Executive Assistant to CEO (Contract to Hire)
- AI
- GPT
Not enough detail in this posting to match
Seer is a remote first agency andCertified B-Corp with team members working across the country. If an office environment is more your style, this position can also sit in our HQ office, Philadelphia. We can only consider candidates based in the US who are able to work continental US based hours.
The Role: You're not coming into this role already knowing how to do it, you're coming in ready to figure it out. This is a hands-on, high-trust seat supporting Wil Reynolds, our Founder and CEO, and it starts with the fundamentals: his calendar, his inbox, his travel, the small stuff that keeps a busy person's day from falling apart. But it doesn't stay there. This role is built for someone who treats every task, big or small, as a chance to earn more trust and more responsibility, and who's hungry enough to keep pushing for that growth rather than waiting for it to be handed over.This is a contract-to-hire position: your first 90 days are a real, mutual trial, for you to learn fast and prove what you're capable of, and for us to see where you land.
Role Highlights
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
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
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
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
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
Support non profit board logistics, including meeting coordination and materials
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
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
Daily & Personal Support
AI Systems & Tools
Board & Nonprofit Support
Key Relationship & Recognition Management
Calendar, Scheduling & Meeting Coordination
Business Development & Client Relationships
Travel Management
Conference & Speaking Circuit
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
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
Bonus
30/60/90
- 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
- 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
First 30 Days — Learn
60 Days — Build
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
- Your final offered compensation will be determined by your skills and experience
- This will be a 1 month contract to hire based on ability to complete the role
- Evaluation of comp at least once a year after that
- Benefits (eligible after conversion)
As aB-Corp Certified organization, we are committed to creating an inclusive environment and are proud to be an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, or veteran status.
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Executive Assistant to CEO (Contract to Hire) · Seer Interactive