Executive Assistant (Part-Time) (Calgary)

Chris Jones is one of a small number of Expert EOS Implementers in the world — and his Calgary-based practice is busy. A full slate of active client relationships, a second Implementer, two growing ventures, and a full conference and session calendar mean the operational demands here are real and constant. The guiding values are: humbly confident, grow or die, help first, do the right thing and do what you say. The previous EA grew into this role and came to own it — calendar, clients, sessions, inbox, invoicing, everything. That's the standard we're hiring to match, and ideally exceed. This is not a task-execution role. It requires judgment, proactivity, and the emotional intelligence to work alongside a high-output entrepreneur who measures success by outcomes, not activity. If you have supported a fast-moving executive or entrepreneur before — and you know what it looks and feels like to run things without being asked twice — this role was built for you. What Your Days Look Like - Owning Chris's calendar — staying 2–4 weeks ahead at all times. Session readiness, travel logistics, prep buffers, follow-up deadlines, invoicing due dates. Nothing surprises him. - Managing the inbox — triaging email three times daily, responding on Chris's behalf, escalating what needs him, and resolving what doesn't. Timely, skilled, and clear every time. - Running EOS session logistics end-to-end — confirmation (14 days out), client homework tracking (2 days out), invoicing (QuickBooks Online), room setup, materials, parking logistics. Every session, without being chased. - Managing the Leadership Centre (ARTC boardroom) — readiness, supply inventory, boardroom bookings and invoicing. - Supporting client relationships — every interaction reflects on the practice. Warm, professional, and on time. - Maintaining CRM records and EOS reporting obligations (EOSi Hub, Ninety.io) — training is provided. - Coordinating travel — booking, itineraries, and logistics via TripIt. - Processing invoices and routine financial administration in QuickBooks Online and Dext — training is available. You Bring - 3+ years supporting a senior executive, entrepreneur, or small business owner in an EA, Operations Coordinator, or comparable role — with demonstrated ownership, not just task completion - Proven ability to manage a complex calendar, a high-volume inbox, and client-facing communication simultaneously, for someone who does not have time to supervise the details - Full proficiency in Google Suite (Gmail, Google Calendar, Google Drive) — this is daily use at a fluency level, not occasional familiarity - Clear, professional written communication — you edit your own work before you send it, and your correspondence reflects well on whoever you support - Experience in an entrepreneurial, fast-moving, or professional services environment; candidates from large corporate or heavily structured environments will need to demonstrate they can shift to a different pace and culture Bonus Points For - Familiarity with EOS (the Entrepreneurial Operating System) — or experience working inside an EOS-run organization - QuickBooks Online (QBO) experience — training is available for the right candidate, but prior experience is welcome - Experience supporting multiple business entities simultaneously - Background in consulting, coaching, professional services, or a high-trust client service environment What We Offer - $25–$35/hr (CAD) based on experience — positioned at the median-to-75th percentile for experienced EA support in Calgary - 25 hours per week, Monday–Friday, flexible daily schedule — this is the full scope of the role; permanent part-time - Hybrid work model — approximately 80% remote, 20% on-site for session prep, ARTC management, and key meetings - Work that is genuinely varied and visible — what you do directly shapes how a high-functioning practice operates - A clear working relationship with a principal who values ownership, appreciates discretion, and does not micromanage About the Practice Chris Jones is an Expert EOS Implementer based in Calgary — one of a small number of practitioners globally to have earned EOS Worldwide's Expert designation, which reflects both volume of client engagements and depth of implementation skill. Chris works with leadership teams across a range of industries, facilitating the Entrepreneurial Operating System to help organizations gain traction, clarify their vision, and build the accountability structures that allow them to grow. He also holds ownership roles in two growing companies: Outgrow and Simple Solve AI. The practice is professionally run, client-driven, and built around doing excellent work. Pay: $25.00-$35.00 per hour Perks: - Flexible schedule Work Location: Hybrid remote in Calgary, AB T2L 2K7 Apply on Kit Job: kitjob.ca/job/2pj81y