Facing Adversity with a Growth Mindset with Keegan Riley


In this episode of the Sales Hacker Podcast, we have Keegan Riley, CRO at Sysdig, a cybersecurity startup, and philanthropist on the St. Jude Chicago Advisory Council. Join us for a raw and personal conversation on leadership, adversity, grit, and a growth mindset.

Bonus: In this episode, we hear music from Baba Brinkman, Founder at Event Rap.

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If you missed episode #180, check it out here: Talent Retention with Whole-Person Benefits Package

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What You’ll Learn

  • How Keegan fell into B2B tech sales
  • Creating a context for people to succeed
  • Facing adversity with a growth mindset
  • Finding joy in life with passion and perseverance

Show Agenda and Timestamps

  1. About Baba Brinkman & Event Rap [3:39]
  2. About Keegan Riley & Sysdig [7:02]
  3. Leadership learnings from massive company growth [18:09]
  4. Job training beyond college: a growth mindset [22:33]
  5. Facing adversity with courage and joy [24:39]
  6. Music by Baba Brinkman [33:12]

About Baba Brinkman & Event Rap [3:39]

Sam Jacobs: Welcome to the Sales Hacker Podcast. Today, we’ve got Keegan Riley, a long-time sales executive and chief revenue officer who’s led enterprise sales teams all over the world. And we’ve got a special surprise for you, so keep listening because it’s fantastic.

Before we get there, we want to thank our sponsors. The first is Outreach. A long-time sponsor of this podcast, we’re excited to announce their annual series, Unleash Summit Series, is back. This year’s theme is The Rise of Revenue Innovators. Get more details and save your spot at summit.outreach.io.

We’re also sponsored by Pavilion. Pavilion is the key to getting more out of your career. Our private membership gives you access to thousands of like-minded peers, Pavilion University, and workbooks, templates, scripts, and playbooks to accelerate your development. Pavilion members get hired 22% more quickly, are paid 14% more, and get promoted 32% more rapidly. Unlock the career of your dreams by applying today at joinpavilion.com.

Finally, Demostack. The product demo is make or break for your deal, but tailoring the story is tedious work. Demostack turns weeks into minutes so you can deliver custom demos at scale. See how world-class sales orgs use Demostack to accelerate revenue at demostack.com.

Today on the show, we’ve got two very special guests. The first is Keegan Riley, CRO for Sysdig, a San Francisco-based cybersecurity startup, with over 200 million in VC funding. Before joining Sysdig in 2018, Keegan was VP and GM of North America data storage at Hewlett Packard Enterprise, running a $1.5 billion P&L.

We’ve also got a special guest on the show, Baba Brinkman. Baba is going to be doing a performance for us. He’s going to be synthesizing what we talk about and coming back at the end of the show to do a musical performance.

Founder and CEO, rap artist Baba Brinkman began his rap career in 1998 freestyling and writing songs in his hometown of Vancouver, Canada, the home of hip-hop. In 2004, he premiered a one-man show based on his master thesis, The Rap Canterbury Tales, to critical acclaim at the Edinburgh Fringe Festival. He’s gone on to create award-winning solo rap theater shows about evolution, consciousness, religion, and climate change, and a new company and project that he’s going to be talking about. Baba, give us a little bit of a snapshot. We call it the baseball card. Tell us a little bit about yourself.

Baba Brinkman: I was doing science communication rap, that’s been my little niche. I do one-man shows, and I release records.

When the pandemic hit, I was like, “What am I supposed to do now?” I started reaching out to people I knew in enterprise and software companies, saying, “Hey, I’ll jump in your meeting and rap about whatever you’re talking about.” I developed this virtual custom rap show that I did over the course of 2020. The main one is a wrap-up, which I’ll do at the end. It’s where you come in with nothing prepared, listen to a whole conversation, it can be a sales meeting, conference, whatever, and you’re writing the rap in real-time, responding to everything you hear, and then you kick the lyrics at the end and wow everybody with a cogent rap summary.

I started reaching out to some rappers and saying, “Would you be interested in some of these virtual gigs?” and I founded Event Rap. I represent 10 rap artists who do customer commission writing projects, freestyle, and do their thing but in a specific technical/ utilitarian context. We’re here to liven up meetings, and we do podcasts, too, so I’ll be showing you a demo.

Sam Jacobs: That’s awesome. We’re looking forward to it. My company might be interested in using Event Rap, so I’m glad we got a chance to connect.

Baba Brinkman: Boom. I’m hacking sales.

About Keegan Riley & Sysdig [7:02]

Sam Jacobs: Keegan, you’re CRO of Sysdig. You told me that you guys are absolutely killing it. What do they do in your words?

Keegan Riley: Sysdig is capitalizing on a platform shift that’s occurring in terms of how companies build applications. Increasingly, companies are building cloud-native applications, leveraging containers and Kubernetes, and built completely in the cloud, whether it’s AWS, Google, or Microsoft. Any time there’s a major platform shift like that, legacy tooling tends to break, so the security tools from the old-school on-prem data center world don’t work for cloud security. Sysdig was founded around the premise that container and cloud security is going to be a big market in the future. It’s not just a startup that’s invented a better mousetrap, it’s a startup that has made a market in terms of container and Kubernetes security.

