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When is it a good time to hire your first CTO? Or, how to help Founders understand that they’re not ready to hire you!

By CTO Toolbelt, Executive

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 bored.  We are also problem solvers, of the technical and the business kind.  There are many of them out there who simply want to help startups out.
  • Someone who is well connected is someone who can introduce you to future engineering or product resources you may need.  They could hopefully also introduce you to your future CTO.
  • Someone who is willing to spend 3-5 hours a week on your startup.
  • Someone who isn’t talking to you about advisor shares or equity.  This doesn’t mean that you don’t offer them a little something, but it’s not the main topic of conversation.

Your advisor is not writing code!  But if they want to that’s ok but be careful, you’re not looking for another developer, you’re looking for the leader of developers and process.  Their time is best spent on the following:

  • Meeting with you for an hour or two a week discussing your own business goals and customer challenges
  • Reviewing developer contracts, scopes of work and any documentation that you’ve generated
  • Checking with your dev team/technology resources for 15-30 minutes a day
  • Possibly joining your team collaboration tools like Slack or Teams

3. Find a Product Lead

This is the step that might be the least intuitive, but I would prioritize a product lead over a technical lead at this stage.  Once again, the assumption is that with the help of you technical advisor from step 2, you’ve increased revenues, or perhaps you’ve secured a cash infusion.  Don’t go running to a CTO but rather look at your CPO/Product VP/etc. options.  Here are my top reasons for going this route:

  • If you as the founder have been playing the product role up until now, you are undoubtedly distracted by what the business needs in order to operationalize it’s revenue.  This is a very nice way of saying that you’re probably not that great at this job anymore.  I know, I know, it’s like telling a coder that they’re better at managing now than coding.  It stings.  But truth is, as CEO/founder you need to focus on bringing in the people that will build your products while you make sure that the company rocks it on the culture front without running out of money.
  • I really love classically trained product managers.  They will fight for engineering empathy and more customer advocacy as they seek to focus the attention of the company on exactly what needs to be built.  A word of caution here, I think that there are many engineers turned product people that aren’t really suited for the role I am speaking of here.
  • Since you’re probably emotionally tied to the product up until now, you need someone that will be a strong counter to your ideas in the C-Suite.  I like the idea of hiring a CPO and not just a product manager.  This is literally a person who is going to say “No!” to many of your pet projects, are you ready? 🙂

For the longest time I thought that good CTOs would also be good product people but I am no longer in that camp as a rule.  Yes, obviously there are the exceptions, but I like to think that separating the “what” from the “how” to be really important.  If the CEO is a strong product person, I would recommend that the product lead report into the CEO even if there is a CTO onboard.

4. Find a CTO

And finally, we are in the quadrant where we have a very solid product market fit with revenues to show for it.  The need for technical leadership is probably felt by everyone and this is a great time to bring in a CTO.  When you’re in this quadrant you’ll probably feel the following burn:

  • deliverables lack in the quality they used to have, i.e. it seems like with every release you have more bugs
  • delivery has slowed down, also known as velocity
  • your development expenses seem to have gone up

These are just a few canaries in the coal mine indicating that there is a consumer mentality towards implementation and this ends here.  Find a person to occupy the CTO role, report directly to the CEO and help firm up the product engineering in order to satisfy your customer’s needs for high quality products.  What would the CTO focus on, you ask?  Let me highlight a few aspects that I consider to be important out the gate:

  • Team: your CTO needs to earn the trust of the existing leadership team (think emotional intelligence) and start focusing on bringing your technical competence in house.  As mentioned before you’re probably paying too much for the dev shop and quite frankly, the dev shop needs to know that there’s a new sheriff in town.  If the dev shop is still working for you, then the CTO will help stabilize cost and delivery estimates.
  • Tools: your CTO will help with the overall tooling in your company from sales and marketing tools all the way down to the financials integrations and the stuff that makes engineers happy.  These can be technology tools but also just best practices aimed at increasing the productivity and effectiveness of your people.
  • Scale: this could be another reason your costs are growing since you’re having to work with more customers and team members.  The CTO helps you scale your organization’s technical team and product availability so that customers never complain about downtime and your team never complains about the size of your backlog.
  • Strategy:  if you have your business and product voices in the C-Suite, it’s important to have that technical voice to round things out.  I think a lot of innovation relies on knowing what can and can’t be done and I love CTOs who are able to fly with the ideas and vision of their C-Suite to see how they can make things happen.  It’s also important to know when to hit the breaks and this requires a ton of communication that a good CTO is all too willing to do.

