Customer Spotlight

Leaning Into Leadership: How Bigeye’s CEO Delegates to Focus on Growth

Customer since 2021
CEO & Co-Founder at Bigeye
Data Observability Platform
50+ Employees
Kyle Kirwan

A Harvard study found that, on average, a CEO works 9.7 hours per weekday and even squeezes work into 79% of their weekends. The grind is real.

What makes a CEO’s job even more stressful is how a leadership role evolves. As a company scales, it becomes more complicated to balance operational tasks and strategy.

Bigeye Co-Founder & CEO Kyle Kirwan needed more time to focus on leadership as his business took off. We sat down with him to find out how delegating to an assistant boosted his impact.

Guarding Time: The Decision to Work With an Assistant

Like many startup founders, Kyle grappled with a sharp shift to focusing more heavily on strategic leadership functions. He explained his experience to us this way:

The flip side of being in leadership is not being able to get hands-on as much. Before Bigeye, I was a Product Manager and loved sitting next to my users, then with designers, then with engineering, and getting my hands dirty in the product process. Now, I have to be extremely guarded with my time because we have amazing folks who can do all of those things, and I have to ensure I’m dedicating time to the things that allow them to align and deliver and not get into the details myself.

Protecting his time is a critical element of productivity for Kyle. But as things got busier, it became difficult to manage his schedule. Interestingly, he can pinpoint the exact moment he realized he needed help getting control of his hours.

I was eating a Cliff Bar before a customer-facing call. It was the afternoon, and I hadn’t made any space in my day to eat lunch, so I was starving and didn’t want to be ‘hangry’ in front of a customer. I realized I needed some support getting my schedule under control.

Kyle concluded that an executive assistant could shoulder some of the workload and organize his schedule.

Delegating Daily Operations to a Double Helped Renew Focus

Kyle started working with Double to give himself and his team more time to focus on growing the business. His assistant (aka, Double) Debbie was able to take over critical administrative tasks and run daily operations.


Debbie has an experienced background in assisting executives across various industries, so she was able to help with schedule management as well as other more advanced projects like planning and organizing corporate events. She acts as a shared resource for the leadership team, so her impact is team-wide.

Debbie helps us with a ton of logistics involved in daily operations. She helps us schedule both internal and external calls, especially when a bunch of hard calendars need to align. She’s also helped plan and execute in-person summits and gatherings where hotels, food, and activities had to be sorted out. She’s super thoughtful and makes sure the details are handled, which gives my team and me energy to spend on the business.

While having an efficient assistant is great, a trusting, positive working relationship is the key to the most productive outcomes. What we loved about Bigeye’s story was the relationship the team built with Debbie.

When we asked for her thoughts, Debbie told us, “Working with the Bigeye executives and this team is right up there with my best experiences. They are hard-working, brilliant, and so creative while being some of the most down-to-earth people I’ve had the pleasure of meeting. Being able to help in any measure that is the ‘business Jenga’ they each work through daily is very rewarding for me as an administrative professional.”

How a Successful Founder Spends His Day With Double

By delegating ten hours per week, Kyle is able to direct his hours to the most impactful, strategic work that helps him serve customers and grow the business.

Debbie has helped me ensure my week contains space for deeper thinking and isn’t totally dominated by back-to-back calls that end up feeling exhausting.

Since he started working with Double, Kyle has built a daily routine that works for him:

A typical day is meeting-heavy, but I try to ensure there are uninterrupted blocks in the week where I can do deeper work. That means a few days are meeting-heavy, where I’m helping our leadership stay in sync and other days where I can sit down and do thoughtful work.

Kyle tries to balance a busy work life with meaningful personal time: "If I don’t go to the gym in the morning, I usually can’t make it happen at all, so chores have to fit into the evenings or weekends. My wife and I try to preserve a date night once a week, but she’s a tenure track professor, so sometimes we both end up breaking the rule.”

As hectic as things can get, Kyle genuinely loves his job. He truly believes in the mission of his business and loves helping customers: "I love supporting my team and watching them deliver for our customers. Nothing makes me happier than feedback from a customer that Bigeye is helping them earn trust from their organization that the data is just right. Being able to help my team delight our customers is a special privilege, and I’m grateful for it every day."

About Bigeye

Bigeye is a data observability platform founded in 2019 by Kyle Kirwan and Egor Gryaznov. The platform helps enterprise data teams keep their analytics and machine learning fed with fresh and high-quality data, no matter how complex their data pipelines are.

In 2020, Sequoia led Bigeye’s $17 million Series A, with participation from Costanoa Ventures, and in early 2021, Coatue led Bigeye’s $45 million Series B, with support from Sequoia and Costanoa Ventures. Today, Bigeye serves clients like Zoom, Lyra, and Udacity.

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