Deputy Chief of Staff

Curaleaf•Stamford, CT

2d•Onsite

About The Position

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.

Requirements

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

Nice To Haves

MBA or advanced degree preferred.

Responsibilities

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.