Recovering Gartner Analyst: Year One

Sysdig is my first startup, and this week is my one-year anniversary. I got here by way of a meandering path through academia, research, consulting, and ultimately Gartner. If you have the chance to work at Gartner as an industry analyst, you should absolutely take it, even if only for a couple of years. It’s like going to Harvard or working at NASA. You will collaborate with the highest caliber of people, you will learn more than you didn’t know you didn’t know, and people who have never worked at Gartner will think you’re a wizard. What’s cool about Sysdig is that the people we hire here are cut from the same type of cloth, even though we are not yet a world-renowned powerhouse of a company.?

Why Sysdig?

I had two reasons for joining this company: I believe in the product, and I believe in the leadership team. Don’t ever join a startup without seeing a demo of what they have so far and collecting some intel on the founders, executives, and investors. I had the unfair advantage of covering this space as a Gartner analyst for 6 years, so it was my job to know this stuff, but anyone can do a little homework to save themselves heartache down the line. I suggest finding answers to at least these questions:

• Which market does this product play in, and can it win? Sysdig plays in cloud and container security, which is one of the hottest markets of our time. I think we can win because we’re one of the very few who understand the full scope of the problem.
• Who is running this company, and do they seem to know what they’re doing? Sysdig’s leadership team is a delightful combination of utterly stunning intellectual prowess (Loris), impressive technical-business acumen (Suresh), and a solid mix of senior leaders, all of whom have done this successfully before.
• Who invested and how much? Sysdig has raised over $700M in funding from very reputable sources. We’re also very careful about the valuation the money is raised at and how that money is ultimately spent, which helps protect us from unpleasant financial maneuvers in rougher economic times.???
• Who are the existing customers? Sysdig’s customers include the largest enterprise companies in the world and the most cutting-edge engineering and security teams. More importantly, these customers have stuck with the product through the years (our NRR is >135%), indicating that the company continues to deliver on its promises.

Surviving at Startup Speed

I avoided startups in the earlier stages of my career because I am a fairly risk-averse person. I didn’t want to burn out before turning 30. I didn’t want to live to work. In retrospect, it was the right decision for me. But if you’re ambitious and the prospect of cashing out in a sweet IPO makes you giggle with delight, here are a few things to think about before you dive right in.?

Boundaries and Work-life Balance

We all need boundaries, in our personal and professional lives, but it’s notoriously difficult to set and enforce them, especially at work. I follow a simple rule for myself: I don’t let work bleed into my personal time unless I messed up or it’s a serious emergency like a zero-day vulnerability disclosure.

It takes a LOT to build a successful company from scratch, and thus startups often attract the most passionate, driven, committed, and moderately obsessive people. Sysdig in particular is late-stage enough that it maintains a lot of its startup energy while learning to operate at scale, so it’s in a really fun phase.

I’m somewhat prone to “saying yes” and doing too many things, but I also hugely value my mental health. One thing that keeps me sane is having a boss who viciously defends my boundaries. He’s an incorrigible workaholic, by the way, but he understands that he and I don’t have to have the same boundaries, so he enforces his for him and mine for me. Find that type of boss (or become one).

Culture

Sysdig is quite a happy place, but not every day is puppies and rainbows (although there is a Slack channel full of adorable dog photos, and the dancing parrot emoji gets deployed with great frequency). We’re building a very intricate product here that has many moving parts, and we’re building it to address some truly novel use cases. We’re also moving very, very fast. Regardless of where you work, sometimes things can go a bit sideways. One thing I love about working here is that we laugh all the time, on good days and bad days. It feels much less hierarchical and much more genuine this way. I’m a snarky, silly, bold person. I can’t thrive in a place that’s all suits and management tiers. If I can’t be myself at work, I’m not happy. Whatever your work personality is, you want a job that matches it. Find a team that makes you laugh.?

Relationships

If you spend enough time in any industry, you’ll notice that everyone knows everyone. This is weird because an “industry” includes hundreds of thousands of people. But it’s actually not weird at all because the best people know and remember each other, and that’s how you get companies like Sysdig. You want to be one of these people. You want to join companies that not only attract high-performing individuals, but all of their high-performing friends as well.???

Sysdig’s current crew includes the co-creators of Wireshark, the former CEO of Nimble Storage and his team, the former CTO of Endgame, a group of serial Israeli startup founders, a handful of former Gartner analysts, and tons of alumni from places like Google, Mandiant, US government agencies, and more.

So if you’re thinking of joining us, remember that this may be the coolest job you ever have, but it won’t be the last. The people you meet here will be worth holding onto long after our private island exit.