AI Strategy Trainer - Transformation Senior Manager (Remote)

DataAnnotation; Wellesley (MA); Remote; USD 142,000 - 202,000; Full time

Job summary

DataAnnotation is seeking an experienced Management Consultant to train AI models by testing them on real business problems from your practice. You’ll judge outputs with a consultant’s eye and clearly explain where they struggle and how to improve.

You’ll write client-style briefs, critique model responses for problem framing and rigor, and flag issues. You’ll compare options and select the best to present to leadership, shaping next-gen AI tools with your judgment and standards.

Qualifications

• Fluency in English.
• Experience in management consulting, strategy, PMO, or deal advisory.
• Experience at a top strategy firm, Big Four advisory practice, or boutique consultancy is a strong plus.
• Skilled at building and critiquing work for senior stakeholders.
• MBA or other postgraduate degree is preferred but not required.

Responsibilities

• Write client-style briefs from engagements you know well and run them through AI models.
• Review each response like an associate’s work before it reaches a partner: problem framing, structure, analytical rigor, insight, storyline, and whether it answers the client’s question.
• Flag concrete issues such as unsupported claims, faulty numbers, buried recommendations, or vague AI-sounding conclusions, and explain your reasoning.
• Compare responses head-to-head and pick the one you’d put in front of a leadership team.

Skills

Write briefs

Review responses

Flag issues

Compare responses

Job description

DataAnnotation is seeking an experienced Management Consultant to train AI models by testing them on real business problems from your practice. You’ll judge outputs with a consultant’s eye and clearly explain where they struggle and how to improve.

You’ll write client-style briefs, critique model responses for problem framing and rigor, and flag issues. You’ll compare options and select the best to present to leadership, shaping next-gen AI tools with your judgment and standards.