Full-Time

Enterprise Context Architect

Dropbox

Dropbox

1,001-5,000 employees

Cloud storage, file sync, collaboration platform

Compensation Overview

CA$129.2k - CA$174.8k/yr

Remote in Canada

Remote

Remote within select locations in Canada.

Category
Data & Analytics (1)
Required Skills
Atlassian
ServiceNow
RAG

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Requirements
  • At least 7 years of experience designing how information is structured, owned, and maintained at enterprise scale, including at least 2 years applying that work to AI retrieval and grounding.
  • Direct experience preparing content for AI consumption, with working fluency in retrieval-augmented generation, grounding, semantic chunking, embeddings, vector search, and citations.
  • Hands-on experience with knowledge graphs, ontologies, or semantic models that structure content for machine consumption.
  • A track record of building federated operating models across functions outside direct reporting lines, with evidence of metadata standards or authoring frameworks adopted at scale.
  • Demonstrated ability to influence senior stakeholders across Engineering, IT, Legal, Security, and business functions.
  • Sound judgment on balancing central standards with domain expertise.
Responsibilities
  • Define the source-of-truth strategy for enterprise knowledge, including which systems are authoritative, what is indexed centrally versus fetched live, what is eligible for AI use, and what is archived or excluded, informed by an assessment of the authoritative sources behind the highest-value workflows.
  • Define enterprise standards that make content AI-ready across structure, metadata, provenance, and access, including where semantic models or knowledge graphs are warranted and where they are not, and translate them into authoring patterns adopted across domains.
  • Design the control model for AI actions, including eligibility rules, preconditions, approval boundaries, escalation paths, and rollback requirements, so systems that act on enterprise knowledge stay traceable and safe as AI capabilities evolve.
  • Lead platform and connector strategy across the content stack; drive decisions on what is refactored, migrated, indexed in place, or consolidated; and partner with IT and Engineering on connector architecture and how AI systems are granted access to tools and sources.
  • Build the federated operating model for enterprise content, including stewardship across functions, domain accountability for accuracy within shared standards, and lifecycle policies covering review cadence, expiration, material-change triggers, and retirement tied to business criticality.
  • Define content quality in an AI context; establish retrieval and grounding evaluations for priority use cases; extend measurement to workflow traces and policy conformance as systems begin to act; and route findings back into the content lifecycle.
  • Co-own criteria for AI content eligibility, sensitivity classification, and permissions modeling with Legal, Privacy, and Security, including access boundaries for the tools AI systems can reach.
Desired Qualifications
  • Hands-on experience with enterprise platforms such as ServiceNow, Atlassian, Microsoft 365 or Copilot Search, Slack, or Notion.
  • Familiarity with structured authoring such as DITA, controlled vocabularies, or knowledge operations methodologies such as KCS.
  • Experience with AI evaluation tooling and frameworks for measuring retrieval quality, groundedness, and answer relevance.
  • Background working in regulated, policy-heavy, or high-risk content domains.
  • Working knowledge of NIST AI Risk Management Framework, OWASP Generative AI guidance, or comparable risk frameworks.

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

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Simplify Jobs

Simplify's Take

What believers are saying

  • Q2 2026 revenue rose 0.9% to $631.5 million, returning to growth.
  • Dropbox raised 2026 free-cash-flow guidance above $1.07 billion and bought back $900 million.
  • Over 150,000 users connected Dropbox integrations with Claude and ChatGPT by August 2026.

What critics are saying

  • Google launched Dropbox Business migration tools in November 2025, accelerating customer churn.
  • Entangled Media’s patent trial against Dropbox remains scheduled for September 8, 2026.
  • Dropbox Sign breach litigation and arbitration keep trust damage alive through 2026.

What makes Dropbox unique

  • Dropbox Dash unifies search across Google Workspace, Slack, Notion, and ChatGPT in 2026.
  • Dropbox’s remote-first model drove 74% of 2026 hires to cite flexibility as decisive.
  • Dropbox still owns a profitable file-sync platform with 2026 operating margins near 40%.

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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

-1%

2 year growth

-2%
Yahoo Finance
Aug 16th, 2026
Two profitable stocks with strong fundamentals and one to avoid

Financial services firm Ares Management and commercial asset marketplace operator RB Global have been highlighted for their strong fundamentals and profitability, whilst cloud storage provider Dropbox faces challenges. Ares Management has demonstrated exceptional revenue growth of 24.3% annually over the past two years, with earnings per share compounding at 19.5% annually over five years. The company maintains an operating margin of 21.8%. RB Global, formerly Ritchie Bros. Auctioneers, has achieved 27.4% annual revenue growth over five years, with EPS growing at 19.3% annually. The company generates a free cash flow margin of 14%. Dropbox, despite a 26.6% operating margin, showed flat billings and faces weak demand outlook. Wall Street expects flat revenue over the next 12 months.

Dropbox, Inc.
Aug 10th, 2026
Introducing Dropbox Dash for Business — AI-powered Universal Search That Finds Anything and Protects Everything at Work | Dropbox

Dash for Business makes it easy for teams to find, organize, share, and secure company information by combining universal search, organization and sharing capabilities, and in-depth content access control for businesses of all sizes SAN FRANCISCO--( BUSINESS WIRE )--Today, Dropbox, Inc.

Business Insider
Aug 10th, 2026
Dropbox new co-CEO vows to maintain remote-first policy despite industry RTO mandates

Dropbox is maintaining its remote-first work model under new leadership, according to incoming sole CEO Ashraf Alkarmi. The cloud storage company adopted its "virtual-first" policy in 2021, focusing on workforce flexibility. Alkarmi, who joined Dropbox in 2024 and became co-CEO in May alongside founder Drew Houston, called the structure an "incredible model". He told Business Insider that "flexibility and autonomy are the ultimate currency in modern work". The company reports significant benefits from the policy. Applications per job were nearly seven times higher in 2025 than before virtual-first implementation. Dropbox has also seen its highest offer acceptance rates and lowest attrition rates under the model. Additionally, 74% of new hires in 2026 cited virtual-first work as a reason for joining. The policy includes in-person gatherings like annual hack weeks and leadership off-sites to maintain team connections.

Business Insider
Aug 4th, 2026
Dropbox co-CEOs use keyword 'final' to resolve workplace disagreements

Dropbox co-CEO Ashraf Alkarmi has shared how he and co-founder Drew Houston resolve workplace disagreements using a specific keyword system. Alkarmi, who joined Dropbox in 2024 and became co-CEO in May, said he continues challenging ideas until Houston uses the word "final" to signal a decision has been made. Until then, the discussion remains open for debate. The approach builds on trust, data-driven arguments, and radical candour. Alkarmi emphasised the importance of backing perspectives with clear reasoning and communicating directly rather than passive-aggressively. Once Houston makes the final call, Alkarmi fully commits to the decision, embracing Jeff Bezos's "disagree and commit" philosophy. "Whether it works or not, it's not his opinion or my opinion. It's what we both fundamentally actually ended up agreeing on," Alkarmi said. Alkarmi will eventually become Dropbox's sole CEO.

Business Wire
Jun 11th, 2026
Dropbox Completes New Secured Credit Agreement; Announces $1.2B Stock Repurchase Program

Dropbox, Inc. (“Dropbox” or the “Company”) (Nasdaq: DBX), today announced entry into a Credit and Guaranty Agreement providing the Company with up to $2.0 bi...