Head of Engineering

LeafLink

Head of Engineering leading LeafLink’s B2B cannabis platform. Shaping technical strategy, scaling engineering teams, and delivering reliable cloud-native software.

Posted 8/14/2026full-timeRemote • 🇺🇸 United StatesLead💰 $240,000 - $270,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in leading engineering organizations, establishing technical architecture, and managing security and compliance programs. Proven ability to translate strategic objectives into actionable engineering roadmaps while fostering a strong engineering culture.

Highest-signal resume keywords

12+ Years Software Engineering Experience7+ Years Leading Engineering ManagersAWS-Managed Services ExpertiseExperience with Infrastructure as CodeStrong Experience with CI/CD Tooling

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Technical ArchitectureEngineering Organization DevelopmentBudget ManagementAPI ManagementCode Quality PracticesOperational LeadershipTechnical Vision SettingRisk ManagementDistributed SystemsSecurity Compliance (SOC 2)

Soft Skills

Strategic ThinkingCommunication with ExecutivesTalent DevelopmentTeam LeadershipContinuous Improvement Mindset

Tools & Technologies

AWS (EKS, ECR, R53, SES, ElastiCache, RDS)TerraformAnsibleDockerKubernetesJenkinsCircleCIArgoCDSpinnaker

Industry Keywords

Marketplace PlatformsEnterprise PlatformsHigh-Growth EnvironmentsMission-Critical EnvironmentsEngineering Metrics

Tech Stack

Tools & technologies

AnsibleAWSCloudDistributed SystemsDockerJenkinsKubernetesSpinnakerTerraform

About the role

Key responsibilities & impact

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

What you’ll need

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

Comp & perks

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