Becoming Mobile First

It was a Wednesday, mid-summer 2019. I don’t know which Wednesday specifically, but I know that it was a Wednesday because I was attending Artsy’s weekly all-hands meeting. Two hundred colleagues were also there (many dialing in remotely) and we were all listening to Artsy’s new CEO talk about the company’s direction. Mike Steib had […]

It was a Wednesday, mid-summer 2019. I don’t know which Wednesday specifically, but I know that it was a
Wednesday because I was attending Artsy’s weekly all-hands meeting. Two hundred colleagues were also there (many
dialing in remotely) and we were all listening to
Artsy’s new CEO talk about the company’s direction.
Mike Steib had only been around for a few months at that point, getting to know the business. He was talking about
the product direction, and I was listening intently.

With Artsy’s iOS app, I knew there were only really two directions we could go. As I listened, I reflected on how
we had gotten here.

When I joined Artsy in 2014, I joined the Mobile Team. It was an amazing team. While we were called the “mobile”
team, we only worked on Artsy’s iOS apps and not the mobile website.

By 2016, Artsy Engineering had grown to the size that having only a “mobile team” and a “web team” was no longer
working well. We dissolved both teams and distributed the engineers into
new product teams, focused on
vertical aspects of Artsy’s business. Auctions. Partner Success. Editorial. And so on. The idea was that each team
would have total autonomy over building products to support their slice of the business, and each would have the
engineering and design resources to build new features across both our web and iOS canvases.

That structure worked well, and continues to work well today (we have continued re-organizing ourselves into new
teams to better meet business goals). But once we dissolved the mobile team, there was no longer anyone looking at
our iOS software holistically. The app had become a series of silos – each silo was internally consistent, but
distinct from each other. Often each silo was written in distinct programming languages (we had also started
adopting React Native).

New iOS technologies had been created by Apple, but our teams weren’t taking full advantage of them. We would
update to support the latest versions of Xcode and iOS in the free time between other tickets. It wasn’t ideal. Of
the five original members of the Mobile Team, everyone else had moved on except
me.

As a product, the app was languishing.

Yet despite this, it was also hugely popular among our users and very important to Artsy’s business. Art collectors
love our app! It gets a large percentage of our total sessions. Also, users place an outsized number of auction
bids and artwork inquiries using our app relative to the number of sessions on our website. In fact, the highest
value artwork transaction ever to take place on Artsy was made on an iPad, running software that I helped build.
I’m still pretty proud of that.

So, Wednesday all-hands. I stood there, not sure of what would happen next. I could see Artsy either making a
massive investment in the app, or I could see Artsy cutting its losses and focusing on the software that we already
knew how to build. Which direction we took largely depended on this new CEO, who was now standing in front of us
all and describing the direction Artsy’s product would take next.

The Dream

Mike said something that caused a lot of raised eyebrows in the crowd. People were excited. I was excited.
Artsy’s product organization would shift to adopt a “mobile-first strategy.”

Someone asked “does this mean the app will reach feature parity with Artsy’s website?”

Mike responded: “No. It means that features are going to launch first on the app. If anything, it’s the website
that will be catching up to the app.”

I was kind of blown away! I mean, this had been the spirit of our original re-org in 2016, but that hadn’t really
materialized. The app had continued to trail the website. At most, only one product team was ever building new
features for the app (usually which ever team I happened to be on). Shifting to this mobile-first strategy would be
a massive undertaking, but I was keen.

In August, an email landed in my inbox from Artsy’s head of software. He wanted to spin up a new team to focus on
the app: the team would be responsible for supporting Artsy’s new mobile-first product strategy. He wanted to know
what I thought, and he wanted to know if I was interested in leading the team.

Honestly, it was a dream come true.

Screenshot of the RFC for creating the Mobile Experience team

Here we are, a year later. This is the story of how Artsy created its Mobile Experience team. How we recovered a
languishing iOS app. How engineers helped shift the product organization to a mobile-first product strategy. And
how Artsy grew from sometimes having a team working on the app, to usually having every team working on it.

Another screenshot of the RFC for creating the Mobile Experience team, describing frequently asked questions

Getting Our Bearings

When Artsy created its new Mobile Experience team, we were already resource-constrained and so the new team would
need to be nimble. We had three full-time engineers (myself as tech lead, and two others), assisted by a designer,
product manager, and data analyst, who would each be spending only half their work time on the Mobile Experience
team. We needed to be scrappy. I’m really proud of the work that that early team accomplished, and I look back
fondly on those first few months working with Sam, Joanna, David, Kieran, and Ani.

