Deputy Chief of Staff

At Curaleaf, we’re redefining the cannabis industry with a strong commitment to quality, expertise, and innovation. As a leading global cannabis provider, our brands—including Curaleaf, Select, and Grassroots—offer premium products and services in both medical and adult-use markets.

Join us at Curaleaf to be part of a high-growth, purpose-driven company that champions corporate social responsibility through our Rooted in Good initiative, supporting community outreach and positive change. Here, you’ll have the opportunity to make a meaningful impact, drive innovation, and help shape the future of cannabis.

Title: Deputy Chief of Staff

Location: Stamford, CT (on-site)

About the Role:  

The Deputy Chief of Staff is a strategic partner to the CEO and Executive Leadership Team, helping drive the organization’s most important priorities from strategy through execution. This high-impact role sits at the center of the business, working across functions to create alignment, accelerate decision-making, and ensure critical initiatives move forward.

The ideal candidate is a highly strategic, analytical, and results-oriented leader who thrives in a fast-paced environment and can move seamlessly between big-picture thinking and hands-on execution. This role offers broad exposure to the business and the opportunity to work closely with senior leaders on initiatives that have meaningful enterprise-wide impact.

What You’ll Do:

• Partner closely with the CEO and Executive Leadership Team to drive execution of strategic priorities and key business initiatives.
• Lead high-impact, cross-functional projects from strategy and planning through execution and delivery.
• Coordinate and drive accountability around Executive Leadership Team priorities, ensuring alignment, clear ownership, and progress against key objectives.
• Prepare executive briefings, presentations, Board materials, and other strategic communications for senior leadership.
• Monitor enterprise KPIs and business performance, identifying trends, risks, and opportunities to inform executive decision-making.
• Translate complex business challenges and data into clear insights, recommendations, and actionable solutions.
• Build strong relationships and influence leaders across functions to drive alignment and execution.
• Identify roadblocks, anticipate risks, and work collaboratively across the organization to remove barriers and improve organizational effectiveness.
• Support special projects and strategic initiatives on behalf of the CEO and Executive Leadership Team.

What You’ll Bring:

• 5–10 years of progressive leadership experience, with a track record of increasing responsibility and impact.
• Strong strategic thinking and business acumen, with the ability to understand the broader business while maintaining a focus on execution.
• Proven experience leading complex, cross-functional initiatives and influencing stakeholders without direct authority.
• Exceptional analytical and problem-solving skills, with the ability to synthesize complex information and develop clear, actionable recommendations.
• Strong executive communication skills, including experience developing presentations, executive briefings, and other materials for senior leaders.
• Ability to build trust and credibility with leaders and stakeholders across all levels of an organization.
• Demonstrated judgment, accountability, integrity, discretion, and a strong results orientation.
• Highly organized with the ability to manage multiple priorities in a dynamic, fast-paced environment.
• Bachelor’s degree required; MBA or advanced degree preferred.

Why This Role?

This is an opportunity to work at the center of the organization and partner directly with senior leadership on some of the company’s most important priorities. The Deputy Chief of Staff will gain broad enterprise exposure, tackle complex business challenges, and play a critical role in turning strategy into results.

Connecticut Hiring Range$150,000—$175,000 USD

What We Offer:

• Career Growth Opportunities
• Competitive Pay and Benefits
• Generous PTO and Parental Leave
• 401(K) Retirement Plan
• Life/ Disability Insurance
• Community Involvement
• Referral Bonuses and Product Discounts

Benefits vary by state, role type, and eligibility.  

Follow us on Social Media: 
Instagram: @curaleaf.usa
Twitter: @Curaleaf_Inc
LinkedIn: Curaleaf LinkedIn

Curaleaf Holdings, Inc. (TSX: CURA) (OTCQX: CURLF) ("Curaleaf") is a leading international provider of consumer products in cannabis with a mission to enhance lives by cultivating, sharing, and celebrating the power of the plant. As a high-growth cannabis company known for quality, expertise and reliability, the Company, and its brands, including Curaleaf, Select, Grassroots, Find, and Anthem provide industry-leading service, product selection and accessibility across the medical and adult-use markets. Curaleaf International is powered by a strong presence in all stages of the supply chain. Its unique distribution network throughout Europe, Canada and Australasia brings together pioneering science and research with cutting-edge cultivation, extraction and production. Home | Curaleaf | Cannabis with Confidence

Our Vision: To be the world's leading cannabis company by consistently delivering superior products and services and driving the global acceptance of cannabis. 

Our Values:

• Lead and Inspire.  
• Commit to Win.  
• ONE Curaleaf.  
• Driven to Deliver Excellence.  

Curaleaf is an equal opportunity employer. Curaleaf recruits, employs, trains, compensates, and promotes regardless of race, religion, color, national origin, gender identity, sexual orientation, physical ability, age, veteran status, and other protected status as required by applicable law.

We will ensure that individuals with disabilities are provided reasonable accommodation to participate in the job application or interview process, to perform essential job functions, and to receive other benefits and privileges of employment. Please contact us to request accommodation.

Individuals adversely impacted by the war on drugs are encouraged to apply.

Current Curaleaf employees should apply for open positions through our Internal Job Board, which can be accessed via the link on The Leaf. 

***Please note that U.S. immigration rules and regulations are governed by federal law; not state law.  Although Curaleaf operates in states that have legalized and decriminalized marijuana, it is still considered a controlled substance under federal regulations and thus illegal under federal law. For this reason, unless and until federal law changes, Curaleaf is prohibited from offering sponsorship for any non-immigrant or immigrant visas. 

***Please also note that while candidates who are Lawful Permanent Residents (such as those with Green Cards) are eligible for employment with, and are hired by Curaleaf, working for a company engaged in a business that grows and sells a product that is illegal under federal law might compromise the candidate’s immigration status. Before a Lawful Permanent Resident accepts an offer of employment, Curaleaf recommends that the candidate seek the advice of an immigration lawyer.