Head of Engineering

The Role

LeafLink is seeking a Head of Engineering to lead our entire engineering organization. This role owns the technical vision, architecture, and health of every engineering function and is accountable for how well our teams turn strategy into shipped, reliable software. You'll report directly into executive leadership, partner closely with Product, and represent engineering at the leadership table.

As Head of Engineering, you are the senior-most technical leader responsible for building the org itself: hiring and developing engineering managers, setting standards for how we plan and execute, and making the calls on architecture, tooling, and headcount that determine whether we can keep moving fast without breaking things. You'll work with modern technologies and concepts such as containerized and serverless design patterns, Python, Kubernetes, AWS-managed and self-hosted services, third-party integrations, and event-driven and distributed architectures. This is a rare opportunity to shape not just a roadmap, but the operating model of an engineering org at a pivotal size, big enough to need real structure, small enough that one leader can still touch everything that matters.

Ideal candidates possess a strategic mind for solving unique challenges with fitting solutions, and a track record of building high-performing teams and the managers who run them. They should be personable, decisive, flexible, and communicative, with a strong desire to implement change, grow the org thoughtfully, and bring a genuine passion for their craft. This role comes with the opportunity to define engineering leadership at a fast-paced, dynamic, and quickly growing company.

What You'll Be Doing

• Translate company, product, and technology objectives and goals into a 1 - 3-year engineering plan, operating model, organizational structure, and execution roadmap. Lead rebuild versus refactor decisions related to platform enhancement and integration across all of our platforms
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• Create the right engineering organizational structure and lead the engineering team. Recruit, develop, and retain top engineering talent and set the bar for how the engineering team operates day to day
• Set engineering-wide standards for planning, estimation, and delivery, and hold teams accountable to them without turning process into bureaucracy
• Establish engineering metrics, operating rhythms, and governance that provide executive visibility into execution. Own and manage the technical architecture, infrastructure, security and  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, ensuring engineering capacity, sequencing, and constraints are represented in roadmap decisions and the team delivers features that have measurable customer impact and move adoption., ensuring 
• Manage the engineering budget: headcount planning, vendor and tooling spend, and cloud cost, with a clear view of TCO
• Establish company-wide engineering practices for code quality, testing, CI/CD, and on-call/incident response as the team scales past the size where informal norms hold
• Own SOC 2 and broader security/compliance posture across engineering, partnering with IT and any external auditors
• Create long-term sustainable mechanisms such as feedback loops, retros, postmortems, and eng-wide metrics for continuous improvement across performance, scale, delivery and org health.
• Build and protect engineering culture as headcount grows: the norms around ownership, blameless problem-solving, and technical excellence that are easy to lose past 80 people
• Champion agentic AI, LLM-powered code generation, and multi-agent orchestration to reimagine how services are built and operated at scale, compressing delivery timelines and raising engineering velocity.

What You'll Bring to the Team

• 12+ years of experience in software engineering, with 7+ years leading engineering managers (not just ICs)
• Experience in working in marketplaces or enterprise platforms and building and developing large-scale infrastructure or distributed systems. Experience in e-commerce, B2B SaaS, or marketplace businesses (and their mobile counterparts) a plus
• Direct experience building an engineering org from the ground up or through a major scaling inflection point, you've made the "when do we add a second team" calls before
• Strong track record setting technical vision and translating it into a roadmap that executive leadership and the board actually trust
• Strong balance of technical depth, strategic thinking, and operational leadership. Extensive experience communicating engineering strategy, risk, and resourcing to non-technical executives and board members
• Proven experience building and scaling engineering organizations in high-growth or mission-critical environments balancing execution versus management
• Hands-on background (even if not day-to-day anymore) with modern cloud-native architecture: AWS-managed services (EKS, ECR, R53, SES, ElastiCache, RDS, etc.), infrastructure as code (Terraform, Ansible), and containers (Docker, Kubernetes)
• Experience owning security and compliance programs, including SOC 2 controls and audit management
• Strong experience with CI/CD tooling and practices (Jenkins, CircleCI, ArgoCD, Spinnaker, or similar) and a point of view on developer experience
• Experience with API management and service-oriented, API-driven architectures, and the operational challenges they create at scale
• Proven ability to manage budget, vendor relationships, and cost efficiency for an engineering org
• A genuine passion for developing people, you measure your success by the managers and engineers who grow under you

• Flexible PTO - you’re going to be working hard so enjoy time off with no cap!
• A robust stock option plan to give our employees a direct stake in LeafLink’s success
• 5 Days of Volunteer Time Off (VTO) - giving back is important to us and we want our employees to prioritize cultivating a better community
• Competitive compensation and 401k
• Comprehensive health coverage (medical, dental, vision)
• Commuter Benefits through our Flexible Spending Account

LeafLink’s employee-centric culture has earned us a coveted spot on BuiltInNYC’s Best Places to Work for in 2021 list. Learn more about LeafLink’s history and the path to our First Billion in Wholesale Cannabis Orders here.