I first announced that I was building CTOBox in late February.

Since the first announcement, I kept working on it as much as I could, prioritizing this initiative over other engagements. As the tool is shaping up for the first public release, I thought it would be a good time for a long-overdue update on its progress.

For the folk who are new around here, let's start with a quick summary of what CTOBox is:

As I said in my original post:

I want CTOBox to be the suite of tools I have always wanted to have at hand through all my experiences leading engineering teams.

In essence, I'm building a tool for engineering leaders at all levels, especially those aiming to reach the executive ranks one day. The tool I'd always wanted to have available as I was going through my career.

When I first announced it, CTOBox only included a module called Team Compass, focused on running effective 1-to-1s with your team members.

Thanks to the first round of early testers, I was able to collect and act upon a ton of feedback. That has allowed me to improve the functionality way beyond what I originally envisioned.

If you missed the original announcement, I recommend you check it out before continuing:

Will CTOBox help you become a better leader? Sergio Visinoni · Feb 26 Read full story

Besides working on improvements around Team Compass, I've spent a significant amount of time iterating on the second major module: Career Architect.

Introducing Career Architect

Let's start with the problem to be solved, or the job to be done.

Back in September 2023, I wrote a somewhat provocative piece on what I saw as a common startup sin: not having an engineering career ladder.

Common Startup Sin #1: No Engineering Career Ladder Sergio Visinoni · September 28, 2023 Read full story

After talking with numerous engineering leaders, I realized two major things:

• Many don't even know they need one, as they assume this is mainly HR bureaucracy

• Of those who realize they probably need one, most have no idea how to get started and end up procrastinating indefinitely.

That's why with Career Architect, I aim to simplify the task of defining and operationalizing a ladder — or framework, if you prefer — for an engineering team, especially for those leaders who have never done this before.

Like everything else in CTOBox, Career Architect is and will be opinionated. If you want full flexibility, you should probably look at using a spreadsheet, but then you'll mostly be on your own.

With Career Architect instead, I want to guide you to build a sane and solid starting point that you'll then be able to evolve and customize at will.

How it Works

Enough sales pitch, let's look at some concrete stuff. Those of you who have access to CTOBox will be able to access Career Architect from the main menu.

It's helpful to clarify some terminology before we get into the mechanics.

Let's start with the terms specific to the structure of a ladder

• Branching Point: The tool focuses on dual-track / Y-track career paths. This refers to career tracks that aren't linear, and instead allow the employee to progress either on the Individual Contributor (IC) or the Manager track. Obviously, the first part of the track is shared as only IC levels are available up to a certain point. The point above which the two tracks split is referred to as the branching point. The most common branching point for software engineering ladders is the senior level.

• Company Structure: This concept refers to the underlying structure that your company uses to define levels. Typically, a company will define a certain number of levels, e.g., 10, and that applies to all disciplines and departments without distinctions. Your ladders need to respect such a common structure.

• Career Ladder: This is the framework you use to define levels, titles, with their respective expectations for skills and competencies.

There are also a handful of concepts specific to the competencies part of a ladder.

• Categories: Categories in this context are a way to group competencies under a common area or theme. Categories are generic by definition, such as "Technical Skills" or "Team Management".

• Competencies: They are the broad set of abilities and expertise you want to define expectations for at various levels. They are grouped into categories and provide a high-level overview of the type of competencies you expect from people in your team. Examples might include "Coding & Testing", "System Design & Architecture", or "Mentoring and Coaching".

• Key Skills: This is the most granular level at which you're defining the required skills at various levels. They are grouped into competencies and provide a very detailed list of expected abilities from people in your team. Examples here might include "Coding Patterns", "CI/CD", or "Performance Feedback".

The process that helps you go from zero to having a complete ladder in place is guided and should be intuitive enough not to require any particular guidance.

A typical process will look as follows:

1. You start by defining a Company Structure to be used for all your ladders. You'll be presented with sane defaults and the ability to customize them.

2. Once you have the first structure in place, you can create one or more ladders. This is a multi-step process that involves:

   1. Define the ladder name, description, and which structure to use (in case you have more than one)

   2. You'll then be presented with a view of the Y-ladder, where you can customize roles and titles.

   3. You'll then be presented with a proposed list of categories/competencies/skills that you can also fully customise.

   4. A review step in which you'll confirm that it all makes sense before saving the new ladder

Once you've done all that, there is one more thing you can and should do: assign levels on the ladder to the team members you've already configured in Team Compass. You'll be able to do it via the newly added Career tab in the person's view. Of course, you'll see the full history of the evolution of your team member in the company.

What's Missing

Though I feel Career Architect is ready for initial private testing, there is still a lot of ground I want to cover before opening CTOBox up for the public. That includes:

• Allow the user to edit Categories/Competences/Key Skills once the ladder has been defined (WIP).

• Introduce a detailed text for each competency and level, in which specific expectations are spelled out. This will be added as soon as the edit functionality is completed.

• Evaluate your team members against the ladder to identify areas of development.

• Define personal development goals based on current gaps and ambitions, and connect them with the recurring one-to-one discussions, actions, and follow-ups.

Once those are complete, I believe CTOBox will offer a comprehensive set of tools to help engineering leaders proactively manage the lifecycle and performance of their employees, providing clear guidance and expectations and helping them grow.

I believe that will be enough to make it the first public version of the product, while I'll keep working on covering many other aspects of engineering leadership, starting with offering a way to help leaders define effective tech strategies for their teams.

But that is something we'll talk about in another article!

Join the Testing Group

Many people helped with testing the first iteration of Team Compass, and I'll be forever grateful to them.

Now, with Career Architect taking shape, I want to invite another cohort of private testers. If you're interested in getting free access to CTOBox and helping me shape its future while being able to benefit from it in your current job, you can sign up for the waitlist here.

Join the Waitlist!

I process the waitlist in batches, and as soon as you've been granted access, you'll receive an email inviting you to sign up.

I'm convinced that with your help, I'll be able to launch a great product in the upcoming months.

As a sign of gratitude, I can already disclose that I'll be offering temporary free access to the tool once it becomes paid to everyone who helped out.

I haven't ironed out all the details yet, but I'll be offering something generous in exchange for your precious time.

Thanks in advance for all your feedback!