Role: Online Customer Success Trainer

Priority Location: South Africa

Working Hours: 9AM - 5PM (Mon - Fri) EST

Salary Range: $2,500 - $3,500 USD per month (The final offer is at the client’s discretion and depends on the candidate’s interview result, skills, and experience.)

Type of contract: Independent Contractor

Type of job: Remote

Role Overview:

As a Customer Success Trainer, you deliver the live product learning sessions that teach institutions how to use our software confidently and get the most out of the platform. Your focus is training on the system itself—walking administrators through how the product works and how to run their day-to-day tasks in it.

Every school runs on an academic calendar, but no two schools run it the same way, and the details differ widely from one institution to the next. A big part of this role is learning to read each institution—understanding how they operate, relating to the people you’re training, and adapting your sessions so the guidance fits how that particular school works.

You won’t be expected to redesign a school’s internal processes or make complex configuration decisions on your own—our senior Customer Success team owns that consultative work, and you’ll hand those questions off to them. Over time you’ll build deep product expertise and take on more, but you’ll be set up to succeed from day one with training, materials, and a team behind you.

Responsibilities:

Product Learning & Training Delivery

Deliver live, virtual product learning sessions—onboarding walkthroughs, feature refreshers, and group “office hours”
Teach administrators how to use the software’s core workflows, guiding them hands-on until they can run tasks on their own
Tailor sessions to different audiences: housing directors, front-desk and RA staff, and campus IT
Answer how-to product questions in the moment, and hand off complex configuration or process-design questions to senior Customer Success

Understanding & Relating to Each Institution

Learn each school’s context—how their academic calendar, housing setup, and day-to-day operations work—well enough to train them effectively
Recognize how institutions differ from one another and adjust your sessions and examples accordingly
Build genuine rapport with the people you train, so sessions feel approachable and supportive

Content & Materials

Help build and maintain training decks, quick-reference guides, walkthrough videos, and session agendas
Keep learning materials current as the product evolves and new features ship
Follow a repeatable curriculum so every customer gets a consistently excellent training experience

Cross-Functional Collaboration

Partner with Customer Success Managers to align training to each account’s onboarding plan
Share recurring questions and friction points back to Product and Support to improve the platform
Coordinate scheduling and follow-up so sessions run smoothly and customers stay on track

What Makes a Great Candidate:

You’re a natural teacher who is energized by helping people succeed. You pick up new software fast, you can explain how something works in plain language, and you’re genuinely curious about the different organizations you work with—quick to pick up on how each one operates and how to relate to them. You stay patient and upbeat, and you care that people leave your sessions more capable than they arrived. You don’t need to already be a housing-software expert—we’ll train you—but you do need to love learning and teaching.

Required Skills & Experience

Excellent live presentation and facilitation skills—clear, warm, and easy to follow on a video call
Strong digital fluency and the ability to learn new software quickly and thoroughly
A knack for reading people and organizations, and adapting how you communicate to fit them
Understands how people learn and how to teach effectively—whether from teaching, training, tutoring, or enablement experience
Fluent, articulate English communication, spoken and written
Able to work consistently within U.S. business hours
Reliable high-speed internet and a quiet, professional environment for video sessions
Organized and self-directed: manages a schedule of sessions and follow-ups without being chased
Operates with ownership: no excuses, no blame, just results

Nice-to-Have

Experience with student housing—as an RA, student staffer, or campus housing/residence-life employee
Experience training on or supporting a SaaS product
Background in higher education, admissions, or campus operations
Experience creating training videos or written documentation

Personal Qualities

Patient, encouraging, and genuinely enjoys helping people learn
Positive, resilient, and motivated
Curious about both the product and the institutions you work with
Brings energy without taking yourself too seriously

Compensation:

Base salary based on experience and qualifications.
Benefits include: Paid Time Off commensurate to local customs in the contractor’s home country

Online Customer Success Trainer - 65260425231