I often get calls from founders who feel that they’ve been at it long enough and that the time has come for them to hire, promote or invite a CTO into their startup.

The challenge

When starting out, the founder is faced with one problem, will they be able to build a product that solves a pain for somebody, hopefully many, people in this world.  Although this might be a daunting thought for many of us, the founder, a visionary, is most likely at the easiest part of their startup journey, and that is, to find a means by which to build a product.  They need to define their feature set and match that with an engineer, a dev shop, a cloud tool, or whatever to get that first solution in the hands of a human.

But what happens when that cycle turns into a happy outcome that now increases it’s appetite for faster technical development?  Two things:

  • the founder feels overwhelmed because their startup went from an MVP side project, to now also having to develop customer, build the business and possibly start wooing investors
  • the founder is being bombarded with technical decisions that need to be made that they don’t feel equipped to handle
  • the product market fit starts suffering because their customers love the product, but would love it even more if they saw a few additional features that weren’t really on the roadmap

The misconception

This initial success, especially for the first time founder, drives the urgency for technical leadership and technical leaders are called Chief Technology Officers no?  Well yes, but technical leadership comes in many forms and hiring a CTO is an involved process that I’ll write about in the near future.  I am huge fan of incremental changes where possible and bringing in a CTO is not an incremental change.  In fact, you might be focusing on one aspect of your business that needs the least amount of change or attention at this stage.  Hear me out.

Zig-Zag your way to a CTO

In the video above I explain the Zig-Zag method towards hiring a CTO and I’ll list the zigs and the zags here:

1. Find your Fit

Find your fit by any means possible.  I tell founders that there are plenty of ways to figure out if someone is going to pick up what you put down without breaking the bank.  Here are a few ways:

  • The No Code route: Build your concept using existing tools and then use zapier to integrate those tools.  This doesn’t require coding and there are plenty of resources that aim to solve this problem.  The upside is that you get to spend endless hours converting your ideas into reality which will often lead to you rethinking some of your assumptions.  The downside is that these solutions are harder to customize or build upon.  The main idea here is to see if you can help a prospective customer understand the solution you’re presenting for their pain.
  • The Dev Shop route: You’d be surprised at what you can build for $20k or less.  I’ll let you in on a secret.  Dev shops aren’t enticed by lump sums, they are enticed by retainers.  When they have retainers, your project is more predictable from their business standpoint and it’s easier for them to ramp up developers and keep them.  Great ways to get started is to ask, “can we get started with $3k or $5k/month?”.  This is a solid route if you’re totally clear on what features you want built and have wire frames accordingly.  This is definitely not the way to do things if you only have a vague idea of what you want built.
  • The Friend route: You can always tap into friendships or family to get your product build started.  I’ll just add that whatever is said about business ruining friendships is mostly true but your mileage may vary.  I may write something about how to go about this at some point.  A tip for how to do this would be to keep the business and equity and future conversations out of this and try make it a fun experience, eg. spend a day together in a fun location and grind something out.  Keep it to exactly what it is, friends who like to hang out.

2. Find an (active) Advisor

When founders reach this stage they have proven product market fit and can show revenues, usually less than $20k/m.  When you see money coming in, my suggestion is to not see this as a means to bringing in your first CTO.  I would much rather see you bring in an advisor.  Here are my requirements for what type of advisor you should look at:

  • Someone who is gainfully, and happily employed in the role of CTO and wants to help out some startups, otherwise known as help solve other people’s problems.  CTOs get b