There are plenty more aspects to the CTOs role that I won’t cover in this article but hopefully this gives you a sense of what is important for you to focus on.


The days of viewing your CTO as the “IT guy” are over.  You can’t afford to think that all you need is someone who knows how to code and understands which tools are out there.  Your CTO is not your “first engineer” hire.

Let me know how this all works out for you and always open to your feedback.



Top CTO Podcasts

By Executive

Here is a list of regularly updated podcasts that the Chief Technology Officer, regardless of company size or experience, should keep an eye on. In between all the incredible technology talks and episodes that fuel our geekiness, there lies the podcast focussed on helping engineers turn into leaders and grow into visionaries.

There is definitely something for everyone here so take a look and let me know if I’ve missed anything!

Modern CTO

Average length: 50 minutes
Topics include: CTO Role, Scaling, Organization, Growing Leaders
Style: 1-on-1 interviews via video conference

Joel Beasley is doing a stellar job, not only finding ALL the CTOs, but as someone who has experience as CTO and as a developer, his conversations are engaging and fun! The gold lies in the banter between general leadership and growth topics when all manner of tools, trends and books are casually discussed.

If you’re interested in learning how people grew into their roles as CTOs, tackle coaching and development of middle management roles like directors and lead engineers then Joel and his guests are definitely a table you’d want to sit at.

Killer Innovations

Average length: 40 minutes
Topics include: Ideas, Creativity, Innovation
Style: Interviews and coaching

Phil McKinney reads my mind! As CTOs we have rich imaginative conversations in our heads especially when the going gets tough.  Don’t you wish that you could go talk to someone who’s been there, done that sometimes?  Well, this podcast is like having coffee with an advisor who not only gets you out of your head but also gives you solid actionable advice.  This podcast has a nice balance between interviews and 1-1 coaching which I really like.

The CTO Advisor

Average length: 30 minutes
Topics include: Just enough tech to keep CTO on their toes, Personal, Technology Trends
Style: Conversational

I love listening to Keith Townsend and his crew. I feel like he is really close to all the topics CTOs are thinking about. I also get a sense that if I were to meet them at a party, I would be jealous of the camaraderie and rapport they have with each other.

This is one of those podcasts where it’s not that important *what* people are talking about, but rather the trust you feel for *who* is doing the talking. This is not to say that the topics are weak by any means at all. But if you enjoy freestyle banter between people who are obviously very well informed, super experienced and comfortable with each other, this is a great show to add to your subscription list.

CXO Talk

Average length: 30 minutes
Topics include: Tech
Style: 1-on-1 and panel interviews

In our roles as CTOs we are members of a C-Suite and I love this podcast for giving me a glimpse into the minds of my fellow company leaders. In an age where collaboration and emotional intelligence is a significant differentiator, host Michael Craigsman guides us through very interesting conversations that fuel empathy.

The true value of this podcast lies in various experts’ opinions on topics that are relevant, and most essential, to the role of CTO.  CXO Talk has also been around the block so it has a nice air of confidence in the way it’s produced and backed by sponsors.

CTO Think

Average length: 40 minutes
Topics: Product Development, Leadership
Style: 2 “recovering CTOs” talking, no interviews

This podcast has more of an episodic vibe tracking the journey of two “recovering CTOs”. The gold in this show lies in the fact that both hosts, Don Vandemark, and Randy Burgess are currently building products and seem to be in leadership roles at their companies so the topics give you a glimpse into their decision making processes and navigation of real-world situations on a weekly basis.

The benefit that comes with not having guests on a show is that you grow comfortable with the hosts and they tend to speak to their audience more directly rather than hosting a talk show in which they have to guide a guest through a conversation that provides value to their listeners.  In this case, you have two extremely knowledgeable, hands-on CTO types checking in with each other every week and we all get to listen in on that conversation.

CTO Colloquium

Topic: Wide ranging
Style: Live presentations to audiences of CTOs

I’m a lover of live music where the authenticity of the moment trumps the production of perfection and so here you have a unique TED stage meets indie conference vibe that brings CTOs out from their workplace and onto the public stage. Sometimes it sounds like the speaker is referring to slides but overall, the topics are absolutely focused on what Chief Technology Officers should be thinking about and offer a whole plethora of frameworks, models, and systems for getting work done while scaling your organization.

