Chief of Staff - Freelance, Remote

The Impact you’ll make

• Own and optimize the founder’s calendar; protect deep-work blocks, resolve conflicts, and ensure meeting readiness
• Build weekly operating cadence and prep briefs so the right decisions happen at the right time
• Anticipate founder needs and be two steps ahead on next actions

• Triage and prioritize email; draft responses and manage stakeholder expectations
• Maintain clear, timely communications across internal/external partners
• Produce executive-ready updates, summaries, and decision memos

• Run task boards; set deadlines, drive follow-ups, and unblock teams
• Track deliverables across departments; escalate risks early and propose solutions
• Coordinate vendor/partner workflows, including scheduling and light contract/admin support

• Draft/polish decks, memos, customer letters, SOPs, and executive talking points
• Capture live meeting notes; translate into clear action items with owners and dates
• Maintain a clean source of truth for decisions, plans, and status

• Pull basic reports; distill key data points and insights for fast executive decisions
• Create simple dashboards or summaries to monitor priorities and progress
• Identify operational bottlenecks with data and recommend improvements

Skills, Knowledge and Expertise

• Previous Chief of Staff or senior Executive Assistant (founder/CEO-facing) experience in a fast-paced, high-growth company
• Proven track record running cross-functional projects and owning executive operating cadence (calendar, comms, task boards)
• Exceptional written communication; demonstrated experience drafting decks/memos and executive-ready materials
• High judgment, confidentiality, and accountability under pressure; thrives in high-intensity, rapidly changing environments
• Strong tooling fluency with modern productivity and project systems (e.g., Google Workspace/Microsoft 365, Asana/Notion/Monday, Slack/Zoom)
• 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

• Hard skills: executive calendar/inbox mastery; project management and follow-through; concise executive writing; note-taking to action conversion; light reporting and synthesis
• Soft skills: proactive, two-steps-ahead operator; bias to action; excellent stakeholder management; calm under pressure; ruthless prioritization; ownership mindset

• You love being the force multiplier for a founder—anticipating needs, removing friction, and creating clarity
• You thrive in startup speed and ambiguity, and you hold yourself to outcomes, not activity
• You are highly organized, detail-obsessed, and can switch contexts without dropping balls
• You communicate crisply, protect focus time, and are comfortable being the point of escalation
• “Everything is your job” resonates with you—no task is too small if it moves the mission forward

• 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
• Approximately 9am–6pm ET, 40 hours/week

• $8 per hour
• No benefits package included

Benefits