Executive Assistant to CEO (Contract to Hire)

Seer Interactive•Philadelphia, PA

4d•$65,000 - $100,000•Hybrid

About The Position

Seer Interactive is a digital marketing consultancy that harnesses compassion, data, and technology to make a mark on our communities. We are a remote-first agency and Certified B-Corp with team members working across the country. This is a hands-on, high-trust seat supporting Wil Reynolds, our Founder and CEO, starting with the fundamentals of his calendar, inbox, and travel. This role is built for someone who treats every task as a chance to earn more trust and responsibility, and who is hungry for growth. This is a contract-to-hire position with a 90-day trial period for mutual evaluation.

Requirements

Persistence: ability to keep pushing on something even after initial failures.
Coachability: ability to take direct feedback and visibly change approach quickly.
Resourcefulness: ability to find solutions without full context, authority, or experience.
Comfort earning trust incrementally.
Curiosity about AI tools and self-teaching their use.
Comfort with detail-heavy, repetitive work as a means to prove oneself.
Comfort with direct, frank communication.
Ability to work continental US based hours.
Must be based in the US.

Nice To Haves

Experience in a fast-paced, quota-driven, or rejection-heavy environment (sales, recruiting, business development).
Experience teaching oneself to use an AI tool for something outside of school or work.
Genuine interest in eventually growing into full executive or business partner support.

Responsibilities

Support the full speaking pipeline for the Founder, from inquiry tracking through logistics to post-event follow-up.
Handle speaker-specific logistics: bio, headshot, W9, vendor forms, ground transport, expense tracking, and 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.
Price, book, and monitor travel tied to speaking engagements and business travel.
Learn the Founder's preferences for airport timing, routing, and hotel standards, and anticipate them.
Sit in on sales calls as access and trust grow, starting as note-taker and observer.
Practice turning what is heard into follow-up and next steps, with feedback and coaching.
Review call transcripts and project context to help synthesize key accounts.
Support calendar management and scheduling.
Learn to produce a weekly briefing with context for upcoming meetings.
Catch and help resolve scheduling conflicts.
Support logistics for VIP contacts and relationship-building touchpoints.
Learn the goodwill and recognition cadence the Founder cares about, and help build it into a more repeatable, AI-supported system.
Support non-profit board logistics, including meeting coordination and materials.
Learn and use existing AI-powered systems that support this role.
Propose small improvements to existing systems and build personal workflows.
Handle day-to-day logistics, meals, errands, and home needs.
Maintain inbox access for utility purposes, with growing responsibility.
Support monthly expense tagging and categorization.