Transcript: Bonus Episode with Greg Conklin: Navigating Hyper-growth and Tech Debt at Groupon and Dropbox

0:00 Brad Is four years enough time to build tech debt?

0:01 Brad Like I tell you, that's plenty of time.

0:22 Greg So can I ask you about Dropbox?

0:24 Greg You heard Dropbox and Groupon because kind of dual question for both of them.

0:29 Greg Talk about two organizations that had hyper growth.

0:33 Greg I mean, I saw Groupon from the outside as a consumer. It was a cultural phenomena,

0:38 Greg right?

0:39 Greg And Dropbox, I don't think was as much of a cultural phenomena, but I think was explosively growth.

0:46 Greg And then like very technically complex,

0:49 Greg I would imagine because you've got all this data.

0:51 Greg um

0:53 Greg and like tell us about those experiences sure

0:57 Brad particularly like the hypergrowth phase.

1:01 Greg or any part of it but i just think it's you know not everybody gets the opportunity to ride a to be on a ride like a groupon or a dropbox ride

1:08 Brad Oh, it's super fun. I highly recommend it.

1:10 Greg i mean i would i mean i would imagine groupon grew like 10 000 x in a in a year or something like that it was enormous

1:18 Brad It probably...

1:19 Brad It probably did.

1:21 Brad I mean, it grew.

1:23 Brad Let's see, where do I sort of begin there?

1:25 Brad I mean, we could talk about building out these teams, and I think Groupon and Dropbox had different approaches to building out teams. And what I found worked well in both cases was that method.

1:44 Brad was very much aligned to the strategy and the mission and what how the company wanted to operate so for example Groupon uh was a rather Amazon culture like a lot of what went to sort of gain traction and was growing a lot of the Amazon a lot of the leadership at Groupon was was very Amazonian and it lended itself well yes we had

2:07 Brad The deal of the day phenomenon,

2:09 Brad which was our first kind of hook that really grew the company enormously,

2:13 Brad but the overall strategy was build out a series of secondary products. Okay, sure.

2:21 Brad Nail salons and restaurants,

2:24 Brad then travel,

2:26 Brad then maybe physical products,

2:28 Brad then experiences. And it led itself to a more two pizza team GM model.

2:34 Brad everywhere.

2:35 Brad And so the hiring strategy there was find a leader,

2:39 Brad have them build the team.

2:42 Brad And so it was very distributed.

2:46 Brad I had to trade off you would sort of expect from that in terms of like a very heterogeneous culture to put it sort of specifically.

2:55 Brad four years enough time to build tech debt like I tell you I tell you that's that's plenty of time particularly we have engineering you know independent engineering teams all sort of building out separate set of products where where speed was was super important but we had mechanisms in place and the engineering leadership would come together all the time to understand where exactly we needed to

3:19 Brad put something together and call it a platform component or where we're just going to let let it rip and then dropbox was was was quite different um it was growing very quickly but the nature of dropbox needed to be secure it needed to be private right um drew house and the founder of dropbox would say

3:44 Brad You know, your house is burning down what you go back in to get. It's your kids,

3:48 Brad your pets and your family photos.

3:50 Brad And Dropbox kind of has one of those.

3:52 Brad And so it really set the culture there around security,

3:58 Brad privacy,

3:59 Brad getting it right,

4:00 Brad never lose a bit of data was super important. So as you built the engineering teams at Dropbox.

4:07 Brad That is sort of what we focused on when it came to the cultural aspects of the hiring process,

4:13 Brad the behavioral aspects of it.

4:18 Brad So yeah,

4:19 Brad both were very, very different.

4:20 Brad And I was sort of struck by how they matched the way they tried to grow with what they were trying to build as a company.

4:29 Greg At Groupon, was there a fairly thick platform layer for all those two pizza teams to work on top of,

4:36 Greg or was there a lot of

4:37 Brad No.

4:37 Greg duplicate stuff going on?

4:38 Brad I mean, my judgment was no. And maybe some former Groupon colleagues will hear this and give me a hard time about it.

4:49 Brad I remember,

4:50 Brad and this is sort of a tongue-in-cheek sort of joke.

4:54 Brad Your platform,

4:55 Brad you would file, if you're a team and you needed a database, you would file a JIRA ticket and the ops team would respond back with an IP address.

5:05 Brad And it was just an image of a host with a MySQL database on it.

5:11 Brad And that was it.

5:14 Brad We had an ops team that was managing data centers, we had an SRE team that was small but mighty,

5:20 Brad but largely it was pretty much a bunch of startups.

5:24 Brad We had some platform teams that owned, let's say, like the web framework,

5:34 Brad for example.

