Training Specialist - Remote

You're not running a classroom. You're building the EAs our clients count on, one person at a time. Why does this role exist? You're an in-house Magic employee, full-time from day one, and not a freelance or client-placed role. Every EA who steps in front of a client has to be ready, not "probably ready," actually ready. That's what you're here for. You run the sessions that turn new hires into confident, capable Executive Assistants, and you're the one who calls it when someone is or isn't there yet. This isn't about lecturing from a slide deck. You're facilitating, assessing, coaching, and constantly tightening the program itself because "how we've always done it" isn't good enough if it's not producing EAs who can hold their own with US clients. You'll work closely with the Assistant Training Manager, but the day-to-day judgment calls, including how a session goes, whether someone's ready for their mock client call, and what feedback actually lands, are yours. What Winning Looks Like You run daily virtual sessions that trainees rate as clear, engaging, and genuinely useful, not just "completed." You grade every assessment against the rubric, not your gut, and your calls hold up under review. You synthesize checkpoint scores, mock interviews, and day-to-day notes into a readiness call that's right more often than not. You flag performance risks and program gaps early before they become a trainee's problem in front of a client. You ship at least one program improvement a quarter that measurably moves engagement or retention. What You'll Actually Do Training Facilitation & Trainee Readiness You lead daily, trainer-led virtual sessions for each assigned batch, and you keep every scrap of training documentation accurate and current. You run rubric-based assessments at each stage of the program, graded on defined criteria, not impression, and you resolve trainee questions and concerns as they come up, on the spot. EA Assessment & Coaching You run mock client intro calls and mock interviews to pressure-test readiness beyond checkpoint scores, then pull all of it, such as checkpoints, mock performance, and facilitation notes, into one clear readiness read per trainee. You coach on presentation, communication, and the mental shift from "doing tasks" to "providing strategic support," and you call out each trainee's specific strengths and gaps with targeted next steps. Program Design & Improvement You work with the Assistant Training Manager to review what's working and what isn't, then build the agreed-upon fixes, including content, structure, and delivery. You design simulations and role-play scenarios that mirror the real situations EAs actually run into with clients. Coordination & Reporting You keep the Assistant Training Manager and Training Supervisor looped in on trainee progress and project status in real time, and you flag roadblocks before they become missed deadlines. You escalate unresolved issues or performance risks to the right person — Supervisor first, Assistant Training Manager when it needs a call only they can make — and you help onboard new team members when needed. Required Experience Your Superpowers Rubric-Driven Evaluator Confident Facilitator Adaptive Coach Fast Learner Detail-Obsessed Calm Under Pressure What You Bring 1+ years of virtual training experience with a proven track record of success 1+ recent year working as a VA/EA with US clients Working knowledge of Google Suite, Discord, and Slack for delivery, coordination, and documentation Solid presentation skills — comfortable building in Google Slides, Canva, or similar tools Experience in using Claude, ChatGPT, or other similar AI tools in a professional work environment A real understanding of different learning styles and how to teach to them, not just one script Experience running mock interviews and giving structured, constructive feedback What's In It For You Benefits Monthly gross compensation: ₱37,000 – ₱42,000 Full-time employee benefits, including government-mandated benefits, paid leaves, and HMO Before You Apply — Quick Gut Check Can you grade someone against a rubric even when your gut says something different? Are you comfortable being the one who tells a trainee they're not ready yet, and telling them why? Can you run a live virtual session solo and adjust on the fly when it's not landing? Do you actually enjoy the process of coaching someone from "learning the task" to "owning the outcome"? Are you comfortable using AI tools and teaching trainees how to use them in their respective tasks? If that sounds like you, we'd love to hear from you. Training Reality There's no formal training program for this role — onboarding is personalized, 1:1 with your managers and team members. Schedule is fixed from day one: Weekdays, 9 PM – 6 AM PHT. Our Hiring Process Application → HR Initial Interview → Skills Assessment → 2nd Level Interview → Final Interview → Job Offer About Magic Magic is a leading modern outsourcing platform that connects SMBs to high-quality remote workers, from SDRs to virtual assistants and more. With roots in Silicon Valley and backing from top venture capitalists, our workers are supercharged with a combination of the latest AI technology and training. We came out of Y Combinator in 2015, have grown to 1,000+ remote workers, and are backed by Sequoia Capital with over $30M in funding.