Screaming in the Cloud - Democratizing Software Development on Stack Overflow with Prashanth Chandrasekar
Episode Date: May 20, 2020About Prashanth ChandrasekarPrashanth Chandrasekar is Chief Executive Officer of Stack Overflow and is responsible for driving Stack Overflow’s overall strategic direction and results. Pras...hanth is a proven technology executive with extensive experience leading and scaling high growth global organizations. Previously, he served as Senior Vice President & General Manager of Rackspace’s Cloud & Infrastructure Services portfolio of businesses, including the Managed Public Clouds, Private Clouds, Colocation and Managed Security businesses. Before that, Prashanth held a range of senior leadership roles at Rackspace including Senior Vice President & General Manager of Rackspace’s high growth, global business focused on the world's leading Public Clouds including Amazon Web Services (AWS), Microsoft Azure, Google Cloud Platform (GCP) and Alibaba Cloud, which became the fastest growing business in Rackspace’s history. Prior to joining Rackspace, Prashanth was a Vice President at Barclays Investment Bank, focused on providing Strategic and Mergers & Acquisitions (M&A) advice for clients in the Technology, Media and Telecom (TMT) industries. Prashanth was also a Manager at Capgemini Consulting where he managed Operations transformation engagements and consulting teams across the US. He holds an MBA from Harvard Business School, an M.Eng in Engineering Management from Cornell University and a B.S. in Computer Engineering (summa cum laude) from the University of Maine. Prashanth is married and has two children.Links ReferencedTwitterRackspaceStack OverflowStack Exchange
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Welcome to Screaming in the Cloud.
I'm Corey Quinn.
I'm joined this week by relatively recent Stacks Overflow CEO Prashanth Chandrasekhar.
Prashanth, welcome to the show.
Thank you, Corey. Pleasure to be here. Thank you for having me.
Your history is fascinating.
Before you joined Stack Overflow as the first non-founder CEO, to my understanding,
you came out of a relatively lengthy tenure back at Rackspace.
That's right. Yes, Rackspace is a tremendous company and experience. I'm so grateful for that
as part of my career and just really having worked with a tremendous number of amazing people at the
company down in Texas and around the world. Yes, so my journey at Rackspace was all about
how do you redefine the company
in the context of a fairly competitive landscape in the cloud?
If you remember, Rackspace was originally,
it started in the context of a managed hosting company
well before I joined there.
And when I joined in 2012,
we had our own public cloud, the OpenStack public cloud,
and going head-to-head against Amazon Web Services,
which was our primary
competitor. And, you know, as we know today, you know, obviously AWS is a leading public cloud
capability and, you know, still growing just a massive, massive, you know, success by Andy
Jassy and team. And so back in 2014 or so, our company decided that we wanted to effectively
not compete based on infrastructure and just
based on a price wall, which is obviously going to go to zero, which didn't make any
sense.
And that...
Who could lose money the slowest and be the last person standing?
Yeah, indeed.
And then Amazon, being the company that it is, relative to Rackspace, its relative size,
it didn't make a lot of sense for us to compete based on that dimension.
So what we had to do is some soul searching to determine what we were truly good at.
And we decided that we were really good at what we call fanatical experience or fanatical
support, what we used to call it back then.
And that was all about providing services.
And so that's what we ended up doing, saying, why were we so specific about providing services
only on our cloud or our infrastructure? Why wouldn't we do it on any kind of infrastructure, much like we
would support Linux or Windows in the operating system context? So that's when we made a strategic
decision in the company, one of the most important decisions in the history of the company to support
Amazon Web Services. And then, you know, soon after Microsoft Azure and Google Cloud. And so
that was just a, you know,
I would say a huge pivot for the company.
And, you know, I was part of the founding team
that did that and then also helped lead that business
to a multi hundred million dollar business
over the course of just a few years.
And that ultimately was called
the Managed Public Clouds business at Rackspace.
And that was, I would say,
just a tremendous experience in building something
very rapidly, scaling it very rapidly,
enabling a lot of people,
both on the product engineering side
plus also the go-to-market side.
So just an all-around,
just a great experience that I'll never forget.
Oh, absolutely.
It's fascinating talking to you,
just because for those who aren't privy
to all of the ins and outs
of my various career twists and turnings,
you and I went to undergrad
at the University of Maine and Orono at the same time.
