Head of Engineering

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 - 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 prefer being a lone wolf instead of building a team
• 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 all, it’ll be a 1-hour read
• What We Value and How We Live

Soul

• Doing the right thing, even when no one is watching. We put our heads on the pillow in peace.

Heart

• We bring joy, passion, and love into everything we do.

Growth

• We grow ourselves, improve our services, and uplift ChessMood Family members. Every day. One step at a time.

Serve

• We serve with our soul and heart, sharing joy and knowledge. To each other and to the ChessMood Family.

Excellence

• We don’t pursue perfectionism. But we keep “a minimum 8 out of 10 standard” in everything we do.

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.

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 click the “Apply” button 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

Originally posted on Himalayas