6 minutes

Sticking The Drop — My Journey to Obsidian

Stay On or Hop Off?

It’s been about six weeks since I made the jump from working for the UK Government to Obsidian Security, an early-stage startup in Newport Beach, CA. I wanted to write some quick thoughts to explain what it’s been like to anyone thinking about doing the same!
For me, my journey to Obsidian started in April 2017. My wife and I were staying in a log cabin in the Welsh mountains having our first weekend away alone since having our daughter two years before. I took a book I’d long wanted to read, “How Google Works” by Eric Schmidt, Jonathan Rosenberg, and Alan Eagle. In the book, they describe their personal philosophy about technology careers. They say that technology careers can be thought of like surfing (this appeals to me primarily because I like to think of myself as a surfer though my brother-in-law would say otherwise!). The key to accelerated development is to surf the gnarliest waves you’re capable of surfing — the waves where your board feels like it wants to fly out from under your feet — but you manage to stick it.

While reading this book I had a really successful project that was coming to an end. To stick with the surfing analogy, you never ride a wave to the beach unless you want to get out. As soon as the wave has lost power you hop off the back and find the next one. It’s a really hard thing to recognize in the moment, but I knew it was time to hop off the back and look for a new exciting wave that would push me beyond my limits!

Hunting the Wave

So I started my search. It turned out to be far harder and longer than I thought it would be. I had a few key principles to guide me:

  • Join an early phase startup, where the decisions and technology choices hadn’t all been made yet
  • See a company grow from a small tight team into a giant
  • Believe in the founders’ vision
  • Be surrounded by people more capable than myself
  • Find people solving a new problem, not cranking the handle on something tried and tested

In short, I set an extremely high bar for my would-be future startup.

After an exhausting search, I found Obsidian. After reading an article entitled, “How to build your dynasty: Hire for passion, train for skill, coach for performance” by Obsidian’s CTO Ben Johnson, where he outlined Obsidian’s philosophy for hiring I was sold. After further research including watching some YouTube videos of the founders Ben, Glenn, and Matt presenting at conferences and talking about Obsidian, it felt right. Obsidian was the team I was searching for.

Paddling for The Wave

Next was the tricky challenge of landing myself an interview and getting hired. I wanted to put my best foot forward so I analyzed all of their website content, news articles and job descriptions, and tailored my CV and cover letter to be a strong fit. But it is well known that sending your CV in cold is rarely successful. Thus, I tried to temper my expectations and was prepared that Obsidian might be a wave that I wouldn’t catch. However, two weeks later I had phone screens with Ashley, Obsidian’s Director of Operations and Matt the Chief Scientist.

Speaking with both Matt and Ashley confirmed that Obsidian was right for me, but the discussions also led me to believe that I was right for Obsidian. I had relevant experience and our conversations went well so they invited me for a full interview. I wanted to give myself maximum preparation time so I tried to delay the interview as much as I could without appearing to be disinterested. After a productive interview, Matt phoned me to offer me a spot on the team!

Dropping In

I was now at the top of the wave staring at a near vertical face thinking how on earth am I going to stick this drop. Being part of a startup is incredibly exciting and completely different from what I had done previously. The company has doubled in size in the last three months, going from 15 when I interviewed to over 30 today.

Joining the data science team has been a humbling experience to say the least. The standard is incredibly high as every single teammate could get hired in most companies as a software engineer, mathematician, machine learning engineer or data scientist. Across the rest of the company, the standard fails to disappoint. And while you may think this would lead to an arrogant and hero culture, the opposite is true. Obsidians (as we call ourselves) are always willing to learn, to listen, and to consider ideas. There’s also a healthy dose of constructive criticism that supercharges personal development and makes for a better product.

Finding Your Ride

The next few years will be super exciting for Obsidian and myself; learning new technologies, pushing the boundaries of information security and AI. All whilst being a part of an all-star team of engineers, leaders, researchers and thinkers.

If you are thinking about paddling out to the break and trying to stick a monster wave like an Obsidian, I would offer you the following advice:

  • Immerse yourself in the startup world and talk to as many people as possible— look to see which teams excite you, find the people that are leading and changing the industry
  • Have a solid CV and cover letter tailored for the company (1–2 pages no more)
  • Get ready to be knocked back, if you’re not getting rejected you’re aiming too low
  • Don’t aim to be a big fish in a small pond, find teams who intimidate you with their brilliance
  • Train, always train — startups look for versatility, passion and curiosity above all else
  • And finally, enjoy it, it’s an amazing adventure!

If you think that Obsidian might be the monster wave you’ve been waiting for, we’re hiring and would love to hear from you.

Best of luck, see you in the lineup.