How Stripe thinks about comms & customer delight
Edwin Wee Arbus on delighting customers, understanding users, and handling trolls
Ask any developer their opinion on who does marketing and comms best, and I’m willing to bet they’ll answer Stripe.
Communications (particularly developer comms) is not unlike DevOps: done well, you don’t even notice it.
It appears effortless, but in my experience, is meticulously crafted. The placement of an emoji in a Tweet is hotly debated. A landing page header is workshopped for hours. A service email is drafted and re-drafted.
And in the end, it all feels…natural.
Stripe is like that. They take craft, and utility for their users, seriously – through every UX touchpoint, email or tweet someone encounters.
To understand how Stripe achieves this, I spoke with Edwin Wee Arbus. You may remember him from Hacker News (“Edwin from Stripe here.”)
Edwin led Stripe’s community efforts for nine years, translating his experience in politics to tell the story of the company to their user base.
I learned so much about comms and delight from this interview:
How Stripe measures Comms success (it’s different from what you might think)
Stripe’s philosophy on customer delight & how founders should delight their users
The top mistakes startups should avoid when communicating with users
Note: I spoke with Edwin before he announced he’d be completing his epic run at Stripe this month, so the interview is written in present tense. We cannot wait to see what Edwin does next!
You are part of the Stripe Comms organization. What is the “job” of comms at Stripe, and how’s the team structured?
The mission of the comms team is to tell the story of Stripe, its products and its users. The way we’ve structured it is broadly:
Community Comms: Telling our story on the internet. Making sure that users understand what Stripe is and how to use it.
Corporate Comms: Your more traditional PR or crisis response.
International Comms: Stripe in international markets.
Internal comms: Making sure all Stripes have the information they need to thrive at Stripe.
Brand comms: Oversees Stripe Press, publishes lots of cool books.
And these teams are very, very small. There are only three people on my team, and we’re hiring a couple more.
You run Community Comms. If you’re doing your job well, what is different?
What’s interesting about community is that you get instant feedback. Everything we publish is on Twitter, YouTube, LinkedIn – so we know immediately when something is different.
As an example, we recently published a video with the founder of Perplexity.AI, and we could immediately see it get lots of views and new YouTube subscribers.
For Black Friday last year, we published a website showing all our transaction numbers. The conversation around Stripe on the internet that day was just off the charts.
You can immediately see if we’re having an impact.
How do you think about metrics of success for your role?
Stripe is weird: a lot of companies measure success through the number of likes or how many new followers they get. But that’s pretty antiquated these days, and it’s sort of a 2008-type way of thinking about impact on the internet.
What we do is maintain a minimum engagement rate. We look at average engagement through a quarter, and see if we’re hitting it this quarter. That number is also our baseline metric for when we publish something. We have set it to be unreasonably high.
It’s not incentivizing posting more. A lot of companies feel like they have to fill out a content calendar where they have to post every day. When there’s a hole in the calendar, they post some random fluff.
But in actuality, if you look at engagement for those random things, they bring engagement down. People aren’t really interested in that type of thing.
We’ve flipped it around and said let’s not look at it from an absolute numbers perspective, let’s look at how engaged our audiences are.
Stripe does comms differently (I’d argue better) than other companies. How is Stripe’s approach unique compared to your peers?
We see our users as a huge component of who we’re talking to, and developers are the largest component of that. Other companies might have communications for users in a separate part of their business [outside of Comms], or they might belong in Marketing.
We recently published the annual letter. When other companies publish annual letters they’re meant for shareholders, but our users are our shareholders, and so we write for them. We email it to every single user.
We also ran it past many users before we published to get their feedback. We do this quite often. Every single blog post, before we publish, we make sure users read so that we incorporate their feedback.
You can really tell that utility for users is a core goal of how Stripe communicates.
Every time we write a tweet, we ask ourselves, “if we received this as a push notification, would we like it, or would we just block Stripe?”
How should startups be thinking about comms for developers? Or communicating to users in general?
There are playbooks out there for first-time founders, and people use them to follow what they see in the market already – but it doesn’t cut through the noise, because it all seems like the same fluff.
The most important thing is to try to do something differently. That’s the hook for our readers.
