There is one role that almost every CEO I speak with needs but doesn’t know when to hire: an executive assistant. There is no right way to work with an executive assistant but I often find that CEOs are uncertain about this role more so than most other functional roles. Perhaps it feels like an unnecessary expense for a company that has fought hard to find PMF. In most cases, I advocate to hire an EA and thought I would share  some of my reflections on this very important role:

Hire early. Once you have ~20 employees or have raised a Series A, you should think about this role. Every company is different so CEOs need to adjust for their needs - in some cases, you may want to hire an EA even earlier. Many CEOs struggle with measuring the value of this role and balancing that with a limited runway. One way that I frame the value / trade off in this role is if the company has raised $8m, a good EA might cost just 1% of the capital raised. Would I get enough value and bandwidth for that 1% trade? Most CEOs I know would trade 1% of their capital for getting a good portion of their time back.  

In an ideal world, the CEO is only doing things they are good at and enjoy doing. The remaining tasks would be delegated to another member of the team. Obviously in an early stage startup this is rarely possible. The CEO acts as a catch all, picking up all the tasks that must be done but don’t have a clear owner. If this sounds familiar, an EA may be able to provide immediate value. 

Use your EA to give you leverage. Have your EA do the things that don’t require your cycles but have ended up on your plate. Take an inventory of all the tasks you are responsible for and in particular, the things that you don’t enjoy and don’t need to do. These are prime items to hand off. An EA can also help with office management and potentially assist with HR (recruiting, policy, etc) if bandwidth permits. You can also use their help to drive your internal communications to a higher level by having them join key meetings (management team and board meetings) to take notes that can be circulated internally afterwards.  

Prepare to spend a good amount of time teaching and training. Block off time (perhaps a daily sync to start with) when you can actively train your new hire. I’ve found that to get the most leverage from this role, you need to be able to easily communicate feedback bi-directionally. Make sure you hire an EA whose work style fits with yours and figure out the best way to exchange feedback early. 

Some FAQs on EA roles:

• Should you look for a career EA or someone who might want to expand their role in the future?

It depends. I have had success with both - at an earlier stage in the company, an EA who wants to transition into another role can be a great fit given the need for talent as the company grows. At a later stage, you might prefer having more stability in the position. 

• Should you ask your EA to do PA (personal assistant) work as well?

My unpopular belief is that you should craft the role to give you the most leverage possible. In my case that meant the role included some personal assistant work as well. I believe strongly that your time and mental bandwidth are scarce resources and offloading anything that might weigh you down is worth exploring. 

• Who should this role report to?

Initially having your EA report to you is the simplest path. Over time as the rest of the organization is built out, having a direct or dotted line reporting structure to biz ops or people ops may make sense.