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Remote Executive Assistant to Founder - Startup

Remote / Online - Candidates ideally in
Chicago, Cook County, Illinois, 60601, USA
Listing for: FreedUp
Full Time, Remote/Work from Home position
Listed on 2026-11-05
Job specializations:
  • Administrative/Clerical
    Office Administrator/ Coordinator, Virtual Assistant/ Remote Admin, Business Administration, Executive Admin/ Personal Assistant
  • Business
    Office Administrator/ Coordinator, Business Administration
Salary/Wage Range or Industry Benchmark: 1000 - 1700 USD Monthly USD 1000.00 1700.00 MONTH
Job Description & How to Apply Below
Position: Remote Executive Assistant to Founder - Startup Support

Freed Up is seeking a proactive Executive Assistant to support the Founder of Orderly AI, an early-stage AI startup currently raising its seed round. The founder is juggling fundraising, investor and VC networking, product marketing, and customer-facing work — and needs everything that isn't fundraising, networking, or selling taken off his plate.

This role starts on lower-agency, clearly-scoped tasks (calendar management, follow-ups, meeting prep, drafted-not-sent emails) with the expectation that trust and scope grow quickly as the assistant proves reliable. The founder has never worked with an assistant before, so this person should be comfortable building context fast, working independently, and earning delegation of higher-agency tasks over time rather than waiting to be handed them.

This is a full-time, remote position that requires strong written communication, organizational excellence, and accountability.

Location: Fully Remote

Job Type: Full-Time

Salary: $1,000 - $1,700 per month (based on experience)

  • 3+ years of experience as an Executive Assistant, Executive Coordinator, or similar role supporting a founder or senior executive — startup experience is a strong plus.
  • Excellent written English; comfortable drafting emails and messages in someone else's voice.
  • Highly organized, with the ability to track a large volume of ongoing conversations, follow-ups, and introductions without anything slipping.
  • Comfortable working closely with a first-time founder who is still building trust in delegation — patient, clear, and consistent rather than needing everything spelled out twice.
  • Tech-savvy and comfortable with Google Workspace, Slack, and similar tools.
Key Responsibilities
  • Calendar Management:
    Own scheduling across a high volume of virtual and in-person meetings — VC meetings, networking, demos, and customer onboarding calls.
  • Follow-Up & Relationship Tracking:
    Keep track of the "endless web of conversations" — who's owed a follow-up, who needs an introduction, and make sure nothing is dropped.
  • Meeting Prep:
    Prepare the founder for VC meetings, customer calls, and networking conversations.
  • Email Support:
    Draft emails and messages on the founder's behalf based on quick verbal direction, with a review-before-send step on anything sensitive (e.g., investor communications).
  • Investor Updates:
    Support drafting and coordinating monthly investor updates.
  • Light Personal/Business Admin:
    Take on ad hoc admin and logistics as trust builds — this may expand over time as the founder gets comfortable delegating.
  • International experience
  • Opportunity to work remotely from anywhere
  • Supportive and collaborative team environment
  • Learning and development opportunities
  • Potential Performance Bonuses
  • PTO
  • HMO after 3 months
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