The evolution of HEY: from humble beginnings to a multi-platform email service

Two weeks ago we released HEY into the world, the culmination of 2+ years of explorations and intensely focused work.

It goes without saying, but I’ll say it anyway: inventing a new product from scratch is one hell of a challenge. It’s the toughest thing you’ll ever do as a product team. There are a million reasons why it won’t work, and zero guarantees that it will, so the whole project is a massive gamble. You just have to buckle up and trust that you’ll figure things out.

Since HEY made a big splash on arrival, I thought it’d be fun to share the backstory of how we ended up reinventing email. Because we certainly didn’t start by wanting to reinvent email. (That sounds hard and intractable!)

For the past several years, even pre-dating the work on HEY, we noticed some ongoing communications problems at our company. They all revolved around external email: things like going back and forth with lawyers, working with benefits providers, dealing with press outlets, accountants, and stuff like that.

It was too hard to keep the right people in the loop, because we’d have lots of email threads scattered around with different participants, and none of them had the complete story. It was too hard to get caught up on a project that someone else was working on with a vendor. And too hard to hand work off when someone went on vacation or parental leave. At best, you’d end up with a steaming hot pile of forwarded emails, and it was all a chaotic mess.

This was in total contrast to our well-tended internal communications, which all lives tidily in Basecamp (the app), and suffers none of those problems. But Basecamp is mainly a company tool, and it’s not so reasonable to ask our miscellaneous vendors to join Basecamp just to communicate with us. So what’s the equivalent of Basecamp for the outside world?

Well, it didn’t exist! So we began thinking about how we might solve these problems with a new product.

At first, we were considering making a successor to our older CRM product, Highrise. Highrise was our first take on the external communications world, but it doesn’t do nearly enough to cover all the scenarios we wanted to solve.

And thus, HEY started its life as a prototype for a possible Highrise 2. It was originally focused around work problems—not personal email problems.


In May of 2018, Jason and I kicked off the first work on a prototype, built in Jekyll, which was code-named Haystack. We were intent on addressing real-life situations right away, so I asked our Head of People Ops, Andrea, to find the gnarliest vendor email threads she’d been involved with recently. She forwarded all the emails to me, along with any internal chats she had about those emails. Using that source material, I painstakingly reconstructed all the conversations into seed data for our prototype. That way we’d have some real stuff to judge our ideas against.

We started by designing how these internal/external threads might look and work, then gradually worked our way out to the Inbox view, and finally filled in various supplemental ideas around the edges. We focused specifically on email pain points, and discarded any notion of how email “usually works” in favor of the way we would ideally want it to work, while also considering what we could realistically foresee building.

After a few months of prototyping, it looked like this.

Having explored lots of different examples and core ideas (including the nascent version of The Screener, the All Files view, and contact pages), we felt like we had something promising.

None of it really worked, there were still a million unknowns, and loads of features we hadn’t figured out yet, but there was one thing we were sure about—it had evolved far beyond just a better Highrise. If we were going to build it, it needed to become a complete email service. And if it was going to be an email service, it needed to have a personal version, of course!


Phase 2: Building it

By early 2019 we started the process of making HEY real. At first we used the prototype’s general skeleton as a foundation to start wiring things up, but we continued to hone the app’s visual design. Our brilliant marketing designer Adam joined up, and he helped us shed all the experimental cruft from the original design, paring things back and making the whole thing more minimal.

Adam also developed the original color palettes and menu gradients that became iconic—those bright pops of color are sprinkled throughout and give the app a lot of friendly personality without being too overwhelming.


Phase 3: Tightening up, adding features, and doing all the hard work

Designing with a team where everyone has autonomy is a bit like playing in a band. Someone seeds an idea, and then someone else builds on it and takes it somewhere else, then those changes get promoted into little systems, and over time the best ideas persist through all the changes. Harmonies prevail.

You can see that taking place in the screenshots above, but it really picked up steam from mid-2019 on, when the whole the company started working in earnest. For a while there was a lot of tug-of-war design and development between the web and mobile teams, where all of us bent and stretched the system for what we needed on our respective platforms. Since HEY is a hybrid web app, we ended up building a ton of new tech to optimize for UI patterns that would work equally well on a phone or a laptop (we’ll be sharing a lot more about that soon.) Conor led the way on a lot of those efforts.

By early 2020 we had worked out most of the fundamentals. We had Reply Later and Set Aside, and we had The Feed, which at that time was called “Slowbox”.


From then on, the remaining work was a recurring cycle of polishing what we already had, and using the product ourselves to figure out what was still missing. For example, in January I noticed I was having trouble filing the gobs of junky capitalism emails I constantly receive, so I pitched the idea of a special place just for that, and the Paper Trail was born.

Pitch for the Paper Trail (originally Baconbox 🥓)

We spent the remaining months adding all the many, many, many things you need to release something to the outside world, like: billing, trials, onboarding, exports, cancellation, security settings, 2FA, password resets, contact imports, forwarding settings, and a seemingly endless parade of email rendering challenges.