The first thing we did was define our own mandate. What was this team responsible for? What was it not
responsible for? “Mobile Experience” is pretty vague, and we had to answer a lot of upfront questions. Would we be
responsible for all of Artsy’s iOS software? No, just the main collector app. Would we be responsible for Artsy’s
mobile website? No, that’s too far-reaching. What about Android? Well, yes, eventually…

After we decided on our mandate, the next step was to get really familiar with the existing app. We storyboarded
out all the existing screens and their connections to one another.

Screenshot of all the screens in our app laid out to discuss

Screenshot of a brainstorm for app ideas

No one on our team had complete knowledge of every screen in the app, not even me, so exploring it together was a
great way to uncover what needed immediate attention. One example was our partner page, which displayed information
to our users about Artsy’s partners: galleries, museums, auction houses, etc. We learned that the app actually used
an ancient web view, and it didn’t even show the partner’s artworks. The artworks! Probably the most important
thing for it to do!

Screenshot of a presentation showing the old partner page

Screenshot of a presentation showing the new partner page, which looks much nicer

This is where “being scrappy” started to take root. Usually when developing new features, Artsy designers iterate
on a design before we plan on execution, then we implement, test, and deploy. The nice part of replacing something
that was obviously broken was that we didn’t feel beholden to this usual process; whatever we built would be
better than what we had. One engineer and our designer started the new partner page with a quick pencil sketch,
using the app’s existing UI abstractions to design something that we could quickly build. Once we had a prototype,
the engineer and designer iterated. The whole project took only about three weeks.

Early Wins

Learning about the app itself was critical, but equally important was learning about how our users used the app.
We scheduled user interviews and, in the mean time, looked into our anonymized user analytics. Our data analyst
found a few representative sessions and we walked through each action that a user took. One big lesson here was how
much our app users relied on the app’s search feature, which was still written in Objective-C and hadn’t been
updated in a long time. We found that users would often search for the same query several times in the same
session. For example, users would search for “banksy”, wander off exploring some art, and then return to search for
“bansky” again. And again. And again.

Our search implementation didn’t show users their own recent searches, which would have greatly reduced the amount
of friction users experienced while exploring the art world in the app. Our other engineer took point working with
our designer to migrate the app’s search to React Native. We also added some other features to our search page,
like adding entity subtitles so users would know if the result they were tapping on was an artwork, and artist, a
gallery, and so on. The whole project took about a month to complete, and we have continued to iterate on the app’s
search.

Screenshot of a presentation showing the new search

In early conversations with company leadership, the Mobile Experience team settled on an… interesting strategy to
what we would prioritize. Our mission was “to make the app not suck.” This might seem harsh! But it came from a
place of caring. We knew how much better the app could be and we were motivated to make that a reality. In the
spring of 2020, the team felt like we had reached a point where the app no longer “sucked” – our goal now was “to
make the app amazing.”

During 2020, we made a lot of changes to the app. We had built a new home page, a profile tab for users, granular
push notification settings, Sign In with Apple, and more.

Screenshot of a presentation showing the new home page

It was really exciting to show off our progress to the rest of the company at our monthly Demo Day, especially in
those early months. The product team makes up only a quarter of our company and it was really cool to hear gallery
liaisons complementing our new partner page, or sales people complementing our refreshed home feed. I think that
people had gotten so used to the app not moving much at all that this sudden high velocity of development was as
exciting for them as it was for us.

Setting Up Others To Succeed

Artsy’s goal for the Mobile Experience team was explicitly not to centralize all our iOS feature development, and
so our mandate included much more that just working on iOS software ourselves. We wanted to sit between a typical
product team and a “platform” team, to provide infrastructure and assistance so any team at Artsy could develop
their own iOS feature. This was a big challenge, and required work at the individual and team levels.

The first step was apparent before we even created the Mobile Experience team. Artsy Engineering runs skills
surveys every six months, and we knew that building iOS software in React Native was something Artsy engineers
weren’t really familiar with, but that they really wanted to learn more about. I worked with the Engineering team’s
Peer Learning Working Group to design a curriculum – big shout out to Christina and Adam for their help here!

The iOS Learning Group took four weeks to deliver four lessons.
The learners were mostly web engineers, so I emphasized the familiar parts of writing React Native software. I also
provided weekly office hours for learners to get assistance with homework. I even stretched my wings as an
educator, developing new skills around curriculum design and delivery. After the course, learners responded
positively to the experience and we have integrated lessons learned from the iOS Learning Group into subsequent
peer learning groups.

