Head of Engineering

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LeafLink

WebsiteLinkedInAll Job Openings

201 - 500 employees

Founded 2016

📦 Logistics

📣 Marketing

💼 Consulting

💰 $100M Series D on 2023-02

Logistics • Marketing • Consulting

LeafLink is a leading technology platform that connects cannabis businesses for modern, wholesale e-commerce. LeafLink facilitates streamlined commerce by providing a platform for brands to increase exposure, process orders from buyers, and access analytics. For retailers, it offers the ability to discover new products and order all brands in one online cart for free. LeafLink's ecosystem includes marketplace solutions, payments, logistics, advertising, and insights to optimize workflows for both brands and retailers. Catering specifically to licensed, wholesale cannabis operators, LeafLink simplifies processes such as payment tracking and order management, leveraging integrations with top ERP and CRM systems. Operating in over 30 markets primarily in the United States, LeafLink stands as a central hub for wholesale cannabis transactions.

📋 Description

• Translate company, product, and technology objectives into a 1–3-year engineering plan, operating model, organizational structure, and execution roadmap • Lead rebuild-versus-refactor decisions for platform enhancement and integration across platforms • Create the engineering organizational structure and lead the engineering team • Recruit, develop, and retain engineering talent • Set engineering-wide standards for planning, estimation, and delivery • Establish engineering metrics, operating rhythms, and governance for executive visibility • Own technical architecture, infrastructure, security, technical debt, speed, and long-term stability • Improve engineering velocity while reducing technical debt and operational risk • Partner with product and business stakeholders to translate customer requirements into engineering priorities and roadmap decisions • Manage the engineering budget, including headcount, vendors, tooling spend, and cloud cost • Establish practices for code quality, testing, CI/CD, and on-call/incident response • Own SOC 2 and broader security/compliance posture, partnering with IT and external auditors • Establish feedback loops, retrospectives, postmortems, and engineering-wide metrics for continuous improvement • Build and protect engineering culture as headcount grows • Champion agentic AI, LLM-powered code generation, and multi-agent orchestration

🎯 Requirements

• 12+ years of experience in software engineering • 7+ years leading engineering managers • Experience with marketplaces or enterprise platforms and large-scale infrastructure or distributed systems • Experience building an engineering organization from the ground up or through a major scaling inflection point • Strong track record setting technical vision and translating it into trusted executive and board-level roadmaps • Technical depth, strategic thinking, and operational leadership • Experience communicating engineering strategy, risk, and resourcing to non-technical executives and board members • Experience building and scaling engineering organizations in high-growth or mission-critical environments • Hands-on background with AWS-managed services, including EKS, ECR, R53, SES, ElastiCache, and RDS • Experience with infrastructure as code using Terraform and Ansible • Experience with Docker and Kubernetes • Experience owning security and compliance programs, including SOC 2 controls and audit management • Strong experience with CI/CD tooling and practices, such as Jenkins, CircleCI, ArgoCD, or Spinnaker • Experience with API management and service-oriented, API-driven architectures • Ability to manage budgets, vendor relationships, and engineering cost efficiency • Passion for developing managers and engineers

🏖️ Benefits

• Flexible PTO with no cap • Stock option plan • 5 days of Volunteer Time Off (VTO) • Competitive compensation • 401k • Comprehensive health coverage (medical, dental, vision) • Commuter Benefits through a Flexible Spending Account