Program Manager, Learning & Development

Role Description

As an experienced Learning & Development Program Manager at Dropbox, you will lead the strategy, planning, execution, and continuous improvement of high-impact learning programs across the employee lifecycle. Working in partnership with our Learning Design team, your portfolio will span programs focused on leadership development, general and VP onboarding, technology-enabled learning, the company-wide coaching program, and more.

You will manage and evolve multiple learning initiatives simultaneously—bringing strong systems thinking, learning operations expertise, and a learner-first mindset to your work. You will serve as a key liaison between the L&D team and stakeholders across the business, including senior leaders, and will bring your project and program management experience, executive presence, strong judgment, and clear communication to every interaction.

In this highly cross-functional role, you’ll partner closely with Learning Designers, People

Analytics, external vendors, and leaders across Dropbox to deliver scalable and insight-driven learning experiences. You’ll define and operationalize the learning metrics strategy, using data to inform continuous improvement and strategic prioritization.

This is a role for a collaborative doer who is energized by complexity, passionate about enabling growth, and motivated to bring Dropbox’s Learning Philosophy to life.

Responsibilities

• Lead the detailed planning and execution of multiple concurrent L&D programs, including leadership development, general & VP onboarding and skill-building for general employee populations.

• Partner with Learning Designers to refresh and evolve programs based on learner feedback, UX and user journeys, behavioral data, and organizational priorities.

• Own and operate the logistics of Dropbox’s coaching program from manager to VP level: manage vendor partnerships, facilitate intake and coach-matching, and oversee program evaluation and communications

• Define and implement Dropbox’s learning metrics strategy, turning engagement and impact data into actionable insights that align with business priorities.

• Manage integrated platforms, program calendars, dashboards, and planning processes, ensuring visibility, prioritization, and alignment across stakeholders.

• Deliver and own technology-enabled learning experiences that scale effectively in a Virtual First environment (e.g., LMS platforms, Slack-based workflows, self-paced content, AI).

• Foster strong cross-functional partnerships at the senior level to ensure aligned and high-quality learning experiences.

• Approach your work with an innovative lens, offering recommendations for AI-integration and enhancement and continuous improvement across the organization.

Requirements

• Bachelor’s degree or equivalent experience in Organizational Development, Psychology, Education, Business, Learning and Development, or a related field.

• At least 5 years of experience in L&D, program and project management, employee experience, or HR strategy, preferably in a distributed or tech-enabled organization.

• Proven ability to manage and evolve learning programs and/or coaching and leadership development initiatives across multiple stakeholder groups.

• Demonstrated success in leading multiple large-scale, cross-functional programs, with strong attention to strategy, timelines, and execution.

• Experience designing and operationalizing metrics and evaluation strategies for learning programs, and translating insights into iteration.

• Executive presence and the ability to engage with and influence senior stakeholders, aligning learning initiatives with leadership and company priorities.

• Experience working with instructional designers and user researchers to help shape and iterate learner experiences.

Preferred Qualifications

• Project Management Professional (PMP), Certified Professional in Learning and Performance (CPLP), or similar credentials

• Familiarity with adult learning principles, leadership development frameworks, or behavior change models

• Experience with modern LXP/LMS platforms and integrations

• Proficiency in project and data tools such as Airtable, Asana, Google Workspace, and Tableau (or equivalent)

• Interest in or experience applying AI tools to learning and productivity in ethical and impactful ways

Compensation

Canada Pay Range
$94,400—$127,600 CAD