Head of Engineering

About LeafLink LeafLink is the largest unified B2B cannabis platform, providing licensed cannabis businesses a suite of tools to manage their business more effectively, sell or order from their favorite brands and accelerate growth. We are one platform, one solution and we’re defining the way thousands of cannabis brands, distributors, and retailers streamline their operations. With thousands of brands and retailers across 30+ markets in North America, we are setting the industry standard for how cannabis businesses grow together. LeafLink processes more than $5 billion in wholesale cannabis orders annually. Our team, backed by funding from leading VC's, including Founders Fund, Thrive Capital, Nosara Capital, and Lerer Hippeau is poised to define the cannabis supply chain through technology. LeafLink was named one of Inc. 5000’s ‘Top 5000 Fastest-Growing Private Companies’; one of Fast Company's 'Top 10 Most Innovative Companies in Enterprise for 2020', joining the ranks of Amazon, Slack, and VMWare; one of Built In NYC's 'Best Places to Work in 2021'; 2024 Fast Company’s Best WorkPlaces for Innovators for Banking, Finance, and Fintech category; 2024 Green Market Report Award for Best Fintech in cannabis - and we're just getting started! 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 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 eng…