And that is the last time
we ever really had anything in common.
You wound up graduating summa cum laude
with a BS in computer engineering.
You got a master's in engineering
and engineering management from Cornell,
and then an MBA from Harvard Business School.
Whereas I failed out of undergrad, discovered my high school diploma was not accredited.
So on paper, I've been walking around with an eighth grade education that no one can ever take away from me.
The path not taken, as it were.
But you've had a fascinating career trajectory and now have landed as the first non-founder CEO of, whether we think of them as a cloud company or not,
I would argue that the cloud would not exist without Stack Overflow in its current form.
Yeah, no, by the way, on the background, yes, you know,
it's just a fantastic coincidence that we both went to the same undergrad schools.
And obviously, listen, everybody has their own path, right,
to their own kind of finding their own true purpose and what they end up doing in life.
So no, nothing's right or wrong.
It just happens to be what the path to be chose.
So I would say, you know, I think that, yes, Stack Overflow throughout my time at Rackspace was just a, you know, such a loved entity and a loved community.
All my technical teams always historically use Stack Overflow.
We've always known about it.
I've known about the company for a long time.
And then more towards the end of my time at Rackspace was approached about the role, saying
that, hey, this great foundation exists of this community.
It still has something like 50 million users that come to the website every month.
Just on Stack Overflow, if you include Stack Exchange, there's another 70 million folks
that show up to the Stack Exchange websites. That's about 120 million people that show up every month.
We have something like 150,000 new signups on Stack Overflow every month. So just a tremendous
amount of scale at 12 years or 10 years after, 12 to 10 years after founding the company.
And that foundation is just, I would say, would say there's not, there aren't a
lot of companies that actually have that sort of a phenomenal foundation. And on top of that, you
had these great products that the company was beginning to build and had built over the past
few years. Talent product, which is our job listings product where big companies can post
their jobs on our website. And obviously we have the world their jobs on our website.
And obviously, we have the world's developers on our website,
about 25 million.
All of them are pretty much used for a daily basis.
So they're able to match jobs and applicants.
And then you've got the ads business that basically is an ability for big companies
to showcase their developer-centric products.
So think about, for example, in the case of Google Cloud, it could be BigQuery and how
ads on that so that developers can leverage the product.
And then finally, the latest SaaS product that we have is called Stack Overflow for
Teams product, which is just a tremendous way to share knowledge and collaborate within companies across their development teams,
their product teams, their security teams, IT teams, et cetera,
to make sure that they have the latest and greatest content internally around their feature releases and, you know,
code snippets, et cetera, and all be available for teams like go-to-market teams and other teams that need to be very close to,
you know, the core information.
And that product has really been a tremendous growth engine for Stack Overflow.
So we've seen that business double year over year.
And we've got companies like Microsoft that have something like 70,000 users on Stack Overflow for teams.
So that whole story and why Stack Overflow is sort of an inflection point in its history.
It's helped build the cloud, to your point, by enabling developers around the world to really rapidly build out capabilities across AWS, Azure, and Google, but also now helping them become even more efficient as part of their developer workflow and adding value, like helping them find jobs and awareness about various products.
So hopefully that's a good,
it's a helpful overview for you.
Oh, it absolutely is.
It's always interesting when you see a company
that is effectively a household brand,
has a management or leadership shakeup in different ways.
For example, when Google acquires something,
the immediate knee-jerk reaction is,
oh no, they're going to kill it.
When Stack Overflow effectively changed leadership, it was the biggest reaction I had as a full Stack Overflow developer myself is, oh my god, there might turn off copy and pasting, and then where will I be?
So just for the record, there is no current plan to disable copying and pasting on Stack Overflow, Stack Exchange, or any of the affiliated Halo sites?
Oh my goodness, no.
I think that we want to do more things for our community, not less things.
We want to make life easier for our community members versus the opposite, so absolutely not.
Just to think about a lot of what we're planning on doing this year is about one of
our top priorities is community engagement and inclusion.
So we really are trying to make sure that we get more and more developers and hobbyists,
et cetera, that are, you know, and people are writing code earlier and earlier in their
lives.
