How to be a startup CEO: 6-25 employees

5 min read
11 Dec 2018

ow that your company is chugging along, it’s time to put in place some structures aimed at institutionalizing your values and establishing your leadership teams

This article was written by the original owner of, Ryan Allis, and published on his website in 2012. Read more about why Ryan was happy to hand over his website domain to us here.

Congratulations. You have six employees. You’re running a real business. You have revenues approaching $25,000 per month (you’d better, or else what are you doing with all those employees?!). If you took a month off, the business would probably still be there when you got back.

Now, it’s time to:

1.Put in place some basic systems and tools to automate your operations and prepare for growth.
2.Figure out your customer unit economics so you can determine whether it makes sense to raise outside capital to scale your customer acquisition.
3.And as your revenue growth allows: hire really good people to own marketing, customer service, sales, product development, bookkeeping and administrative duties.

Ask yourself, what is your specialty? What are you good at? Most early-stage CEOs are either really good at sales, marketing, and product vision or really good at technology and research and development. Find someone to own what you’re not good at.

You should never have more than seven direct reports. So once you get to eight employees including yourself, you’ll have to create your first layer of management.

Most often this is done by functional area, with all the support reps reporting to the Director of Support, the developers reporting to the CTO, the sales reps reporting to the Director of Sales, etc. and all the Directors reporting to you.

Instead of starting out by naming every early employee a Vice President (VP) like we did, I would recommend avoiding the VP title for the first couple years of your business.

While you’re still under 25 employees, just call someone a Director or Manager if you can. Only once you have more than 7 directors will you need a VP title. This title structure will help you reduce the chances of having to later demote early VPs to Director roles as the organization scales.

Creating a basic meeting rhythm

As you move beyond working in a single room, creating a basic meeting structure will be helpful.

When we had 6-25 employees at iContact, we simply had a weekly staff meeting with everyone in the company – back when we could actually fit everyone in one room!

Every week, we reviewed the company’s weekly results (sales, trials, conversions), tracked progress against each of our quarterly priorities, and reviewed the status of each of our company-wide projects.

We eventually came up with Key Performance Indicators (KPIs) and quantitative measures of success and started marking each KPI as red, yellow, green, or supergreen based on how we were performing.

We were as objective as possible about results, and did our best to leave subjectivity out of the assessments. By making it clear in advance which metrics individuals were responsible for and would be compensated on, we had an easier time assessing performance later.

Defining your company values

Back in 2006, we defined our company values. For three years we had a list of ten company values. We printed them up on big cardstock boards and had everyone sign the back at each iContact Day.

There was only one problem. No one could remember them. I once tried to recall the values without looking at the sheet and got to four before my memory failed me.

We had to re-do our values – and make them unique to us and easy to remember.

On a Thursday in December 2009 in Chapel Hill, our Senior Leadership Team met for a two-day offsite to create our first ever One Page Strategic Plan (OPSP) following a format that comes from the book The Rockefeller Habits.

The OPSP has a very visible section on the left side in which you name your values. We took the entire first day to redefine our company’s values.

Our facilitator, Patrick Thean, started out by asking us to write down the five words that we felt most described our company culture. When we were done, he wrote all the words, perhaps thirty in total, on a flipchart. He found the commonalities amongst similar words and got us down to eight words that defined our culture. He then had us each vote for three.

Patrick took the tally and it was clear what our top values were. There was a tie between five and six and so we debated for about an hour over which one was truly more important and more descriptive. We eventually settled on incorporating number five, “Have Fun and Be Wacky,” into the descriptive language underneath another value.

A vision is something you strive towards in the future. A mission on the other hand, is how you serve your customer today.

Finally, we needed to create an acronym that would make it easy for everyone in the company to remember the values.

We started out with

“Wow the Customer”

“Operate With Excellence”

“Act With Urgency”

“Treat People With Respect”

“Act Like an Owner”

We didn’t want to have WOATA be our values acronym! After two hours of restructuring we came up with:

Wow the Customer”

Operate With Urgency”

Work Without Mediocrity”

Make a Positive Wake”

Engage as an Owner”

We got it. Our values acronym was WOWME! Much better.

We rolled out WOWME a few weeks later on January 9th, 2010, and immediately integrated our values into everything we did, from our training to employee recognition system to our performance reviews. We made sure chanting WOWME was a key part of every company-wide meeting.

To help the values spread, we implemented a WOWME Awards program in which employees would nominate other employees for either wowing the customer, operating with urgency, working without mediocrity, making a positive wake, or engaging as an owner.

We automated the nomination system using our CRM tool We put an annual amount of $40,000 into the awards pot and split the winnings between the employees who received at least three approved nominations for all five letters.

Defining your vision and mission

One of the CEO’s most important roles is to communicate the vision of the organization. This becomes even more important as the organization grows. If you have a vision but don’t communicate it, you might as well not have a vision.

iContact’s vision was “to build a great global company based in North Carolina for our customers, employees, and community.”

A vision is something you strive towards in the future. A mission on the other hand, is how you serve your customer today.

This is the third in a three-part series of articles which give an overview of how to be a startup CEO while growing as a company. Read the first part, how to be a startup CEO in the early stages, here.

Main photo: Unplash/ Alex Kotliarskyi

*This article was originally published on October 17th, 2018 and updated on December 11th, 2018.