Senior AI Trainer, Customer Success Managers

About The Role
Apply senior enterprise Customer Success expertise to create, evaluate, and refine realistic training tasks for advanced AI systems.
What You'll Do
Produce high-difficulty tasks and gold-standard solutions involving onboarding, adoption, retention, renewals, account health, stakeholder management, and value realization.
Review and calibrate peer work, own day-to-day quality, and escalate genuine edge cases or rubric ambiguities.
Requirements
8-15 years of Customer Success or account-management experience, primarily in enterprise SaaS.
Ownership of strategic enterprise accounts across complex customer lifecycles, renewals, retention, and revenue growth.
Experience designing health-score frameworks, renewal playbooks, risk processes, success metrics, and onboarding, adoption, value-realization, retention, and expansion strategies.
Bachelor's degree or equivalent practical experience. AI evaluation or related analytical experience is preferred but not required.
Engagement Details
Short-term contractor engagement for up to 9 weeks. Commit at least 4 hours per day and up to 40 hours per week, including 4 hours of overlap with Pacific Time.
Compensation
$10.50 USD per hour.