We're trying to make sure that they feel extremely welcome to leverage the community to utilize the
resource that's there. How do we, you know, have even more productive ways to intersect our public
community Q&A platform and our private Stack Overflow for Teams product so that, you know,
there's even more, you know, kind of a workflow integration, developer workflow integration,
so people don't context switch, etc. All those things are in the spirit of making sure that life is easier for community members
like you.
Because today, most people like you go to Google, type in a question about whatever
could be a Python question or Amazon Web Services question, and you land on Stack Overflow.
Or copy and paste an error message directly in and cut out the middle person.
For whatever reason, that seems to be a less common approach than it really should be
given how many problems it seems to solve for.
Exactly, yeah.
So that happens more often than not.
And we just believe that it should be
a lot more seamless of an experience
for users like you.
And that's why we're integrating with,
in the community, we integrated with GitHub last year.
For our Stackable for Teams product,
we have integrated with Slack and Microsoft Teams,
and we're about to announce our integration
with Jira and GitHub Enterprise.
So there's just a lot that we're hoping to do
to make sure that the developer workflow
is highly, highly integrated
and ultimately indispensable as part of that.
I would say that, for better or worse,
whether or not companies know
that they're dependent upon Stack Overflow, they absolutely are.
In that it has saved so many person years of time in the past decade or so, however long it has been in business.
It feels like forever, but I understand that it's not.
The awareness of the passing of time is a slippery thing.
But it has been a transformative place to solve things i mean i will say that i've
dabbled a little bit as a part of the community and found it wasn't really for me and for the
best of all reasons namely that giving an answer should not be a facile one or two line response
there's expected to be some depth and some exposition and explaining not just what the
right answer is but why it's the right answer.
And when I'm trying to do this late at night from a phone in a hurry, that doesn't really lend itself to the same thing.
I mean, I rarely have the attention span to finish writing a complete tweet, let alone a full, deep, technical dive into something.
So that highest community standard is absolutely one of the differentiating virtues of the entire community.
Yeah, no, spot on on that. absolutely one of the differentiating virtues of the entire community.
Yeah, no, spot on on that.
I think that there is a very, you know, you've got to give our founders just a tremendous amount of credit, right?
Both Joel and Jeff Atwood have built this system that is, you know, sustained for so
long.
And despite what could be perceived, maybe harsh realities of, you know, downvotes or
kind of like a very binary experience
or very specific experience. It works. It just works. And that's the whole point of it is to
make sure that people get the right answer very quickly and they're on their way. And that does
come with some downsides with regards to sort of the friendliness element. And if you're a newcomer,
you might feel may not be kind of like the easiest way for you to get going.
You know, I remember when I was dabbling myself in the community, even before I joined the company, you know, I would say it was sort of a harsh reality of actually participating as a brand new member.
It's not the easiest way to get started.
So we are testing and iterating on several ways to make sure that we're a lot more welcoming, making sure that people don't feel intimidated. One of the more recent things we've done is
actually make sure that people asking great questions also get as many points, if not
relative to answering questions. And then we also are making sure that we remove negative comments,
and we've actually made some tremendous progress over the past quarter on that, almost half the
negative comments relative to the prior period of measurement.
So we are doing many things to make sure that
despite the very objective binary system that's in place,
we are making sure that we're making it more welcoming
for new users.
You've also made significant changes in the past year
around how you're handling diversity conversations,
representation from different groups in the community. And what's, I guess, fascinating to me
is how public you've been about some of this. It hasn't been something that you give lip service to
it once a year and then it vanishes. We're starting to actively see changes in the community happening
and percolating out. You haven't been trumpeting it from the rooftops, but you also haven't been secret about it or working non-transparently to get there. It's fascinating. And I'm curious as
to how that's, I guess, how that came to be and how we can start seeding that in more companies.
Yeah, I know. I think, you know, we just believe that Stack Overflow, given kind of like the level
of influence that we have around the world, you know, we are very much a platform, a community platform that represents our users, the user base across the
world, right? So the world's developers leverage our platform. But we have a long way to go in
terms of even making sure that everybody signs up for an account and is active, etc. So there's
plenty of work to do. And part of when we do our developer survey, for example, our yearly developer
survey, it's just very, very interesting for us to see some of the results that, you know, some of them
stood out to us, right? Whether that's, hey, you know, most developers are, 80% of the developers
are coding as a hobby. And there's a diversity element there, right? Like how do we make sure
that even newbies or people that are new to programming feel included as part of this? Or the fact that you
have, you know, people that are less than 17 years old, 18 years old, we're talking about at least
50% of the people that we polled were less than, globally, less than 18 years old. So we're talking
about a demographic, an age demographic inclusion metric that's very important to say, how do we
welcome youngsters into the flow of
making sure that they are participating? Or even more specifically around gender diversity, right?