Aligning Product Releases

Now that engineers had a solid grasp of how to build software in our application, we could re-align our product
development process around iOS. I can’t speak to the design side of this, but from a product perspective the most
critical milestone was defining a regular 2-week app release cadence. Let me explain.

Prior to the Mobile Experience team, we released the app pretty irregularly. We would release whenever we had
something big to release, basically. There are two major flaws with that approach. The first problem is that since
each release was bigger, each release was scarier. No one really felt confident releasing app updates. The second
problem was that large pieces of work tended to get coupled together. This came to a head last summer when we were
blocked from releasing an redesigned artwork view because we were waiting for a major overhaul to Artsy’s GraphQL
API to be completed. Without guidance or structure, different teams were building big projects and both had their
changes in our default branch – it was a bit chaotic.

These two problems are incidental to how we worked at Artsy but there is another, inherent problem to developing
mobile apps:
deploying iOS software is weird.
Engineers, designers, and product managers at Artsy are used to being able to quickly and cheaply deploy software
to the web, not the App Store. iOS software is deployed to our user’s hardware, not to servers we control, which
introduces the possibility that users might not upgrade. Software we shipped years ago is still being run today –
we have the analytics to prove it. Not to mention that every app update has to go through Apple’s App Store review
process. Getting our product team aligned on a release schedule might also help us get aligned on the weirdness of
deploying iOS software.

As the Mobile Experience team formed, I reached out to other mobile teams to find out about how they structured
regular releases. Matt Greenwell from BuzzFeed was really helpful in particular,
outlining their experience of the pros and cons of a regular release cadence. We implemented a two-week release
cadence so that all product teams could align their own feature development and testing around this predictable
structure. We also created documentation for teams to hide their in-progress work behind feature flags. And
finally, we refined our app QA process; teams would QA their own features and bug fixes while the Mobile Experience
team would used a QA script to test the app generally, every other Monday, before submitting an update to the App
Store.

Calendar describing our cadence on an example sprint

Making Deploys Not Scary

To further help teams get into the habit of developing and releasing iOS software often, we created nightly betas.
We also adopted a clever idea from our web colleagues: deploy blocks. In case of a technical reason to not release
a beta, we create a block and the CI job that deploys the beta would fail with a descriptive message. This reduced
a lot of chatter in Slack where engineers would ask “could I make a new beta?” Instead, engineers usually just wait
for the nightly beta. And if they get impatient, they now default to action (their beta deploy will fail if we set
up a block).

All of this was automated through fastlane on our CI provider. We had been using fastlane
for a long time at Artsy, but the Mobile Experience team took the time to share knowledge of how it worked. Any
engineer at Artsy can now make a beta (make deploy) or promote the latest beta to an App Store submission
(make promote_beta_to_submission).

We deploy more often and, consequently, each deploy is less scary. And everyone is aware of the need to hide
in-progress work behind feature flags. At this point, updates to our app are mundane, predictable, and boring. Just
the way we like them.

Being Generous With Our Time

Our QA and deploy process touches on something I want to go into more detail about, which is how the Mobile
Experience team helped support other product teams. I described earlier how Mobile Experience sits somewhere
between a normal product team and a platform team, and we leveraged that to our advantage. It would have been easy
to become primarily a supportive team, and leave feature development up to others. However, that would leave us
unaware of how day-to-day development feels in the app. We own the platform, and that includes the developer
experience. By sitting in this ambiguous in-between state, we stayed aware of both the needs of everyday
developers, and the needs of our platform.

I would encourage engineers from other teams to ask us for help, which led to a lot of pairing sessions. To be
honest, I think it probably interfered with our productivity, but it was worth it. A half hour of my time spent
pairing with a colleague might save them three hours of banging their head against Xcode. But it’s not the time
saved that I care about, it’s the head-banging. I want engineers at Artsy to feel empowered to build their own iOS
software, and that’s only going to happen if they feel comfortable and supported.

When the Galleries team kicked off their ambitious Viewing Rooms project, we helped them get started by lending an
engineer to them for a few sprints. When they ran into problems, we were generous with our time by pairing with
them. When they were nearing completion, we helped them test the new feature. This all culminated in a smooth
release.

Screenshot of a presentation showing the new home page's new loading indicator

Speaking of Developer Experience, we took a keen interest in standardizing our best practices and modernizing the
codebase. We
documented how we wanted the app’s codebase to look
and set up
processes like lint rules
to encourage developers to follow our best practices. We also invited any engineer at Artsy to join our
twice-weekly Knowledge Share meetings (I’ll discuss these in-depth shortly). We looked for bottle necks in the
development process and found many problems, which we addressed.
We combined the Native iOS and React Native repositories (which had
historically been separated). We overhauled the CI configuration to
leverage heavy caching – average build times dropped from fifteen minutes to less than five.
And we adopted stricter TypeScript compiler settings so that engineers
would be forced to deal with nullability and other causes of bugs. (Hey, sometimes you need a carrot and sometimes
you need a stick.)

