Will CTOBox help you become a better leader?
Before you ask WTF is CTOBox, read through today's article where I'm sharing the latest experiment I'm running to improve the life of Engineering Leaders.
The primary reason I decided to leave stable employment at the beginning of 2024 and embark on my solopreneurship journey was the desire for greater autonomy.
Autonomy over how I invest my time, which types of activities I want to engage with, and ultimately, when I'm going to work and when I'm not.
Even though the journey started with doing good old consulting to companies in various shapes and forms, the choice of calling this new stage solopreneurship was deliberate. I intend to build a thriving business around myself, one that will allow me increased degrees of autonomy as I add more recurring sources of income to my portfolio.
I'm in for the long game: I know this will take time, and I care more about being on a positive trajectory than the absolute numbers. As long as the trajectory is positive, I'll eventually get to a place where the need to do consulting work will become secondary and finally unnecessary.
I've shared previously that B2B consulting represented about 94% of income in 20241. By all accounts, this is the lion's share. Yet, the remaining 6% is the signal in the noise, considering it was nonexistent the previous year.
For 2025, I want that percentage to grow into the comfortable double-digit space between 15% and 20%.
One of the key drivers will be the community product I opened up in August last year, which is performing above expectations in terms of engagement and retention. The name of the game for it will be acquisition this year.
If you're interested in such a product, there will never be a better moment to join.
As I follow a schema where I progressively increase the price as more people join, you'd better secure your seat at the current price. This will save you some ranting against inflation later.
You should check it out here if you still don't know what it is. We're having a great time there and learning from each other in a safe and supportive environment.
While the community is naturally adjacent to the work I've been doing so far2, I intend to conduct more far-fetched experiments.
One of them is CTOBox, and I'm glad to present it to you all, even though it's still in private beta.
The reason is simple: you, my reader, are the ideal customer profile… at least in theory.
How much that's true is precisely what I intend to figure out.
The rationale behind CTOBox
Whenever I consider launching or testing a product, I ask myself: What am I reasonably good at?
There is only one thing I know how to do decently: run engineering organizations and represent them on the executive team.
One thing has been a constant in my different gigs as Engineering Manager, VP of Engineering, or CTO.
I regularly had to implement bespoke tools and frameworks to do my job.
Part of it was due to the disease that affects everyone and their mother in this industry: the Not Invented Here syndrome3, aka NIH. But NIH was only half the story. The second half was a lack of tools opinionated enough to not only allow me to perform specific tasks as I wanted but also guide me so that I'd do them right, or at least well.
I love opinionated tools as they force you to focus on getting the job done instead of getting constantly sidetracked by doing the meta-work of creating frameworks.
As much as I love using tools such as Notion or Anytype due to their inherent flexibility, I regularly find myself spending time trying to build the perfect system—which doesn't exist—at the expense of getting work done.
Granted, working on processes and tools is fundamental. Building your bespoke system is fantastic and can boost your productivity significantly.
But I believe it shouldn't be a hard requirement.
Anyone should be able to start with something existing that does well 80% to 90% of the job and give you some room to tweak the rest.
This realization gave me the initial idea for building CTOBox.
That, and some free time caused by the shittiest month in my business last year4, which led to a serendipitous encounter with a full-stack framework named Wasp5.
What is CTOBox
In essence, I want CTOBox to be the suite of tools I have always wanted to have at hand through all my experiences leading engineering teams. The current tagline, which I'll probably change a hundred times in the upcoming months, is the following:
The CTO Toolbox, a suite of tools for modern CTOs, VPs and Engineering Leaders.
The ultimate tool you'll need to succeed leading engineering teams, from Engineering Manager to CTO!
Yes, there's a lot of room for improvement in my marketing copywriting. I'm working on it, I promise!
Now, that tagline is the declaration of intention, or if you prefer, the vision.
Today's incarnation of CTOBox is the closest thing you can think to an MVP of that idea.
True to my own advice and recommendations, I forced myself to build something usable—far from perfect—that I could put in front of potential users and get early validation… or crickets.
The MVP is built on a single macro feature called Team Compass. It's intended to give you an overview of your team's health through one of my very opinionated approaches: one-to-one meetings6.
In CTOBox, you can add your team members and start tracking 1-to-1 meetings with them. But that is something that you can do with any note-taking tool.
The value added is a couple of things:
Out-of-the-box insights based on the history of reported mood. Something I've factored in my one-to-ones for quite some time
AI-generated follow-up topics, highlights on the person, and recommended actions. One area where so-called Generative AI does well is summarizing existing information rather than generating content.
CTOBox leverages this approach to ensure you are on top of what is going on with your team members and have the most relevant information available when needed: when you're talking to them.
As a picture is worth a thousand words, here are a bunch of screenshots showing the team-compass capability.
I could add plenty more capabilities and features, such as automated import of past meetings, calendar integration, reminders…, and the list goes on and on.
But building all of them now would have meant a more significant investment and a longer time to market. Before I know if I can afford further investment, I need to figure out if and how people are willing to use the tool.
That's why, on Friday last week, I whitelisted the first few people who had signed up for the waitlist long ago.
I received interesting feedback, questions, and bug reports in the first few days.
That is precisely what I was looking for.
This feedback will be instrumental in determining whether it's worth furthering the investment.
True to the principle of building in public, I'll share every step of the decision-making process on these pages.
How to get your seat
If you believe you could be an early tester for the tool and are willing to endure the annoying quirks of an immature tool—friction, inconsistencies, a lack of features, and the occasional bug—you can sign up for the waitlist at this address.
At the time of this writing, there is no guarantee of whether and when you'll be whitelisted, as it all depends on how the early testing goes.
Similarly, current early adopters have access to the tool entirely for free, as I consider they're doing me a favor by trying it out. This is also a logical step in the validation process: if I don't get people to use it for free, there is no point in adding a paywall and hoping that users will magically flock to it!
I want to manage your expectations as I manage mine. In six months, CTOBox might no longer exist.
That's why I've deliberately decided not to set up a top-level domain for it yet. It's only available as a subdomain at https://ctobox.sergiovisinoni.com.
I don't need a top-level domain to get user feedback.
If the product succeeds, I can always find a fancy TLD in the future… probably not ctobox.vip though.
If it doesn't, that's one less thing to consider in the aftermath.
While you patiently wait to be admitted to the exclusive club, you are welcome to leave comments on why you'd like to try out such a tool or what features you'd love to find in it.
That may or may not get you priority access to the next batch of invites.
There is only one way to figure it out.
If you enjoyed this
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Sharing it with others helps immensely in growing it.
Engaging with my professional services is a great way to ensure I can continue dedicating many hours each week to producing what I hope to be high-quality content.
Those services articulate around three legs:
Fractional CTO or Advisory roles for B2B companies. Find out more on this page.
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Here, you can find a detailed post with my 2024 recap.
The original announcement post shares a lot of the reasons behind the decision to launch the community.
September 2024 was pure crap. I've written about it in this post.
Can you believe one of the very first articles I published talks about that topic? It's true, and you can find it here.
