AI Upskilling Coach

The Workaround Collective · Remote (USA) · Remote · Part-time

REQ-2026-9561 · Hiring manager: Connie L., Founder

Job Title: AI Upskilling Coach (Remote, 1-on-1) The Mission AI tools are quickly becoming standard in today's workplace, yet most job seekers have never been shown how to actually use them. We are looking for a hands-on AI Upskilling Coach to help job seekers build real, job-ready fluency with the AI tools employers are already using — like ChatGPT, Google Gemini, Microsoft Copilot, and Claude. You will provide remote, personalized guidance that turns "AI" from an intimidating buzzword into an everyday skill, so job seekers become more competitive and can hit the ground running the moment they step into a new role. What You Will Do * Provide 1-on-1 remote sessions that coach job seekers on the leading workplace AI tools (ChatGPT, Google Gemini, Microsoft Copilot, Claude, and similar) — from first-time setup to confident daily use. * Teach practical, job-ready applications: drafting and editing documents, summarizing information, research, data cleanup, email and communication, meeting prep, and building simple workflows. * Help clients apply AI to their own job search — tailoring resumes and cover letters, preparing for interviews, and researching companies and roles. * Coach clients on responsible, ethical AI use: verifying outputs, protecting privacy and sensitive data, and avoiding plagiarism. * Meet learners at every skill level with patience and zero jargon, tailoring guidance to the tools common in their target industry or role. * Contribute digital content 1x a week to our in-platform digital library. * Build your brand and drive bookings by hosting free small-group discussions or workshops on AI upskilling in our in-app virtual rooms. Who You Are * Hands-On AI Practitioner: You use multiple workplace AI tools in real professional settings and stay current as they evolve. * Natural Teacher: You can explain a tool to a total beginner and have them using it confidently by the end of the session. * Modern & Tech-Savvy: You understand how AI shows up in everyday office work and how to apply it effectively and ethically. * Empathetic Guide: You understand the emotional and financial toll of unemployment and support clients with patience and encouragement. * Digital Communicator: You excel at building trust and delivering impactful, actionable guidance over video software. * Credentialed (a Plus): A professional certification, credential, or degree demonstrating knowledge of AI or digital skills is a welcome bonus — though demonstrated hands-on skill matters most. Why Join Us * Direct Impact: You will give job seekers in-demand skills that make them more competitive and ready to hit the ground running. * Total Flexibility: Work from home anywhere in the US * You set your hours and your booking rate * Create content and teach job seekers about a topic that you are passionate and knowledgeable in * Purpose-Driven and Mission-Driven Culture: Join a team that truly values the meaning and power of human community and connection. About The Workaround Collective The Workaround Collective is a newly formed 501(c)(3) tax-exempt nonprofit headquartered in Bryan, TX. Our mission is to leverage the power of human connection to support job seekers through the demands and challenges of their job search. We connect them to educational, wellness, and career-support experts, mentors, peers, and educational and financial resources through our in-house digital library and (future-planned) grants-assistance programs. Because we are newly launched, we are intentionally starting small as we ramp up. This role is a great fit if you want a fun, creative, and inspiring place to work — fully remote, with flexible hours and the freedom to build a meaningful side hustle while helping to build a community that cares. The minimum hours required to start is to be available at least 4 hours per week for 1x1 virtual sessions with job seekers. The long term vision is for the Workaround Collective to transition our experts to direct staff as the organization expands and funding grows. If you want to make a real difference in the lives of job seekers and to grow and contribute to the vision and future of the organization, we'd love for you to apply to join our team!