Director of Engineering

Director of Engineering at Leafwell

As Director of Engineering at Leafwell, you will own the technical direction, delivery, and health of our engineering organization. Reporting directly to leadership, you will manage a lean, high-impact team that includes in-house engineers and an external contracting partner, shaping how we build and ship the products that power our mission to transform the medical cannabis industry.

This is a hands-on leadership role. You will spend meaningful time in the codebase—architecting systems, reviewing pull requests, and writing code alongside your team—while also setting engineering strategy, managing people, and driving process improvements. You will be the connective tissue between product vision and technical execution, ensuring the team delivers reliably without sacrificing code quality or developer experience.

Leafwell is investing heavily in agentic workflows and intelligent automation. You should bring genuine curiosity about these paradigms and a point of view on how to integrate them thoughtfully—balancing innovation with the discipline required to maintain and evolve a production platform serving hundreds of thousands of patients.

Key Responsibilities:

• Lead, mentor, and manage all engineers across the organization, including in-house staff and a contracted engineering team of 2–3 developers.
• Set technical direction and architectural standards for Leafwell's platform, built on Node.js, TypeScript, React, and AWS (Lambda, AppSync, EventBridge, S3, CloudFormation, CDK, and related services).
• Remain hands-on: contribute to architecture decisions, conduct code reviews, and write production code in critical areas.
• Own engineering planning and execution—sprint cadence, release management, incident response, and capacity planning across in-house and contract resources.
• Drive the adoption of agentic development frameworks and intelligent automation, evaluating tools and patterns (e.g., LangChain, CrewAI, or similar) that improve workflows without introducing unnecessary complexity.
• Partner closely with Product, Design, and business stakeholders to translate roadmap priorities into well-scoped technical plans.
• Establish and evolve engineering best practices: CI/CD pipelines, testing strategy, observability, documentation, and on-call processes.
• Manage the relationship with our contracting partner, ensuring alignment on priorities, quality standards, and delivery timelines.
• Build a culture of ownership, continuous improvement, and pragmatic innovation within the engineering team.
• Oversee infrastructure and DevOps practices, whether directly or through a dedicated infrastructure-focused engineer, ensuring reliability, security, and cost efficiency on AWS.
• Contribute to hiring decisions, performance management, and professional development for all engineering team members.

Why Leafwell?

When you join Leafwell, you'll be part of a passionate and driven team that is dedicated to making a meaningful difference in people's lives. We believe our employees are the backbone of our success, and as such, we strive to create a supportive and engaging work environment that nurtures growth and fosters innovation.

At Leafwell, you'll have the opportunity to:

• Work alongside industry experts, thought leaders, and like-minded individuals who share your passion for medical cannabis and its life-changing benefits.
• Contribute to ground-breaking research and data-driven insights that shape the future of medical cannabis treatment and improve the health outcomes of our customers.
• Grow professionally and personally in a dynamic, fast-paced environment that embraces diversity, inclusion, and creativity.
• Be part of a mission-driven organization that values your ideas, your well-being, and your long-term success.

Join us at Leafwell, where your passion meets purpose, and together, we can revolutionize the medical cannabis landscape to improve patient's quality of life and overall health.

Benefits Highlights:

Our benefits include, but are not limited to:

• Remote first - Most of our employees are 100% remote. Positions requiring travel enjoy a hybrid environment.
• Paid time off - Generous paid time off, including vacation and sick leave (every employee needs time to unwind, refresh, and renew their mind).
• Health & Wellbeing - Comprehensive health package, including medical, dental, vision, FSA/HSA, and other ancillary products.
• 401K - company-sponsored 401k with 4% match; fully vested after 90 days!
• Growth - Our employees advance with us!
• Training and Development - We foster a culture of learning. We encourage our employees to take part in educational, training, and development opportunities.

Leafwell is dedicated to bringing together people from diverse cultures and perspectives. We work hard to provide a welcoming atmosphere where everyone may flourish, have a sense of belonging, and collaborate effectively. As an equal opportunity employer, we do not tolerate any illegal discrimination against job applicants based on their race, color, religion, veteran status, sex, parental status, gender identity or expression, transgender status, sexual orientation, national origin, age, disability, or genetic information. We are committed to going above and above in creating diversity within our firm and following the regulations upheld by the EEOC.

Our Ideal Candidate: Skills and Qualifications:

8+ years of software engineering experience, with at least 3 years in an engineering leadership role (Engineering Manager, Director, or equivalent) where you managed engineers directly.

Deep, hands-on proficiency with Node.js, TypeScript and React in production environments. You can still architect a service, debug a gnarly issue, and ship a feature.

Strong experience with AWS core services (Lambda, RDS, DynamoDB, CloudWatch, S3, ECS, CloudFormation, CDK) and cloud-native architecture patterns.

Demonstrated experience managing mixed teams—coordinating across in-house engineers and external contractors or agencies.

Familiarity with agentic or autonomous system frameworks and a genuine interest in exploring how AI-driven workflows can improve engineering productivity and product capabilities.

Familiarity with Ruby on Rails or similar frameworks is a plus for maintaining legacy services during migration.

Solid database experience (PostgreSQL, DynamoDB, MySQL) and comfort designing data models, writing performant queries, and managing schema migrations.

Experience designing and scaling RESTful APIs (GraphQL experience is a bonus), with a strong understanding of authentication, authorization, and API security.

A track record of establishing or improving engineering processes—sprint planning, code review practices, CI/CD, incident management—in a growing organization.

Excellent communication skills. You can translate between technical depth and business context, and you build trust across functions.

A pragmatic, low-ego leadership style. You are comfortable rolling up your sleeves when the team needs it, and you empower others to do their best work.