And if you look at that, it's heavily lopsided in terms of males and females. And we say,
I think approximately only 11% of our survey, US survey respondents, you know, were women this year. It was a slight
improvement from last year, about 9% last year, but still very, very small. And if you think about
that, that just seems, you know, it's not representative of the world's developers.
You know, I grew up in India. And just within that country alone, you know, the number of
women developers that are emerging into the workforce is just a fascinating number.
Right. And obviously, I moved here for college and joined you in Maine when I was 17.
But the point is that it's just an important statement and kind of a piece of work that we need to make sure that we represent what's truly in the world.
And so we are very committed to making sure that diversity and inclusion is a top priority for us. This starts, by the way, at, you know,
at our own company, like the people that we hire, my own leadership team. So, you know,
we're just making a very conscious effort to make sure that we are very much reflecting
our community in a way that is, you know, fully representative of, you know, the true
user base that's out there to make sure we lead by example. And you will see us do many things
this year to make sure that we make progress on this key initiative that we'll keep you posted on.
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How do you wind up effectively balancing between two very important
but almost inherently oppositional goals?
One, to wind up continuing to drive change within the community
and make the product offering and discourse, frankly, better,
versus the other side of avoiding the dig
or what seems to increasingly be the Reddit trap
where a redesign drives the community members away.
Or any time you start changing a community,
there's a large group of people out there,
and often I'm one of them,
who despises change or anything that smells of change
because we delude ourselves into thinking
that the world will hold still long enough.
Yeah, phenomenal question.
I think that, you know, there are a couple of things
to note here.
I think one is we are very much convinced
that it is important for us to make sure
that we seek input from a very broad set of folks, just like our developer survey that I mentioned.
You know, we are we've got new mechanisms in place that like the loop survey, which we've launched, which really expands the number of voices that we have in terms of the voice of the community, so to speak.
So we really understand what people want to make their experience even better. And so that change, or set of changes, because historically, you know,
we have completely relied on just mechanisms and forums like Meta, which is, you know,
home to a tremendous power user base and the folks that are such highly, highly valued members
of our community. But it does represent a very specific portion of our community and doesn't necessarily include
the entire population that we want to kind of really hear from.
So that is important.
You know, we want to make sure that we are making sure that we make changes to the question
asking process, you know, questions of asking wizard, unfriendly robot and others.
And this has, you know, really led to some really strong results.
So more people are asking questions without seeing a dip in the question quality. And we cut the
number of negative comments nearly in half without seeing any sort of reduction in the overall
comments. And ultimately, December was our best month ever in the history of our company in terms
of new signups. So there are things that we are doing
that are resulting in, I would say, positive traction. Now, to your point, not everything is
easy to be managed in terms of change. So we have to articulate, we need to do a much better job,
by the way, as a company of articulating how and why we're including these new mechanisms.
What is the role of existing mechanisms like Meta? Because they're obviously
very valuable for us as we continue to evolve the community. How do we make sure that our power
users are part of the journey of helping us get to the overall goal of making this community even
more impactful? Because clearly they care about that. So there's a lot to going to manage around
that. But I think that we are very committed to making sure that we have a robust listening process to make sure we listen to our community and also to have bi-directional feedback and to make sure folks like me and others are going to be very active to make sure that the community is always in the room when we have a key conversation.
We're going to make that happen. One thing that, I don't know if it was a problem or a change that I was somehow
tripping over based upon asking stupid questions, but it seemed for a while
that every third time that I googled for a particular error
message, the top result was always something on Stack Overflow.
And that was always a conversation that was closed as off-topic or marked as a
duplicate, yet somehow it was always at the top of Google search results to the point where it became a recurring joke.
I don't see that happen nearly as much anymore to the point where when I do, it feels like it's almost an oddity in its own right.
