🤓 Nerding Out: An Interview with Derek Williamson

I interviewed Derek Williamson, CEO of HigherMe, a company focused on helping employers hire and onboard employees quickly and seamlessly (9 min read)

Homescreens is a weekly publication about how we interact with our most intimate possession, our phones. Each week I interview interesting people across industries, and we reflect on the apps they use, how they’re organized, and their philosophy on notifications and mindfulness.

I met Derek at a Techstars Startup Weekend in late 2017. I had just pitched a concept for a gamified classroom management system — it drew zero votes. If you’re not familiar with how a startup weekend works, this means that unless I wanted to work alone, I had to join another team.

After shuffling through groups of eager, would-be entrepreneurs, I found Derek. A small crowd was around as he pitched his idea for a niche marketplace aimed at helping busy movers. He was on to something. I quickly joined the team, and over the course of the three-day competition I got to know Derek well.

Derek is a former Marble Slab franchise owner before joining HigherMe, a startup that aims to help employers find and hire talent easily. Since joining as a consultant, Derek has served various roles — Director of People and Partnerships, Recruitment Process, COO — and now serves as HigherMe’s Chief Executive Officer.

When you look at Derek’s phone you can tell a lot about him. It’s hyper-focused. There’s communication apps, there’s Twitter for staying in-the-know with industry news, and there’s Google’s productivity suite. Organized and deliberate.

What follows is our interview, edited for length and clarity.

When we first met you were doing consulting work for HigherMe, and now you’re the CEO—very cool! Tell me about that?

I was honestly a glorified intern. It was like—come in and see where you’re useful. It’s interesting, I found in a startup you need some specialists, and then you need some generalists, right? You need a few people that know what’s going on that can pull things together.

I had seen all the different parts of the business, I had done product management, I’ve done sales, then at one point we didn’t have anyone in marketing for a while so I was like—Hey we should probably update our social and blog—so I said I’m just going to do that. Some people have got to be the garbage collector and clean up loose ends.

Rob [Read his interview here] a couple of years ago was exploring the idea of Lexria and the idea of maybe moving on, so we did the transition about a year ago. We balance each other well, I’m much more internal focused—I like to have one-on-ones with the team and focus on the nitty-gritty process stuff. Whereas Rob, as you know, loves to pitch and do all of that. We’re on a good path. Aside from COVID and this global pandemic things are going pretty good!

That’s great, congrats again. I see you have Twitter right smack in the middle of your home screen. Are you a big Twitter user?

I’m not a big poster yet, I don’t have many followers but maybe six months ago it became my go-to. The beauty of Twitter is you can just follow anyone. There’s no mutual accept or anything. And because I haven’t used Twitter I don’t have a bunch of people I went to high school on it—it’s a blank slate. I just use Twitter to follow people who I really like their ideas and thoughts, right? So it’s kind of curated. I follow a bunch of authors, VCs, a lot of companies that post interesting stuff, startup founders. I’ve definitely found a lot more people in the tech-space are more active on Twitter than any other medium, even more so than LinkedIn.

Who are some interesting people you’ve followed recently?

There are a few interesting accounts—I know it’s super cliche with tech people, but do you know Naval Ravikant? He founded AngelList and is just a super interesting dude. I feel like you and I have a lot in common so it may resonate with you. He’s got an amazing podcast that was originally a tweetstorm, where he basically published an essay of bite-sized tidbits on Twitter, then made the podcast to expand on all of the ideas he shared in the tweetstorms. There’s a lot of depth to it. I like things where you listen for two minutes then have to pause and think about it for ten minutes. That was one of the early ones that made me go—Hmm maybe I should get on Twitter.

Then there’s an author named Derek Sivers who’s pretty cool. He founded a company called CD Baby. It was an early dot com thing that was for independent musicians, you could upload your music and then sell your album to your fans. He’s very mindful, very stoic, and just has a very good view of the world. Just seems at peace.

Then there’s VCs like Ben Horowitz, although I don’t think he tweets much. How about you, who are you following?

You know, I literally just re-made my Twitter account and if you look me up I don’t think I’m following anyone yet. I have mostly just been living in the trending section.

