Chief of Staff

Job Description:

Yutori Method™ is managing the recruitment for this role.  

This position is a full-time, in-person leadership role based in Frederick, MD. Candidates must be willing to commute.

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About the Key Ventures

TCS Interpreting and Captioning — A leading provider of American Sign Language (ASL) interpreting and captioning services, TCS delivers high-quality, reliable language access solutions for clients across sectors. Known for its professionalism, accuracy, and commitment to accessibility, TCS serves as a trusted partner for organizations requiring clear and effective communication for Deaf and hard-of-hearing communities.  

Young Entrepreneur Council (YEC) — An exclusive, invitation-only community for high-achieving entrepreneurs. YEC provides members with access to a trusted network, publishing opportunities, private events, and a robust suite of business resources designed to accelerate success.

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About the Role

This is a unique and exciting opportunity for a high-caliber operator to serve as the true right hand to a successful entrepreneur, guiding the future of multiple thriving businesses including TCS Interpreting and Captioning, YEC, and other ventures. The Chief of Staff will shape priorities, lead strategic projects, and drive alignment across diverse business models — translating vision into action, managing cross-functional execution, and protecting the CEO’s time for her highest-leverage work.  

If you are execution-first, thrive in fast-paced, multi-venture environments, and can lead with discretion, clarity, and trust, this role offers the chance to make a lasting impact and grow long term.

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What You’ll Do

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1. Business Development  

• Lead strategic planning and go-to-market execution for multiple ventures.  
• Drive new revenue opportunities through partnerships, events, and brand expansion.  
• Oversee market research and performance reporting to inform business decisions.

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1. Operations  

• Design and optimize systems, workflows, and SOPs across ventures.  
• Implement and manage tools for project management, CRM, and analytics.  
• Resolve cross-functional bottlenecks to ensure on-time, high-quality delivery.

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1. People Leadership  

• Lead and coach key team members, ensuring accountability and alignment.  
• Oversee hiring, onboarding, and role optimization across ventures.  
• Monitor morale and performance, making proactive adjustments to strengthen culture.

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1. CEO Enablement  

• Manage the CEO’s priorities, time allocation, and delegation decisions.  
• Prepare the CEO for high-stakes meetings, communications, and events.  
• Oversee personal and household systems to free the CEO for strategic work.

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Knowledge & Skills

• EOS or similar framework (REQUIRED)  
• Project management, CRM systems, budgeting, KPI tracking (REQUIRED)  
• Business plan & go-to-market development (REQUIRED)  
• Google Suite, Microsoft Suite, Asana (REQUIRED)  
• ChatGPT or similar AI tools (INTERMEDIATE)  
• Familiarity with ASL/Deaf culture (PREFERRED)

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Logistics & Compensation

• Location: hybrid or remote and comfortable traveling 1-2x per quarter to office (office is in Frederick, MD)  
• Compensation: $100,000 – $130,000 base + performance bonus  
• Benefits: Comprehensive benefits package shared with finalists; participation in leadership training and programs  
• Work Hours: 9:00 AM – 5:00 PM EST (flexibility required)  
• Authorization: Must be authorized to work in the U.S. without sponsorship