How to Fire Yourself as CEO: The Resource-Strapped-Company Edition

Andy Cook
Andy Cook
December 14, 2017
octopus wearing a captains cap high five with crab

The other day I ran into a friend during a ride-share. She’s a local entrepreneur who’s just getting her company off the ground and we got to chatting:

Her: “How’s Tettra going?”

Me: “Pretty good. We’re almost profitable.”

Her: “That’s great! So where are you spending your time?”

Me: “I’m running marketing, sales and support.”

Her: “You’re doing all three of those? That seems like a lot…”

Indeed it is a lot, but there really isn’t another choice at the moment.

As the CEO of a resource-constrained company, my job is to take on any role that needs to get done. When people ask me what I do at Tettra, I often joke that I’m the Chief Janitor, cleaning up everything that no one else has the time to do.

Yesterday, I read Jeff Seibert’s post on the most important job of the CEO in Hackernoon. His thesis was that any CEO should “fire themselves” from any job they’re doing and hire someone else to do it instead.

Initially, I nodded my head in agreement with him as I read the post. Then the truth sunk in…

I can’t actually follow that advice because it assumes that we’ve raised millions of dollars to spend on hiring new teammates. We’ve only raised under $1M from angel investors. That funding amount and our revenue barely covers our lean, mean team of six people.

My friend Jason Evanish echoed a similar sentiment, asking what if you haven’t raised at all?

When you’re a resourced constrained CEO, you’re not doomed to have to do soul-sucking work 24/7, you just have to be more creative about solving problems.

Below are some ideas on how to make it easier to replace yourself as CEO if you’re not following a VC-funded path. I’ll warn you that there are no silver bullets here, but hopefully some of this helps.

Do less and leverage technology

We recently decided to change our sales model at Tettra from live demo-driven sales to product-driven sales to fit our funding situation better.

That means we have no one specifically accountable for sales on the team anymore. You can probably guess what happened next— in steps the Chief Janitor.

My first instinct was to pick up all the deals where we left off to convert them into sales. I thought, “we still need to make money, which means we still need someone selling to the prospects in the pipeline.”

I then took a step back and thought, “do we really need to keep doing it this way or can we get prospects what they want by doing something else?”

Eventually, I settled on using video to do demos. Record once, reuse indefinitely.

What happened next genuinely surprised me.

I learned our prospects actually prefer video. They can watch it on their own time. They don’t have to schedule time for a call, sit through a presentation to learn what they want and be pushed by a salesperson to make a decision to buy.

It was a good reminder that not all work is created equal. A reusable asset like a demo video or support article is just like code. It’s a repeatable way to solve a problem without having to invest more of our team’s time.

From there, I ruthlessly starting cutting tasks from my calendar and asked the team to help me automate anything repetitive. We fixed bugs that customer frequently run into, updated our support docs and made videos to help with support and sales.

That freed me up to truly focus on a couple of bigger tasks each week that would move the needle. My output improved, the quality of my work improved, and as an added benefit, I’m happier than ever because I don’t have to constantly switch context between dozens of small tasks.

Working more doesn’t always result in more progress. Instead of replacing yourself with people, replace yourself with machines by automating everything that’s frequent and repetitive.

It’s actually good to do it all, all at once

Cross-discipline thinking forces your brain to ooze creativity. One of our investors at Tettra, David Cancel has a great outlook on why he reads multiple books at once for this very benefit:

“I try to read books of different types all at once. Several nonfiction books, usually business or person growth related. Then I try to read some fiction. And then I try to read, in the non-fiction category, a lot of biographies…

The reason I try to do all of these different types at once is … I found that the more books that I have going on at once … these different ideas from different places come together and then new innovations are born of that … Innovation that I’ve seen is usually applying ideas that exist from different realms, different genres, together into a new application, and that is the innovation.”

Just like the way David reads multiple books at once, there are synergies between doing marketing, sales and support all at once too.

Doing sales calls and answering support tickets makes the patterns for what the market demands recognizable. You’ll hear the actual words your prospects use to describe their problems. You’ll be forced to face objections head on and figure out how to overcome them. You’ll see the real-life ways people are trying to solve their problems with your product.

All those conversations make marketing much easier. You can use these learnings to reach your target audience using their own language, nix sales objections on your product website, and preemptively train customers on how to think about using your product too.

Good marketing gets more people in the door, which creates more opportunities for sales and support conversations, which then helps you iterate on your marketing by learning from your customers. It’s a virtuous cycle.

But what’s the CEO’s job after she has replaced herself in every functional role?

The most important job of the CEO after she fires herself from every functional role is to set the company vision. That’s something only she can solely do because she has insight into the entire company.

The reality of most founder’s vision is that they don’t start off correct and some of the most successful companies ended up in dramatically different places than where they started. PayPal started as a way to send money through PDAs. Slack started as an online video game. YouTube started as a video dating website.

There’s no faster way to figure out the vision and calibrate your way there than talking to customers. And there’s no easier way to “hide” from your customers than to hire other people to talk to them instead.

Be patient

The reality of entrepreneurship is that most companies fail. Those that don’t usually take 5–7 years to ultimately be successful. That’s a long time.

When you’re resource constrained, everything feels like it takes longer.

Building the product takes longer and you’ll watch your funded competitors launch dozens of features while you focus on one or two really critical ones each month.

Sales are slower and revenue growth takes longer. You’ll have to be smart and leverage scrappy, scalable systems while your competitor’s brute force revenue growth by hiring reps to do outbound sales.

Marketing takes longer. You’ll probably only have the bandwidth to focus on one or two really good pieces of content instead of hiring a team of marketers to pump out articles that get you ranking in the search results.

It’s frustrating to see competitors moving faster than you, but it’ll all be ok. Learn to manage your psychology and remember: It’s a big world and there’s plenty of opportunities.

Not having resources might mean you’re doing a lot of jobs yourself for awhile, but it also means you really know those jobs inside and out when you do inevitably hand them off by hiring someone else. You’ll be able to better vet candidates from doing the hard work to learn the job. And you’ll also build real muscles for growth as a company that doesn’t rely on VC-funded steroids.

Constant progress on the right things compounds. Eventually, you’ll be growing so much you can scale the team and start firing yourself. Be patient on getting there and enjoy the journey.

Find a co-founder

This is my #1 piece of advice. It’s dangerous to go alone! Find a co-founder.

There’s dozens of reasons to have a co-founder, but the main one is that in a growing startup, there’s just too much to do for one person to handle.Having a co-founder means you can divide and conquer on at least some of the tasks.

If you’re slammed, you can ask your co-founder for help. This is exactly what I do with my Tettra co-founder, Nelson Joyce. When I have too much to do, he will help pick up some of the slack for me or at least help me prioritize on what’s actually important vs. what can wait vs. what isn’t worth doing at all.

Trying to do it all alone would have probably crushed me by now and I probably would have given up from the pressure. Find someone to go along for the journey with you.

As a bonus, having a co-founder makes the good times more fun and the hard times less shitty.

At the end of the day — Build a “real business”

If you can’t raise money or don’t want to, then there’s only one alternative — revenue.

Knowing that the only way you’ll be able to transfer an overwhelming set of operational tasks off your plate is hugely motivating. Focus on growing revenue and doing whatever it takes to make money, and the rest will fall into place for you to start replacing yourself.

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