Executive Assistant to CEO (Contract to Hire)

People & RecruitingOperationsHybridContract

Seer Interactive is hiring a Executive Assistant to CEO (Contract to Hire) in Philadelphia, Pennsylvania (hybrid, contract). Posted 29 September 2026. Apply directly on Seer Interactive's own careers site — no account needed.

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Seer Interactive is a digital marketing consultancy that harnesses compassion, data, and technology to make a mark on our communities - our coworkers, our clients, our industry, and our neighbors. We believe in relentlessly pursuing (and sharing) the truth – bringing together millions of data points from quantitative and qualitative sources to base our decisions on. Our purpose is to unlock potential for our communities mentioned above. Our vision is a world where it’s easy to do the right thing throughout those communities. If you’re ready to uplift others, challenge your ego, commit to the truth, and be better than yesterday – keep reading.

Seer is a remote first agency and Certified 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

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

Have questions about recruitment at Seer? Check out our Custom GPT: Guide to Talent Acquisition at Seer to drop in your questions! You can ask it anything about our hiring process, and how to best prepare for an interview with us.

As a B-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.

Not ready to apply but want to keep in touch? Stay connected via our monthly Career Update newsletter! We'll share curated content on Seer, open roles, industry insights, career advice, events you don't want to miss, and more (so you never miss a beat).

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