does an assistant make me look bureaucratic?

Editor’s Note: Each week Maynard Webb, former CEO of LiveOps and the former COO of eBay, will offer candid, practical, and sometimes surprising advice to entrepreneurs and founders. To submit a question, write to Webb at

Q. At what point should a startup CEO hire an executive assistant? Our business has not yet raised a Series A round, yet I’m struggling to carve out time to focus on strategic work just purely based on hours in the day and energy levels. I would love some advice on what to do. 

-Scrappy startup CEO

Dear Scrappy Startup CEO,

Ensuring that you have the bandwidth and space to focus on what really matters is super important. There’s not one set answer on how to do it. There are options, which may include hiring, or delegating, or restructuring.

I think I understand why you may be feeling some hesitancy about hiring an executive assistant. Startups are supposed to be scrappy, and as a founder you may feel pressure to do everything on your own and not hire support staff until you reach a certain level of success. An inclination towards scrappiness is a good instinct, but at the same time if you have more work than the bandwidth to do it and if you have the cash available to hire assistance, it may be smart to do so. Without this support you will continue to be limited, which in turn could limit your company’s growth.  

Let’s look at the barriers you may be facing:

Bandwidth: Are you constrained by time and unable to work on what is most important? If you are sapped of time and energy is there someone else who can take on some responsibilities for you? Can someone else do it better than you?

Resources: How much cash do you have? How much do you want to burn before you reach the next round of funding? Hiring someone is going to cost. Let’s say this position will be compensated with a significant salary and potentially some stock. You have to ask yourself, is this where you want to spend the money? At this point you have to keep your limited resources in mind. If you hire this person, you likely won’t be able to hire someone else. What do you need? Would an engineer who could build out your product or a salesperson who knows how to get your first 50 customers get you further? 

Perhaps some founders see it as bureaucratic or “unstartup”-like. But it’s your job to solve for work you can’t get to. If you can afford to hire someone in this role and it will free up cycles for you, it may make sense. Also keep in mind, this person could do jobs beyond scheduling, and they could be dedicated to help other people as well. It’s common for everyone at a startup to wear many hats and this role is no different. 

Being a startup CEO is an all-consuming job. You are supposed to feel like your hair is on fire most of the day. But if you are not able to get to what is most important and what you are uniquely qualified to do, it’s time to find other ways to get it done. You need to find a way to get more out of the hours in the day, more money in the bank, and faster growth to make it to the next round.