Engineering Team Lead Applied AI

Engineering Team Lead, Applied AI (Internal Automation) at WorkFlex

At WorkFlex, we don’t just "allow" remote work, we enable it for the world. We are building the automated operating system for international travel compliance, tax, and duty of care. We are a remote-only company. You can work from anywhere and take up to 183 days of workations per year. We value your output and your "Architect’s Mind," not the hours you spend in an IDE or a physical office.

The Role: The Automation Practice Lead

You will lead a high-autonomy, distributed squad of 3 Applied AI Engineers. This is a Player-Coach role designed for an experienced engineer who wants to lead a team while keeping their hands in the codebase. Your engineers operate semi-autonomously, embedded in different departments (Compliance, CS, Ops). They don't work on the same daily codebase. Instead, you run this team like a "Guild" - fostering async collaboration, code reviews, and shared AI prompting strategies. While your "clients" are the operational departments, your home is the Engineering organization. You’ll spend half your time as an individual contributor - building complex, cross-departmental automation workflows and standardizing the deployment pipelines (Docker, CI/CD) for your team. The other half is dedicated to people leadership, stakeholder management, and tracking the impact of your team's work.

The Way We Work: Agentic & Async

We are not a traditional "code-monkey" shop. Our workflow is heavily driven by AI agents (Claude Code, Cursor). We expect you to lead your team in using AI as a high-leverage tool to build scalable internal tools at 4x speed. We operate with an async-first culture. We protect your time so you can focus on leadership and the bigger picture.

What You Will Do

• Define the ROI Framework: Establish the metrics framework to quantify how many hours of manual work your team is saving the company each quarter.
• Stakeholder Partnership: Collaborate directly with Department Heads (Compliance, Customer Success, etc.) to identify the highest-impact automation opportunities and prioritize the pipeline for your team.
• Pave the Road: Define the technical standards, ensuring a unified, secure approach to API integrations, deployment, and data handling.
• Force Multiplication: Technically mentor your engineers and handle all classical people management topics: 1-on-1s, performance reviews, career growth, and salary negotiations.

What You Need to Succeed

• Traditional Engineering Roots: Strong foundational background in Computer Science or Software Engineering. Deep experience in backend technologies (Python, Node.js/TypeScript, Docker, API design) to audit and guide AI-generated architectures. Be the ultimate "BS-checker" for AI output.
• The Lead Experience: 1-2+ years of experience in people management, including growing engineers and managing performance in a remote, highly autonomous environment.
• AI-Native Instincts: Power-user of LLM tools and orchestration frameworks (n8n, agentic workflows with Claude). Know how to use the best tool for the job.
• Consultative Communication: Ability to translate non-technical executive needs into a technical roadmap and confidently report on success metrics.

Why WorkFlex?

• True Global Mobility: Work from anywhere. Truly. 183 days of workations per year.
• High Leverage: Use all the AI tools on the market. We don't just permit them; we require them.
• Equity: Virtual Stock Options (VSOPs) so you own a piece of the mission.
• Flexibility: Monthly budget for co-working or fitness, and a "results-only" work culture.

Ready to lead the agentic revolution? If you have the technical depth of an architect and the empathy of a leader, we want to talk. We value ambition and a "builder" mindset over a perfect CV.

Key skills/competency

• Applied AI Engineering
• Team Leadership
• Automation
• Python
• Node.js
• TypeScript
• Docker
• API Design
• LLM Orchestration
• Remote Work Culture