Is that something that was a change on your end?
Was that just I learned to Google for better questions?
Or was there a flare
up in that that suddenly just wound up getting fixed, but everyone thought that was how it was
supposed to be? Yeah, this is interesting. This is about basically improving our code of conduct
and educating our moderators and power users. So it's making sure that we are very specific
about how we improve on a day-to-day basis. We make sure that people are evolving
how they actually operate in the community and how we bring along the community for that ride.
So that's effectively what you're seeing there. And to make sure that our moderators are
enabled with the right sort of information and we're really trying harder to make sure we
help new users and beginners and not to be too zealous about our gatekeeping so that people are more welcoming here internally.
It definitely seems to have had a meaningful impact.
Now, I have to assume that there's more to your company as far as revenue models,
as far as what you folks do, than providing the answer to me frantically Googling while on a phone screen,
how do I fizzbuzz? What are you folks beyond the community, which is the way that most of us tend to interact
with you? Yeah, thanks, Corey, for that question. I think that the Stack Overflow is mostly known
for the community that we've established over the past decade, right? So the 50 million folks that
show up to our website every month, the additional 70
million that show up to our Stack Exchange websites, and then the 150,000 people that
sign up every month for new accounts. But what's not well understood and perhaps not
as recognized is the fact that we are a true company, a SaaS company. And so very much like
how GitHub had its own enterprise journey, we've been on that journey for a few years, just a couple of years.
And that's one of the reasons why I'm also on board, which is to make sure that we really build a sustainable and long-term and successful business at Stack Overflow.
In addition to obviously the core mission of making sure that we really help our developers and our technical workers.
So in terms of the products, we have our talent business, which is really, you know, we have
something like 40,000 jobs were posted on Stackable for jobs in 2019, which is, you know,
matching against or close to a million searchable profiles of developers who are interested in
being contacted by a job on Stackable for talent.
So that's our first business, the talent business.
It's a big area.
And we also, you know, we have a second business which is called the advertising business,
which is something like a million developers found new and useful tools after seeing a
company advertise on one of our sites this past year.
So think about Microsoft advertising about Microsoft Azure or Google advertising about
BigQuery,
those sort of examples.
And then our third product is our true SaaS product
called Stack Overflow for Teams,
which really allows developers and product folks, et cetera,
to really collaborate and ship products really fast
within their organizations.
And so we've had hundreds and thousands of engineers
who have leveraged our product in 2019.
As an example, Microsoft has something like 70,000 developers on Stack Overflow for Teams.
So those products are just the beginning of, you know, I would say our commercial journey.
And some of those products, especially Microsoft, the Stack Overflow for Teams rather, is growing at a very rapid rate, right? And we have all the, you know, the Fortune,
Fortune 100 companies, really some phenomenal logos like Bloomberg and Microsoft and a whole bunch of other fast-growing startups like Expensify, et cetera, that are all leveraging
Stack Overflow for Teams and are just amazing use cases internally within these companies.
So we're really tagged against, you know, the future of work, if you will. So we integrate with Slack and Microsoft Teams and very soon with GitHub Enterprise and Jira
to make sure that we're really part of the developer workflow so that we help developers
go faster and faster as they ship products. As you take a look across the larger ecosystem
and community, what do you think is the most misunderstood about the company in the common case?
Yeah, it's a great question.
I would say it's probably the notion
that Stack Overflow is a community
and it's really not,
people don't really truly understand
the other products that we have
that are also tremendously valuable.
I think most people just know us about the community
and assume that we don't have a revenue model,
when in reality we have a very robust revenue model
that's in many ways, you know,
just about to really explode in a good way.
So that's just, I would say the biggest,
I would say lack of understanding.
And I think the other part is I think just,
people just don't realize the scale at which we operate.
Right, I think people just don't understand that we are pretty much,
I would say, the life force of the internet.
I mean, everybody, there's not a single developer in the world
that does not use Stack Overflow.
I mean, that is not a kind of a brash claim.
I think that it's hard to come across a developer
that has not used our website one way or the other.
It is the new way, or if you will.
Well, many of us may not admit it,
but absolutely, we use it.
Exactly.
And so I think that is, I would say,
one of the unsaid kind of statements.
