Executive Assistant to CEO (Contract to Hire)

Digital Agency Jobs; Sheffield; On-site; GBP 32,000 - 52,000; Full time

Job summary

Digital Agency Jobs is seeking a proactive assistant to support our Founder with scheduling, travel, and client relationships in a fast-paced environment. You will learn and operate AI-powered workflows while building trusted, incremental access to critical calendars and communications.

You will contribute to meeting coordination, materials preparation, and post-call follow-ups, with opportunities to take on more ownership as trust grows.

Qualifications

• Persistent and resilient, pushing through obstacles until completion.
• Coachable and able to adapt quickly to feedback.
• Curious and asking sharp questions to uncover needs.
• Resourceful, finding solutions with limited context.
• Able to earn trust incrementally and gain autonomy over time.
• Curious about AI tools and learning new ones independently.
• Enjoys repetitive, detail-heavy tasks as a path to mastery.
• Communicates directly and candidly when needed.

Responsibilities

• Support full speaking and logistics pipeline for the Founder from inquiry to post-event follow-up.
• Handle speaker logistics: bios, headshots, forms, transport, expenses, deadlines.
• Build and manage the presentation tracker and start direct organizer communications.
• Learn and maintain travel preferences; book and monitor travel for engagements.
• Join sales calls as a note-taker and observer, then turn insights into next steps.
• Assist with calendar management and weekly briefings for upcoming meetings.
• Support VIP relationships and nonprofit board logistics as needed.
• Use AI-powered systems to improve workflows and propose small improvements.

Skills

Persistent

Coachable

Curious questions

Resourceful

Trust-building

AI tools curiosity

Detail-oriented

Direct communication

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