Full-Time

L&D Innovation Strategist

Learning and Development, Innovation Strategy

Posted on 8/9/2025

Dropbox

Dropbox

1,001-5,000 employees

Cloud storage, file sync, collaboration platform

Compensation Overview

CA$114.3k - CA$154.7k/yr

Remote in Canada

Remote

Remote work is limited to select locations within Canada.

Category
Education
Required Skills
UI/UX Design
Product Management
Data Analysis
Requirements
  • Bachelor’s degree or equivalent experience in Instructional Design, Learning Technology, Computer Science, Human-Centered Design, or a related field.
  • At least 8 years of experience in learning innovation, L&D strategy, instructional design, or product management of learning technologies.
  • Proven track record of launching and scaling AI- or tech-enabled learning solutions, with measurable impact on experience or performance.
  • Strong understanding of learning technologies, including LMS/LXP platforms, content authoring tools, AI integrations, and analytics systems
  • Demonstrated experience building and executing innovation pipelines or structured experimentation cycles.
  • Excellent collaboration skills—able to bring together cross-functional teams and co-create with Design, Delivery, Tech, and external partners
  • Strong presentation and storytelling skills, with the ability to influence decisions through compelling narratives.
  • Experience integrating AI tools or automation into workflows to enhance efficiency, personalization, or insight generation in L&D or operational contexts.
  • Proven success applying HR as a product approaches to program design or delivery, with a focus on driving learner outcomes and operational excellence.
  • Comfort with UX/design thinking principles to co-create, test, and refine learner-centric experiences in fast-moving, data-informed environments.
Responsibilities
  • Lead Dropbox’s L&D innovation strategy: develop and manage a sustainable pipeline for exploring, evaluating, and scaling AI-enabled and tech-forward learning solutions.
  • Build and implement a process for ongoing research and innovation—identifying learning trends, surfacing opportunities, and converting insights into pilot programs.
  • Manage the L&D technology ecosystem—assess tools, recommend upgrades, and oversee vendor relationships to ensure scalable infrastructure.
  • Pilot and scale innovative learning methods, collaborating with Design and Delivery to ensure strong learner experience and alignment to Dropbox strategy
  • Drive development of learning technology platforms, including platform enhancements and AI-powered features to increase personalization and impact.
  • Develop and deliver AI-enabled learning experiences, including microlearning, adaptive content, or in-flow nudges that meet learners where they are.
  • Build team-wide fluency in the future of learning—keeping the team informed on evolving tools, methods, and insights.
Desired Qualifications
  • Background in strategic foresight, innovation strategy, or product innovation within L&D, HR, or EdTech.
  • Experience developing learning experiences that incorporate natural language processing, generative AI, or adaptive learning systems.
  • Skill in trend analysis—translating macro trends in work, technology, and learning into actionable L&D opportunities.
  • Ability to translate future-facing insights into near-term strategy and practical action.

Dropbox provides cloud storage and file synchronization for individuals and organizations, with features for storing, sharing, and collaborating on documents. Users upload files to online storage; the service syncs them across devices and makes them available in shared workspaces, with links, comments, and real-time collaboration. It differentiates itself with a simple interface, strong security, reliable syncing, and a growing ecosystem of integrations and partnerships including DocSend and HelloSign. Its goal is to support remote and distributed teams by offering a straightforward, secure way to access and work on files from anywhere while growing its subscription revenue.

Company Size

1,001-5,000

Company Stage

IPO

Headquarters

San Francisco, California

Founded

2007

Simplify Jobs

Simplify's Take

What believers are saying

  • Mobius Labs acquisition enhances Dash search capabilities announced in 2026.
  • OpenAI partnership integrates Dropbox tools with ChatGPT for AI work hubs.
  • Q1 2026 raised guidance projects $2.5 billion revenue by 2029 via AI.

What critics are saying

  • Microsoft 365 bundles OneDrive with Copilot, eroding Dropbox's $2.5B ARR now.
  • Paying customers drop to 18.07 million as ARPU declines in Q1 2026.
  • Convertible debt maturities exhaust $1.5B buyback, forcing dilution by 2028.