Sam Jacobs: Helping enterprises transition from on-prem to the cloud with the confidence that they’ll have the right security systems in place?

Keegan Riley: Modern applications are built in a fundamentally different way. The old waterfall approach, that’s not how applications are built anymore. Now, most organizations deploy using continuous integration, continuous deployment, where the code changes multiple times a day, and containers, which are the building blocks of cloud-native applications, very ephemeral in nature. We’ve brought a product to market that’s highly differentiated in this new space.

I was one of the first 30 employees, and we were just under five million in ARR. We’re about 300 employees today. We’re more than 10X growth on ARR, and we raised our last round. We closed it in April of this year at a $1.2 billion valuation.

Leadership learnings from massive company growth [18:09]

Sam Jacobs: When you think about the keys to your success and the keys to leadership, what comes to mind?

Keegan Riley: Leadership is about creating a context in which people can do great things beyond what they thought possible. If you foster that environment, hire the right people, find people that are gritty and passionate about what they do, willing to persevere even when things get tough, and are relentless in their approach, that’s a recipe for success. If you get those things right, it’s hard to fuck it up. If you get those things wrong, it’s hard to succeed.

Culture and the term “hiring for cultural fit,” in some ways, can be misunderstood. It’s been misinterpreted by a lot of companies as shorthand for hire people that look like me and think like me and root for the same sports teams.

At Sysdig, there are three pillars, our core values:

  • The first is love our customers and put them at the center of everything that we do.
  • The second is trust in the team, we’re a meritocracy and we’re going to keep the bar high. We’re only going to hire A players who are going to get shit done.
  • Then the third element is dig deeper, hiring gritty people and fostering an environment of grit, where people are passionate about what they do and have the ability to persevere over long periods of time in pursuit of an ultimate high-level goal.

You’ve got to be explicit in your expectations. You’ve got to build a business plan and communicate what the vision is, align everyone behind the vision, and then treat it as a process.

Job training beyond college: a growth mindset [22:33]

Keegan Riley: There’s no one straight ladder to success like there used to be, for a variety of reasons. Online learning and the free flow of information allow self-starters to educate themselves. I’m a true believer in that, but there’s no one size fits all answer. There’s a ton of value in college. There’s a ton of value in graduate school.

You’ve got to have a growth mindset. Educate yourself and be open-minded to continuous learning for your entire life and career. When I look at folks as potential employees, partners, or investors, I don’t care how they got there. I care that there’s a track record of success, of finding a way to get the job done successfully.

Facing adversity with courage and joy [24:39]

Keegan Riley: Overcoming adversity is not something you’re born with. It’s a skill that you develop. You’ve got to let your kids fail. They’ve got to learn to lose, to be competitive, and to dust themselves off. But I had a bit of a tragedy in my family. My little brother passed away unexpectedly about three or four weeks ago.

It’s the most painful thing that a family can go through. There’s a great quote from Adam Grant, a psychologist at Wharton: “Personality is how you respond on a typical day. Character is how you show up on your worst day. It’s easy to demonstrate fairness, integrity, and generosity when things are going well. The real question is whether you stand by those values when the deck is stacked against you.”

You don’t know when your time comes, so you’ve got to realize that life is precious, and you’ve got to make the most of the time that you’re given, and you’ve got to live a full life. I’m proud of my family, and I’m proud of the way that they’ve all chosen to respond, focusing on immense gratitude for the time spent together, faith that he’s still with us in spirit, and a serious commitment to doubling down on living a life that would make him proud and bringing him with us.

Sam Jacobs: What’s the best way to get in touch with you?

Keegan Riley: LinkedIn, Keegan Riley. Direct messages on LinkedIn are probably the best way to go about it. My email’s keegan@sysdig.com.

Music by Baba Brinkman [33:12]

Sam Jacobs: Baba, that was fantastic. If folks want to hire you, what’s the best way to get in touch?

Baba Brinkman: The website is eventrap.com. It’s Event Rap Inc. across various socials. We’re building this industry from the ground up. Hit me up, I’m on LinkedIn.

Sam’s Corner [38:47]

Sam Jacobs: Hey, folks, Sam’s Corner. What an episode! We got a special rap performance from Baba Brinkman, he took all those notes during my conversation with Keegan, he delivered it, and we need to use it to promote Sales Hacker because it was absolutely fantastic.

Keegan’s an incredible guy and Baba’s an amazing lyricist, creator, and artist. I really enjoyed this episode.

Before we go, we want to thank our sponsors:

  1. Outreach. Save your spot at summit.outreach.io
  2. Pavilion. Apply today at joinpavilion.com
  3. Demostack. Accelerate revenue at demostack.com

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If you want to get in touch with me, you can email me, sam@joinpavilion.com. I’ll talk to you next time, thanks for listening.

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