Why Early Employees Make Great Operations Leaders 
February 11, 2021

Employees that join early stage SaaS companies are a different breed. And I’ll make no bones about it, I truly admire this type of person. 

I’m certainly biased, because as you can guess I’ve spent my fair share of time at startups. But I just think there is something so special about people who are willing to put themselves in positions of complete chaos with the promise that if this thing goes well, you will fail more times than you care to imagine. And once you fail, you are going to be asked to brush off that failure, learn from your experience, and keep moving forward. 

It’s not to say that those working at larger companies can’t be as hardworking, determined, or growth oriented as those at startups. But inherently, startups offer more uncertainty than companies that have been around for longer and have more structure in place.

At a startup, the range and pace of potential decisions you are processing can be mind-numbing no matter how many years of experience you have under your belt. The twists and turns of product pivots, new go-to-market strategies, and crucial hiring decisions can be the difference between success and failure.

These high-stakes decisions amidst significant levels of uncertainty, highlight the abilities of early employees to process information quickly and make decisions others would shy away from. Interestingly enough, these are some of the same qualities you would find amongst many of the best Strategy and Operations Leaders. 

For those that have never been at a startup, let me just give you a glimpse into what life can look like in the early days. 

Early on your company has a big vision, but it’s going to take some time to actually reach that vision. It’s a constant balancing act. We have to stay true to what we are building, while also realizing this is a business that needs to deliver in the here and now. And for each employee, they have a main directive, maybe it is customer success or sales. But unlike a larger company that has resources dedicated to supporting you in the sales process, you don’t have that. So you think, ‘Wow, a case study would be great!’ Well, guess who just signed up to put together a case study. Or you might be thinking, ‘If only I had a demo environment that highlighted this cool new feature!’ Hate to tell you, but engineering is heads-down building the actual product. 

This is usually the part where folks start to realize whether early stage companies are for them. 

Everyone is asked to flex into areas that were never part of their job description, but you figure it out. You learn. 

At a startup, you don’t have the luxury of processes being in place or departments having well-built channels for communication. 

The handoff process from sales to customer success doesn’t exist, someone has to build it. Nor does the hubspot process for tracking upsells on existing accounts. The best early stage employees intuitively understand that they have to create the connective tissue that allows the business to grow and thrive.  

As I sat down with leaders for our Aspiring Ops series, what I found is that so many of them were at one point or another employees at startups. And it finally clicked. 

From what I can tell, most COOs or Chiefs of Staff don’t go to school and get a degree in ‘Operations.’ However, take a look at the successful employees in the Chief of Staff or Head of Operations role at your favorite SaaS company. My guess is that many of them didn’t start out in operations. They likely started out in another area of an early stage company, or even at that exact company, and found their home in operations. 

Think about the customer issues that come up in the early days for companies. Who do you think handles the frontline support, and turns disappointment about a product feature into a learning that makes the entire company stronger? Or who is it that helps provide the healthy tension in a conversation that needs to be had when discussing building one product feature vs another? 

Whether it is knowing how to bring up a tough conversation, making the difficult decision others don’t want to make, or the ability to let go of yourself and think about the bigger vision, early employees are inundated on a daily basis to the types of environments that the best Strategy and Operations Leaders thrive in regularly. 

So this post is for all of the early employees out there looking for direction or trying to understand why they don’t fit into the cookie cutter departments that we’ve been trained to think our career paths should take. Businesses need great leaders who can think outside the box and run towards chaos. 

You might not have set out to end up here, but Operations might be your home.