What makes Dropbox unique

  • Dropbox Dash enables AI-powered universal search across Dropbox, Slack, and Jira.
  • Dropbox Sign from HelloSign acquisition provides electronic signatures and workflows.
  • Dropbox Spaces offers organized hubs for collaboration in 500,000 global teams.

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Benefits

Competitive medical, dental & vision coverage

Competitive 401(k) Plan with a generous company match & immediate vesting

Flexible Time Off/Paid Time Off

11 Company-wide PTO days

Volunteer time off and more

Life Insurance, Disability Insurance & Travel benefit plans

Perks Allowance

Parental benefits

Mental Health & Wellness benefits

Free Dropbox space for your friends and family

Growth & Insights and Company News

Headcount

6 month growth

1%

1 year growth

0%

2 year growth

0%
Yahoo Finance
Apr 6th, 2026
Dropbox beats profit expectations but remains slowest-growing productivity software peer

Dropbox reported revenue and EBITDA above analyst expectations for early 2026, closing 2025 ahead of guidance whilst showing accelerating customer growth despite slight year-on-year revenue decline. However, the company remains the slowest-growing major productivity software peer, creating tension between improved profitability and lagging revenue performance. The company continues significant share repurchase activity, allocating billions of dollars across multiple authorisations to amplify earnings per share whilst revenue remains under pressure. Dropbox is betting on AI tools like Dash and operational discipline to offset flat or declining revenue. Analysts project $2.5 billion revenue and $494.6 million earnings by 2028, implying 1.1% yearly revenue decline. The key question remains whether Dropbox can reignite sustainable growth before competitive pressures and customer churn impact earnings power.

Yahoo Finance
Apr 2nd, 2026
Dropbox reports slowest revenue growth in productivity software sector with $636.2M Q4

Dropbox reported Q4 revenues of $636.2 million, down 1.1% year-on-year, though exceeding analyst expectations by 1.1%. The company added 10,000 customers, reaching 18.08 million total, and beat EBITDA estimates whilst demonstrating accelerating customer growth. However, Dropbox delivered the slowest revenue growth amongst 16 tracked productivity software stocks. The broader sector reported strong Q4 results, beating revenue consensus estimates by 1.9% on average, though share prices declined 8.9% following earnings. Appian led the sector with revenues of $202.9 million, up 21.7% year-on-year and beating estimates by 7.2%. Dropbox shares fell 4.8% following the results and currently trade at $23.54.

Yahoo Finance
Jan 20th, 2026
Dropbox faces structural decline as Microsoft and Google dominance erodes $2.5B ARR business

Dropbox faces structural challenges in a commoditised file storage market dominated by Microsoft and Google, according to a bearish thesis from Inwood Capital. The company reported $2.5 billion in annual recurring revenue and 18 million paying users in Q3 2025, but is experiencing declining user growth and market share erosion. The platform's standalone cloud storage offering struggles against Microsoft 365 and Google One, which bundle storage with broader ecosystems and AI tools. Dropbox has responded with cheaper pricing tiers, indicating deteriorating pricing power. Diversification efforts through products like Dash have underperformed, whilst acquisitions including HelloSign and DocSend have failed to deliver. Management has guided for revenue contraction in 2026 with no margin expansion. With EBITDA margins exceeding 45% and upcoming convertible debt maturities constraining share buybacks, the analyst views the stock as overvalued.

SiliconANGLE Media
Oct 23rd, 2025
Dropbox Enhances Search with Mobius Labs

Dropbox Inc. has introduced new AI features to enhance file search capabilities on its platform and announced the acquisition of Mobius Labs GmbH, an AI model developer. The acquisition aims to improve Dropbox's search features using Mobius Labs' technology. Both announcements are centered around a tool called Dash, launched in 2023, which allows users to search for files across Dropbox and third-party services like Jira.

Business Wire
Sep 10th, 2025
Dropbox Amends Secured Credit Agreement; Announces Additional $1.5B Stock Repurchase Program

Dropbox, Inc. (“Dropbox” or the “Company”) (Nasdaq: DBX), today announced an amendment to its existing Credit and Guaranty Agreement providing the Company wi...

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