All of that infrastructure work is an amazing achievement for our small team. Creating a reliable, robust, functional email service is no joke. We obviously had big ideas, and wanted to do something new and inventive, but we also had to do something old and unsexy: make the thing actually work as well as products like Gmail. Those platforms have been around for 15 years and have massive amounts of engineering talent backing them up—and we’re just a handful of people working our tails off to make the best thing we could. It took the full force of every single person at Basecamp to make this happen, especially our R&D, Ops, and Security teams, who had to invent loads of new systems for us.


We pulled it off 😅, but we’re still just barely getting started. You can see little hints of where we might be going next, so stay tuned for a lot more good stuff in the coming year!

Curious about our design process or anything else? Hit us up in the comments below, or ask me a question on Twitter.

And if you want to give HEY a try, you can sign up now over at hey.com.

34 thoughts on “The evolution of HEY: from humble beginnings to a multi-platform email service

  1. It’s fun to see the iterations of the names throughout the development process, like “The Bouncer” (which sounds incredibly intimidating).

    1. Ha, that’s one trick we use while we develop ideas — we give them over-the-top names. The name helps communicate the idea really clearly when there’s no other certainty about what it is, or how it should work.

      Sometimes those names stick around, but usually we go through a couple iterations before settling on the production name.

  2. That people icon, though. Nice little detail and tribute to the O.G. 37s!

    Also, interesting to see that, at least initially, there was some archiving capability. Something I still have to get used to after using Gmail for so long.

    1. Yes! I still want to get that 37signals nod back in there somewhere 🙂

      We did have archiving at one point, but ultimately decided we didn’t have a story to tell about what it’s for. It was just “yet another place” for emails to go, and more work to do for the same result—a big pile of old email. Previously Seen accomplishes the same thing with no effort.

    2. > We did have archiving at one point, but ultimately decided we didn’t have a story to tell about what it’s for.

      Yes, I have the same feeling. Stopped archiving my Gmail many years ago. Keeping the inbox empty is just hamsterwork.

    3. Super interesting read. Thank you for sharing. I’m confused on the archive though – to me the archive has nothing to do with the active act of archiving something, actually the opposite.

      By not having an archive, you’re really forcing me to consider what I want to do with every email on my first read, because if I don’t, it’ll just get lost in the pile of “read” emails. Problem is, I’m rarely in a headspace to take any action on my first read. I’d much rather get back to it later, and consider whether it deserves another read or a reply at that time.

      By having an archive, I know that everything in my inbox + read, I’m not yet finished with. Once I am, I can safely archive them without having to worry that I forgot about them. I really miss that in Hey.

    4. I do miss archiving. I don’t want to see things I’ve already seen, not even in the corner of my eye. It distracts me. For me, archiving is about getting rid of distractions. (I don’t label or use folders).

  3. Fascinating read. Thanks for writing it (and for all the work on creating Hey).

    I’m interested in the behind the scenes on the back and forth with Inbox vs. Imbox.

    1. Thanks Dave!

      We did go back and forth on Inbox/Imbox a few times, and had a whole lot of internal debate about it (we’re well aware that Imbox is a little weird.) We also floated several other name ideas, but kept coming back to Imbox.

      In the end, we felt it was worth differentiating HEY’s inbox view from all the other grody email inboxes out there. Calling it “Inbox” would do it a disservice, because it’s not just any old inbox. People hate their old inboxes. This is something else.

      Imbox worked because it’s close enough that people can understand it’s basically an inbox, but it’s different enough to draw your attention, and it communicates the core concept of the view (which is: “only your Important emails should go here.”)

    2. I suggest that it may be a good idea to style “Imbox”…it is supposed to be different from Inbox but looks the same.

      IMbox or IM-Box or colors. Maybe by introducing it at the start of onboarding process will minimize confusion…

  4. I am loving the idea of HEY– but a blocker for me would be missing a calendar– any idea of when / if that will make it on your dev roadmap? Thanks!

    1. Hey! We don’t have a roadmap, we come up with what to work on every 6 weeks (see http://basecamp.com/shapeup). A calendar would be really fun to work on, and it feels like it’s long past time to tackle that old thing with new eyes, but it’s a massive project so it wouldn’t be anything we’d be able to get to this year. Who knows about next year – it’s so far away!

  5. Always neat to see the beginnings of a product design. Thanks for sharing!

    I listened to the Rework podcast on the original Hey designs and you had mentioned some drastically different design approaches early on (I think a ‘timeline’ was mentioned). Any chance you will share those down the road?

    1. Thanks! You can kind of see it in the prototype screenshots above…the email thread views were mini-timelines, with annotations on the left, sticky dates on the right, and various different objects displayed chronologically in the middle.

      We also originally had an “Activity” view which was a timeline showing a list of all emails across all threads shown in reverse chronological order, but it didn’t really work out.

  6. Hi!

    First of all, HEY is so cool.

    It looks like a lot of the screenshots are from actual prototypes as opposed to design software like Sketch/Figma. Does the team pretty much just design on the prototype itself and evolve on the spot?