And most people, you know,
I don't know if everybody realizes that, realistically.
Yeah.
Well, what would you do if you had this problem in an interview?
Well, I'd Google it.
Well, what if Google is down?
That's okay.
I already know Stack Overflow's address.
We're good.
It becomes one of those fun, exploratory things.
I guess, what are you seeing or concerned about
as a CEO who is not a founder of the company,
effectively their first external CEO?
What's top of mind as you step into
what are admittedly some very big shoes?
Yeah, so I think that a lot of what I've done so far
is to really listen to all our employees,
our community members, and our customers of our products.
And constantly, every week,
I'm talking to a large number of them on a regular basis
just to really make sure that I have the full context
to really make the right decisions in terms of the types of products that we build,
what we need to evolve as a company, et cetera.
So a lot of what we're, you know, I think what we're trying to accomplish,
I think even in my first 90 days of the company, one of my observations is that I think a lot of,
well, the external community and the tech industry has very rapidly evolved.
You know, if you think about the cloud, and you know this better than anybody,
which is between Amazon Web Services
and Microsoft Azure and Google Cloud
and concepts like Kubernetes, container orchestration,
you know, Lambda with serverless,
you know, there's just a whole world
where infrastructure and DevOps
and software engineering, software frameworks, all of those things are sort
of, you know, very much colliding and really the lines are blurring. And so even for sort of our
experience on the community or in our community websites, I don't think have evolved as much as,
you know, the end customer, the end community member has evolved in terms of what they do on
a daily basis. So there's a lot of what we have to improve in terms of the experience between our Stack Exchange websites and our Stack Overflow website.
And to make sure that, you know, people have all the things at their disposal, whether that's DevOps concepts or cloud concepts or, you know, Stack Overflow concepts, you know, all questions and answers at their fingertips.
As an example, we have 182,000 questions on Azure
and we have 87,000 questions on AWS
and 20,000 questions on Google.
But it's actually not well understood or well recognized
because it's actually sitting in Stack Exchange
sort of in a corner with a bunch of other websites that we have there and phenomenal properties.
But it's away from Stack Overflow.
And most people just go to Stack Overflow.
And we also have, by the way, communities like information security and DevOps and data science and so on.
So there's just a lot that we can do to make sure that we bring those to the forefront so people actually are able to leverage all these great resources. So that's really, I would say,
a lot of what we're thinking about,
making sure that one of the things
that I've noticed
that we have not necessarily evolved
just like the external developer,
external meaning outside our company
has evolved very rapidly
and we need to do a much better job
of doing the same on our end.
Fantastic.
Last question before you go.
And I just wanted to get your take on this. A while back, Joel had a blog post. I think it was a blog post. It could have been a bunch of the best companies in the world to work at.
And this is going to sound petty or like I'm being sarcastic, but I swear I am not.
The fact that every engineer there gets the option of having their own private office
is mind boggling to me. I have worked in too many startups where you're sitting cheek to jowl with
everyone next to you that holds still long enough. And just the idea of a private office is hands down one of the best opportunities to differentiate yourselves.
I don't know why other people don't do it, but it is one of the most aspirational aspects of Stack Overflow culture that I think I've ever heard of.
Yeah, no, absolutely.
I obviously can't take credit for that. That's all Joel and his, you know,
his philosophy and his, which I totally agree with, by the way, which is really making sure
that we provide an environment for our engineers and our developers to make sure they're highly
productive in the same vein of what I've discussed, you know, kind of our various products, etc.
But it's the physical environment. How do you make sure that they actually have the space
for them to be sort of in the zone, so to speak, to be able to really contribute at their highest level?
And so that's, you know, I think it's very distinctive about our culture.
One of many things, by the way, that makes Stack Overflow such a great place to work
for.
And so, you know, we welcome, we're always hiring, by the way.
So if anybody's listening here, we're always looking for new and talented stackers, as
we call them.
So please, please reach out to us.
Thank you so much for taking the time to speak with me today. I really do appreciate it.
Same here, Corey. Real pleasure and great to reconnect with a fellow Black Bear.
Yes, eventually those scars will one day fade as soon as the main shill gets burned from my bones.
Prashanth Chandrasekhar, CEO of Stack Overflow. I'm Corey Quinn, and this is Screaming in the Cloud.
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