Wilco gamifies your path through your software engineering career

Israeli startup Wilco describes itself as “an immersive upskilling platform for software developers,” and snuck out of stealth this week with its first public version and a stash box with $7 million worth of fresh seed funding. It’s just weird enough that it’s the kind of thing I completely love.

The problem the company is trying to solve is the bewildering array of options available to a freshly minted, wet behind the ears software developer. It turns out that being able to write software is only a small part of the job. In addition, you need to develop a wide set of skills that are not writing code but just as important. These might include strategies for debugging complex systems, team communications and responding to high-pressure crisis situations. The theory is that these skills are both hard to get without experiencing in the real world, and they can be daunting. Why not do the same thing airline pilots need to do before they take the steering wheel on a plane? (Can you tell I’m not a pilot?) That’s right, Wilco developed a simulator of sorts.

On Wilco’s platform, developers join a made-up tech company and are put through their paces in a game-like experience designed to accelerate their professional growth. At their “new workplace,” engineers go on quests that challenge them to navigate complex life-like scenarios while utilizing real tools and technologies.

One quest begins with the developer being notified via the workplace messaging app about a mysterious issue with the company’s application. The developer must analyze data to identify the affected users, recreate the issue on their own device, find the problematic code and push their fix to the company’s code repository on GitHub. When needed, guidance from virtual co-workers is provided through the messaging app, simulating a modern remote work environment.

Wilco’s various quests help you through your developer journey. Image Credits: Wilco

“One of the critical challenges I’ve faced throughout my career as an engineering leader is finding ways to nurture talent and ensure the continuous growth of every team member,” said Farhan Thawar, VP Engineering at Shopify and an angel investor into the company via one of Wilco’s press contacts. “That’s what got me so excited when I tried the Wilco platform — the realistic environment brought me back to my early days as a dev team contributor and the engineering scenarios addressed precisely those abstract skills that are so hard to teach.”

I interviewed the company’s CEO, On Freund, to learn more.

TC: Why are you excited about this company?

OF: When we were just getting started, my co-founder Alon said that if Wilco had already existed, he’d simply join the company rather than start a new one. That’s really how we feel — we didn’t get into it to be founders; we’re in it because we believe in what we do. We see the passion developers have for our problem space. Almost everyone we talk to immediately gets it — they’ve all experienced how hard it is for them and their teams to develop new skills. The use cases we see are all net positive for the individual — helping them develop themselves professionally in an innovative manner, but there’s also a broad social benefit to Wilco in making professional development opportunities more accessible and equitable.

What’s currently broken about training for software engineers?

The best way developers have to improve their skills today is on the job, but that is both slow and inefficient. You need to wait for a particular situation to arise in order to practice a skill. It isn’t often though that you need to completely redesign a legacy app component or set up a new pipeline on the fly because your product is experiencing an unexpected surge in popularity. You have to wait for a production crisis to naturally occur in order to learn how to handle it (I do not recommend creating your own :) ). Even when a crisis does happen, chances are the person who will handle it is someone who’s seen this a thousand times.

That’s only the first problem though — when you do get a chance to “practice,” you’re not really in a practice environment, and you have to live with the fear of breaking something. Software mistakes can easily end up being costly.

Last but not least, practicing only on the job has an equal opportunity problem. Two developers starting at the same time but landing in different teams can have a vastly different outcome based on the people who work alongside them, the mentors they have, the types of assignments they’re getting and their employer’s willingness to tolerate costly mistakes in order to train them. When it comes to people from underrepresented groups, it’s less common for them to get to the kind of teams that enable them to quickly close the experience gap and reach their full potential.

In your opinion, why is now the right time for Wilco?

Building Wilco would have made sense even a decade ago but after COVID-19 forced the world into a remote working environment it’s more relevant than ever. We do “real” work remotely, so why not simulate a remote workplace to master and learn skills?

What was the fundraising experience like?

There’s a cliche that investors always want to see traction, and the right amount of traction is just a bit more than what you have. That’s why we immediately started pitching Wilco to every engineer and engineering manager we could talk to. Being able to show both bottom-up and top-down interest made fundraising significantly easier.

