Head of Engineering - ChessMood

What do most companies do after crossing $1 million in annual recurring revenue? They raise a glass, then raise their prices, then chase 2… then 5… then 10 million.

That’s not what we did.

We’re in control of our future, and we can decide to do it differently - because we’ve built a company that’s profitable, without VC ownership.

So, we don’t have to rush off the cliffs that kill so many startups.

For us, 2025 is the year of the backward move - the year of transformation. We’re strengthening our foundations so we can go much faster after.

We’re hugely ambitious about our product - and so our small but mighty team is looking for an engineering leader who will bring a deep heart to their work, be hands-on with building in our current phase, and keep growing with us on the adventure of a lifetime.

Our customers love our product. But we have so much more work to do with it.

Making it ready for our upcoming AI Coach that will completely revolutionize how people learn chess. Making it ready to serve millions of chess lovers who come to ChessMood to improve their game.

Maybe you could be the person to help us do that?

⚒️ What You’ll Do?

Probably, start by auditing everything and telling us where we should begin? 🙂

Here are the things we already have in mind:

• Audit our existing architecture and decide what to rebuild vs. refactor
• Build, coach and grow a modern engineering team for the AI era
• Set technical standards, systems, and deployment practices
• Collaborate directly with the CEO on product strategy and priorities
• Work closely with our AI Coach and product teams to bring new features to life
• Make technical decisions with a long-term ownership mindset
• Ensure speed, reliability, and scalability across the entire platform
• And do everything else needed to shape ChessMood ’s next stage of growt

✅ YOU MIGHT BE THE RIGHT FIT IF YOU HAVE…

• Love and deep interest in chess! We’re serving an audience of 600+ million chess players. The deeper your interest in chess, the more first-hand empathy can go into our product, and the domain knowledge will help you to work effectively with our in-house GMs and IMs as we build our AI coach.
• Experience and pragmatism with AI-written code. We want to be efficient and nimble as we scale. As frontier LLMs continue to improve, you’ll be iterating how our team uses Cursor / GitHub Copilot / Windsurf (etc.), to manage its downsides but also take advantage of its appropriate use cases.
• Emotional intelligence with strong communication skills. You’ll be working with lots of us - engineers, the CEO, and cross-functional peers - and so it’ll help if you can communicate and build relationships across all areas.
• Ideally: full-stack competency. Whilst we might grow our team with specialists, you’ll be hands-on across our stack at the start -