We are direct and approach things in a slightly different way. People don’t get fatigued when they see comms from us because they know it’ll be something new and different each time.
My warning for early-stage founders is not to fall into the trap of doing what everyone else is doing for content, which may or may not be AI-generated fluff.
What are the most important activities a startup thinking about comms & marketing should do?
Speaking to users. Having real-life conversations is the most important thing, because it really informs how you communicate. If you want to understand your audience, you have to get really close to them.
This is part of my remit at Stripe: to literally get as close to our users as possible, to understand how they think, and to know what they think is interesting.
I have a goal of talking to a user every week, either IRL or through text message. I don’t find Zoom that useful for this. Typically it’s in person, maybe over a meal at the office.
I’ll run random ideas by them, like “what’s the most interesting thing you saw Stripe do recently?” just to see if it’s something my team put out. Or, “what would you like us to do?” This helps inform questions like what to announce, and how to announce it.
Why don’t you like Zoom for user feedback?
As a conversion mechanism, [Zoom] doesn’t feel casual enough for someone to put down their shield.
If you’re sitting across from someone and ask what feedback they have, you can give them a few minutes to think about it. If we just sat here [on Zoom] for 30 seconds of silence, it would feel awkward. But if we were sitting over lunch, it wouldn’t.
What other ways should founders get closer to their users?
They need to understand the problem they’re solving, but also how their users want to receive information.
The push notification example I gave: that wasn’t because of some internal philosophy. It was literally us sitting next to our users – again, in real life – and we saw how they were consuming information from Stripe.
Slack had an integration with Twitter, so everything we tweeted would get piped directly into a #stripe Slack channel. That information helped inform how we craft our comms.
Besides that, identify a few tastemakers in your industry. We have a list of tastemakers – people who we trust. There actually aren’t that many people on it. A lot of them are friends who have integrated Stripe at their startups.
They may not be your most active user, but these are people who understand how your company may be perceived in the market.
We get their unfiltered advice on things. Find people who really understand your problem space – they don’t have to be an expert in the nitty-gritty of the technology, but they should be active in the communities you’re trying to speak to. They can help gauge whether something is cringe or not.
So basically, think of tastemakers as community-level analysts.
Yeah, exactly.
I’m interested in the relationship between comms and support. You’ve become the de facto Stripe Hacker News guy. “Edwin from Stripe” is almost a Hacker News meme at this point. Did it happen organically?
It did. It wasn’t in my job description, but it kind of just fell on my plate. For a while if you tweeted at Stripe, I’d be the person responding, so I already had a really broad exposure to the most common questions from users as well as the ability to talk to people on the internet – even if they’re Hacker News trolls.
We want to be as responsive as possible to people on HN, especially if they are an active user.
Stripe first launched on Hacker News – Patrick [Collison] submitted it as a link – and our first users came from that submission. And obviously, Stripe is a YC company.
It is our most important channel. A lot of people think of distribution channels as Twitter or LinkedIn, but Hacker News is our number one. When you look at the metrics for our blog posts, we see Hacker News is a big [traffic] driver.
We also know the HN community very well and at this point we recognize quite a few usernames. Sometimes it’s a random indie hacker, and other times it’s a developer from a Fortune 500 company.
We want to talk to developers. Hacker News is where they go, and we want to meet them where they are.
Talk me through the logistics of this. Is there a system behind the mechanics of Stripe on Hacker News? Is it just you firing things off?
There’s no system! People ask me this quite frequently. We’re very fast. We’re just constantly refreshing Hacker News.
When we jump into something on Hacker News, it could be a friend sending it to me, another Stripe flagging it to me over Slack, or it could be [my team] refreshing the page. There’s an RSS feed that we occasionally listen to.
There’s no API – like with Twitter, our Support team uses the API to pull in the Stripe mentions and triage from there into different inboxes.
But [with Hacker News] it’s literally just us, in Chrome, refreshing.
Given it’s such a public forum, is there much behind-the-scenes workshopping of how to approach certain answers?
Most of the time, I just write directly into the comment box and fire it off. Sometimes we need to check with the team to make sure we don’t overpromise anything and that we’re being accurate.