Another thing that worked well for us is a very targeted approach — we knew who the right investors for Wilco were and that made the pitch so much more effective. While this might not be the best time to raise a round, I do believe that carefully picking the investors you’re pitching to can go a long way.

Are you happy with your investors? Why?

Very much so! And no, I’m not saying it because I feel obligated to. Each of our investors not only understands Wilco’s potential and believes in our mission but has given us strategic guidance along our journey. I believe we’ve selected partners who are right not just for this stage in our journey but for the years ahead. With everything that’s happening in the industry these days, I’m more confident than ever in our choice of investors.

What are you personally most excited about with Wilco?

Alon, Shem and I have known each other for many years, and what we’re building together comes from solving a need we’ve experienced firsthand in previous roles. While each of us tackled this from a slightly different angle, we all wished we had some way to get our developers to constantly practice their skills.

Additionally, I’m honestly just really excited about the team we’ve brought in and the culture we’ve all built together. One of our objectives is to build a fun and supporting workplace, and we really invest in making that happen.

What are you hoping to accomplish over the next 18 or so months?

The most important thing we want to accomplish is to provide validation for the continuous impact Wilco can make on an engineer’s professional development. By inviting hundreds of developers to try out the platform prior to launch, we got strong validation of Wilco’s ability to provide immediate value. Now we want to see that over a year and a half, we can accelerate developers’ growth and continuously help them acquire and practice new skills. Practically, we have a lot of things to do — including expanding our catalog and adding quest creation tools — and there’s a business edition to think about. We also want to bring in additional business partners to co-create quests with us. We think Wilco is a great way for developer-facing companies to provide their developer communities hands-on experience with their products.

If Wilco hits every goal, dream and milestone, how will the world be different five years from now?

What we want is for engineers to be able to develop themselves professionally using Wilco throughout their careers. What would it look like? Here are a few examples:

After learning to code, a recent graduate or self-taught engineer will have the chance to acquire skills even before they get their first job, improving the chances of acing their technical interview and getting into a team that reflects their potential rather than the opportunities they’ve been given previously.

Engineering teams will not have to wait until crises arise or new challenges are handed down by the roadmap. They’ll be able to continuously upskill, practice for real-life scenarios and expose themselves to the newest technologies.

Experienced engineers will have less desire to move on from a job they really like simply because it doesn’t expose them to new challenges. It’s a very common scenario: You love the company, love the team, but professionally it’s no longer the right place for you because you’ve stopped evolving and growing. With Wilco, you won’t find yourself torn between those two competing motivations.

We talk about unlocking engineers’ potential a lot. I know it probably sounds a bit like marketing-speak, but think about it: It is indeed something that needs to be unlocked. People aren’t born with the knowledge of how to run a development life cycle or how to find bugs in production, and theoretical knowledge that you pick up in a course or a classroom is just half of the equation — there’s the on-the-job muscle they need to train by being exposed to scenario after scenario. Professional flight simulators do that for pilots, making air travel safer for everyone. What will Wilco’s impact be if our “flight simulator for engineers” works at scale? I can’t wait to find out!

You mentioned that you are building partnerships with “real” companies for Quests. What are these quest partnerships?

Apart from building our own quests, Wilco will offer quests built together with other companies, such as New Relic, JFrog and Applitools. These companies are already investing heavily in developer advocacy, but blog posts, podcasts, videos and the like can only take you so far. With Wilco, they can create content that is both engaging for third-party developers and provides them with hands-on practice.

For the individual developer it means that if they want to get better at a skill like observability, they can get hands-on experience utilizing real production tools to solve a life-like problem, using quests developed by the top experts in the field.

Thank you to On Freund for being willing to do the interview over email in a busy week where we couldn’t find any time to talk on the phone.

Personally, I’m a self-taught software developer, and I can totally see how, if I wanted to make the move back into software development, getting a taste for what life is like on the coalface of software development would be fantastically valuable; it’ll be interesting to see how the company evolves and grows.

The funding round was led by Hetz Ventures, with participation from Vertex Ventures, Flybridge Capital Partners, Shopify’s VP Engineering Farhan Thawar and others.

I managed to convince the Wilco team to share its pitch deck with me as well, so be on the lookout for a Pitch Deck Teardown to see what the company did to raise its round in the next couple of weeks!