September 15, 2020

Improving the Developer Hiring Experience, with Headlight’s Wayne Gerard

By Wes Winham

Today’s a really exciting day for us. Our startup just acquired a New York City-based tech hiring platform called Headlight.

We’re sitting down with Wayne Gerard to talk about this transition. We wanted to know what they’ve learned while uncovering some of the best software engineers in New York City. Over the past two years, they’ve uncovered hidden gems and made the hiring process better for both developers and hiring managers. What’s more, they did it in one of the nation’s most competitive job markets. We could all learn something from their story.

In this episode, we cover:

  1. The work Etsy put into perfecting their “take-home assignment”
  2. Why Headlight decided to partner with Woven
  3. The next steps for the Headlight team

Listen to the full episode here

Wayne thank you for joining us today on Scaling Software Teams.

Thank you. Happy to be here.

So tell us the Headlights story.

So at Etsy, Jason – my co-founder – and I were part of the interview process for a large number of candidates and over time we started to have opinions on the hiring process.

That tends to happen, yes.



Wayne: Something we did at Etsy that we took a lot of pride in was something called the “take-home assignment” – which, if you’re not familiar with, is usually a small contained project that candidates are asked to complete. It’s supposed to demonstrate their expertise and you know, kind of allowed them to show off. Basically, show what they know.

Of course, that has its own problems. It really optimizes for people with free time; obviously if you’re not bounding it in some way. So if you have 40 hours you can put together something really amazing even though it was meant to be done in about two to three hours right. So, as you can imagine if you’re a parent or even just someone in any kind of a relationship you probably don’t have that much free time – especially if you’re thinking about applying to multiple companies at the same time. I mean, if you’re spending six to seven hours on each take home assignment and you’re applying to four or five companies, it could be a real time sink.

So we really like this idea of take homes, especially done as blind reviews, because it lets candidates demonstrate their expertise without answering traditional whiteboard questions in a really high pressure situation. But we didn’t like the unboundedness of take homes because it sort of introduced what I considered to be a sort of an arms race. You know, candidates felt pressured to spend tons of time on take homes because they knew that other candidates were spending lots of time on take homes, and that’s what they’re gonna be judged against.

Wes: Right, if I’m competing with someone that spent 40 hours, I’m gonna want to polish and polish and polish and add that extra feature.

Yeah! And it just makes sense that you would be more impressed by something that someone spent 40 hours on. You don’t consider the fact that they spend 40 hours on it, you just see the final product and think, “this is amazing” right? But it’s really unfair to people who just have other commitments, and typically those are the kinds of people you’re trying to hire anyway. I mean, you don’t always want just the person who has tons of free time, you want people of diverse backgrounds and who are coming in from various life experiences.

So we started Headlight to try and turn this into a process, [in order] to provide small but time constrained and strictly enforced challenges that let candidates demonstrate their ability without feeling like someone is watching over their shoulder the whole time and judging them like they would be in an interview, or if they were competing against a recent college grad who had 40 hours of free time and just managed to put together something spectacular. That was the inspiration for Headlight and is sort of how we got to where we are today.

You don’t always want just the person who has tons of free time, you want people of diverse backgrounds and who are coming in from various life experiences.

— Wayne Gerard

You and Jason have been working at this for almost two years now. What have you learned about how candidate experience impacts developer hiring?

As you can imagine candidates are really sensitive to the hiring pipeline. I think a lot of companies are really struggling to hire mid-level and senior level developers, but they don’t think about how the interview process actually impacts that their ability to recruit [them]. I can say, personally, that I have been turned off by major companies having gone through their interview process because it seems haphazard or it’s unclear what I’d be hired to do – things like that. And certainly I get the the story from the other side where hiring managers feel like they don’t really know how to recruit senior developers or how to manage that interview process and it ends up being a mess on both ends, basically.

As you can imagine, good candidates are sensitive to the hiring process, and if you don’t have a good candidate experience they’re likely to just drop off immediately.

