Chief of Staff, Internal AI Optimization

Chief Of StaffThe 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 RoleServe as truest advisor to Zack and the executive team, providing strategic guidance and supporting key initiativesLead special projects across business development, operations, and strategic growth initiativesEfficiently manage key processes and systems, including email inbox, Slack, and other tools, resulting in increased productivity and operational efficiencyExecute strategic projects and tasks for the CEO such as decks, business plans, and longer-term initiativesCommunicate daily with the CEO to optimize the planning and execution of his various commitments and responsibilitiesManage all administrative duties for the CEO, including owning the calendar and scheduling all meetings and eventsServe as a key representative of the executive team both inside and outside of the companyHandle confidential information, write correspondence, and support the CEO and teams across global time zonesCoordinate travel and related logistics on behalf of the CEOLead & organize quarterly team onsitesAct as a liaison between the CEO and other key stakeholders, both internal and externalOwn 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 teamLead the initiative to ingest all Firefly company videos into an AI knowledge base, enabling intelligent coaching and insights to be automatically surfaced to the teamOversee the pipeline that transforms Firefly video content into personalized coaching outputs delivered via email and broader team communicationsChampion AI adoption across the organization from identifying opportunities to automating workflows, enhancing productivity, and embedding AI tooling into day-to-day operationsLead projects do internal AI optimizations across the companyEffectively integrate subsidiariesCompetencies810 years in a role supporting executives and/or C-suitesVery high EQ and people skillsCreativity and open-mindednessGreat project management skillsExcellent written and verbal communication skillsAbility to synthesize various viewpointsHigh empathy and ability to make team members feel heard and acknowledgedGreat listener and ability to absorb informationStrategic thinking and problem-solving abilitiesComfort with ambiguity and flexibility to adapt to changing priorities and deadlinesDemonstrated experience with AI tools, CRM platforms, and emerging technology (strongly preferred)Ability to manage and implement AI-driven workflows and communications systemsCultural CompetenciesMust be able to work primarily between the hours of 9:30 AM - 6:30 PM ETMust have a player/coach mentality, willing to both execute and leadAbility to juggle multiple projects concurrently and set and meet deadlinesSkilled at receiving and providing direct feedbackCollaborative mindset and great teamwork skillsEntrepreneurial & adaptable; great learning skillsCurious, research-minded, data-informedAble to search for possible solutions and apply themCreative confidenceProactive communicatorA sense of humor and a love of online cultureThrives in a start-up cultureBenefitsCompetitive SalaryHealth, Dental and Vision InsuranceAnnual Performance BonusPaid Time OffCompany HolidaysFlexible work schedule401k