Challenge
Microsoft's Enterprise Technical Specialists needed a scalable way to validate technical discovery and objection-handling capabilities before high-stakes customer engagements, but traditional role-play exercises couldn't provide the volume, consistency, or real-time feedback required for global teams.
Approach
Led the end-to-end design and deployment of generative AI-powered simulations using Second Nature's conversational AI platform. This involved:
- Simulation Architecture: Designed eight distinct customer personas (e.g., CIO, CFO, IT Director) with role-specific objections, technical concerns, and decision criteria across industries including healthcare, financial services, and manufacturing
- Prompt Engineering: Authored system prompts that enabled natural multi-turn conversations while maintaining character consistency, realistic pushback patterns, and appropriate technical depth
- Assessment Framework: Built evaluation rubrics measuring discovery effectiveness, objection handling, value articulation, and technical accuracy-with automated scoring and human-readable feedback
- Pilot Execution: Coordinated technical deployment, user onboarding, and feedback collection across pilot cohorts
- Iteration & Refinement: Analyzed conversation transcripts and success metrics to refine persona behaviors, scoring logic, and simulation difficulty
Collaborated cross-functionally with AI researchers, enablement leads, product managers, and field stakeholders to ensure simulations aligned with Microsoft's customer engagement methodology and real-world selling scenarios.
Outcomes & Evidence of Impact
- First enterprise deployment of generative AI role-play for technical capability validation at Microsoft, establishing a scalable model for AI-enhanced practice environments
- Delivered pilot results showing measurability of technical discovery quality, with automated feedback reducing dependency on human evaluators while maintaining assessment rigor
- Informed executive strategy on AI simulation capabilities through demos and presentations to program leadership, influencing FY25 enablement investment decisions
- Created reusable frameworks for persona design, prompt architecture, and scoring models now being adapted for additional customer-facing roles
- Demonstrated 25% reduction in time required for practice scenario administration compared to traditional facilitator-led role-plays
Tools & Platforms
Second Nature AI, Azure OpenAI Service, Seismic Enablement Cloud, Microsoft Teams
Key Capabilities Demonstrated
Prompt engineering, LLM evaluation design, conversational AI architecture, simulation-based learning, technical enablement, cross-functional program leadership