CEO Rapidfire: Monte Carlo's Barr Moses On Why Tech Trends Are Like Avocados

Welcome to CEO Rapidfire, fast-paced questions with today’s most successful founders and CEOs. Be sure to look for these special Q&A editions of my newsletter, where I’ll share insights from the amazing leaders in my network.

This week I chat with Barr Moses, who doesn’t put much stock in five-year plans. (To find out why, keep reading!) 

Barr is co-founder and CEO of Monte Carlo, a data reliability firm. Monte Carlo created what's considered the first end-to-end data observability platform, which lets companies in a wide range of industries detect, resolve and even prevent issues with their data. “Our mission is to help accelerate the adoption of data by reducing what we call data downtime, which is periods of time when data is wrong or inaccurate,” Barr says.

Monte Carlo was recently named the No. 1 data observability platform by product review site G2, for the fifth straight quarter. The first company in its category to reach a $1 billion valuation, it’s backed by Accel, IVP, Redpoint Ventures and other top Silicon Valley investors. Founded in 2019 by Barr and her husband, CTO Lior Gavish, Monte Carlo serves customers including Affirm, CNN and Sonos.

Barr began working with data early in her career, focusing on data analysis in the military context. She then moved to the US to earn a BS in math and computer science from Stanford University. Barr went on to become a management consultant with Bain & Co., then a VP at customer success platform Gainsight, before launching Monte Carlo.

As a remote-first company, Monte Carlo is known for having an exceptional culture where team members are challenged and rewarded. Newcomers, for instance, go through what’s called a Week One Ship. “Within your first week at the company, you’re shipping something to production and making an impact on customers right away,” Barr explains. 

Here’s what Barr shared in our CEO Rapidfire interview: 

The one secret to succeeding as a leader, in 5 words or less: Speed and focus. 

What was the most exciting “minute” of your leadership journey? You can’t beat the first moment when you realize you’re making an impact on your customers. I’ll never forget when one of our first customers shared with me that at any given time, she had three tabs open: Gmail, BigQuery and Monte Carlo. That was pretty powerful. 

One truth you wish you knew about leadership before starting? Building and maintaining a strong, scalable culture at a remote-first company is an underrated superpower. It requires intention and focus to make Monte Carlo an inspiring, fast-paced, challenging and rewarding place to work. I’m blessed to have an incredible leadership team and people team and culture team that is taking that to the next level and beyond. 

If you had to do battle with a giant, what weapon would you use? As a data nerd, I’ve got to say my brain. Can’t be too tough to outsmart a giant, right? 

If culture is one superpower a successful CEO must have, another has to be conviction. Without it, your company will go nowhere. 

Your worst mistake as a leader (and what you learned from it): One of our investors, Steve Loughlin from Accel, once told me: Don’t listen to advice. Instead, listen to your customers, the data and your gut. And he was right. If culture is one superpower a successful CEO must have, another has to be conviction. Without it, your company will go nowhere. 

Top 3 websites, blogs, or podcasts you can’t imagine your day without: The Data Chief podcast with Cindi Howson for great learnings from enterprise data leaders; Data Engineering Weekly to keep up with the latest in the data space; and the AI in Business podcast for the most insightful and thought-provoking content and conversations about AI in the real world.  

Technology trends are like avocados. When you buy them, they’re not ready. You go to use it the first time, still not ready. Second time, still not ready. Then all of a sudden, they’re perfect, then in the blink of an eye they’re past their prime.

What popular leadership advice do you disagree with? Create a five-year plan. Companies need to be ruthlessly focused on the short-term future — if GenAI teaches us anything, it’s that the best laid plans often go awry. One of our investors recently shared a fun analogy with us: Technology trends are like avocados. When you buy them, they’re not ready. You go to use it the first time, still not ready. Second time, still not ready. Then all of a sudden, they’re perfect, then in the blink of an eye they’re past their prime. The strongest companies are the ones who are quickest to react when the avocado is still ripe. 

One life hack you can’t live without: Can I say ChatGPT?  

One soft skill that you’ve realized is supremely important: Listening with intent. You can't run a billion-dollar company if you don’t have an ear to the ground. I’ve learned my most important lessons about our product from listening with intent to our customers, and I’ve learned my most important lessons about my leadership by listening to our employees and my team. 

The one thing that makes a good leader great is:  Transparency. We have monthly AMAs where employees are encouraged to bring their toughest questions for me and my leadership team to answer — the spicier, the better. If I expect my team to be working toward a common goal, they need to have all the information and clarity necessary to do that work.  

Your secret to building a great team is: Give your staff responsibilities that map to their skills and where their energy is at, not their job titles. If I could go through life without job titles, I would. We encourage our people to try new things, flex new muscles, grow new skills, and contribute in bold and different ways that may be outside what their job description entails. 

Lean into what works, and don’t boil the ocean.

The key to navigating hypergrowth is: Lean into what works, and don’t boil the ocean. Monte Carlo was built on a pretty simple premise — to help companies accelerate the adoption of reliable data. And while we’ve certainly grown and have found new ways to apply that principle to help our customers, that singular goal has remained the same.  

Every leader must read... The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers by Ben Horowitz. As Ben explains in the book, there’s no playbook, no secret recipe, no dummy’s guide for running a high-growth tech company. Instead Ben focuses on the mindset, the potential pitfalls and the lens with which to view leadership that really helped me in my journey as a CEO and founder.  

What are you most excited about at work right now? We’re continuing to grow and expand the data observability category, and that alone is enough to get me out of bed and light a fire underneath me. Our customers have really brought us in close as they navigate the rapid adoption and propensity of GenAI, and solving those challenges alongside them is an honor and a thrill every day.  

Your one “non-negotiable” in business (or life) is... Treat people with respect. Whether it’s your peers, your customers, your employees, your neighbors — everyone deserves respect. 

Thank you, Barr, for sharing your leadership thoughts this week. To learn more, follow Barr on LinkedIn.

Thank you for reading! I'm interested in hearing your thoughts in the comments below. For more insights from my experience as a serial entrepreneur and how we can harness the power of software to change the world, be sure to subscribe to Entrepreneurship and Leadership.