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Director of Engineering


Leaflink is seeking a Director of Engineering over our core platform to join our remote-friendly team, headquartered in NYC, who is passionate about working with teams rapidly solving interesting and large-scale problems.

This role will primarily be responsible for owning the infrastructure, the technical foundation for our user-facing applications, and security roadmaps. They will also focus on team growth and the partnership between DevOps, QA, Engineering, and IT stakeholders to ensure our platform and processes meet our organization’s needs to build and serve high-quality and reliable products to our customers. 

As a member of our engineering team, you will have a direct and lasting impact everywhere in the business. Your contribution will be immediate and have positive ripple effects across not only our business but each customer’s business, as well!

This role will be the leader of our new Platform team that brings our existing app platform, SDETs, DevOps, and Cloud Engineers together as one team and one platform that focuses on the performance, reliability, quality, security, and scalability of our systems and infrastructure while enabling product teams to build rapidly and efficiently.

As the Director overseeing this crucial function and team, your role has the opportunity to help shape and grow the team, strategy, and processes as a whole. You will 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. It’s an exhilarating time to join our engineering team!

Ideal candidates for this position should possess a keen mind for solving unique challenges with fitting solutions and partnering effectively with various team members along the way. They should be personable, efficient, flexible, and communicative, have a strong desire to implement change, grow, mature, and have a passion and love for their work. This role comes with the opportunity to be a high performer within a fast-paced, dynamic, and quickly growing department.

What You’ll Be Doing

  • Work with the VP of Engineering, Principal Engineer of Platform, and department stakeholders to properly plan short and long-term goals and execute a technical roadmap that continues to evolve LeafLink’s infrastructure and core Platform capabilities and functionality to meet the needs of our platform users
  • Communicate effectively with engineering and product leadership to manage expectations, remove blockers, and ensure adequate resourcing to meet commitments
  • Advise technical and non-technical leadership on technical product strategy, quality and reliability vulnerabilities, and what is needed to scale current products, keeping in mind TCO and current capabilities
  • Mentor and manage a team of engineers and managers, focusing on both their day-to-day responsibilities as members of the Platform team and also their career growth, interpersonal and leadership skills, and future-facing goals
  • Plan, lead, and help ensure the delivery of projects, partnering closely with technology peers and external stakeholders
  • Oversee the architectural design and development objectives and processes for our growing suite of tools and services based on a flexible infrastructure and architecture roadmap alongside your IC leaders 
  • Successfully see the rollout of our new testing automation framework that enables product engineering to plug and play into and improves the overall test coverage of our distributed architecture and experiences
  • Establish clear goals and success criteria for the various projects being worked on so KPIs can be measured and reported accurately to determine project health
  • Participate in and lead quarterly goal planning and execution sessions with both your direct reports and your peers, working closely with tech leadership to craft challenging but reachable goals for each
  • Interview and contribute to the growth of the LeafLink engineering org, focusing on finding and then retaining candidates that will continue to elevate and diversify our ever-expanding set of in-house engineering talent
  • Partner effectively with other teams within engineering and IT that are responsible for supporting our security and additional products and business lines today
  • Help cultivate and advance a collaborative culture that values ownership and finding the best solution to a given problem while also emphasizing the importance of automation and enablement
  • Give our product and data engineering teams a best-in-class user experience through an internal developer platform that encompasses developer documentation, automation, toolchains, libraries, and workflows that developers use to write, test, and roll out their code with efficiency
  • Experience managing SOC 2 Controls and assisting on audits

What You’ll Bring to the Team 

  • 10+ years of experience in software development roles with a proven record of working with DevOps, SRE, Cloud, and QA teams
  • 5+ years of experience leading teams and managing individuals, including managers.
  • Experience with strategic planning and technical road mapping that takes into account business and product stakeholders
  • A passion for building and retaining teams of individuals who are highly motivated and excited about the work they’re contributing to
  • Extensive experience communicating estimations and project visibility to senior management and stakeholders
  • Experience managing project processes, resourcing, timelines, and delivery efforts with cross-functional teams
  • Experience working in and advocating for agile environments
  • Extensive experience working within AWS and with its managed products (EKS, ECR, R53, SES, Elasticache, RDS, etc.)
  • Strong experience working with infrastructure as code (Terraform, Ansible, etc.)
  • Strong experience with containers (Docker, Compose, ECS, Kubernetes)
  • Strong experience with various managed and self-hosted CI/CD tooling (Jenkins, Travis, CircleCI, Spinnaker, Harness, Flux, ArgoCD, etc.)
  • Strong experience with API Management and Gateway tools (Kong, AWS Gateway, Mulesoft, Postman, etc.)
  • Extensive experience working in service-oriented, API-driven application tech stacks and working knowledge of the challenges and gotchas that can bring to the SDLC
  • Exceptional written and oral communication skills
  • Exceptional documentation skills
  • Experience with vendor and cost management
  • Experience driving efficiencies through automation, toolchains, and workflows developers use to write, test, and roll out their code
  • Passionate about data-driven decision-making and continuous iteration and delivery
  • Experience working with and leading teams within e-commerce, B2B, and their ancillary systems as well as their mobile counterparts a plus

LeafLink Perks & Benefits

  • 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.

Base Salary Range

$230,000—$270,000 USD

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