We also try to get the PMs themselves to respond as much as possible, so we can put them in front of the user directly. I might flag minor style nits to them, like a missing comma, but there’s no “war room.”
What’s your advice for when a startup should respond to a user complaint publicly – knowing that by responding you risk drawing more attention – versus responding privately or ignoring?
Here’s what comes to mind for me here. Satoshi’s Bitcoin whitepaper was published to Hacker News when it first came out.
And if you look at the comments, it was just people trashing on it – like, “this will never work.” And look where we are now – Bitcoin is at an all-time high. The internet sometimes loves to breed negativity, so sometimes you just have to ignore it.
The way I think about when to ignore it is to play out [the interaction] like a game of chess. You have to think about the next move someone is going to make. “If I respond here, what is the other person going to respond with? And what will I respond with to that?”
You have to think forward a few steps. Three responses from now, is this going to be a productive conversation? If not, then it’s not worth responding to.
If we want to clear something up, or we think the person will understand our response, then it is worth responding to. We try to respond to everything, but a couple of times it’s been clear that someone is coming from a bad place and nothing we do is going to convince them otherwise.
Sometimes we just let them rant if we think we can’t have a productive back-and-forth.
Let’s talk about customer delight. Stripe is known for sending hyper-personalized gifts like a custom motorcycle helmet, alarm clock, and (my personal favorite) handmade dumpling rugs by artist/Stripe designer Cynthia Chen. Tell me about your philosophy.
Stripe has done this since the very beginning. John and Patrick sent a handwritten card to every single beta user when they first launched in 2012. We have carried that forward as much as possible.
Our mission is to increase the GDP of the internet, but the amount of trust users place in us to do that…they’re really placing their livelihoods on us. We want to make sure they know that we know that and that we don’t hold their trust lightly. We are always watching for moments where we can recognize and surprise users.
This has been a wonderful way for us to get closer to our users. There have been so many times where a user has posted about crossing a business milestone, and we go on their Instagram page to see what they’ve recently posted about.
We made custom tennis balls for Pat Walls because we saw pictures of him playing tennis. So when I say we want to get to know our users, I really mean it.
Stripe cares about craft in everything that we do, not just craft in our software. In every interaction a user may have with Stripe, we want to have approached it with care.
There are so many Stripe users. How do you decide who gets to be delighted in that way?
It’s actually all random.
We don’t look at their Dashboard data or their revenue data. We just follow a lot of users all over the place – LinkedIn, Twitter, Indiehackers.com, Hacker News. We’ll see people post something like, “I’m really excited, I almost hit my revenue milestone!” or “Once I hit 500 subscribers, I’ll have a sustainable business.”
We’ll share it in our Slack channel and say, “We’ve got to keep an eye on this guy.” We kind of obsess over it.
It’s really fun to see the user get excited to hit their milestone, and then they get excited again because they get recognized by Stripe.
What’s your favorite example of a customer delight moment?
Last year, Logology shut down. So this was not a recognition of them hitting a revenue milestone, but a recognition of them trying to start a business on Stripe. We sent them a little book, like a children’s picture book, showing moments of them building in public and the ups and downs throughout it.
We just wanted to thank them for putting themselves out there and going to market with Stripe. It also signals okay, maybe it didn’t work out this time, but in the future maybe you can build a business with us.
It was my favorite moment because it was the opposite of the other examples, where you’re talking about successful businesses. Most startups fail, so this was a moment of recognizing failure rather than success. It’s good to recognize those moments as well.
What should founders do to delight their customers?
Physical mail and handwritten notes break through these days. With everything digitized and over Zoom, things can feel impersonal.
When we launched Payment Links, we hand wrote a letter to literally every single person who tried out our demo. We even wrote the mailing address on the envelope. And the reception was pretty incredible to see.
It doesn’t have to be that method, but finding your own way to put a personal touch on things – especially in this category of product – is important.
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Edwin Wee Arbus led communications at Stripe for nine years. Previously hailing from political campaigns, he's brought high touch retail politics to B2B tech, communicating complex ideas to wide audiences—and keeping those audiences engaged. Follow Edwin on Twitter.