Chief of Staff/Executive Assistant - Freelance, Remote

The Impact you’ll make

• Own and optimize the calendar; protect deep work time; resolve conflicts and last‑minute changes
• Triage inbox; flag urgent items; draft responses; manage stakeholder expectations and SLAs
• Ensure on-time meeting starts; anticipate logistics; proactively check executive status and readiness

• Own task boards and project trackers; maintain clear priorities and deadlines
• Prepare agendas, docs, and resources for upcoming decisions; ensure follow-ups are completed
• Drive cross-departmental coordination; “firefight” blockers on behalf of the executive

• Draft/polish decks, memos, SOPs, customer letters, and internal updates
• Create concise summary reports and executive briefs from complex inputs
• Maintain a consistently high standard of clarity, tone, and brand alignment

• Schedule with partners; prepare materials; support contracts and onboarding
• Maintain relationship maps and key contact cadences for the executive
• Track deliverables and ensure external commitments are met on time

• Pull light reports; summarize key data points for quick executive decisions
• Capture live meeting notes; track action items; circulate clear summaries
• Handle occasional personal admin tasks that enable executive focus

Skills, Knowledge and Expertise

• Demonstrated Chief of Staff experience (or equivalent) in a fast-paced startup or high-growth environment
• Prior Executive Assistant (or equivalent) experience supporting a C-level executive
• Mastery of calendar/inbox management and meeting ops across tools like Google Workspace, Slack, and a PM tool (e.g., Notion/Asana)
• Proven cross-functional project ownership with measurable outcomes
• Ability to work full-time, 40 hours/week,  9:00 a.m.–6:00 p.m. Eastern Time
• WFH Set-Up:
  • Computer with at least 8GB RAM, an Intel i5 core processor/AMD Ryzen 5 Processor and up.
  • Internet speed of at least 40MBPS
  • Headset with an extended mic that has noise cancellation and a webcam
  • Back-up computer and internet connection
  • Quiet, dedicated workspace at home

• Anticipation and prioritization: staying two steps ahead; protecting focus; time‑boxing
• Executive communications: concise writing, stakeholder tone-matching, drafting email/memos/decks
• Project management: task boards, dependencies, deadlines, and follow-through
• Real-time situational awareness: monitoring schedules, nudging participants, resolving conflicts
• Analytical synthesis: distilling data into clear, decision-ready insights
• Relationship management: vendors, partners, and internal stakeholders
• Calm under pressure, high accountability, discretion, and sound judgment
• Bias to action: proactively filling the pipeline with high-impact work without micromanagement

• You thrive in a fast-paced, high-accountability startup industries
• You love being the force multiplier—acting as an extension of the executive while helping manage the business
• You’re relentlessly proactive, keep multiple balls in the air, and stay two steps ahead
• You take ownership, follow through without being asked, and you’re comfortable with high stress and rapid context switching
• You measure yourself by outcomes—not activity—and you build systems to remove friction

• Remote position
• Must have a reliable internet connection and a quiet workspace
• Required to provide own computer with Intel Core i5 or something similar or higher operating system

• 40 hours per week
• 9:00 am - 6:00 pm (Eatern Time)

• $8 per hour
• No benefits package included

Benefits