Chief of Staff

Company Overview

@‌woods is where teams escape the noise, reconnect with nature, and unlock their full potential. Our next-gen resorts combine immersive learning, meaningful team-building, and the restorative power of the outdoors. Our private tech retreats are being developed worldwide and are designed exclusively for team building, networking, learning, coding, planning and creating breakthroughs.

Our first retreat location, a 130-acre facility in the Catskills, will be opening in fall 2026.

Position Overview

@woods is seeking a dynamic Chief of Staff to work closely with Founder and CEO Jessica Rovello, a seasoned and visionary entrepreneur with a proven track record of building and scaling successful companies. Jessica’s leadership as the co-founder of Arkadium, a company celebrated for its innovative culture and sustained growth, exemplifies her commitment to creating meaningful businesses that thrive. This is a rare opportunity to join @woods at the ground level, collaborating with a founder whose reputation as a trailblazer is matched only by her passion for revolutionizing the future of work.

Initially, this role will be part-time (three days per week), with plans to transition to full-time in Q3 2025. As Chief of Staff, you’ll help scale operations, support fundraising efforts, and act as a strategic partner to the CEO. No two days will be the same—this role offers exposure to all aspects of the business, from design and business development to marketing and HR. It’s an unparalleled opportunity for someone eager to help shape the future of work.

Key Responsibilities

• Organization and Collaboration: Collaborate with Jessica to prioritize initiatives, and translate ideas into actionable plans that drive the business forward.
• Fundraising Support: Play a pivotal role in preparing and managing fundraising efforts, including market analysis, managing investor-ready materials, and engaging potential investors and lenders to secure resources for growth.
• Research & Analysis: Conduct research on industry trends, competitors, and market opportunities, offering insights that inform @woods’ strategies and decisions.
• Operational Scaling: Design and implement systems and processes to streamline operations, ensuring the company is equipped for rapid growth.
• Partnership Development: Identify, establish, and nurture collaborative partnerships with various stakeholders, organizations, and community entities.

Qualifications

• Experience: A minimum of 5 years in a strategic or operational role, ideally within the tech industry or a startup environment. Knowledge of fundraising is preferred; experience in real estate or hospitality is a bonus.
• Skill Set: Exceptional organizational, communication, and project management skills, with a proven ability to juggle multiple priorities and execute tasks with precision.
• Entrepreneurial Spirit: Self-motivated, adaptable, and comfortable with ambiguity. You’re not afraid to wear multiple hats and embrace new challenges with enthusiasm and a bias for action.
• Mission-Driven: A deep passion for @woods’ vision of blending team development and nature to support tech companies in building a better future.

Why Join @woods?

This role offers more than just a job; it’s a chance to help shape an entirely new way of working. Guided by Jessica Rovello’s expertise and backed by a mission-driven approach, you’ll be an integral part of building a business that redefines team connection and innovation. If you’re ready to take on this once-in-a-lifetime opportunity, we’d love to hear from you.

This is an in-person role in the Flatiron neighborhood in New York City