    My other question is, we’re often told that designing for ourselves is a bad idea. But HEY was designed to be very opinionated with just feedback from Basecampers. Were you scared at any point that this wouldn’t resonate with outsiders? How do you modulate between having a clear internal vision and trying to validate it?

    Thanks! 🙂

    1. That’s correct, when we do prototyping it’s rarely in the form of static mockups. We have a (very old!) post about that here: https://signalvnoise.com/posts/1061-why-we-skip-photoshop

      As for designing for ourselves…part of it is having a really strong sensibility about what we’re willing to do and not willing to do. We have 20 years experience making software, so we’re not starting from zero in understanding the broad challenges and potential market (but as I said, it’s always a gamble!)

      For a brand new product, we had to define the boundaries of what we were interested in building first. Getting more feedback at that time wouldn’t be helpful, because it would just add to the overwhelming pile of potential problems we hadn’t figured out yet.

      Once that basic foundation was in place, we started absorbing feedback from people at the company, and we also quietly shared the ideas with friends, beta testers, floated ideas on Twitter, etc. HEY evolved in a lot of major ways based on that. It’s not a total vacuum.

      Once the product is out there in the world, then we do a lot of customer research. We’ve spent many years talking to customers and learning more about Basecamp, so we can understand how people are using it in ways we never imagined. With that info, we can tune it to work better for specific situations.

  7. It is always interesting to get a glimpse of behind the scenes of a new product or service. Thank you for providing these insights and I look forward to more.

    This comment is for Baconbox. I love this name and already named a folder in my email system Baconbox replacing my Paper Trail folder, idea I stole (oops inspired) from you guys.

  8. Thanks for sharing these screenshots—-very interesting to see how early you arrived at some of the principles! Viewing CRM as a feature layer on top of email seems right to me, as much as I liked Highrise back then, although I always found the deals and cases UI pleasurable to use and hope something analogous appears in Hey for businesses.

  9. Highrise, huh?

    That had me look at the contact page in Hey, to see if I could add a sticky note there. Then remembered about sticky notes on a message thread, which I see I can do.

    Anyway, just sharing that reaction I had.

    1. Just ran into this inkling again… having a chat with a new person in a Slack community… would like to save our back and forth someplace. Thought of creating the contact in Hey and copy/pasting that into a note there, but realized I’d first need an actual email thread to hang that note on…

  10. I remember Jason saying in an interview that the real competitor at the time to basecamp was actually email. 🙂

  11. Congratulations for Hey! It really offers a lot of new features. That’s probably the most difficult part for adoption : you need to change your habits to make the most of Hey. Habits you’ve had for decades are not easy to change though.
    I think you really did a great job for the imbox and screener.
    I’m a bit less enthusiastic for The Feed and Paper Trail. It’s a bit of a hassle to delete a message once you’ve expanded it. You need to move up to the top of the message to do it. Would love some new features to help managing (reading and deleting) newsletters. Maybe something a bit similar to “Focus & Reply”.
    Currently, you even don’t have any information of what you’ve already red or not. It’s just a list of messages with no intelligence. I know you can do better Basecamp team! 🙂

  12. I’m sorry, but I don’t find the description of Hey compelling.

    First of all, I don’t want to change my email address. I have had my email address since 1995.

    Although my email address has a custom domain, it is handled by GMail. GMail has an excellent spam filter. So good, in fact, that spam is pretty much a dead issue with GMail.

    GMail also has filtering. I can filter emails from a particular person or from a domain. I recently started a project where I started to get a flood of Git checkin emails for projects that I’m not working on. These were poisoning my inbox. Filtering saved the day. I could rout these emails to their own folder.

    The thread feature of Hey sounds really useful. But again, no so useful that I’m going to give up my email address. Really, there isn’t anything that Hey could offer me that would be worth changing my email address.

    The solution here seems obvious: change Hey so that it can access GMail and I can use it as a front end to GMail. Of course for all I know Google disallows this since it would step on their email kingdom.

  13. i love hey. i feel that i will never go back to the old again. i have waited to a revolution that’s on my side, not on the business side. and, for the record, i am the type of person who has lived moneyless for years and with little drops of pay since then for years. i don’t have much, financially speaking. every cent is counted. and hey will get a huge junk of my tiny budget because there no better place where i would invest my money to. i am honored to be apart of this journey with hey.

  14. Congrats for Hey. I am sure to use it. The evolution of Hey is really inspiring. It was really hard for those initial days but you come out positively.

  15. “ it’s not so reasonable to ask our miscellaneous vendors to join Basecamp just to communicate with us.”

    Actually this has become our way to select external vendors : if they are not ok to work in basecamp with us via the “client side” we drop them. Seems a missed opportunity to me that HEY started solving this problem and wandered off to solving something else (which is still a good thing though !)

    The client side is decent but guess what it doesn’t interface well with all other shared inboxes vendors are using to link external / internal communications. Something like a better in/out email parsing / dispatching / responding / threading pipeline we would pay for.

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