CTO and Co-Founder Talk

Average length: 1 hour
Topics include: Startups
Style: 1-on-1 interviews

An often neglected aspect of the role of CTO is whether it also includes co-founding the company. What I love about this podcast is the perspective Dave Albert brings by interviewing people that help CTOs who also wear the ownership hat. A key differentiator for this audience is the requirement to help with sales.

So, there you have it, our list of podcasts that we think every CTO should listen to.  There is one final podcast that I would be remiss not to add to this list but it’s focus lies more with the entrepreneur founder and is not a technical podcast per se.  But every time I listen to How I Built This, I feel inspired.

Go check all these out and please let me know what else CTOs should be listening to!

4 Steps To Gain and Solidify Your Executive Role As CTO in the C-Suite

By Executive, Leadership

I have come across so many CTOs who have lost their executive decision-making power in the C-Suite.   Or even worse, they never had it to begin with.  This often happens as a result of CEOs not fully understanding the role of the CTO, but it could also happen because of repeated failures to deliver on promises made.  Eventually, this leads to a lack of trust, diminished responsibilities, and overall job dissatisfaction.

If you find yourself in this situation, there is great news!  You stand before a perfect opportunity to break through the stereotypes often associated with the role of CTO.  The framework I’ll discuss with you not only helps with how you see yourself but also educates your C-Suite on the role of the CTO in your organization.

Having served as CTO for multiple organizations, I have fallen into the trap of taking a back seat when things didn’t go my way in the executive sync-ups and I can honestly say that the following framework had a radical impact on my results as CTO.

The CTO Authority Ramp

1. Frame

Those who know me know that I am a huge fan of Oren Klaff’s “Pitch Anything”.  In the book, he talks about frame control.  Frame control is giving someone else the lens to see what you see.  The first step in the CTO Authority Ramp is to take control of the frame.  If you don’t control the perspective, you’ll end up debating, contending and even arguing against a point of view that will leave you unfulfilled and feel unheard.  Here are a few ways to take back control of the frame:

  • Don’t react. If you’re starting sentences with “Yes, but..”, “It depends…”, you’re in reaction mode.
  • Don’t commit. If you’re committing to anything as a reaction, you’re in trouble.
  • Don’t agree. There’s nothing wrong with disagreeing even if you can’t articulate the exact reason why in the moment.

Instead, inform the alpha dog that you will carefully consider their comments and get back to them.

2. Focus

There is a reason “retrospectives” have their place at the end of a sprint in the agile software development processes.  It is because they are not productive before, or during the sprint.  In the same way, it is almost never a good idea to focus on the past, or on “what got us here” in your executive sync-ups.  If you find yourself explaining and re-explaining how we got into a situation, you’re wasting your breath (and losing the frame).  Keep your focus on the current reality and the steps needed to advance in order to achieve maximum results.

3. Forecast

Always be forecasting.  The absolute best way to ramp up your authority is to demonstrate that you are firmly rooted in the present, focussed on the future and pursuing attainable results.  I highly recommend a 1/1/1 approach:

  • 1 month. What should we focus on in the next month?  This is a very important unit of measure because payroll is tied to it.
  • 1 quarter. Most companies pick a strategy for the year.  Breaking it down into quarters is a great way for people to understand progress against the overall strategy.  It is also easier for people to tactically visualize 3 months out into the future.
  • 1 year.  As CTO you’re always aligning your technology with future goals.  Constantly demonstrate that you have an eye for the future, securing your company’s technological viability.

Another tip for your forecasting exercise is to stay away from using many many words in a document with many many bullet points and sub-bullet points.  Instead, use a presentation format with simple shapes like a circle, some squares, and many many colors.

4. Fund

And now for the most important step in establishing your authority in the executive suite: bet on yourself.  Put your money where your mouth is.  Be willing to suffer the consequences if you don’t hit your targets.  If you’re blaming anything or anybody but yourself, you’re playing the victim card and perpetuating the back seat stereotype.

Are you ready?

You may say that you are too introverted to match your C-Suite using the CTO Authority Ramp, or that you do not have enough information to go build a forecast, not to mention backing it.  But here is my encouragement to you, if you do this, you stand to gain a lot more leadership clout from your team.  The potential for higher reward skyrockets.  Don’t shy away from doing this and if you don’t have access to numbers, budgets or planning, go with your best guestimates.


Here’s how you’ll know that you’re ramping up your authority in the C-Suite: you’ll be consulted more frequently, if not incessantly in strategic decision making.  You’ll be awesome.  Enjoy 🙂

Please send me feedback on how this framework has helped you and as always, I would love to help you any way I can.