Executive Assistant to CEO (Contract to Hire)

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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