Senior Director of IT

LeafLink New York, NY, USA 2022-01-27 $150k - $270k -
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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 $4.4 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 Built In NYC's 'Best Places to Work in 2021', as well as one of Fast Company's 'Top 10 Most Innovative Companies in Enterprise for 2020', joining the ranks of Amazon, Slack, and VMWare - and we're just getting started!

What We're Looking For

LeafLink is seeking a Senior Director of IT to join our growing Tech organization who is passionate about working on teams that solve interesting, large-scale problems at a rapid pace. As the leader of the IT function at LeafLink, you will be in a position to have a direct, lasting impact everywhere that technology powers our business.

LeafLink's IT footprint has grown considerably over the past year and we're looking to expand our IT leadership to include someone who can focus on the evolution of our IT practice, grow and mentor a team of highly-engaged, passionate individuals, and ensure the needs of our workforce are consistently met or exceeded. It's a very exciting time to join our team!

Ideal candidates for this position should possess a keen mind for solving tough problems with the ideal solution, partnering effectively with various team members along the way. They should be personable, efficient, flexible, and communicative, possess a strong desire to implement change, growth, and maturity, and have a passion and love for what they do. This role comes with the opportunity to be a high performer within a department that's fast-paced, dynamic, and quickly growing in all areas.

What You'll Do

• Manage daily operations of the IT department in close partnership with the VP of Engineering and People Operations team and to properly plan short and long-term goals and execute on a technical roadmap that continues to evolve LeafLink's IT infrastructure

• Communicate effectively with department leadership to manage expectations, remove blockers, and ensure adequate resourcing to meet commitments

• Mentor and manage a team of managers and IT professionals, focusing on both their day-to-day responsibilities as members of the IT department and also their career growth, interpersonal and leadership skills, and future-facing goals

• Ensure seamless onboarding for new hires to LeafLink's existing IT systems and hardware

• Ensure seamless day-to-day operations for all LeafLink staff members from a technological perspective

• 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 OKR planning and execution sessions with both your direct reports and your business stakeholders, working closely with department leadership to craft challenging-but-reachable goals for each

• Automate manual tasks; create and improve small tools that help make team operations more efficient

• Interview and contribute to the growth of the IT org, focusing on finding and then retaining candidates that will continue to elevate and diversify our ever-expanding set of in-house talent


• A strong leader with proven experience building teams and applications that drive a company forward in its objectives and initiatives

• Experience with strategic planning and technical roadmapping that takes into account business and product stakeholders

• A passion for building and retaining teams of individuals that are highly motivated and excited about the work they're contributing to

• Extensive experience communicating estimations and project visibility to senior management and stakeholders

• Exceptional written and oral communication skills

• Expert knowledge of hardware technology, concepts, and connectivity

• Expert knowledge of networking principles and how to apply them in a business setting

• Extensive experience with office expansion, A/V setup and maintenance, remote work tooling and support, helpdesk operations, and other IT lifecycle workflows

• Proven track record of practical, thoughtful problem solving

• An interest in the cannabis industry and/or the LeafLink brand


• Flexible PTO to give our employees a little extra R&R when they need it

• Competitive compensation and 401k

• Comprehensive health coverage (medical, dental, vision)

• Commuter Benefits through a Flexible Spending Account

• A robust stock option plan to give our employees a direct stake in LeafLink's success

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