So what’s on your home screen, by the way? I feel like you shared it before, but I can’t remember.

Derek flips the interview onto me

I try and keep it productive. I have Audible, Blinkist—which I just downloaded, Numerical calculator app, Pocket Casts, Headspace, and Notion. Have you used Notion before?

Yeah, it’s perfect. A year or so ago we moved our entire knowledgebase over to it. I mean it probably gets harder to manage if you have 1,000 people but for a small company, it’s perfect. I try to get everyone to not put things in Google Docs because it’s just going to live in some folder somewhere—put it in Notion! It’s searchable, it’s always there, and if you want to share something with someone outside the company you can just publish it as a website—which is such a cool idea.

Have you heard of Hey? Like Hey.com?

I really liked it, I used it for a while as my personal account and I debated after the demo if I wanted to pull the trigger but I haven’t yet, being that it’s $99. Do you use it?

Exact same thing. It’s funny how we perceive value. Email is something we use every day, right? I said the same thing—man it’s $99, I don’t know—our conception of price is so weird. It’s anchored to “email is just free.”

Exactly. Are you using Slack to basically run your day-to-day?

Yep, 100% We still use Zoom though, Slack’s calling isn’t great, I’m big on not having unnecessary meetings. We don’t have a meeting if it could be a Slack message. For things like standups, we automated and got a Slack bot that will send you the questions and just puts it in a channel. All of that stuff can be done asynchronously, then for meetings, it’s like—okay what do we actually need to talk about? You cut out all the other steps. I think I stole that actually from the guys at Basecamp. Have you read Rework?

No, but isn’t that by the founder of Basecamp?

Yeah, it’s really good. Even today it’s pretty contrarian to a lot of the “startup mantras.” For example, we glorify failure too much. Someone’s failure is their problem, and their argument is that we sometimes use it as an excuse to fail, cut corners, or just do a poor job.

I have to stop our team all the time, like if we're going to release a feature and there are bugs and they go—well yeah, it’s the first version—no, we control the appearance of it. You don’t release something that looks like shit. That’s not what “fail fast” means. It still has to be a true minimum viable product, actually testing the experience.

They [Jason Fried] relentlessly kibosh meetings. So much time is wasted in meetings—so many inefficiencies. You’re doing things that could be done asynchronously, especially when we have all these great tools.

Anyways, my phone is kind of boring though, eh?

I’m the same way, you’ve seen my phone. There’s nothing on it.

You know what, I’ve got a good one—I can’t remember if this was on Product Hunt but I just started using it, it’s called Reclaim.ai. It’s a calendar manager. There’s another app called Undock which you may have seen, I’ll have to show you both.

Undock is going to be close to the “Superhuman” of calendar scheduling. Both of these work well together. Reclaim.ai is more for managing your personal time and your deep work time. The concept is that you can set things that you want to do every day or week. For example, I want to have a thirty-minute lunch every day, and I want to have it sometime between 11 o’clock and 2 o’clock. It will put a placeholder in your calendar, and as things get added to your calendar it will move it around. If your calendar gets too tight it will lock-in an invite, and you can set rules around that.

I love that, this is something I’d certainly use.

Right, so that’s one. Then there’s Undock which I keep nerding out about. It’s kind of like Calendly, where you can create a meeting link and you set your availability. There’s a bunch of configuration options. The cool thing though, is that you can download a chrome extension, and it lives in your email. So if I want to book a meeting I just hit backslash and it will bring it up at any time.

They’re still at a stage where the founders are doing the onboarding, so I was chatting with them, and they are going to be layering a meeting tool system on top of it. That way if I have Undock and you have Undock, it will find the ideal meeting times based on both of our settings. Super cool. I always felt Calendly was clunky for that. I highly recommend it!

Very cool! Thanks Derek, this was great, I appreciate you taking the time to do this. We should catch up more often.

For sure, thanks for having me! Cheers!


Thanks for reading my interview with Derek. Find him on LinkedIn, Twitter, learn more about HigherMe, and find out about his side project Deployee.

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