Engineering Manager, LeafLink
$200-215k
+ A robust stock option plan that gives employees a direct stake in LeafLink’s success
React
AWS
Docker
Kubernetes
TypeScript
JavaScript
Node.js
Senior and Expert level
Remote from US
Wholesale marketplace for legal cannabis
Be an early applicant
Wholesale marketplace for legal cannabis
101-200 employees
B2BMarketplaceLogisticsPaymentsSupply ChainWellbeingeCommerce
Be an early applicant
$200-215k
+ A robust stock option plan that gives employees a direct stake in LeafLink’s success
React
AWS
Docker
Kubernetes
TypeScript
JavaScript
Node.js
Senior and Expert level
Remote from US
101-200 employees
B2BMarketplaceLogisticsPaymentsSupply ChainWellbeingeCommerce
Company mission
To provide growing cannabis businesses with the tools they need to manage their businesses more effectively and accelerate growth.
Role
Who you are
- 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
- 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
What the job involves
- 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
- 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
Our take
Cannabis is the most widely produced and consumed drug in the world, but until relatively recently this market remained underground. An increasing number of US states, however, are opting to legalize cannabis, opening up a highly lucrative market opportunity that businesses are looking to capitalize on.
LeafLink has cemented its position as one of the major supply chain players in the growing legal cannabis market, connecting suppliers with retailers through its wholesale eCommerce marketplace. Currently, it commands over half of the US cannabis market, as well as having strong VC backing, and surpassing the $1B transaction threshold.
Since 2016, it has helped over 12,000 companies in 37 states build relationships, process payments, and ship products to retail, and it isn't slowing down any time soon. The company acquired Leaf Trade and Dama Financial, putting it in an even greater leadership position within the cannabis industry. Now the company looks set for an even greater future.
Steph
Company Specialist at Welcome to the Jungle
Insights
Top investors
74% employee growth in 12 months
Company
Funding (last 2 of 7 rounds)
Feb 2023
$100m
SERIES D
Jul 2021
$40m
SERIES C
Total funding: $229m
Company benefits
- Healthcare, dnetal, and vision coverage
- 401k plan
- Company equity
- Unlimited PTO + 5 days of Volunteer Time Off (VTO)
- Learning and development stipend
Company HQ
Financial District, New York, NY
Leadership
Ashwin Raj
(CEO)Previously President & CEO at ezCater,Executive Vice President at Lyft,Director at Amazon Payments and was the Vice President of Global Products at Visa.
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