There’s this interesting dynamic where companies largely want senior developers but it turns out senior developers tend to be older; they have more going on in their life. They might be married with children and things like that, so they have less free time to do things like spend 20 hours on a take home assignment, or to do six phone interviews. Plus, they’re less patient with experiences like that, so it’s this weird Catch 22 where companies have these stringent hiring processes because they feel like that’s how they get the best developers, but it turns out the best developers really push back against things like that, and want a smooth, human process.

Sounds like you’ve been able to kind of thread that needle and give the rigor that creates a good hiring process by enforcing a time limit, while also building a process that senior developers who have lives and don’t want to spend 40 hours will actually take.

Yeah. And you know it’s not perfect, obviously. I mean we certainly had stories from people who who have small, infant children, and even spending an hour and a half sometimes is a struggle – babies obviously can’t be timed or told to be quiet for an hour and a half. So it’s certainly not perfect but we hope it’s at least more humane than the existing processes they go through.



That’s one of the things I struggle with – I hear people on Twitter who have opinions. They say, really what you should do is just talk to somebody and if you just talk to them and they feel smart then they’re probably smart. I wish I believed the world worked that way.

You know something I was gonna say about the hiring process is, maybe you might get a good impression just from talking to someone or even doing something like looking at their resume. But we’ve seen candidates with great experience, or who are currently working at somewhere like Amazon, and then it turns out they really don’t know the things that you need them to know.

So yeah, it would be great, obviously, if you could just talk to someone and figure out what their deal is. But it doesn’t always work that way, obviously.

I find that those folks who view the world that way also tend to rely on credentials. If you can’t see what someone can do, then you’re more likely to gauge them by when they worked at Amazon in the past… which… maybe that’s not so great, either.

Yeah, and it turns out sometimes Amazon employees aren’t the best idea for a small, two to three person startup, right? They might be used to that big company infrastructure. So, yeah, I agree it’s tough and there’s no magic bullet –  you’ll find someone who hates basically every part of the hiring process.

Interviewing kind of sucks – like they’re just fundamentally kind of a sucky [process]. It’s just judging and being judged.

It’s really about trying to find the least stressful way of interviewing someone – but it’s never gonna be fun.



Wes: Tell us about why you choose to work with Woven.

Wayne: You know it’s interesting. So we did a lot of competitive research when we were starting up – trying to see what was out there. We did a lot of research on companies that had existed prior to us that tried to take a similar approach. And truthfully we had no idea Woven existed until I read a Hacker News comment about Woven. It was a large thread about take home assignments and, as is the case with Twitter, lots of people were commenting about how much they hate take homes and how terrible the process was.

And someone commented saying that there’s this company, Woven, that’s working on trying to make it more humane and more beneficial for the candidates, instead of just being a black box.

So that was the first time Woven came across our radar and we obviously looked a little bit more into what Woven was about and it felt like are our ideals of trying to make a great candidate experience, or at least as great as it can be for an interview.

Those were ideals that Woven also shared, and it was refreshing to see a company really care about candidate experience. That seems kind of silly because it seems like, of course, everybody would care about candidate experience but I’d say in general that’s really not the case – a lot of companies are really optimizing for “throughput”; they really focus on how they can reject the bad candidates, not how they can find the good candidates. We really felt like Woven was sort of a kindred spirit in that regard.

A lot of companies are really optimizing for “throughput”; they really focus on how they can reject the bad candidates, not how they can find the good candidates. We really felt like Woven was sort of a kindred spirit in that regard.

— Wayne Gerard

Yeah, I remember the first call with Jason just really bonding over hearing you frustrations with the status quo. I think telling someone very quickly that they’re not gonna be successful on the job is useful – and I think there are some good tools out there for that. But I’m glad that we shared the idea that maybe there’s a better way maybe we can tell people that actually, no, you are very good at this job even though your resume might not say that.

