Founder Focus

Now we're live. Welcome everyone to another episode of Founder Focus. I'm your host Jade Wang and I run the Cloudflare for Startups program.

Today we are joined by our guest Christine Spang, founder of Nylas.

Welcome to the show, Christine. Thanks, Jade.

It's really great to be here today and joining on Cloudflare TV. Thank you.

So very briefly, can you tell us about Nylas? Yeah, for sure. So Nylas is a company that I started about seven and a half years ago at this point.

And we really started out by building essentially like a universal API for connecting to mailboxes.

But as is typical with a company, you start out with one niche and as you grow and evolve and talk to your customers, what you're trying to accomplish expands.

And today we really think of ourselves as building communication and collaboration components that you can embed into other software to make it more interactive.

The way we like to phrase it is called productivity infrastructure, where we're building all these building blocks that are essentially infrastructure for being more productive that you can plug into other software to essentially enable people to be more effective.

Can you screen share a demo with us on how someone uses Nylas?

Yeah, for sure. I have a little demo that I'd love to walk through.

Awesome. This works properly. Here we go. Cool. So this is actually the onboarding flow that we put users through when you actually go and sign up for a developer account for Nylas.

So if you go to Nylas.com and you click sign up, you'll be able to go through this flow yourself.

But this walks through a few of the features in a slightly more interactive way than, for example, like making curl requests on the command line, which is not very flashy.

But the core part of our platform that we've shipped from the get-go is what we call our connectivity APIs.

This is the universal API integration layer that makes it so that you can connect any email mailbox, any calendar from any provider in the world, not worry about what protocol it's backed by, what provider the user is hosted on, and access data from their mailbox, from their calendar, and use that to essentially build automated workflows.

This is just showing an example of some of the kinds of data that you could pull using Nylas API from, in this case, email.

So we can move through the flow.

I mentioned previously that we really ship components that allow people to develop features more quickly.

That extends not only from back-end APIs that give you structured data that's really easy to integrate with, but also includes pre -integrated front-end components that make it really easy to ship kind of table stakes features that you need to build these broader workflows.

In this case, we're demonstrating our composer widget, which if you're building any sort of embedded workflow that involves email, you usually need to allow people to be able to compose and send emails.

And there's 100 little features that you need to have like a fully featured rich text editing window for sending.

We provide components that provide all those table stakes features out of the box and make it so that you can just plug in a couple lines of code and really spend your time worrying about kind of the broad workflows and feature set of whatever application you're building rather than how to implement bold texting and send later in a composed window, things like that.

That's just one example. We also have other components around scheduling and things like that, common workflows that are fully white labelable.

They don't say Nihilus anywhere. They just allow you to quickly integrate the features and get on with building the rest of your app.

Awesome. So I'll go. I just have like a couple little things that additionally to highlight.

One is that we've recently launched a bunch of new features kind of on top of our data APIs that we're calling our neural APIs.

These essentially do additional structuring and processing on top of the data backends that we integrate with.

So a couple examples are, it's pretty common to want to be able to display email in a much sort of easier to view way.

But because of kind of the historical context of email, they end up having like quoted texts from different clients, multiple signatures, all this sort of crap that you don't really want to see in like a conversation window.

So we have APIs today that allow you to really simply clean up these messages and just get the meat of what you care about and also do things like structure data that is found within those emails.

So this is just an example that shows that like an email signature that you might find.

There's a bunch of structured data in here that is essentially free form text.

And we've built the learning models that allow you to really quickly turn this into the structured data that you need to actually use that in an application for something useful.

So just a few examples of how we're continuously essentially shipping new building blocks that are higher level that make it easier to build applications that include all these sort of data types and collaboration pieces.

So if a company is, for instance, using the Google suite of Gmail and Calendar and things like that, the company internal teams can use Nylas to build integrations on top of that.

Is that the correct understanding? Yeah.

I mean, there's a whole broad swath of sort of different use cases that people use this for.

For example, people have used Nylas to build out tools around things like recruiting or doing customer support.

It's a little atypical for someone to use it just for like a single provider for internal tools.

So we do have some customers that do that kind of thing.

But larger organizations tend to have multiple different providers or you want to use our more advanced workflows features.

There's a lot of code that you can avoid writing by using an API platform such as Nylas to do that.

So if you think about all of the different jobs that exist in the knowledge economy today, they all have kind of the same core units of work.

