Not every career in tech follows a straight line, and Dereck Fleury’s path is a great example. Over the years, he’s seen Funnel grow and evolve, faced new challenges, and shaped his own leadership style along the way. In this conversation, Dereck shares what his day looks like, the lessons he’s learned, and what keeps him motivated as he helps his team reach new goals.

Can you introduce yourself and your role at Funnel?

My name is Dereck Fleury, and I am currently the Sales Manager for the US Account Executive team at Funnel. I have been in this role for about a year now. Before that, I managed the SDR team for five years, and before that, I was an SDR myself. I am coming up on my seventh anniversary at Funnel, which is crazy to think about, especially considering how small the company was when I first joined.

I actually found the role through a recruiter. At first, it was not even for this job, but once they mentioned a startup called Funnel, it sounded interesting enough to explore. From the very beginning, the interview process felt different. It was a lot less about rigid structures and more about genuine conversations. When I met with leadership early on, it felt real. That same transparency has stayed consistent ever since.

What does a typical day look like for you in your current role?

I'm an avid morning person, so I'm up by 5:30 AM at the latest. I'm currently training for a marathon, so the day typically starts with either a quick gym session or a run outdoors. After that, I take my dog for a walk and get ready for the day. Depending on the weather, I either bike or hop on the train into the office. 

Once I’m in the office, most  days start with a podcast or I’ll listen to a sales call on my way into the office. I like getting a pulse on what prospects are saying or picking up new ideas from others in the industry. Once I am at the office, I check in on performance dashboards, review call schedules for the day, and flag any deals or conversations that may need extra support. If something big is coming up, like a negotiation call, I will connect with the rep to ensure they feel prepared ahead of time.

The first half of the week is packed with one-on-ones. I spread them out so I can really dig into each conversation, whether it is coaching, forecasting, or just checking in on how people are doing. Later in the week, I usually shift into more strategic work, reviewing calls, giving feedback, and planning longer-term development for the team. Of course, there is also a lot of problem-solving in real time. Deals shift, unexpected challenges come up, and part of my job is helping reps adjust and figure out the best next move.

What have been your top 3 learnings since becoming a Sales Manager?

The biggest one, without question, is that sales is way harder than it looks. Coming from an SDR background, I thought I understood what it took to get a deal across the lines. However, when you are not the one carrying the quota, it is easy to think you know how a deal should close. Being in it every day shows you just how many moving parts there are.

The second is that asking the right questions matters more than having the right answers. As a manager, my job is not just to cheer on wins. It is to be the skeptic. I need to push people to think about why a deal might not happen, not just why it should. That way we can uncover risks early and actually do something about them.

Third, and maybe most important for the long run, is that you cannot lead everyone the same way. Different people need different things at different times. Some need coaching, some need directness, and some days they might need both. You have to be able to adjust based on where they are, not just stick to one leadership style and expect it to work for everyone.

How would you describe leadership at Funnel? And how does the rest of the organization support you in your role as a leader?

Leadership at Funnel is a mix of servant leadership and situational leadership. We lead from the front and do not ask people to do things we would not do ourselves. At the same time, Funnel encourages leaders to be flexible and adapt to each person and each situation.

One thing I really appreciate is how much support managers get. CoachHub has been a big part of that. It pairs managers with leadership coaches, and it helped me figure out howI want to show up as a leader, not just what tasks I need to complete. Beyond that, there is a lot of openness across the leadership team. People are willing to share ideas, support each other, and talk about what is working and what is not. You are not left trying to figure out leadership on your own here.

Do you have any role models or leadership approaches that have inspired you?

Internally, Lucie, our VP of Revenue Development, has been the biggest influence on me. The way she leads, balancing high expectations with real understanding of people, is something I try to model in my own leadership. She knows when to push and when to step back, and she genuinely cares about the people she works with. Even now, I still meet with her weekly to keep learning.

Outside of Funnel, I like the mindset that Matthew McConaughey once shared. He said his role model is “himself in ten years and then ten years after that.” This  idea stuck with me and I am always chasing the future version of myself, trying to keep getting better.I want to become the kind of leader others can look up to. That idea keeps me grounded and focused on continuous growth.