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Pinnacle - AI Coaching · 4 days ago

AI Learning Specialist / AI Agent Lead

United States

Full-time

Remote

Mid Level

3+ years exp

Pinnacle is one of the world’s leading AI coaching companies, redefining leadership development for the modern workplace. The AI Learning Specialist / AI Agent Lead will shape how Pinnacle’s AI coach operates in customer environments, designing and iterating on AI agents while also providing leadership coaching to select clients.

Computer Software

Responsibilities

Own and evolve Pascal’s existing AI agents (prompts, structure, tone, memory patterns, guardrails) to support trusted, high-quality coaching relationships

Design, launch, and iterate on new AI agents grounded in real leadership and people-development use cases (discovery → design → deployment → iteration)

Orchestrate how multiple agents work together so the experience feels cohesive, intentional, and human

Rigorously test agents for quality, reliability, and alignment with real customer expectations; diagnose failures and turn them into system-level improvements

Record, investigate, and resolve quality issues, providing detailed feedback to improve outcomes

Collaborate with engineering and product on implementation

Provide executive and leadership coaching to select client leaders, using those relationships as a live signal for what the AI should (and should not) do

Partner with customers on program design, implementation, and change management so Pascal is meaningfully embedded in how teams work—not bolted on

Help clients programmatically design and customize Pascal to support ongoing people programs (e.g., manager enablement, feedback, performance, growth)