Meet The Team: Rik, CTO

Ricardo (Rik) Signes is Fastmail’s CTO. He joined our team in 2015 when Fastmail acquired Pobox in Philadelphia. Get to know Rik!

What I work on

Historically, I have been the primary programmer on Pobox and Listbox, and I did a lot of work in the last few years building the framework of Topicbox. But nowadays, I spend most of my time coordinating the work of the development and operations teams, figuring out who’s doing what and whose work might be blocking whom, so that people aren’t sitting frustrated at their desks.

As CTO, I balance the technology requirements across different groups. Generally we don’t have people who want contradictory things, but sorting out work often requires determining invisible pre-requisites and doing that work first. It requires figuring out the way to get from here to there… And preferably after I’ve already figured out what people are likely to want next.

Figuring out what people will want next is often a natural by-product of talking to people about what they want. As we take things from the abstract to the concrete, I try to stay focused on the goals (and really understanding them!) rather than the suggested technical implementation they’ve requested. Time is often a consideration; a lot of times, just keeping in mind the next logical iteration of the solution you can get today is all the plan for the future you need.

How did you get involved with FastMail?

They bought me? I got involved with Pobox in 2005 when Dieter Pearcey heard me saying I was looking for somewhere else to hang my hat. He and I had debugged some problems earlier that year on IRC, so when he told me to apply, I did. About 8 years later, I met Bron at OSCON. We were having a beer when super-connector Paul Fenwick realized we worked at Pobox and FastMail, respectively, and asked if we were going to brawl. We did not; we ended up discussing the common problems and solutions of our load balancers and user migrator implementations. About a year after that, we started the long process of acquisition. A year after that, it happened. 16 months after that, I was the CTO.

I took a photo at the time, recording our meeting for posterity.

What’s your favourite thing you’ve worked on this year?

In technical terms, it’s Topicbox. When building Topicbox, we treated it like a greenfield project. We didn’t reuse many of our standard components, but the technical decisions I made were based on years of using our tools and thinking about how I would do it if I did it from scratch. As many of those plans were borne out in successful technical solutions, it was really rewarding — a pleasure to build and see used.

But, more than that, I have loved organizing the technical team. It’s a really talented group of people, with many unique areas of expertise. Orchestrating all of them requires having a handle on what everyone is doing. Doing it successfully also requires I have at least a basic understanding of what everyone is working on. It is either an excuse or demand for me to be learning a little more all the time, which is great! It forces me to get off the same old path.

What’s your preferred mobile platform?

I use iOS. I don’t have really strong feelings about it. It has a bunch of things I prefer, but … I’ll use anything that has Spotify.

What other companies, people or projects inspire you?

The Rust language project is really inspirational. Like most technical projects, they’ve always striven to have a technically excellent product, but they also decided early on that they were unwilling to compromise on their community to get it. So, the community is not the toxic, or even merely odious, community that you can get in other projects with a lesser commitment to community.

Julia Evans, who is an endless prolific source of interesting and instructive material, who is always positive in attitude, is the kind of technical role model I aspire to be. She says my favorite thing, which is that computers are not magical; you can start from first principles and figure out what is going on, always.

Companies are impressive for lots of reasons, but I’m pleased when companies doing interesting work make it clear what their values are, especially when you can see it’s true. They make it clear they have a direction beyond just making money. They promote that the direction they’ve chosen has value to them. They make it easy to guess what it would be like to work there, and what kind of work and behavior would be rewarded. Netflix and Stripe are two examples that come to mind; I hope I do my part to expose a similar ethos here at FastMail.

What’s your favourite FastMail feature?

I like FastMail’s push support, because it makes clear that FastMail really is fast. It looks like a super simple feature, but the technical details are way more complicated than they should be. It’s technically interesting and you can always get Rob N to tell a good story about it!

My favorite Pobox feature is the RSS feed of spam reports, which lets you review the small amount of mail Pobox isn’t quite sure about. I like it both because RSS is something that I wish had gotten wider adoption, and because I like having it in a separate place than my email or the web (which are the two other places you can review it.)

My favorite Topicbox feature is organization-wide search! Topicbox makes it easy for team members to create new groups, which is awesome for making sure all the right people are included in a discussion. But as soon as you start having enough information that you can’t see in one screen, you want to search for it. The Topicbox search technology is based on FastMail’s, so it’s fast, thorough, and easy to refine. You find the full thread… and the conclusion. Organization-wide search is, to me, the best reason to move your organization’s email discussions to Topicbox. (And, yes, we can help you import from an archive or a even a personal mailbox!)

What’s your favourite or most used piece of technology?

My bicycle! It embodies everything I think of as technology. It lets you solve a problem that you could probably solve without it, but much more efficiently. It also rewards curiosity. You don’t need to know how it works to use it. But it’s really easy to learn how to take it apart, fix it, and make it better. Also, like most of the technology I like, I don’t use it as often as I’d like.

This isn’t my bike. It’s a photo I took while on a trip to the Australian office. It’s a sculpture of three bicycles occupying the same space!

What are you listening to / watching these days?

I’m finally catching up on Song-by-Song podcasts, which discusses every Tom Waits song, one per episode. But that means I’m listening to a lot of Tom Waits again too. It’s good to listen to full albums!

We talk a lot about music at FastMail, and we’ve gotten almost everyone on Spotify. We have a bot who tracks people’s Discover Weekly playlists, looking for duplicates, and determining who has compatible (and diverse!) musical tastes. I’ve found a bunch of good music that I wouldn’t have heard before because staffers have been listening. I also know who has consistent enough taste that I know I can always hit up their weekly playlist for, say, synth pop and 80s hits (Rob Mueller!).

What do you like to do outside of work?

I do coding projects outside of work, too, though less this year than in years past. I used to manage the perl5 project for many years, but now I’m just an active member of the peanut gallery.

I watch a lot of movies. I talk a lot about the horror movies I watch because they are the funniest to discuss, but I actually watch plenty of movies across all genres.

I run a D&D game, and I’ve been playing a lot of Mario Kart on my Nintendo Switch.

What’s your favourite animal?

I used to have pet guinea pigs, so they’re up there! They’re my favorite animal that I would actually consider palling around with. But I’m also a fan of any animal that is really bizarre in some way. It reminds you that evolution goes in a lot of crazy ways.

Any FM staffers you want to brag on?

Everybody’s great! If I was going to call somebody out in particular, though, it would be Bron. We had reached an inflection point in terms of scale, where we needed to rethink the way we organized our work. Bron stepped up to make that happen, and we’re all better off for it.

What are you proudest of in your work?

In my technical work, over many years, I’m proudest we’ve been able to use a slowly evolving set of patterns without finding out they were fundamentally bankrupt. With Topicbox, we were able to test that theory in the biggest way — we started from scratch using those patterns as first principles, and it worked. So that was really rewarding.

On a larger scale than that, it’s always a blast to meet people in a professional setting who have heard of FastMail or Pobox. They will be excited to talk about what they know of the company, and often tell me they think it would be an exciting and great place to work. In large part, that’s because of people and culture we have, and I’m proud to have been part of making that the case!