Onboarding Specialist

Onboarding Specialist
100% Remote | Full-time Contractor
Schedule: Monday through Friday, 8:00am–4:00pm or 9:00am–5:00pm North American hours (flexible if you're in PST, MST, CST, EST)
About Gymdesk
Gymdesk is category-leading gym management software, built for gym owners, martial arts school owners, and studio owners who want to run and grow their business. Thousands of fitness and wellness businesses run on Gymdesk, and we're proud to sit at 4.8 stars on Capterra. We recently closed a $32.5 million growth investment from Five Elms Capital, and we're building out the team to match.
About the Role
Every new Gymdesk customer needs someone in their corner during the first weeks of the relationship: someone who configures the platform around how their business actually runs, coordinates their data migration with our dedicated migration team, and trains their staff so day one feels like day one hundred. That's you.
This is a high-volume, high-trust role. You'll partner with 40 to 50 customers a month across phone, email, and video, and you'll be the reason their first impression of Gymdesk is a great one.
What You'll Own
Project manage onboarding for a full book of customers at once, moving each one from signed to set up to self-sufficient.
Coordinate data migration with our dedicated migration team, making sure customer data lands cleanly and on schedule ahead of launch.
Assess each customer's specific setup and configure Gymdesk to match how they actually operate, not a generic template.
Train new customers and their staff on the parts of Gymdesk that matter most to their day-to-day.
Deliver a launch experience customers remember for the right reasons: efficient, personal, and genuinely helpful.
Act as the voice of the customer back to our Product team, so real feedback from real onboarding calls shapes what we build next.
Spot friction early and manage escalations before they become churn risks.
Work directly with our VP of Customer Success to build out the onboarding systems and playbooks that scale as we grow.
Who You Are
2 to 4 years of experience in onboarding, training, customer service, or project management.
Very strong English speaking and writing skills. You're a clear, confident, and approachable communicator on calls and in writing, and you'll be the face of Gymdesk to customers every day.
Genuinely motivated by helping people succeed. You want the customer's win as much as they do.
Comfortable coordinating with cross-functional teams and confident in Microsoft Excel.
An effective project manager who can keep dozens of customers moving forward at once without dropping the ball.
Detail-oriented and organized, because a missed step in an onboarding plan is a customer's real business on the line.
Comfortable running your day through a CRM, Slack, and other remote-work tools.
Energized by a fast-paced, evolving company, not looking for a fixed playbook that never changes.
A fast learner who can become a genuine product expert on new software.
If you think you'd be a good fit, we'd love to hear from you.

Work arrangement
No