Head of Technology

We're looking for a Head of Technology who can own the technical health and growth of our backend platform. You'll be part architect, part tech lead, part engineering manager. You won't just review code, you'll set the standard for how code is written, how systems are designed, and how the team thinks about quality, cost, and customer impact. This is not a senior IC role where you write code all day. And it's not a pure management role where you're in meetings all day. It's the balance between the two, the person who makes the team better while staying close enough to the code to make good decisions.
The candidate will have responsibilities across the following functions:
System Reliability and Upkeep:
Own the health of a production multi-tenant Node.js/TypeScript backend serving real-time messaging traffic.
Lead incident response, root cause analysis, and post-mortem culture.
Identify and drive the reduction of technical debt proactively, not reactively.
Ensure monitoring, alerting, and observability are in good shape (we use New Relic, Sentry, and Pino structured logging).
Work across multiple backend services and ensure they integrate reliably.
Scalable, Quality Engineering:
Design and review system architecture decisions, schema changes, service boundaries, async workflows (we use Temporal.io), and queue design.
Drive engineering standards: code review culture, PR quality, test coverage, error handling patterns.
Establish and enforce engineering practices that let the team ship fast without accumulating hidden risk.
Evaluate build vs. buy decisions with a clear eye on long-term maintainability.
Cost Consciousness:
Maintain a clear understanding of infrastructure costs (AWS, third-party APIs, LLM usage, DB compute).
Actively flag cost anomalies and propose architectural or operational changes to address them.
Balance engineering investment against business return, and know when "good enough" is the right call.
Team Standards and Culture:
Set a high bar for code quality, not pedantry, but clarity, maintainability, and correctness.
Build a review culture where feedback is constructive, specific, and educational.
Help engineers grow by pair debugging, design reviews, and code walkthroughs.
Define and document coding conventions, architecture patterns, and engineering principles that persist beyond any individual.
Customer Empathy:
Understand that the systems you build serve real D2C businesses that depend on them to communicate with their customers.
Treat reliability issues with the urgency of a customer escalation, not a backlog item.
Stay connected to what support and product teams are seeing from customers, and let that shape engineering priorities.
Communication and Stakeholder Management:
Translate technical complexity into clear, honest language for non-technical co-founders and stakeholders.
Communicate risk, timelines, and tradeoffs clearly, no sugar-coating, no unnecessary alarm.
Manage up: surface the right problems at the right time without waiting to be asked.
Manage expectations both internally with the team and externally with leadership.
Balancing Tradeoffs:
Navigate the tension between shipping fast and building right, and be able to articulate why you chose one over the other.
Know when to take on short-term debt and when to push back.
Make architectural decisions that serve the next 18 months, not just the next sprint.
Requirements:
4-6 years of backend software engineering experience, with at least 2 years in a lead or staff-level role.
Strong command of TypeScript/Node.js in production (our primary stack).
Deep understanding of multi-tenant SaaS architecture patterns.
Hands-on experience with relational databases (MySQL/PostgreSQL), ORM usage (TypeORM or similar), and writing efficient queries at scale.
Experience designing and operating async/event-driven systems (message queues, workflow engines, or similar).
Comfort with cloud infrastructure (AWS preferred) and cost/performance monitoring.
Strong pull request review discipline, you know what makes a good review and what makes a bad one.
Strong Plus:
Experience with real-time systems (WebSockets, Socket.IO, pub/sub patterns).
Exposure to LLM integration, RAG pipelines, or AI feature development in production.
Experience with Temporal.io or similar workflow orchestration.
Familiarity with WhatsApp Business API, omnichannel messaging, or e-commerce integrations.
Prior experience at a startup in the 10-100 person range, where you had to set standards, not just follow them.

Experience
4-6 yrs