Wilco Raises $7M To Help Software Developers Up-Skill Their Careers

The lack of structured, regular opportunities for software engineers to sharpen their skills results in a massive market of corporate workplace training resources targeting them. Wilco, a startup founded by On Freund, Shem Magnezi and Alon Carmel, provides software engineers with a dedicated training platform to help them up-skill themselves through simulations mirroring real-life developer scenarios. The Tel Aviv, Israel-based startup raised a $7M seed round led by Hetz Ventures, with participation from Vertex Ventures, Flybridge Capital, Operator Partners, Samsung Next, Graph Ventures, WeWork Alumni Fund, and angel investors including Farhan Thawar, Dave Bisceglia, Sagi Schliesser, Yoni Assia, Mike Vorhaus and Ariel Tiger.

Sagi Schliesser, cofounder and CEO of CrazyLabs, states, “In all honesty, when I spoke with On the first time, I felt two very strong sensations which led me to ask to invest: the team was amazing talent-, experience- and energy-wise. The second sensation was that I was a longtime CTO and VP of R&D in my past and felt a “Wow!” moment about the market need and product-market fit.”

The startup, founded in August 2021, has twenty-two employees. The seed round closed in September 2021. The Wilco cofounders plan to use the money to further develop an “engaging experience for developers” and create a “community editor” to allow users to craft their own “quest” to sharpen their skills. There are many training products and coding bootcamps to teach and improve developers, but Wilco’s stiffest competition may come from pair programming as a learning technique. However, the perpetual demand for software engineers ensures a massive market with room for multiple startups delivering solutions.

Frederick Daso: What inefficiencies deter software engineers from improving their skills in their day-to-day work environment?

On Freund: Developers improve their skills in their day-to-day work environment, but the way to do it is slow and inefficient. The only time a developer can acquire a new skill is if there’s a situation in which there’s a real need for it. It isn’t often, though, that you must completely redesign a legacy component or set up a new CI/CD pipeline.

If you want to learn how to handle a production crisis, you have to wait for it to naturally occur (we do not endorse creating your own!), and even when it does, chances are the person handling it is someone who’s seen this a thousand times.

So you get to practice new skills very infrequently, but when you do, the stakes could be high, and if you get something wrong, that mistake can end up being costly.

Last but not least, practicing on the job doesn’t provide equal opportunity to all developers. So much depends on the team you get to, the people who mentor you, and the types of tasks you’re getting. If you look at underrepresented groups, they rarely get to teams that enable them to close the experience gap quickly and efficiently.

Daso: Within the overall market for workplace training for software engineers, what size firms are you targeting to sell to initially, and why?

Freund: The Wilco platform is suited for any company wishing to develop its engineers and enable them to reach their full potential. That being said, our PLG approach initially lends itself better to smaller engineering teams of under 100 developers. These teams tend to appreciate self-serve products and are easier to onboard. We plan to go upmarket in the future, though, and we’ll complement this with additional integrations and customization abilities that many larger organizations need.

Of course, any developer in any company can sign up for the community edition.

Daso: Within Wilco’s product, how did you construct realistic tasks that accurately mirror real-world problems that engineers face? Did your design also consider the potential contingencies or trade-offs software engineers face in their profession daily?

Freund: For Wilco to be immersive, developers need to experience many of the same scenarios they encounter daily. To make this work, we created the fantasy company - Anythink - that developers join. Anythink is an e-commerce company with a production environment and its own messaging platform - Snack.

On Snack, users communicate with other “employees” who assign tasks, give feedback, and help them on their journey. This isn’t just for fun; engineers often get assignments in conversational terms and have to be able to break them down into tasks. We also made sure to give those “colleagues” real character.

The scenarios built on this infrastructure are meant to be realistic and engaging. They explore trade-offs such as “Should I deploy a quick-n-dirty fix in this situation, or does this call for something more infrastructural?” or “How do I ensure that my teammates are up to speed on the changes that I’m making?”

Daso: How does storytelling shape and drive the user experience within Wilco?

Freund: The narrative is a key element that makes Wilco unique. So much so that we ensured that one of our first employees has a background in experience design. Smadar, our creative director, has been creating immersive online experiences for projects ranging from games to escape rooms, both online and offline. There’s nothing she loves more than surprising twists that hook the player along the journey.

Wilco isn’t just about improving skills — it’s also about immersing developers into a full world that simulates what they would encounter in a real job in a fun and interesting way.

This makes the difference between “Here’s a function you need to fix” and “Oh no, production is down. Can you figure out what happened?”

Daso: How have you balanced the requirements of the learning specialists, who are in charge of purchasing workforce learning and development products and services, against the needs of the developers, who are the end users?

Freund: While team leads and L&D managers may decide whether Wilco is right for their teams, at the end of the day, it all comes down to developers gaining real value from the platform. We are building the experience for the individual developer, ensuring that the immersive world they enter is a fun and engaging one and helps them hone their skills and learn new ones.

We believe the transition from individual value to team value will be a natural one, and the engineering managers we speak to tend to agree.

Daso: Diversity is a common, recurring issue in the tech industry. How have you buck the trend at such an early stage of Wilco by having a higher than average proportion of your team be women, especially in critical engineering and product roles?

Freund: Alon, Shem, and I have been lucky to work with many strong female leaders throughout our careers. It’s allowed us to hear some of the challenges they’ve faced and ensure that we create an inclusive environment not just for women but for all parents and people from diverse backgrounds. There are a few fundamental principles we’ve instilled in our culture to ensure this: hybrid work and flexible working hours, investing in managers who know how to support people both professionally and personally, ensuring equal ability to voice opinions, and trying to minimize company politics.

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