It's like you're combining data from different places, communicating with people, you're checking in with them.

You might want to send reminders about things you want to schedule meetings.

And those are all kind of the core communication and collaboration pieces that Nylas can provide that are essentially components in these broader workflows.

So you might be building something that is internally focused.

But a lot of our customers actually use us as like a component that's a part of their own product where their product in general does some specific thing for some specific group of people.

And it's just expected that you need to be able to integrate with all of the really useful communication data that's in email.

You need to be able to schedule meetings and it needs to be really seamless.

So it needs to all happen in the same tool.

And Nylas is what makes that really easy. Nice.

So the pandemic has really been a big influence on productivity tools in the past year.

So a lot of teams have been transitioning from working in the office together to remote.

How has that influenced customer adoption of Nylas? Yeah, for sure.

We've definitely seen it accelerate the adoption of Nylas and tools that are built on top of Nylas, which is a virtuous circle that just drives the growth of both folks in tandem.

Pretty much like being forced to have a fully remote team by this external event has made a lot of companies realize that they need to invest more in these digital tools so that people can be productive outside the office, so that stuff is written down and context is shared.

That's huge. If you're not sitting next to someone every day in the office, you need to be able to have shared context with them about what's going on.

And that kind of thing has really just accelerated people adopting Nylas to build those sorts of tools and also just the growth of a lot of our customers as well.

On a related note, what was transitioning to remote work like for your team and how many people are employed at Nylas, just to give people some context?

Yeah, for sure. It's interesting because at the start of 2020, our team was about, I would say like 50 people, and today it's about 150.

If you think about that, two-thirds of the company today has never worked in an office with somebody else from Nylas.

It's a little bit abstract for me personally to think about how big the company is today because I have never face-to-face met a lot of the people that work at Nylas today.

We've obviously done a lot of hiring remotely.

In terms of the impact to the team, I think that the biggest impact that was negative has just been around how do you create community and the fun stuff about a startup in a completely remote fashion.

We've had to figure out new rituals, new ways to hang out.

A lot of playing silly online games together and stuff like that.

Dealing with how do you hang out without being on Zoom all the time.

In terms of just the day-to-day work, I wouldn't say that there was a huge impact on the team overall because we already had multiple offices.

We had a few people that were full-time remote already. The core ways in which we got stuff done didn't need to change a lot.

I'd say we doubled down on writing things down well, but that was a component of the way that Nylas worked that was already in place.

One example is we actually just started a Canadian entity at Nylas about a year ago today.

I think we have about 40 or 50 people who work for Nylas in Canada now.

None of that existed before the pandemic. It'll be interesting, honestly, to see what happens once we get to a point where it is possible for us to open an actual office there and folks can meet each other in the office again.

I know there's some demand for it and we plan to continue being flexible, but we will have a space for people to meet up and collaborate and have the office experience.

Would you say that the whole working remotely thing has actually increased your access to tap into talent pools that aren't located near some of the hubs that people typically set up offices?

Somewhat. We had already had the plan to expand into Canada before the pandemic happened, so that didn't really change the big picture plan.

I guess we've maybe started hiring a bit more full-time remote people.

We actually also started expanding into Europe, but I don't feel like the pandemic has actually changed our thinking there in a major way.

This is kind of inevitable.

We were already in three different cities in North America beforehand, so you have to have some aspects of a remote culture anyway if you have teams that are spanning different locations.

Do you feel like tripling the size of the company in such a short time, has that influenced your work culture at all?

What feels like a Nylas way of doing things or the Nylas culture kind of thing? The thing that I always come back to is that as you're growing and scaling a company, the first thing that breaks down as you go through different phases is communication.

I would say that we've doubled down and had to spend a lot of time and energy and effort just evolving our communication patterns.

For example, the executive team at Nylas has a weekly staff meeting.

We've constantly been iterating on how do we make that a really productive use of our time and have really good cross-departmental conversations and make it not just super book-reporting status updates.

It's a lot of time for a lot of key people at the company to be spending on a call with each other.

A lot of can be done asynchronously if it's just an update.

Can we put those notes together well beforehand, spend a little bit of time reading the time box, the update stuff, which is fun and we like to nerd out about, especially when we're shipping all sorts of new things.

You want to talk about all of the new updates, but that's not actually the point of that meeting.

