Senior AI Trainer – Customer Success Managers

About the role

We are looking for a senior professional with deep enterprise Customer Success experience to design, evaluate, and refine realistic training tasks for advanced AI systems. You will translate real‑world customer lifecycle challenges into high‑quality AI training data.

Key responsibilities

• Create high‑difficulty tasks and gold‑standard solutions covering onboarding, adoption, retention, renewals, account health, stakeholder management and value realization.
• Review and calibrate peer‑generated work, maintain day‑to‑day quality, and flag edge cases or rubric ambiguities.
• Collaborate with AI evaluation teams to ensure training data aligns with product goals.

Required profile

• 8–15 years of Customer Success or account‑management experience, primarily in enterprise SaaS.
• Proven ownership of strategic enterprise accounts across complex lifecycles, including renewals, retention and revenue growth.
• Experience designing health‑score frameworks, renewal playbooks, risk processes, success metrics, and expansion strategies.
• Bachelor’s degree or equivalent practical experience.
• AI evaluation or related analytical experience is a plus, not mandatory.

Required skills

What we offer

• Short‑term contractor engagement for up to 9 weeks.
• Commit 4–40 hours per week with at least 4 hours overlapping Pacific Time.
• Compensation of $10.50 USD per hour.