AI Learning Strategist​/AI Agent Lead

About Pinnacle

Pinnacle is one of the world’s leading AI coaching companies, backed by top venture investors and trusted by enterprise customers including Hub Spot and Ripple. We’re redefining leadership development for the modern workplace.

Leadership today isn’t shaped in courses or quarterly trainings - it’s shaped in conversations, meetings, and everyday decisions. Pinnacle’s AI coach, Pascal, lives inside Slack, Microsoft Teams, and live meetings, delivering real-time, contextual coaching exactly when leaders need it. The result is continuous, practical skill-building that actually changes behavior over time.

We’re looking for builders with an L&D background who care deeply about craft, clarity, and impact, people who want to work on hard, meaningful problems and see their work used every day by real leaders. If you’re excited about shaping a new category, building products that earn trust, and redefining how leaders grow at scale, you’ll feel at home here.

This role sits at the intersection of learning & development, applied AI, product, and customer success. You’ll shape how Pinnacle’s AI coach shows up in live customer environments - designing, deploying, and iterating on a suite of AI agents that impact every facet of the user’s coaching journey. In parallel, you’ll act as a hands‑on leadership coach and L&D partner for select clients, supporting demos, onboarding, and customer customization while ensuring our AI coaching reflects real‑world coaching best practices.

To be effective, you must have had experience in learning & development or executive coaching.

While you’ll already need some practical AI fluency to be effective in this role (ideally you've already built agents others are using, not just used ChatGPT in your work), you don’t need deep technical expertise coming in. We can teach that. You do need strong instincts for coaching & leadership development, a strong logical mind, and genuine curiosity about experimenting with AI to understand what works in practice.

• AI Agent-Building (~70% time)

  • 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.

• L&D work (~30% time)

  • 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)

• You have 5+ years working in leadership development, coaching, or L&D, and you have strong point-of-view about what actually helps leaders change behavior

• You’re already actively experimenting with AI in your work or on your own and have clear opinions about what works, what doesn’t, and why. Ideally, you’ve applied it to build or ship something others have actually used.

• You’re comfortable learning in public: working directly with users, reacting to real feedback, and making judgment calls without a playbook

• You move fast, ship imperfect work, and improve it through use rather than over-design

• 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.