The React Native community has grown a lot since 2016. If Artsy were to begin our adoption of React Native today,
we would be really well-supported by a community that has defined best practices, documented standard approaches to
problems, and a consolidated opinion on what a React Native codebase should “feel” like. None of that existed in
2016, and our early architectural decisions don’t really reflect contemporary best practices. We continue working
to bring our codebase closer to resembling a fresh project created with react-native init.

I’m extraordinarily happy with how things have shaped up, and in the direction we continue to move. This is all an
ongoing process, and should remain an ongoing process. For example, engineers were still facing a bottleneck with
core parts of our app’s routing logic that were in Objective-C, so we recently
moved all routing to TypeScript. Not only does moving code out of
Objective-C make it easier for everyone to build, but it also ladders up to a cross-platform Artsy app.

We still have older practices in the app that we want to migrate away from, like testing with Enzyme. But overall,
things are looking good!

Knowledge Shares

We achieved most of these big, infrastructural changes in meetings called Knowledge Shares, which I mentioned
earlier. I should write a dedicated blog post on these (update: I did write one), but in short: Knowledge Shares are a structured time to
facilitate unstructured learning. Anyone can bring a topic to Knowledge Share, from a ticket that they’re stuck
on to an idea they have to a neat trick they recently learned. We set aside these two hours a week to discuss
whatever the team wants, and we don’t only invite engineers.

New feature designs, product roadmaps, and data analyses are often brought up by our non-engineering colleagues; we
discuss these at the beginning of the meetings to make sure everyone’s time is respected. Throughout the week,
someone will raise a question in Slack. Before we had Knowledge Share meetings, we might schedule a dedicated
half-hour meeting to discussing this question. But instead, we now say “alright let’s chat about this at tomorrow’s
KS.” Usually the discussion lasts a lot less than a half hour, so we save time and needless context-switching.

Knowledge Shares are also a manifestation of my philosophy of tech leadership, which is this: none of us have built
an Artsy before, so instead of optimizing for building an Artsy, let’s optimize for learning how to build an
Artsy. The best Artsy we can build. And as a natural byproduct, an Artsy gets built. But it’s the learning that
is treated as the paramount goal.

Like I said, I owe you a whole blog post on Knowledge Share meetings. I hope I have conveyed how important these
scheduled “structured unstructured learning” times have been for us.

The Results

So where does that leave us? It’s been a year and change, where are we now? Well I’m happy to say that we’ve made a
huge impact. We’ve gone from only having (at most) one product team writing iOS software at a time to having nearly
every product team building iOS software. Artsy is through the woods of its transition to a mobile-first product
strategy. We still have a ways to go, but it feels like we have finally realized the dream we had in 2016 where
every team is fully equipped and empowered to deliver on their own business goals, across all of Artsy’s canvasses.

Our App Store ranking has shot through the roof – not surprising considering our “make it not suck” and then “make
it amazing” approach. Artsy’s iOS app rating now sits at a stout 4.7.

Screenshot of a graph showing an increasing average App Store rating

We’ve also started tracking our iOS developer experience within Artsy. We know exactly where we still need work
because we ask our engineers where they need support.

It’s taken a mammoth effort, and there’s so much more that I could talk about, but this blog post is long enough
already! Looking at the work we’ve done, the ways we’ve done it, and the results of our effort… I feel ecstatic.

Next Steps

All that said, Artsy’s product team is currently embarking on another reorganization. With so much technical and
product debt paid off, Artsy has evolved past the need for a dedicated Mobile Experience team. It’s bittersweet,
but I’m proud to say that the new Collector Experience team is about to be born. Our team will continue to own the
mobile platform, including its holistic user experience and day-to-day developer experience, but we’ll have an
expanded mandate. That mandate includes a cross-platform Artsy app that will work for collectors on Android as well
as iOS.

The Mobile Experience team has grown, too. Since we started last year with just a few engineers and limited product
support, we now boast a full roster of engineers and product support. I want to thank everyone on the team,
currently: David, Sam, Brian, Mike, Brittney, Pavlos, and Mounir. You have made the past year an incredibly
rewarding experience for me as I learn the ropes of technical leadership. I’m so proud of what we’ve built together
and I’m excited for what the new Collector Experience team is going to do next!

Source: Artsy