Chief of Staff

Description:

Role Summary

The Chief of Staff is a high-impact strategic partner to the Founder & CEO and Head of Strategy & Innovation, playing a central role in driving clarity, alignment, and execution across Little Leaf's executive agenda. This role offers a unique opportunity to influence company-wide priorities, lead cross-functional initiatives, support key corporate development and product innovation workstreams, and shape the operating rhythm of a fast-growing organization.

An ideal candidate would be a strategic, analytical thinker who is enthusiastic about working across various functions and projects. This role provides direct exposure to senior leadership and is a launchpad for future leadership opportunities in strategy, operations, finance, or general management.

Core Responsibilities

Strategic Planning & Execution

• Assist the CEO is setting goals and driving execution across the organization
• Support the Head of Strategy & Innovation on key corporate development and product innovation initiatives (e.g. fundraising, product development pipeline, etc.)
• Prepare executive briefs, scenario analysis, financial models, and talking points for key decisions, board meetings, and other external events
• Craft SLT and company-wide communications as needed
• Help identify and optimize existing processes throughout the organization

Executive Operating Rhythm

• Manage annual board calendar and own the preparation of materials for quarterly and ad-hoc board meetings
• Plan, run, and continuously improve weekly SLT meetings
• Design, plan, and help facilitate quarterly SLT offsites
• Coordinate and track progress of quarterly strategic priorities
• Work with Data & Technology team to maintain and improve operating dashboards

Project Management Office (PMO) Leadership

• Lead project management for CEO-prioritized initiatives
• Govern the PMO processes to ensure timely delivery and completion of high-priority company initiatives
• Act as project manager for critical projects where there is no clear owner
• Work cross functionally to identify key project pain points and create solutions

Requirements:

Qualifications

• 4-6+ years of experience in management consulting, private equity, or in a business strategy, operations, or commercial role at a high-growth company
• Excellent analytical and problem-solving abilities with the capacity to synthesize complex information, identify insights, and develop actionable recommendations
• Strong interpersonal skills with the ability to build trust, influence, and foster alignment across diverse teams and senior leadership
• Strong financial literacy and exceptional written / verbal communication skills
• BA/BS required; MBA or relevant master’s degree is a plus
• Demonstrated interest in Little Leaf’s business, industry, and mission is a plus