Chief of Staff, Internal AI Optimization

Chief Of Staff

The COOL company is looking for a Chief of Staff to support the CEO and the rest of the executive team. This role consists of leading special projects, assisting in the development of various areas of business, and acting as a liaison for the CEO as needed. A key focus of this role is driving the company's AI-forward strategy including owning CRM systems powered by AI, integrating all Firefly company videos into an AI knowledge base to generate coaching outputs, and championing AI adoption across the organization.

About the Role

• Serve as truest advisor to Zack and the executive team, providing strategic guidance and supporting key initiatives
• Lead special projects across business development, operations, and strategic growth initiatives
• Efficiently manage key processes and systems, including email inbox, Slack, and other tools, resulting in increased productivity and operational efficiency
• Execute strategic projects and tasks for the CEO such as decks, business plans, and longer-term initiatives
• Communicate daily with the CEO to optimize the planning and execution of his various commitments and responsibilities
• Manage all administrative duties for the CEO, including owning the calendar and scheduling all meetings and events
• Serve as a key representative of the executive team both inside and outside of the company
• Handle confidential information, write correspondence, and support the CEO and teams across global time zones
• Coordinate travel and related logistics on behalf of the CEO
• Lead & organize quarterly team onsites
• Act as a liaison between the CEO and other key stakeholders, both internal and external
• Own and manage the company CRM with AI integration, ensuring the system is continuously optimized, data is clean and actionable, and AI-driven insights are surfaced to the executive team
• Lead the initiative to ingest all Firefly company videos into an AI knowledge base, enabling intelligent coaching and insights to be automatically surfaced to the team
• Oversee the pipeline that transforms Firefly video content into personalized coaching outputs delivered via email and broader team communications
• Champion AI adoption across the organization from identifying opportunities to automating workflows, enhancing productivity, and embedding AI tooling into day-to-day operations
• Lead projects do internal AI optimizations across the company
• Effectively integrate subsidiaries

Competencies

• 8–10 years in a role supporting executives and/or C-suites
• Very high EQ and people skills
• Creativity and open-mindedness
• Great project management skills
• Excellent written and verbal communication skills
• Ability to synthesize various viewpoints
• High empathy and ability to make team members feel heard and acknowledged
• Great listener and ability to absorb information
• Strategic thinking and problem-solving abilities
• Comfort with ambiguity and flexibility to adapt to changing priorities and deadlines
• Demonstrated experience with AI tools, CRM platforms, and emerging technology (strongly preferred)
• Ability to manage and implement AI-driven workflows and communications systems

Cultural Competencies

• Must be able to work primarily between the hours of 9:30 AM - 6:30 PM ET
• Must have a player/coach mentality, willing to both execute and lead
• Ability to juggle multiple projects concurrently and set and meet deadlines
• Skilled at receiving and providing direct feedback
• Collaborative mindset and great teamwork skills
• Entrepreneurial & adaptable; great learning skills
• Curious, research-minded, data-informed
• Able to search for possible solutions and apply them
• Creative confidence
• Proactive communicator
• A sense of humor and a love of online culture
• Thrives in a start-up culture

Benefits

• Competitive Salary
• Health, Dental and Vision Insurance
• Annual Performance Bonus
• Paid Time Off
• Company Holidays
• Flexible work schedule
• 401k