Pinnacle - AI Coaching · 2 weeks ago
AI Learning Strategist / AI Agent Lead
United States
Full-time
Remote
Senior Level
$75K/yr - $100K/yr
5+ years expPinnacle is one of the world’s leading AI coaching companies, redefining leadership development for the modern workplace. The AI Learning Strategist / AI Agent Lead will design, deploy, and iterate on AI agents while providing executive coaching to clients, ensuring that the AI coaching reflects best practices.
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)
Qualification
Required
5+ years working in leadership development, coaching, or L&D
Strong point-of-view about what actually helps leaders change behavior
Practical AI fluency
Experience in building agents others are using
Strong instincts for coaching & leadership development
Strong logical mind
Genuine curiosity about experimenting with AI
Comfortable learning in public
Ability to react to real feedback and make judgment calls without a playbook
Ability to move fast, ship imperfect work, and improve it through use rather than over-design
Preferred
Experience in forward-deployed, solutions, or customer-facing product roles
Exposure to startups or early-stage teams
Familiarity with conversational AI, prompt design, or evaluation
ICF coaching certification or formal L&D training
Company
Pinnacle - AI Coaching
With Pinnacle’s AI Smart Coach, Pascal, your team gets personalized support and career guidance 24/7, directly within Slack and Teams.
2-10 employees
Funding
Current Stage
Early StageCompany data provided by crunchbase