Dropbox is a Virtual First company. For this role, we are currently only authorized to hire candidates from the following provinces: Alberta, British Columbia, Ontario, and Saskatchewan.
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
The range listed above is the expected annual salary/OTE for this role, subject to change.
Salary/OTE is just one component of Dropbox’s total rewards package. All regular employees are also eligible for the corporate bonus program or a sales incentive (target included in OTE) as well as stock in the form of Restricted Stock Units (RSUs).
Company Description
Dropbox isn’t just a workplace—it’s a living lab for more enlightened ways of working. We're a global community of bold visionaries and resourceful doers who are shaping the future of Dropbox—and with it the future of work. Our Virtual First model combines the autonomy of a distributed workplace with the power of human connection, making space for both meaningful work and meaningful relationships. With our start-up mindset and enterprise-level opportunities, you can be who you are and grow into who you’re meant to be. Here, you can own your impact to make work more intuitive, joyful, and human—for you as a Dropboxer and for hundreds of millions of people worldwide. If you're ready to push boundaries—and yourself— Dropbox is ready for you.
Team Description
The Dropbox People Team is designing a workplace where every Dropboxer can thrive. We take a human-centered, HR as a Product approach—treating programs like well-crafted products shaped by employee and candidate needs, informed by data, and backed by actionable insights. Our team continuously innovates to attract, develop, and retain world-class talent while building a culture of experimentation, craft, and community. From fostering connection in our Virtual First model to scaling HR systems and offering personalized learning tools, we build experiences that evolve with our people. We think big, act fast, and adapt with agility—grounded in outcomes, empathy, and clear communication.
Areas of work include Talent Acquisition, HR Business Partnership, Learning & Development, Total Rewards, and Employee Experience.
Benefits
Dropbox is committed to investing in the holistic health and wellbeing of all Dropboxers and their families. Our benefits and perks programs include, but are not limited to:
Competitive medical, dental and vision coverage*
Retirement savings through a defined contribution pension or savings plan**
Flexible PTO/Paid Time Off, paid holidays, Volunteer Time Off, and more, allowing you time to unplug, unwind, and refresh
Income Protection Plans: Life and disability insurance*
Business Travel Protection: Travel medical and accident insurance*
Perks Allowance to be used on what matters most to you, whether that’s wellness, learning and development, food and groceries, and much more
Parental benefits including: Parental Leave, Fertility Benefits, Adoptions and Surrogacy support, and Lactation support
Mental health and wellness benefits
Additional benefits details are available upon request.
- Where group plans are not available, allowances may be provided
**Benefit, amount, and type are dependent on geographical location, based upon applicable law or company policy
Dropbox supports responsible use of AI for preparation, but misrepresentation of skills or experience is not permitted. See our AI philosophy .
Dropbox is an equal opportunity employer. We are a welcoming place for everyone, and we do our best to make sure all people feel supported and connected at work. A big part of that effort is our support for members and allies of internal groups like Asians at Dropbox, BlackDropboxers, enABLE, TODOS (Latinx), Pridebox (LGBTQ), Vets at Dropbox, and Women at Dropbox.
