What do most companies do after crossing $1 million in annual 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 hugely ambitious for our impact and product - and so we're strengthening our foundations so we can go much faster after.

🎯 Head of Engineering

Today, the best teams can do more with less.

We have big plans - centred on delivering our AI coach roadmap that builds on our proprietary 500+ hours of Grandmaster-crafted chess content, for our engaged community of 100k+ chess lovers and the ultimate global audience of 600+ million chess players.

We’re looking for a Head of Engineering to be a hands-on steward, builder and AI agent orchestrator as we massively transform ourselves into a highly lean, effective and AI-native team.

⚒️ What will you do?

You’ll be the architect, orchestrator and steward of our platform, and a key collaborator in our cross-functional leadership team.

Your main responsibility will be to design, implement and manage effective multi-agent AI workflows across the whole engineering stack - giving us 100x capabilities which we can leverage to serve chess players at scale.

💻 What will you work with?

We primarily expect you to be leveraging frontier models and AI coding tools - such as Claude Code, Codex and Cursor - with a view towards their current and future capabilities.

For what it’s worth, before our switch to AI-native engineering, we have used a mixture that includes:

• TypeScript, Python, PHP
• React, Laravel
• MySQL, MariaDB
• Docker, Terraform
• Cursor, GitHub Co-Pilot

You don't need to be an expert in all of these, and we are likely to modernise our stack anyway - as long as you can work quickly and sensibly with AI workflows to build effectively.

✅ You might be the right fit if you have...

• Love and deep interest in chess! We're serving a potential existing 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.
• Proven appetite and experience with AI agent workflows in engineering. We’re looking to be on the cutting edge of high performance teams, and we want someone who will keep us on the edge.
• Emotional intelligence with strong communication skills. You’ll be working with different teammates - the CEO, and cross-functional peers - and so it’ll help if you can communicate and build relationships across all areas.
• Ideally: full-stack engineering competency. You’ll be hands-on across the AI engineering workflows throughout our stack - so you’ll need to know enough to be able to make architectural decisions, create sensible prompts and verify outputs.

❌ You should skip this if...

• You're not into chess
• You want to build a large engineering team that isn’t AI-first
• You’re looking for a standard 9–5 office job with a task list

😍 Why you'll love working here

• Customer love and product pride. We get such strong testimonials, that sometimes people on the outside think we’ve faked them!
• Deeply committed teammates. Most of our team has been here for 4+ years, and we care about each other a lot!
• High trust and autonomy. You’ll be our trusted expert, leader and decision-maker on technology.
• Grow and learn - holistically. We value this far more than skills - we also value wisdom and character.
• And much more… Otherwise if we list them all, it’ll be a 1-hour read :)

♥️ What we value and how we live

1. Soul. Doing the right thing, even when no one is watching. We put our heads on the pillow in peace.
2. Heart. We bring joy, passion, and love into everything we do.
3. Growth. We grow ourselves, improve our services, and uplift ChessMood Family members. Every day. One step at a time.
4. Serve. We serve with our soul and heart, sharing joy and knowledge. To each other and to the ChessMood Family.
5. Excellence. We don’t pursue perfectionism. But we keep “a minimum 8 out of 10 standard” in everything we do.
6. Courage. We don’t do what others expect. We listen to our soul and heart, and act with courage, even when the world doesn’t approve.
7. Family. We change the world by starting from us. We create a beautiful world within the world and inspire others to truly enjoy this gift of life.

📩 How to apply

If your heart is beating faster after reading all this, you feel “OMG, I want to join ChessMood” — please apply below, and tell us about yourself.

We can’t wait to find that ONE person and scream,

“YEAH, FINALLY!”

With best wishes and love,

ChessMood Team