Learning & Development Program Manager

Okta•Toronto, ON

12d•Hybrid

About The Position

This role is an opportunity to act as a key architect for AI-driven modernization and serve as the lead for Toronto’s Talent, Development, and Experience (TDE) ecosystem within the global L&D team. The position bridges the gap between local employee experience and global AI enablement, moving internal processes from manual design to scalable, AI-assisted models. This role is critical in moving the organization from manual, program-based learning models to intelligent, scalable, AI-assisted systems of development. This role is ideal for someone who thrives operating across the full spectrum of talent development — one day facilitating a manager workshop, the next designing scalable AI-powered learning solutions that shape the future of how we work.

Requirements

5+ years of experience in leadership development, learning strategy, or program management
Demonstrated experience leading complex, enterprise-wide learning initiatives
Experience integrating AI tools and technology into learning design and/or workflow enablement strongly preferred
Strong background in instructional design with a focus on measurable behavior change
Experience designing and scaling manager development programs (feedback, coaching, performance enablement)
Organized with exceptional attention to detail
Strong consulting, communication, and facilitation skills
Data-driven mindset with the ability to define and measure impact
Ability to anticipate challenges and proactively drive solutions
Adaptable and comfortable operating in ambiguity

Responsibilities

Own the strategy, delivery, and evolution of Toronto's learning and talent experience.
Lead end-to-end execution of programs for the Toronto site (onboarding, manager development, employee experience).
Serve as the local extension of the global onboarding strategy, ensuring programs scale effectively while meeting site-specific needs.
Embed learning into day-to-day workflows to drive sustained behavior change, not one-time participation.
Own manager capability programs locally.
Partner with Workplace and senior leaders to activate the office as a culture and development hub.
Track engagement, adoption, and business impact at the site level.
Drive AI modernization across design and delivery.
Help define and operationalize an AI enablement strategy.
Identify high-friction workflows and redesign them using AI-assisted solutions (e.g., copilots, automation, content generation, knowledge retrieval).
Source, test, and model AI solutions (LLMs, content automation, workflow enablement).
Move the organization from AI awareness to measurable adoption.
Apply AI tools to accelerate learning design, personalization, and program iteration.
Advise senior leaders on AI-enabled learning innovation.
Reframe requests into solution pathways (e.g., workflow redesign, manager enablement, AI augmentation, or targeted learning).
Facilitate working sessions to help teams identify friction points and redesign how work gets done.
Advise teams and leaders on AI-enabled talent strategies, manager effectiveness, and future-of-work capabilities.
Balance local needs with global priorities, ensuring alignment while advocating for site-specific solutions.
Partner closely with senior leaders, People Business Partners, and cross-functional stakeholders to ensure learning initiatives directly support business outcomes.
Act as a strategic advisor on AI enablement and manager effectiveness.
Build strong, trust-based partnerships across global teams.
Thrive in a fast-moving, evolving environment with shifting priorities.
Serve as a reliable, proactive communicator, ensuring transparency on timelines, risks, and impact.