Customer Success Manager - Ai Training – Remote

Job Type: Contractor Location: Remote Role Description We’re looking for senior Account Manager / Key Account Manager professionals who understand complex account planning, executive communication, and renewal strategy. You’ll challenge and evaluate advanced language models on account management topics to strengthen model reasoning and communication quality. Your Profile

• 3+ years of experience in account management, key account management, customer success, strategic client management, enterprise relationship management, or a closely related commercial role.
• Significant hands-on experience managing high-value customer accounts, executive stakeholders, renewals, escalations, growth opportunities, and long-term relationship plans.
• Deep knowledge of strategic account planning, customer lifecycle management, stakeholder mapping, retention strategy, QBR preparation, and value-based client communication.
• Strong understanding of commercial account metrics such as retention, expansion, churn risk, account health, pipeline influence, renewal probability, customer satisfaction, and lifetime value.
• Proven experience building trusted client relationships, navigating complex organizations, and translating customer needs into actionable internal priorities.
• Demonstrated experience in developing account plans, managing executive communications, handling difficult customer conversations, and coordinating with sales, customer success, product, finance, and operations teams.
• Bachelor’s degree in business, marketing, communications, management, economics, or a related field preferred; equivalent senior professional experience will also be considered.

Key Responsibilities

• Evaluate AI-generated responses for accuracy, relevance, business judgment, and practical usefulness in account management and key account scenarios.
• Challenge advanced language models with realistic account management prompts involving renewals, expansions, executive alignment, churn risk, escalation paths, and customer value narratives.
• Review and refine AI-generated prompts, responses, rubrics, and examples related to customer relationship strategy and commercial account management.
• Provide structured feedback that helps improve how AI systems reason through complex client situations, competing priorities, and nuanced stakeholder dynamics.
• Assess whether model outputs reflect sound account planning practices, including customer segmentation, stakeholder mapping, opportunity identification, risk mitigation, and next-best actions.
• Identify gaps, hallucinations, oversimplifications, or unrealistic recommendations in AI-generated account strategy content.
• Shape AI communication standards for professional, consultative, and commercially appropriate customer-facing language.
• Support benchmarking efforts by comparing model responses against expert-level expectations for senior account management judgment.

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