyway.
JESSICA: I had kept in touch with Shantanu.
And so he he had told me, over time,
about how he was interfacing with this guy named Sal who
was making these YouTube videos, and I just
thought it was really cool.
I had checked out the site, seen that we had all these practice
modules and some analytics behind it,
and just thought what was happening here was awesome.
So I offered up my free time and said,
hey, I'd love to volunteer.
I started doing that.
And then right around the time of the Ted talk,
things kind of got really crazy for you guys.
And I had been helping to try to find, actually,
a different role that you were thinking of hiring at the time.
And then when things got crazy, Shantanu said, hey actually,
you might actually be a great fit.
SAL: Yeah, I think we realized you
were doing more in your free time
than we would have expected from a full [INAUDIBLE].
It was like, maybe Jessica's the right person for this.
And then you've come, and that was 18 months ago.
But it was at an early stage.
I mean, how many people were we then?
JESSICA: Yeah, when I joined, I think I
was employee number six, after Marsha.
She was really early on.
SAL: And now we're at what?
We're at--
JESSICA: We're now, I believe, we're in our early 30's.
SAL: Early 30's.
JESSICA: Early 30's.
SAL: 31, 32 people.
And we have a bunch of interns right now.
JESSICA: Yeah, a bunch of awesome interns.
SAL: We're like five times bigger than we were.
JESSICA: It's incredible how much we've grown.
SAL: Yeah, it is incredible.
Wow.
And what's your takeaway?
What's the experience been like, and where do you
think this is going to go?
JESSICA: Yeah, so my experience has been phenomenal,
I think beyond what I could have hoped.
SAL: I don't believe you.
I'm sure, but anyway.
Continue.
JESSICA: But it's just been amazing.
I think the people here are all just
so thoughtful and so nice and just awesome.
Everyone's brilliant but just humble about it.
And so I just feel incredibly lucky to be
amongst this group of folks.
I think as we've grown, we've been
able to [? main ?] the quirky, fun culture of being
proactive and thinking epic and shipping beats perfection.
Some of our values, we've been really
great at keeping that going.
As we grow, it's interesting.
I think you once posed the question around,
where would we be 500 years from now?
What would that ideal picture be like?
And I think it'd be awesome if Khan Academy still
exists in 500 years and that we're still completely free
and that we have all the content that anybody
could want to learn.
SAL: And plug directly into their brain at that point.
JESSICA: Yes, by at that point, hopefully it's just plug in,
and you're done.
But I think that would be amazing,
if we could leave something for future generations
to be able to use and have a resource, that,
at this point in time, seemed unthinkable that it would be
free and that anybody can access that quality of education.
SAL: You're inspiring me, Jessica.
JESSICA: The feeling is mutual, Sal.