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Dropbox

Cloud storage, file sync, collaboration platform

Support Enablement Engineer Intern - Summer 2026

Summer 2026Updated
CA$23.08 - CA$25.96/hr
Internship
Bachelor's
Remote in Canada
Remote
Software EngineeringBackend Engineering

About the job

Requirements
  • Currently pursuing an undergraduate degree in Computer Science, Information Technology, Information Systems, Systems Engineering, or a related technical field, with an expected graduation date in 2027.
  • Demonstrated interest in solutions engineering, technology enablement, workflow automation, and applying AI-driven solutions to operational problems.
  • Hands-on experience through coursework, projects, internships, or labs with AI, APIs, system integrations, or workflow automation concepts.
  • Foundational familiarity with AI-enabled systems or tools used to support operational workflows (e.g., agent assist, knowledge retrieval, intelligent routing, or similar applications), either through academic projects, tooling exposure, or self-directed learning.
  • Experience with at least one programming or scripting language (e.g., Python, JavaScript) and comfort working in a development or configuration-based environment.
  • Analytical mindset with the ability to interpret data, identify patterns, and translate insights into practical process or tooling improvements.
  • Ability to work independently on well-scoped tasks while collaborating effectively with cross-functional partners in a virtual team environment.
  • Ability to clearly explain technical concepts to both technical and non-technical audiences.
  • Curious, adaptable, and motivated to learn, iterate, and apply new technologies, particularly AI to real-world customer support and operational challenges.
  • Exposure to CX tools (e.g., ticketing systems, knowledge bases, internal tooling) is a plus but not required.
Responsibilities
  • Support the execution and rollout of AI-driven enablement initiatives across Customer Experience (CX) support workflows, working under the guidance of enablement engineers and AI Program Manager.
  • Assist in designing, testing, and deploying AI-powered workflows, such as: Monitor and troubleshoot issues related to CX tools and AI integrations, helping ensure system reliability, performance, and scalability.
  • Analyze support and operational data to identify opportunities for AI-driven automation and workflow improvements.
  • Collaborate with cross-functional partners across CX, Customer Experience & Success (CXS) Tech, and Go-to-Market (GTM) Platforms teams to ensure AI solutions align with real customer support needs and operational constraints.
  • Develop and deploy automation scripts, configurations, or integrations to support AI enablement efforts.
Desired Qualifications
  • Exposure to Customer Experience or support operations: Including hands-on experience with support tooling, case workflows, or service operations environments through internships, part-time roles, or academic projects.
  • Experience building or configuring automation: Including scripts, integrations, or low-code/no-code workflows that reduced manual effort or improved operational efficiency.
  • Familiarity with data analysis or visualization: To measure adoption, performance, or outcomes, using tools such as dashboards, spreadsheets, SQL, or similar analytics platforms.
  • Experience collaborating cross-functionally with technical and non-technical partners to translate requirements into practical solutions.
  • Demonstrated interest in applied AI enablement: Including experimentation with AI tools, prompt iteration, model outputs, or human-in-the-loop workflows in operational contexts.
  • Hands-on experience with modern AI technologies and workflows, such as LLMs (ChatGPT, Claude, Gemini), automation platforms (n8n, Make, Gumloop), building AI agents, API integrations, MCP, AI coding assistants (Cursor, Claude Code), and no/low-code AI platforms (Lovable, Replit, Bolt).

About the company

D

Dropbox

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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, CA

Founded

2007

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Simplify Jobs

Simplify's Take

What believers are saying

  • Q2 2026 revenue reached $631.5 million, with ARR rising to $2.566 billion.
  • Management raised 2026 operating margin guidance to 40.0%-40.5% and uFCF to $1.07 billion.
  • Dash rollout now offsets FormSwift drag and supports higher monetization across Teams.

What critics are saying

  • Core revenue barely grew 0.9% in Q2 2026, exposing mature demand.
  • Google Workspace and Microsoft 365 can absorb Dropbox's remaining use case by 2027.
  • Dropbox's secured collateral and leverage covenants amplify downside if buybacks outrun growth.