It's to have the tough conversations about the problems that we need to solve and things that need to be de-siloed.

We ended up restructuring that meeting so that all of the conversation topics are bubbled up to be up front and themed by our KPIs as a company.

Then the update stuff goes at the end, so we get through as much as we have time for, but otherwise it doesn't really matter.

People can read it later. I think another piece, specifically on the engineering side, has been around, we went from 25 engineers to I think we have about 45 today.

We started thinking about what are the lightweight processes that we need to put in place that just make the team.

Again, it's really about making sure that people don't get too siloed as the organization gets more structured.

For example, we just implemented a really lightweight architectural review process with a template and some guidelines around what sorts of changes ought to go up for architectural review and get feedback and make sure that those kinds of changes were driving alignment across engineering teams.

You don't have the same thing happening in five different ways in different teams, but also that we're making mindful choices about technology stack, architectural patterns, things like that as the company grows because they have a huge impact on maintainability, the future of the product, optionality.

That's something that's definitely been on my mind a lot lately because just the ways that you communicate at different sizes have to change all the time.

Sure. I've been meaning to ask, a long time back I have a recollection of Nautilus being called Inbox and then there was a name change because of Google launching a product with the name.

Can you tell us the story of that name change and also the pivot that happened thereafter?

Yeah, for sure.

That's ancient history at this point. It feels like a whole world ago. The company was originally called Inbox, partially because, well, really more than partially because the first idea for the product was really this unified API for email specifically.

There was a few different pieces of this.

One was the email API was actually a stepping stone and we actually ended up building out this extensible mail client that back-ended to the APIs.

There was this whole different product direction in the beginning where we saw the API infrastructure as being a stepping stone to something completely different than what we do today.

I would say that the short story is that we built out the APIs, we built out this email client, Google launched a different email client that was called Inbox.

We panicked momentarily and just basically we called up our lawyers and our lawyers were like, Inbox is the worst possible name you could have chosen for an email company because, if you're familiar with trademark law, you can't trademark generic names in the same context as they're used.

You can have Apple Computer, but you can't trademark Apple Orchards.

The law doesn't allow for that. There was no way for us to protect this name in the context of a company that works on email stuff.

We just changed the name because you need to have people be able to go to a search engine and type in the thing that will end them up on your home page or you'll never get anywhere.

We figured that competing with Google for SEO was probably a lost cause.

We basically hired some folks to come up with some concept names for us and that's how we ended up with the name Nylas, which basically checked the boxes of pronounceable, sounds cool, we could get the dot-com.

The metaphor story behind it is that Nylas with an I, N-I-L-A-S, is a name for ice that forms on the surface of the ocean.

The metaphor is that it's like icebergs and Nylas the platform. The surface area that you see belies a lot of complexity underneath the surface.

I have this cool slide that I use for a bunch of different things that has an iceberg image with all of the different jargon and crap that you have to deal with in order to build out email integrations if you're not using Nylas.

So that's kind of the secret meaning.

Can you tell us the story of the pivot, how you ended up in the current product direction that you're in?

Yeah, for us it's kind of a unique pivot story in that we started out, the first thing we built was the APIs that are the core of the product today in a much more limited form.

Then we went down this path that ended up being a really just poor business path which was essentially to build a really extensible email client that we wanted other people to integrate into and essentially be this command center for or this kind of knowledge work type tools that Nylas powers today.

So it was related but I just think the vision was wrong. Basically what we found out is that one, people want to own the end-to-end user experience of their product.

They want you to go to www.myproduct.com and spend all their interaction there.

So it's much more compelling to provide components that people can seamlessly and without any way of knowing that it's built by a different company, provide parts of that product than it is to go around and convince other people to build a plug-in for your experience.

It would have been a very difficult thing to accomplish as a startup not least because there's just so much engineering effort required to support all the different pieces of that.

So we weren't able to make that product successful as a business.

So we ended up essentially kind of pivoting back to our roots where we spun off the email client as an open source project and we had enough data from growing and selling the API product kind of on the back burner that we ended up just doubling down on the API infrastructure piece and that has kind of grown and evolved to where we are today.

And in terms of kind of how that ties into the broader company story, so my original co-founder for example, the mail client was really kind of his passion project whereas I'm the infrastructure person.

So when we went through that pivot, we ended up parting ways and another person who'd been with the company very early on stepped up to be my CEO partner in crime.

