Executive Assistant to CEO (Contract to Hire)

1 month from now
US > Philadelphia
Operations

Job Description

Role Highlights

Conference & Speaking Circuit

Support the full speaking pipeline for our Founder, from inquiry tracking through logistics through post-event follow-up

Handle speaker-specific logistics: bio, headshot, W9, vendor forms, ground transport, expense tracking, deadline tracking with organizers

Learn and maintain the shared presentation tracker

As trust builds, begin owning direct communication with conference organizers and the annual re-engagement cadence that keeps our Founder invited back year over year

Travel Management

Price, book, and monitor travel tied to speaking engagements and business travel

Learn our Founder's preferences for airport timing, routing, and hotel standards, and build toward anticipating them without being asked

Business Development & Client Relationships

Sit in on sales calls as your access and trust grow, starting as note-taker and observer

Practice turning what you hear into follow-up and next steps, with feedback and coaching along the way

Review call transcripts and project context to help synthesize what's happening on key accounts

Calendar, Scheduling & Meeting Coordination

Support calendar management and scheduling

Learn to produce a weekly briefing with context for upcoming meetings

Catch and help resolve scheduling conflicts as you learn the patterns behind them

Key Relationship & Recognition Management

Support logistics for VIP contacts and relationship-building touchpoints

Learn the goodwill and recognition cadence our Founder cares about, and help build it into a more repeatable, AI-supported system over time

Board & Nonprofit Support

Support non profit board logistics, including meeting coordination and materials

AI Systems & Tools

Learn and use the existing AI-powered systems that support this role

Start proposing your own small improvements as you understand what's needed, with the goal of building your own workflows over time

Daily & Personal Support

Handle day-to-day logistics, meals, errands, home needs, that keep our Founder focused on high-leverage work

Maintain inbox access for utility purposes, with growing responsibility as trust is established

Support monthly expense tagging and categorization

Essential Skills

You are persistent, you keep pushing on something even after it doesn't work the first, second, or third time

You are coachable, you take direct feedback and visibly change your approach quickly

You ask sharp, curious questions rather than just following instructions

You are resourceful, you find a way to solve a problem even without the full context, authority, or experience you'd normally want

You are comfortable earning trust incrementally, rather than expecting full access or autonomy on day one

You are curious about AI tools and teach yourself how to use new ones without being told to

You feel energized by repetitive, detail-heavy work early on, and see it as a way to prove yourself, not something beneath you

You feel comfortable with direct, frank communication

Bonus

You have experience in a fast-paced, quota-driven, or rejection-heavy environment (sales, recruiting, business development)

You have already taught yourself to use an AI tool for something outside of school or work

You have a genuine interest in eventually growing into full executive or business partner support

30/60/90

First 30 Days — Learn

  • Learn CEO’s calendar, preferences, and daily rhythms

  • Shadow the existing AI-supported workflows already in place

  • Complete your first fully independent task, however small

 

60 Days — Build

  • Take ownership of a defined slice of the daily/personal support workload independently

  • Begin sitting in on select calls or meetings as trust builds

  • Propose one small improvement to an existing process 

 

90 Days — Decision Point

• Demonstrate independent judgment on at least one ambiguous, unscripted situation

• Reach a mutual decision point on converting to a full-time role

 

This might not be the right role for you if....

You're looking for a role where the scope is fully defined on day one

You need a clear path or process handed to you rather than figuring it out yourself

You're not comfortable with a real evaluation period 

You see detail-heavy, repetitive tasks as something to get past rather than something to prove yourself through

You fear receiving direct feedback on your work

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