Position Summary
Mahogany Cowboy Media Group LLC is seeking a part-time Chief of Staff / Senior Operations Manager to serve as the primary operational anchor, executive gatekeeper, and strategic coordinator for executive leadership. Positioned as the internal "eyes and ears" of the company, this role oversees partner relations, master scheduling, vendor procurement, and project budget tracking.
This position operates as a remote, fractional executive role structured for 16 to 20 hours per week maximum. It offers a flexible working window, but requires strict adherence to confirmed calendar schedules, meeting commitments, and deliverable deadlines.
Core Responsibilities & Scope of Duties
1. Executive Gatekeeping & High-Level Partner Liaison: Act as the primary point of contact for key external partners, institutional contacts, and high-level collaborators. Triage incoming inquiries, filter priority communications, and protect executive focus time. Draft professional outreach, external correspondence, and institutional partner updates.
2. Master Calendar Triage & Schedule Management: Manage executive calendars, ensuring zero booking overlaps and adequate preparation time for meetings. Coordinate multi-party virtual meetings, manage calendar invitations, and issue meeting agendas. Track critical project milestones and maintain master company timelines.
3. Procurement, Budget Oversight & Operational Controls: Review project expenditures, vendor agreements, and purchasing requests against approved project budgets. Standardize procurement intake, vendor onboarding, and contract tracking systems. Assist in financial tracking, invoice processing, and quarterly operational expense reviews.
4. Executive Decision Support & Strategic Operations: Serve as a strategic sounding board for company growth, internal workflows, and operational efficiency. Establish clear standard operating procedures (SOPs) across media projects and business initiatives. Audit internal processes to reduce operational clutter and streamline team execution.
Compensation & Hours Breakdown
Compensation: $35.00 per hour.
Weekly Commitment: 16 hours minimum to 20 hours maximum per week.
Location: Remote (with periodic virtual executive check-ins).
Schedule Flexibility: Working hours can be divided into 2 full days (8 hours each) or spread across 3–4 days (4–5 hours per day).
Strict Policy: Schedule & Deadline Adherence
While Mahogany Cowboy Media Group LLC provides flexibility in setting your weekly working schedule, strict adherence to agreed-upon hours, scheduled meetings, and project deadlines is mandatory.
Calendar Commitment: Scheduled executive syncs, partner calls, and operational deadlines must be honored promptly without unexcused delays.
Communication Availability: Designated working blocks must be clearly posted on the master calendar, with prompt responsiveness during those set windows.
Time Tracking: Weekly time logs must be submitted accurately reflecting hours worked on specific operational tasks.
Position Requirements
Proven experience in procurement, institutional compliance, contract administration, or senior executive operations. Advanced organizational skills with demonstrated proficiency in calendar management and budget oversight. Exceptional verbal and written communication skills appropriate for high-level partner engagement. Ability to exercise sound judgment, maintain high confidentiality, and exercise decision-making authority within designated limits.
Please fill out an application below.
Briefly outline your experience managing CEO/executive schedules, prioritizing conflicting commitments, and controlling time allocation.
Describe your background in facilitating internal team syncs or representing senior executive leadership in external partner/community meetings.
List the primary project management, communication, and scheduling tools you use routinely (e.g., Notion, Asana, Google Workspace, Slack).
Context: The CEO’s schedule is severely overbooked across simultaneous priorities—including strict media/production deadlines, a hospitality pop-up launch review, and continuous operational check-ins.
Question: How do you audit and restructure the CEO's calendar to reclaim at least 5 hours of weekly focus time without slowing down key project deliverables? What criteria do you use to decide what gets delegated, rescheduled, or handled by you directly?
Context: The CEO cannot attend a critical external sync with community partners and strategic stakeholders. The meeting requires clear updates on active launches, managing expectations, and firming up next steps.
Question: How do you prepare for, facilitate, and command authority during this meeting on behalf of executive leadership without overstepping bounds or overcommitting organizational resources? Detail your pre-meeting prep and post-meeting CEO debrief process.
Context: Multi-departmental initiatives are falling behind target dates due to disorganized meeting follow-ups and unassigned action items across creative, marketing, and operations teams.
Question: What explicit note-taking, action-tracking, and follow-up protocol will you implement during your first 30 days to ensure 100% team accountability and clear post-meeting execution?
By submitting this application, I confirm that all information provided is accurate and represents my original professional experience.