Head of Engineering
ChessMood
WorldwideremotePosted 23 days ago
Skill Required
Engineering-LeadershipEngineering-ManagementSoftware-Engineering-ManagementHead-of-EngineeringHead-Of-Software-EngineeringDirector-of-EngineeringCTO-Head-Of-EngineeringTechnology-LeadershipEngineeringbuildingwrittenetc.)GitRustGenerative AIandGoAIFulltime
Key highlights
- Role: Engineering Leader
- Company Status: Profitable, $1M+ ARR, No VC ownership
- Key Requirement: Deep love and interest in chess
- Key Requirement: Experience with AI coding tools (Cursor, Copilot, Windsurf)
- Key Benefit: High trust, autonomy, and technology decision-making
- Team Tenure: Most team members present 4+ years
Role overview
ChessMood is a profitable, non-VC-owned company that crossed $1 million in annual recurring revenue and is focusing 2025 on strengthening its technical foundations for long-term growth. The team is looking for an hands-on Engineering Leader to bring deep care to their work, audit and modernize the platform, and build and guide an engineering team to support millions of chess players and launch an upcoming AI Coach.
Responsibilities
- Audit everything and identify where to begin
- Audit 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 the 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
- Do everything else needed to shape ChessMood’s next stage of growth
Requirements
- Love and deep interest in chess (to bring first-hand empathy for an audience of 600+ million chess players and work effectively with in-house GMs and IMs)
- Experience and pragmatism with AI-written code (iterating team usage of Cursor, GitHub Copilot, Windsurf, etc., managing downsides while taking advantage of appropriate use cases)
- Emotional intelligence with strong communication skills to build relationships across engineers, the CEO, and cross-functional peers
- Must be interested in chess (not for people who are not into chess)
- Must want to build and work with a team (not for lone wolves)
- Must want more than a standard 9–5 office job with a task list
Nice to have
- Full-stack competency (hands-on across the stack at the start to make architectural decisions, create sensible prompts, and verify outputs)
Benefits
- Customer love and product pride through exceptionally strong user testimonials
- Deeply committed teammates (most team members have been with the company 4+ years)
- High trust and autonomy as the trusted expert, leader, and decision-maker on technology
- Holistic learning and growth, valuing wisdom and character alongside technical skills
Additional details
- Company Financial Context: Profitable, bootstrapped without VC ownership, crossed $1M ARR.
- 2025 Strategy: Defining 2025 as the 'year of the backward move - the year of transformation' to strengthen foundations before scaling rapidly.
- Product Vision: Preparing the platform for an AI Coach designed to revolutionize how people learn chess and serve millions of ChessMood users.
- Company Values - Soul: Doing the right thing even when no one is watching.
- Company Values - Heart: Bringing joy, passion, and love into everything.
- Company Values - Growth: Daily self-improvement and uplifting ChessMood Family members.
- Company Values - Serve: Sharing joy and knowledge with soul and heart.
- Company Values - Excellence: Maintaining a minimum '8 out of 10' standard in everything without falling into perfectionism.
- Company Values - Courage: Listening to soul/heart and acting with courage despite external expectations.
- Company Values - Family: Creating a supportive internal world to inspire enjoying life.
- Application Instructions: Click the 'Apply' button and tell the team about yourself.
- Source: Originally posted on Himalayas.