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:

• Competitive Pay and Benefits
• Generous PTO and Parental Leave
• Life/ Disability Insurance
• Community Involvement
• Referral Bonuses and Product Discounts

Benefits vary by state, role type, and eligibility.

Curaleaf Holdings,…