5:37 Brad So early on it was a monolithic Rails application and we slowly moved it over to like a SOA style node based express web thing until we had a small team that was managing that.

5:50 Brad But it was pretty light. It was pretty light.

5:52 Brad Dropbox only had it was pretty significant.

5:56 Brad Maybe a third to a half of the engineering team was what you might call.

6:01 Brad platform,

6:02 Brad which is understandable,

6:03 Brad right?

6:04 Brad They were managing and implementing their own massively scalable distributed block storage system, massively scalable metadata and structure data infrastructure and things like that.

6:16 Greg I would imagine Groupon, all those startups in Groupon, they must have shared some things. They shared accounts,

6:22 Greg they shared checkout,

6:23 Greg a handful of things like that must have been shared between travel and

6:27 Brad They shared...

6:27 Greg between travel and nails and cars and whatever else you guys were selling.

6:34 Brad um

6:34 Greg Or no, was it all were they all independent?

6:35 Brad it was complicated it was it was complicated i mean yeah i think accounts were shared i mean one one of the things that happened at groupon was um it grew very very rapidly and one of our early on we tried to internationalize the rails monolith and you know internationalizing something like that is is hard particularly when you had no

6:59 Brad you know very little there to build upon and so the strategy became you remember all these Groupon clones like let's just go country by country buy the Groupon clone and so you and so you ended up with multiple multiple platforms and so yeah that's why I'm kind of like how do I answer the question about single account system no

7:23 Brad There was the European one,

7:25 Brad there was the Japanese one,

7:26 Brad there was the North American one,

7:28 Brad there was the South

7:29 Greg Whereas

7:29 Brad American one,

7:29 Greg Dropbox

7:29 Brad right?

7:30 Greg was far more cohesive it sounds like.

7:35 Brad Dropbox was very,

7:37 Brad very cohesive,

7:38 Brad yes.

7:39 Brad Yeah, for sure.

7:40 Greg I think it's interesting,

7:41 Greg Greg,

7:42 Greg that you're kind of talking about how quickly you can get technical debt and especially like it sounds like with the Groupon approach,

7:49 Greg of course, like effectively it's like all a whole bunch of separate little startups all just move in as fast as they possibly could.

7:57 Greg Do you feel like?

8:00 Greg Do you feel like at kind of the senior engineering leadership level where we're where we're you know if there's more than you know if there's more than two teams like you're already like in your your offset away from the choices they're making how do you how do you think the role or the how do you think a senior engineering leader should should try to address

8:26 Greg Yes.

8:28 Greg Systems to slow down the creation of technical debt,

8:31 Brad Yeah.

8:31 Greg you know, systems tech culture.

8:33 Greg What do you what do you what's our when we're wearing our CTO, our VP of engineering hat,

8:37 Greg what do we do?

8:38 Brad Yeah,

8:38 Brad that's, it is not easy.

8:41 Brad I don't have any magic for that either.

8:43 Brad I think it is understanding where the company is trying to...

8:51 Brad go like is there a reason okay is there a reason why we had different authentication systems for for different parts of the world the answer was yes because we we decided to take an approach of acquiring them like they didn't they didn't build these new authentication systems once they had joined but you need a plan to figure out okay where where is that running into you

9:15 Brad problems or where is that either going to slow us down or be a burden to the business going forward in Groupon's case the burden was North America was running really quickly building features and products and meanwhile international was going slow they were just fewer engineers there so you would look at okay

9:34 Brad Where can we get more engineering velocity? And for example, what we had decided was we're going to create a middle layer, like an API layer that will then abstract out the nonsense below it.

9:49 Brad So while we had different authentication systems,

9:52 Brad inventory management systems,

9:53 Brad order management systems,

9:54 Brad customer service systems,

9:55 Brad we had one global mobile app.

9:57 Brad one website that worked globally right and so that was for example what we ended up deciding was the best way to get the velocity because what we were what we were seeing what we were what we were seeing in North America was a lot of product iteration a lot of product experimentation was getting us a lot of good growth and we wanted to make sure that that was easily transferable to other parts of the other parts of the company other parts of you know the business

10:22 Greg Well, thanks, Greg.

10:23 Greg Yeah, thanks for coming,

10:24 Greg Greg,

10:25 Greg and we'll probably maybe have you back sometime.

10:27 Greg It'd be great to kind of catch up on whatever you're up to next and more learnings will always be fun.

10:33 Brad That was awesome.

10:33 Brad Great.

10:36 Greg This episode of How Many CTOs Does It Take Podcast was edited by Saffron Epigab.

10:40 Greg Our theme song was AI Generated by Brad.

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