There’s plenty of candidates who have very untraditional experiences, but they’re extremely capable and will really nail it if you give them a chance.





Tell us about your next venture. You’ve gotten great traction with something you’re passionate about. How did that happen?

Yeah, you know it was interesting we had an end of year meeting, where we were discussing things, and thinking about the future, and we realized that we maybe wanted to just take a completely different direction.

So full disclosure, we’re taking a super hard pivot and we’re going into esports; which is teams of people playing video games professionally. We’re rebranding the company as a new company called Midgame.

For a lot of these teams, voice communication is really the only way they can communicate. If you’re playing a video game, you can’t use hand signals, you can’t use eye movements or anything like that. And so you can imagine that communication is the number one problem for almost all of these teams – even more so than basic game skills or things like that.

It’s not a natural transition, obviously, since we’re going from hiring to esports but this theme of of trying to help people communicate better, and really thinking about how teams form together or what makes a good team – that’s something that still felt within the realm of things we really cared about and really inspired us to start a new company.

I mean as you can imagine there’s not a lot of tangible things that we’re taking from Headlight and moving over to the Midgame. But the experience of a company and just basic things like sales, marketing – things that we had no experience in – is really valuable and something that we’re really hoping will help us execute better with Midgame.

Having a co-founder of you work well with – that can’t be overstated. I think people say startups fail because they run out of money which is literally true. But when I hear stories, it’s often co-founder relationships.

It’s just really tough to find someone that you work well with.The great startups obviously have great stories. But you know there’s a lot of struggle, obviously, and so someone that you can struggle and empathize with and not be resentful of is a really rare thing. But it’s just really hard to find.

Disagreeing productively. I feel like that’s the story of a startup over and over.

Yeah totally, and making hard decisions and committing to that and not being resentful of the direction you didn’t take.

Yeah it’s very hard. So now that you’re you’re working on Midgame, you’re going to make teams playing sports better and more effective with voice communications. What does that mean for all of Headlight’s current customers?

Yeah. So what we’re doing is hoping to transition our current customers over to the other company that we’re discussing here, Woven, that really emphasizes the candidate experience in a way that Headlight also does.

I don’t know that we’ve come across another company that really cares about the candidate experience in a way that Woven does. I think – not to be too disdainful of other companies – but sometimes it feels like there’s a bit of a grinder there, where they input candidates, and out come two or three candidates who might be really good. But they’re not thinking about what that experience is like. And I know that a lot of Headlight’s customers also care about the candidate experience for the reasons that we talked about.

I mean it’s really hard to hire mid and senior-level developers if you don’t care about the candidate experience. And rarely will a senior level candidate appreciate you sending them a challenge from one of these other companies without any sort of thinking about how they feel.

So we want to transition our current customers to something that’s very similar to the experience they’ve become accustomed to with Headlight, and to another team that cares just as much about candidate experience as we do.

Yeah I’m looking forward to talking to those folks! One last question: what advice would you have for folks who are looking to hire developers in New York City?

Similar to this this idea of haphazard hiring processes, I think it’s really critical for hiring managers to think exactly about what it is they need, or what they’re looking for. And even to just explicitly write it out. I mean, how can you really evaluate a candidate if you don’t even know what you’re looking for in that candidate?

And I don’t think that this is a result of laziness. I think it’s just really hard to nail down exactly what you want from someone. Sometimes hiring managers will say things like, “I want someone who’s a good communicator.” I’m sure you’ve also heard this requirement, too… but what does it really mean, right? How do you test whether someone’s a good communicator?

Say someone’s really great at communicating in person, but they’re terrible at email and in writing… is that okay? What tradeoffs are you willing to make there? So being thorough and deliberate about what it is you’re looking for, and what you’re hiring for is so critical, and it helps so much with the interview process.

Wayne thank you so much for joining us today on Scaling Software Teams.

Thanks. Yeah. Great to be onboard. And really excited about the future.

Me too.

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April 1, 2019