What makes Dropbox unique

  • Dropbox Dash for Business unifies search, sharing, and access controls across connected apps.
  • Remote-first operations attract talent: 74% of 2026 hires cited virtual-first as reason.
  • Secured credit plus $1.2 billion buybacks signal disciplined cash generation and capital returns.

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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

6 month growth

4%

1 year growth

4%

2 year growth

1%
Business Insider
Oct 28th, 2026
Dropbox cuts 9% of workforce, about 200 roles, as chief technology officer departs

Dropbox is laying off about 9% of its global workforce, co-chief executive officer Ashraf Alkarmi said on Wednesday. The cut covers roughly 200 roles in Engineering, Product, Design, and GA teams. Alkarmi said the company is profitable but must concentrate resources on priorities with the greatest potential for customer impact and growth. Its two-year strategy aims to serve larger companies and reach new markets. Chief technology officer Ali Dasdan is also leaving; his last day is November 18. Departing staff will receive 16 weeks of pay plus one week for each year at Dropbox, Q4 equity vesting, and six months of COBRA subsidy for US employees.

Tech in Asia
Oct 12th, 2026
Dropbox launches Protect in Singapore to govern file access across Drive and Microsoft 365

Dropbox has launched Dropbox Protect in Singapore, a data access governance tool that shows information technology and security teams who can access content across Dropbox, Google Drive, and Microsoft 365. The tool lets teams review public links, external collaborators, and risky permissions. They can also automate policies, alerts, and access fixes, and generate reports and audit logs for governance and compliance. The launch comes as Singapore's Personal Data Protection Act requires organisations to make reasonable security arrangements against unauthorised access to, or disclosure of, personal data held electronically. Dropbox Protect competes with data access governance vendors, including tools covering Google Drive and SharePoint. Microsoft also offers governance actions in Defender for Cloud Apps.

Fortune
Oct 7th, 2026
Dropbox CTO pushes full AI adoption across 2,113 employees with bottom-up approach

Dropbox CTO Ali Dasdan is driving AI adoption across the company's 2,113 employees. When he joined in March 2025, less than 40% of engineering, product, and design teams used AI tools. Through training, hackathons, and championing superusers, he achieved full adoption among these groups. The company has made ChatGPT Enterprise widely available to knowledge workers and approved AI features in platforms like Workday, Slack, and Zoom. Non-technical staff use tools like Lovable to create custom applications, with hundreds now deployed across departments. Dasdan says AI enables faster customer support and helps clear technical debt. The company has focused on enhancing Dash, its AI-powered search tool, with improved capabilities for indexing and searching images and video. Dropbox has also integrated Dash into ChatGPT, Claude, and Google Gemini ecosystems to meet customers where they already work.

Yahoo Finance
Sep 16th, 2026
Dropbox co-CEO sells 28,800 shares for $1M as stock generates 15% annual return

Dropbox co-CEO Ashraf Alkarmi sold 28,800 shares of Class A Common Stock for $1 million on 11 September 2026, according to an SEC filing. The sale was executed through a Rule 10b5-1 trading plan established on 12 June 2026, which allows insiders to make pre-scheduled trades. Following the transaction, Alkarmi retains 1,004,081 shares, representing approximately 0.39% of the company. The stock had generated a 15% one-year return as of the transaction date. As of 15 September 2026, Dropbox shares traded at $37.63, giving the San Francisco-based software company a market capitalisation of $9.5 billion. The company reported trailing twelve-month revenue of $2.5 billion and net income of $442.8 million.

Yahoo Finance
Aug 23rd, 2026
Dropbox CFO sells $25M in shares days after raising guidance

Dropbox CFO Ross Tennenbaum sold 20,326 shares of Class A Common Stock on 17 August, according to an SEC Form 4 filing. The transaction, valued at $25.34 million, was executed for tax purposes and does not reflect a change in the insider's assessment of the company's valuation. Tennenbaum continues to hold 759,000 shares directly, valued at $25.7 million based on the 18 August closing price. He also holds restricted stock units scheduled to vest through 15 November 2029, contingent upon continued service. Dropbox operates a software-as-a-service business model, generating revenue through tiered subscription plans for individual users, teams, and enterprises. The company has a market capitalisation of $8.6 billion and reported $2.5 billion in trailing twelve-month revenue.

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