Chief of Staff, Senior Executive Assistant or Operations Manager

Seeking Former Chief of Staff / Senior Executive Assistant for 1-on-1 Executive Operations Coaching I'm starting a new role as an Executive Assistant supporting a Chief Strategy Officer in a highly strategic executive operations role. I'm looking for an experienced mentor who can help accelerate my learning through hands-on coaching while I work on real assignments. I'm looking for someone who has previously worked as a Chief of Staff, Executive Business Partner, Senior Executive Assistant to a CEO or other C-suite executive, or Operations Manager. This is not a traditional tutoring request. I'm looking for someone who can coach me through real work, help me think through problems, build systems with me, and answer questions as they arise. I need help with: Microsoft Excel (beginner to advanced) Microsoft PowerPoint Advance Asana Building dashboards/trackers Creating project trackers Workflow and process design SOP (Standard Operating Procedure) creation Project management Executive reporting Prioritization and task management Executive communication Designing systems from scratch Determining what information executives need to see Creating templates and operating procedures Troubleshooting assignments as they come up What I'm looking for: Live coaching over Microsoft Teams or Zoom Screen sharing while working on actual assignments Someone who explains not only how to do something, but why. A mentor who enjoys teaching and helping others develop Someone available for multiple sessions each week during my first 30–90 days Ideally, you: Have supported a CEO, Founder, Chief Strategy Officer, or other C-suite executive Have built operational systems, dashboards, trackers, and workflows from scratch Have strong experience with Excel, Asana, and PowerPoint Can provide practical, real-world executive operations guidance Please include: Your previous role(s) Your experience supporting executives Your experience with Excel, Asana, and PowerPoint If you have built operational systems, dashboards, workflows, approval processes, SOPs, and project trackers from scratch—not just maintained existing ones. Your availability Your hourly rate Location & Availability Please apply ONLY if you are based in Canada or the U.S. Eastern or Central Time Zones. You must be available for live coaching between 9:00 AM and 5:00 PM Eastern Time. Occasionally, I may need support after business hours for urgent questions, screen-sharing sessions, or troubleshooting, so some flexibility for evening availability is preferred. I may also need on-call support for quick questions, live Microsoft Teams meetings, or screen-sharing sessions during business hours and, when necessary, after hours. Engagement: This is expected to be an intensive coaching engagement during my onboarding period. The engagement is expected to last approximately 30–90 days but may end sooner if I become confident working independently. There is no long-term commitment required, and either party may end the engagement at any time.