Online Customer Success Trainer - 65260425231

somewhere; United States; Remote; USD 28,000 - 39,000; Full time

Benefits offered by this job

Paid Time Off

Job summary

somewhere is seeking an Online Customer Success Trainer to deliver live, virtual product learning sessions and onboard administrators to our software.

You’ll tailor training to housing directors, front-desk staff, and campus IT, reading each institution to adapt examples and rates of learning. You’ll work with the senior CS team on complex questions while building product expertise and materials for future sessions.

Qualifications

• Excellent live presentation and facilitation skills on video call.
• Strong digital fluency; learn new software quickly and thoroughly.
• Ability to read people and adapt communication to fit them.
• Experience in teaching, training, tutoring, or enablement.

Responsibilities

• Deliver live, virtual product learning sessions—onboarding walkthroughs, feature refreshers, and office hours.
• Teach administrators how to use core workflows and guide hands-on until they can run tasks independently.
• Tailor sessions for different audiences: housing directors, front-desk/RA staff, campus IT.
• Address how-to questions in real time; escalate complex questions to senior CS.

Skills

Live presentation

Digital fluency

Reading people

Teaching

Fluent English

US business hours

Reliable internet

Organized

Ownership

Job description

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