Director of Engineering

Legal Templates · Taipei, Taiwan (on-site/hybrid) · Reports to the CEO · Work permit sponsorship and relocation support

Legal Templates is a profitable, bootstrapped legal-technology platform. For over a decade we've helped hundreds of thousands of people a month create the legal documents they need — leases, wills, LLC formation paperwork, contracts — without hiring a lawyer. No outside funding, no runway anxiety.

The role

You'll own the entire technical function — development, QA, and DevOps — leading a senior team of four and reporting directly to the CEO.

This is deliberately hands-on. Expect to spend 60–70% of your time writing and reviewing code. You'll take story points every sprint and debug production issues yourself. Director describes the scope you own, not distance from the keyboard.

You'll inherit a mature, revenue-generating Ruby on Rails and React codebase with real history in it. The mandate is to make it excellent: rock-solid uptime, tight security, clean releases, steadily less debt to carry. Keeping a high-traffic, SEO-dependent, payment-processing application fast and stable while a team keeps shipping to it is hard, high-craft engineering, and we're looking for someone who takes pride in doing it well.

We also want this role to be genuinely forward-looking about AI, in two directions: removing toil from how we develop, test, and operate, so a team of four delivers like a much larger one — and forming a real point of view on how AI makes the product better for customers, brought forward with prototypes attached. You'll have the latitude to run both.

What you'll own

• Uptime, performance, and incident response, against clear targets you set — SLO, p95 latency, MTTR, escaped defect rate.
• The code quality bar. You're the team's most active reviewer, and dependencies stay current rather than falling major versions behind.
• Quality strategy and release criteria, directing our QA engineer.
• Cloud infrastructure, CI/CD, and disaster recovery, working through and developing our DevOps engineer.
• Application security and data privacy obligations (CCPA/CPRA, GDPR) — extended to how we adopt AI.
• The growth of four senior engineers across three specialties.

What success looks like

90 days — Observability gaps closed. On-call and incident process running. Release criteria and bug triage standards defined and followed. You've merged meaningful code and are the team's most active reviewer. You've delivered a prioritized technical debt and upgrade plan with a business case attached, plus a short list of AI opportunities with effort and impact against each.

One year — Uptime and performance are measurably better and consistently tracked. Escaped defects are down. Regression coverage makes upgrades routine. The team ships more confidently, with less firefighting, than when you arrived. At least one AI-driven product improvement has shipped — or been killed on evidence.

What we're looking for

• 8+ years shipping production web applications, including 3+ years leading engineers. A director title isn't required; a strong lead ready to step up works.
• Deep, production-grade Rails. You've upgraded major versions, tuned ActiveRecord, and debugged Rails in anger.
• Strong React. You can review frontend code credibly and write it well yourself.
• Ownership of a mature, high-traffic production system where uptime was your responsibility, and a track record of inheriting a codebase and measurably improving it. Be ready to talk specifics.
• Enough depth in cloud infrastructure (AWS or GCP), Docker, CI/CD, and SQL to set direction, review your DevOps engineer's work credibly, and operate independently in production.
• Daily, practical use of AI-assisted development tooling in a real production codebase, with earned opinions about where it helps and where it gets in the way.
• Fluent English — our working environment is fully English-speaking. Based in Taipei or willing to relocate.

Nice to have: high-traffic SEO-dependent consumer web, subscription billing (Stripe or similar), shipping customer-facing LLM features, regulated domains, SOC 2, Mandarin.

You'll like this role if

• You take pride in systems that just don't break, and get satisfaction from a quiet on-call week.
• You believe a leader's credibility comes from the code they write and review, not the title.
• You want genuine autonomy over a small, senior team by design — not a large org to manage.
• You're already using AI in your own work and want the latitude to bring it into both how the team works and what we ship.

We're an operator-led company that builds and launches software. As the core platform gets where we want it, there's real potential to seed new products — and you'd be involved from the start, from architecture decisions to building the first version.

Compensation and benefits

Competitive, top-of-market compensation. Plus: 15 days paid vacation, 5 days paid sick leave, your birthday off, and all Taiwan public holidays; labor insurance, National Health Insurance, and pension contributions per Taiwan law, plus supplementary group health insurance; work permit sponsorship, relocation allowance, and settling-in assistance; seasonal gifts, team building, and a food delivery budget.

Legal Templates is an equal opportunity employer. All qualified applicants will receive consideration regardless of age, sex, race, color, religion, citizenship, gender identity, sexual orientation, national origin, pregnancy, marital status, disability, or veteran status. Applications are kept on file for future vacancies; you may request removal from our database at any time.