Executive Assistant & Volunteer Lead

THE ROLE

You are the operating layer between two senior leaders and everything else. You protect their time, turn intent into action, and make sure nothing important falls through the cracks.

You also own the volunteer program from recruitment through closeout.

This is not a coordinator role. It is a chief-of-staff-adjacent role that requires judgment, writing chops, and AI fluency.

WHAT YOU OWN

1. Executive Support — Gathering President and Chief Revenue Officer

• Calendar management across multiple time zones, with clear rules of engagement for each leader


• Inbox triage: read, prioritize, surface what needs them, handle what does not


• Pre-meeting briefings and post-meeting follow-ups with owners and dates attached


• Travel coordination, fully owned: flights, hotels, ground transport, itineraries, restaurant bookings, anything needed


• Expense reporting and reconciliation for both, weekly cadence, no backlog


• Draft emails, partner outreach, and internal updates in our voice 


• Maintain a stakeholder file: contacts, history, last touch, open follow-ups
  
  

2. Stakeholder & Relationship Management

You are the first person a partner, speaker, sponsor, or VIP hears from. That sets the tone for every interaction that follows.

• Inbound requests handled fast. 


• Coordinate across the team so Mandy and Brad are not bottlenecks on their own relationships


• Close loops before they become problems


• Hold the line on partner experience during festival week, retreat weeks, and around the podcast
  
  

3. Operations, Systems & AI

This role is built for someone who already works with AI as a teammate and operational partner.

• Use Claude daily: meeting transcripts to strategy briefs, weekly leadership updates, email drafts, financial summaries, partner and speaker research


• Run Notion as the operating system: clean databases, current SOPs, project dashboards, no orphaned pages


• Keep HubSpot data clean: contacts current, pipeline accurate, follow-ups logged


• Build workflows that remove manual steps. If something is done by hand more than twice, it is a system you have not built yet.


• Maintain the prompt library and shared context docs that keep both leaders moving


• Prepare weekly resorts and dashboards


• Stay current on what's actually useful in the AI/tooling space and bring the best of it back to the team
  
  

4. Coordination Across Festival, Retreats, Podcast & Travel

• Festival: support the Operations and Production leads on cross-functional deadlines and workback schedules


• Retreats: Experience Labs and pop-up activations; logistics, briefs, and stakeholder coordination 


• Podcast: guest scheduling, prep materials, asset handoffs


• Run-of-show, contact sheets, logistics grids — built once, maintained always
  
  

5. Volunteer Program Lead

• Own recruitment, screening, and onboarding for the Banff festival


• Maintain, improve and update the volunteer handbook, role-specific SOP cards, training materials


• All volunteer communication from application through post-event thank-you


• Schedule and assign shifts: hospitality, production, VIP, registration, content


• Day-of deployment coordinated with Operations and Production


• Track show-up rates and satisfaction; improve them every year


• Year-one targets: 95% show-up rate, 90%+ volunteer satisfaction


• Build a program people want to come back to. Belonging is the bar.
  
  

CONFIDENTIALITY

You will see compensation, leadership conversations, partner negotiations, financials, and sensitive personnel matters. That stays with you. We take this seriously and so should you.

YOU ARE

• Two steps ahead. The brief is drafted before anyone asks for it.


• A systems thinker. You see a manual process and immediately want to replace it.


• AI-fluent in practice, not in theory. Claude and Notion are part of how you actually work today.


• Calm with multiple plates spinning. That is your normal, not a crisis.


• A strong writer. You can send a senior-level email on the first pass.


• Warm and discreet. Stakeholders feel handled. Sensitive information stays sensitive.


• Hungry for what's next. You teach the team things you found, not the other way around.
  
  

YOU ARE NOT

• Someone who waits to be told what to do


• Someone who does manually what a system can handle


• Intimidated by senior leaders, big-name partners, or high-stakes weeks


• Satisfied with good enough when better is available


• Looking for predictable 9-to-5 hours, especially August through October
  
  

EXPERIENCE & QUALIFICATIONS

• 3+ years supporting senior leaders in an EA, chief of staff, or senior operations role


• Experience supporting more than one leader at a time


• Working knowledge of Claude, Notion, Slack, Google Workspace


• Comfort with HubSpot or comparable CRM, and Motion or comparable project management tool


• Event, festival, podcast, or hospitality coordination is a real asset


• Experience leading a team or volunteer program is preferred


• Strong writing. Partner email, internal brief, and team update — all in the same afternoon.


• Post-secondary education in business, communications, event management, or equivalent work experience


• Calgary-based. In-office 4 days a week. 
  
  

WHAT SUCCESS LOOKS LIKE AT 90 DAYS

Executive Support

Mandy and Brad's calendars, inboxes, travel, and expenses run without friction. Neither is thinking about logistics.

Stakeholders

Every inbound is handled fast and well. No partner has waited longer than a few hours without a response.

Systems & AI

Claude workflows are running. Notion is clean. You have already replaced two manual processes with something better.

Coordination

Festival, retreat, podcast, and travel logistics are fully owned. Nothing lives in someone's head.

Volunteers

Recruitment is open. Handbook is built. You can walk through the program from memory.

Trust

The team trusts you. The leaders trust you completely. You feel like you have always been here.

COMPENSATION

Competitive base salary based on experience.

HOW TO APPLY

We do not want a resume and a cover letter pretending to be a personality test. We want to see how you think.

Send three things:

1. Your resume.


2. A Loom (5 minutes max) walking us through one workflow you have built or automated — what was broken, what you built, what changed. Show your screen if you can.


3. A 1-page first-30-days plan. Imagine you start Monday. What do you do in week one, two, three, and four to get yourself useful fast in this role? No fluff. We want to see how you prioritize.

Send to: [email protected]

Subject line: EA + Volunteer Lead — [Your Name]

If the Loom is missing or the 30-day plan is generic, we won't get back to you.

If it shows us something, we will.

We build with the boldest.

If that is you, we want to talk.