LeafLink - Engineering Manager
Requirements
• 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.
Responsibilities
• 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.
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 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. • $200,000—$215,000 USD
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