Senior Executive Assistant/Chief of Staff

OBB MEDIA is seeking a full-time Senior Executive Assistant to directly support the CEO in leading the company through its next stage of growth. This is a highly strategic and operational role for a driven individual who can execute with precision, streamline communication, and translate the CEO’s vision into clear, actionable priorities across the organization. From high-level strategy to hands-on execution, this person will play a central role in amplifying the CEO’s capacity and impact. The ideal candidate is a resourceful operator, a strong communicator, and a proactive problem-solver with impeccable discretion and a deep understanding of fast-paced, creative environments. This role also includes oversight of the CEO’s executive support team (Executive Assistant and Personal Assistant), ensuring they’re aligned and working in lockstep to maximize the CEO’s time and output. This is an in-person role based in West Hollywood, CA, and requires adaptability, emotional intelligence, and a “no task too small” mentality. Essential Functions:Oversee the CEO’s support team (EA and PA), ensuring strong performance, seamless communication, and alignment across workflows. Own and manage the CEO’s calendar (with support from EA/PA), allocating time strategically and adapting quickly to shifting priorities. Ensure the CEO is fully prepped for all meetings by managing agendas, briefing materials, and necessary action items/follow-ups.Act as a communication proxy and extension of the CEO — drafting emails, updates, decks, speeches, and managing high-priority correspondence. Lead confidential, internal projects for the CEO and COO that require executive oversight or fall outside existing team structures, often involving sensitive or complex issue.Design and implement workflows that reduce operational bottlenecks created by CEO dependency, empowering teams to execute clearly and efficiently without requiring constant top-down direction. Collaborate closely with department leaders through regular check-ins to maintain organizational alignment and drive sustained forward progress. QUALIFICATIONS: 5+ years of experience in operations, strategy, executive support, or project management — ideally within entertainment, media, or a creative/startup environment. Proven experience managing complex executive schedules, preparing leadership for high-stakes meetings, and interfacing with senior-level stakeholders. Track record of successfully managing and mentoring support staff or junior team members. Exceptional communication skills — both written and verbal — with a high degree of emotional intelligence and professionalism. Strong organizational and time management skills; able to balance long-term strategy with immediate needs and shifting priorities. Discreet, trustworthy, and experienced in handling highly confidential information. Self-starter with a “roll-up-your-sleeves” mindset and deep commitment to team success.