Engineering Manager at LeafLink in Remote

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 an Engineering Manager to lead a team of engineers building and evolving the technology that powers our eCommerce marketplace. This role combines people leadership, technical leadership, and delivery ownership, with responsibility for guiding a team through complex technical decisions and ensuring the successful delivery of high-quality products and systems. As an Engineering Manager, you will serve as the technical leader for your team, working closely with engineers, Product Management, Design, and other stakeholders to translate business priorities into sound technical solutions. You will establish technical direction, guide architectural decisions, identify risks and dependencies, and ensure the team has the clarity and support needed to execute effectively. This is not a traditional individual contributor role, but it is a deeply technical one. You will be expected to understand your team's systems, participate meaningfully in design and architecture discussions, review critical technical decisions, and provide hands-on technical guidance when needed. Your primary leverage comes through the team: setting direction, developing engineers, improving execution, and creating an environment where strong technical work can happen consistently. You will work across modern frontend and backend technologies and architectural patterns, including TypeScript, React, Node.js, Python, containerized and serverless applications, Kubernetes, AWS managed services, event-driven systems, third-party integrations, and service-oriented architectures. The ideal candidate combines strong engineering judgment with effective people leadership and operational discipline. You should be comfortable navigating ambiguity, leading complex initiatives, balancing product delivery with long-term technical health, and creating alignment across engineering and product teams. What You’ll Be Doing Lead, mentor, and manage a team of engineers, supporting their day-to-day effectiveness, technical growth, career development, and long-term goals. Serve as the technical leader for your team, establishing technical direction and ensuring engineers make sound architectural and software design decisions. Maintain a deep understanding of your team's systems and technical domain, providing meaningful guidance on architecture, implementation strategy, scalability, reliability, security, and operational readiness. Partner closely with Product Management to define roadmaps, sequence initiatives, identify dependencies, and develop realistic short- and long-term delivery plans. Translate product and business objectives into clear technical strategies, ensuring the team understands not only what it is building but why and how the pieces fit together. Lead the technical planning and execution of complex initiatives from initial discovery and design through implementation, release, and production operation. Work with engineers and technical leaders to ensure appropriate investment in platform health, technical debt, scalability, security, reliability, observability, and developer efficiency alongside product priorities. Identify technical risks, assumptions, dependencies, and delivery constraints early, and work with Product and Engineering leadership to make informed tradeoffs and adjust plans when necessary. Drive accountability for team commitments while creating an environment where risks and challenges are surfaced early and addressed constructively. Coordinate with other Engineering Managers, Staff Engineers, and technical leaders to manage cross-team dependencies and ensure architectural consistency across the broader platform. Establish and evolve engineering practices and architectural standards that address the unique complexities of LeafLink's business while complementing broader organizational standards. Improve team effectiveness by using delivery metrics, retrospectives, operational data, and qualitative feedback to identify bottlenecks and drive meaningful improvements. Ensure the team maintains a healthy, well-understood backlog with sufficient technical discovery and refinement to support predictable execution. Participate in incident response and production troubleshooting, providing technical leadership during complex incidents and ensuring systemic improvements are identified and implemented. Recruit, interview, onboard, and retain strong engineering talent while building an inclusive environment where engineers can do their best work. Foster a culture of technical excellence, ownership, collaboration, pragmatic decision-making, and continuous improvement. What You’ll Bring to the Team Demonstrated experience leading engineering teams and creating measurable impact through technical direction, people development, and effective execution. Strong technical judgment and the ability to guide architecture, system design, and implementation decisions without needing to personally own every line of code. A proven track record of leading complex technical initiatives from ambiguous problem definition through successful production delivery. Experience developing engineers across multiple career stages, including coaching senior engineers and helping technical leaders expand their influence and impact. Strong experience with modern full-stack application development, including frontend applications, backend services, APIs, distributed systems, and data stores. Experience with modern JavaScript and TypeScript ecosystems, including technologies such as React and Node.js. Experience designing, building, or leading teams responsible for service-oriented, API-driven, event-driven, or distributed architectures. Strong understanding of relational databases, asynchronous processing, messaging systems, third-party integrations, and transactional workflows. Experience incrementally modernizing legacy systems while continuing to deliver customer and business value. Experience balancing product delivery with investments in technical debt, scalability, security, reliability, observability, and developer productivity. Strong delivery and project leadership skills, including roadmap planning, dependency management, risk identification, estimation, sequencing, and cross-functional coordination. Experience using delivery and operational metrics to identify patterns, improve team effectiveness, and increase predictability without reducing engineering work to simplistic productivity measurements. Experience with cloud-native infrastructure and modern delivery practices, including AWS, Docker, Kubernetes, serverless technologies, CI/CD, and infrastructure automation. Experience with eCommerce, B2B marketplaces, financial systems, or other transaction-heavy platforms is strongly preferred. Experience working in highly regulated industries with significant compliance requirements—such as cannabis, healthcare, financial services, or payments—is a plus. Strong written and verbal communication skills, with the ability to explain complex technical decisions, build alignment, navigate disagreements, and communicate effectively with both technical and non-technical stakeholders. Exceptional critical thinking and analytical skills, with the ability to quickly understand complex systems, identify underlying problems, and drive pragmatic solutions. A leadership approach that creates accountability, develops technical talent, and enables engineers to take increasing ownership of complex problems. LeafLink Perks & Benefits Flexible PTO—you’re going to be working hard, so enjoy time off with no cap. A robust stock option plan that gives employees a direct stake in LeafLink’s success. Five days of Volunteer Time Off (VTO), supporting employees who want to give back and cultivate stronger communities. Competitive compensation and 401(k) match. Comprehensive health coverage, including medical, dental, and vision benefits. Commuter benefits through our Flexible Spending Account. LeafLink’s employee-centric culture has earned recognition as one of Built In NYC’s Best Places to Work. Join us in building the technology infrastructure that powers the regulated cannabis supply chain. LeafLink’s employee-centric culture has earned us a coveted spot onBuiltInNYC’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 Ordershere. Base salary range $200,000—$215,000 USD