So the company today is kind of like the reborn Nylas but it's kind of funny to go back and think just like it's not that different.

It's very subtle but important. Under the hood, the tool is very similar.

It's just different people using it in different ways.

Would you say that's the difference? Yeah, and just like the interface and kind of like the entry points is really important.

Let's imagine that I invited you to a magical Zoom call with yourself.

Let's say back when, back in your case-wise days, what would that conversation be like?

What would you tell yourself then?

Assuming like you know the paradoxes don't blow up the universe.

You know that like the mind exploding gift?

That's where my head's at right now. Oh no, like connecting the red wire to the blue wire.

Go ahead. Yeah, that's a great question.

I mean so for folks who don't know before Nylas, I worked at this startup called Ksplice that did essentially like kernel engineering for Linux and had this cool security product and that was my first job outside of college.

So first thing that comes to mind is like one, I had no idea what the fuck I was doing then.

So like just like life experience from 30-something me to like 20 -something me.

Yeah, I guess like I'm the kind of person who kind of like you know I view all the like twists and turns in my path as being like you know things that were like really critical to developing me as the person I am today.

So it's not like I would like go back and tell myself to do something different but I think just like you know a thing that's important to remember is that like you know showing up is half the battle and like I guess the one thing I wish that I told myself maybe in the past is to remember to like celebrate successes more.

Like personally I'm like very hard on myself.

I think this is a very common anti-pattern for like high achieving people is that they're like kind of you know they don't give themselves credit for things they probably should give themselves credit for and I think it's the one thing that maybe I would tell my younger self.

Like I've been very good at like being optimistic and like you know looking for the silver linings and also just like you know when things happen that kind of freak you out like um you know the only thing that you have to do is like let the moment pass and and like don't quit keep going.

And like that's something that I think I've done very well but I haven't done very well at like taking a moment to like you know pat myself on the back and like let it really sink in of like you know the things that I've done that are good and like make sure not to like like grind on things too much.

That's a that's a good thing to keep in mind.

Celebrate the successes along the way. Yeah I gotta I gotta thank our um our our CRO now for that.

He always gives me a hard time about like being like okay we did the thing back to the grind.

He's like take a minute to party.

That's so important to uh like enjoy the journey along the way. Yeah and like you know this is like your whole life.

I mean certainly like you know looking back on Nihilus it's now it's coming up on like probably a third of my life.

So um you know if don't do something different as like a part of the journey like you're never going to do it.

Yeah um so generally speaking uh you know women entrepreneurs are very much in the minority and female CTOs are even more rare.

Um would you say that it's been a like is you know some would argue that it's a double-edged sword.

There's both positive and negative attributes to sort of sticking out or being um the rarity.

Um do you think you could comment on either side of that?

Has it helped with recruiting and closing candidates who are diverse?

Yeah yeah that's a good question. Um I mean I think that it's definitely helpful to be like unique in that people remember you more easily.

Um I definitely think that that has helped me throughout the years of just like I got like I'm not someone that people usually meet and then like you know an hour later they're like whatever.

Um so that's definitely been helpful. Um in terms of like the negatives of sticking out I personally like don't really feel like I've had like a lot of or really like any that I can think of like major negative experiences that I like link with like my female identity.

Um and I almost don't think it's like really helpful like to like try to like drill into that too much because like uh I guess I see it as as almost having like more of an impact on me than it does on like the world in general.

It's like if you're like constantly being like oh they only did that because like I'm a girl or whatever then it can just like just lead to like you know you feeling bitter all the time.

Um so it's not. And wasting cycles on it. Yeah it's like I just don't want to think about it that much so like I I default to like the other assumption of like you know they're like that with everyone or you know uh stuff like that.

Um so I I think that like honestly the major the most biggest downside of like being female for me has just been like like working through my own like internal like mental obstacles from being like conditioned like just as a human to like be quiet and deferent.

And just like confidence like you can't get around the fact that like just men as a group have more confidence than women.

I think that it's hard to argue against and that's the product of thousands of years of just like cultural stuff.

But also a good thing to uh to end on because it's something that you know you can build on yourself over time.

Yeah and I think that's why you know we need all those support structures.

For sure. Um well thank you so much for being on the show.

Uh it was really great having you on here and sharing your stories with uh with our audience.

Yeah super fun to chat um and uh hope that anybody who's listening uh got something out of it.

Well thank you.