Fireside Chat: Fair Square Medicare’s BizOps Lead, Lorenzo Carlisle

Neeraj Periwal headshot
Neeraj Periwal
May 24, 2023

Lorenzo Carlisle is the Business Ops Lead at Fair Square Medicare, a Medicare brokerage that helps new retirees choose the right healthcare plan for them. At Fair Square, Business Operations focuses on making the company more efficient and owns data and revenue operations. In this Fireside Chat, we explore how Lorenzo got to where he is, what it’s like to work in his role, and advice he has for other ops teams.

What are you responsible for at Fair Square?

The brokerage is the largest part of our business, but there are some adjacent teams, like engineering and growth. Our role as the business ops team is to solve problems the rest of the company might be facing. We’re a pretty small team — it’s me and two operations associates, and a two-person customer success team — but we’re in charge of a lot. We manage compliance, fin ops, people ops, and rev ops, and we serve as Fair Square’s data team. The company currently has around 50 employees.

How did you get into operations?

I actually hadn’t worked in an ops role before this. An old friend of mine reached out about Fair Square, and as I was interviewing I learned about some of the challenges they faced from an ops perspective and was intrigued. Despite my ops inexperience, I had a lot of transferable skills — prior to Fair Square, I worked in a few different analyst and project management roles, first at a financial services company serving small businesses and then at a water technology company. I figured the core skills I’d developed in my career would serve me well in an operations role, since it’s all about solving problems.

What are your biggest goals and operational challenges today?

My biggest goal is to unblock the rest of the teams at Fair Square so they can be as effective as possible. While this sounds simple, it’s also one of my biggest challenges: making sure everything we do is aligned with the broader needs of the team. For example, if the brokerage department aims to achieve significant revenue growth in the next quarter, the goals of the business operations team should align and contribute to that objective. 

It’s important that team goals flow into individual goals so my team members are excited about their work and have a target to strive for, while being able to critically evaluate their own performance.

Having a team that feels enabled and happy to be there goes a long way toward success in business operations. As a manager, you need to identify and help solve your employees’ problems if they’re going to solve the problems of the business.

What is something you wish you knew before you started your current role?

I wish I knew a big part of the job would be ruthless prioritization.

In my previous roles, it was clear what my responsibilities were, but in this role, I have 15 problems, and they're all important. In the early days, it felt overwhelming and I felt like I was flailing because I couldn't solve all of them or could only solve some of them well. 

I quickly realized that even though there are multiple problems to tackle, one of them is usually the most significant. Write everything down, lay it all out. Just seeing everything in front of you helps you realize that there are only a few real issues that need immediate attention. Ask yourself if you need to be involved in every task or if someone else can handle it. 

At the end of the day, you have to pick the thing that your boss is going to ask about first and foremost. If you’re still unsure, approach your leader with your thoughts and recommendations. It’s always better to be overprepared with several right answers, so come with at least two options and ask for their input. 

What advice do you have for other ops teams?

When it comes to motivating your teammates, it's important to get a sense of what they want to achieve and what their aspirations are. These may not always align with what needs to get done now, but you have to empower them and support their professional development. For instance, if someone’s passionate about learning SQL, give them that opportunity and trust it’ll pay off later on.

One more thing: a truly irreversible solution is exceedingly rare, so don’t get stuck in analysis paralysis. Once you’re pretty sure what you’re working on matters and you have a correct course of action nailed down, pursue it with all the attention it deserves. –Lorenzo Carlisle, BizOps Lead, Fair Square Medicare

This post is part of Avenue's Fireside Chat Series. To learn more, check out our case study with Fair Square Medicare.

Neeraj Periwal headshot
Content Marketing Lead