Is Dropbox fully remote, or will I ever need to go to an office?

Remote is the primary way of working, but Dropbox keeps on-demand Studios and workspaces you can use at no cost, and teams typically gather in person for offsites of 2 to 3 days per quarter, with roughly 5 to 10% travel being typical. In-person time is intentional and community-focused rather than a return-to-office requirement.

What does async by default look like day to day?

You work a nonlinear schedule of your own design, anchored by core collaboration hours that overlap across time zones, and written asynchronous communication is preferred over meetings to protect focus time. Dropbox also publishes free 4-week courses on its careers site teaching best practices for thriving in distributed work.

How does Dropbox set pay for remote roles?

Pay is geo-based: salary ranges are published in job postings, segmented into three US zones plus country-level ranges for Canada, Poland, and Mexico. The zip code of your remote work location determines which metropolitan pay range applies.

Which benefits stand out for remote employees?

Highlights include a 100% 401(k) match up to $6,000 per year, a quarterly perks allowance usable for childcare, wellness, ergonomics, and learning, a $100 monthly gym and wellness reimbursement plus the Peloton Corporate Wellness Program, and up to $145 per month toward phone and internet. Parental leave runs up to 20 weeks for birthing parents and 12 weeks for non-birthing parents.

Do employees actually like the Virtual First model?

Recent internal surveys on the careers site report that 87% of employees are happy with the current balance of in-person and virtual experiences and 90% feel they have colleagues they can trust. It suits people who value autonomy, strong written communication, and deliberate rather than constant in-person contact.

Head of Global Sales Enablement and AI Adoption

Dropbox

Remote

Job Description

Role Description

Dropbox is looking for a strategic leader to build and scale the next generation of Sales Enablement. As Head of Global Sales Enablement & AI Adoption, you will define how our sales organization learns, executes, and performs at scale. You’ll lead the strategy, operating model, and execution for global enablement while leading how sellers and managers adopt AI capabilities to transform the way they work.

This role sits at the intersection of Revenue Operations, Sales, Product, Marketing, and AI adoption. You’ll partner closely with executive leadership to identify the highest-impact opportunities to improve seller productivity, accelerate strategic priorities, strengthen manager effectiveness, and create consistent execution across our global go-to-market organization.

Success in this role requires balancing strategic thinking with operational excellence. You’ll build scalable enablement programs, modern learning experiences, adoption of AI-enabled workflows and tooling, and measurable operating rhythms that improve business performance—not simply deliver training.

If you’re excited about building organizations, influencing executive strategy, and using AI to redefine how revenue teams work, we’d love to meet you.

Responsibilities

Define and execute the global Sales Enablement strategy and multi-year roadmap aligned to Dropbox’s go-to-market priorities.
Build scalable enablement programs that improve seller productivity, manager effectiveness, onboarding, launch readiness, and revenue performance.
Partner with Sales, Revenue Operations, Product, Product Marketing, IT, and executive leadership to drive consistent execution across global teams.
Partner with GTM Technology and enterprise AI teams to identify, validate, and drive adoption of AI-enabled workflows that improve seller productivity, while maintaining responsible AI governance and usage.
Establish measurement frameworks that connect enablement investments to business outcomes, using data to continuously improve programs and prioritize future investments.
Build and develop a high-performing enablement organization and create operating mechanisms that reinforce learning, coaching, and adoption.
Foster a culture of continuous improvement by simplifying complex problems, driving change effectively, and ensuring enablement remains tightly connected to customer and business outcomes.
Drive adoption, enablement, and change management for AI capabilities introduced into seller and manager workflows.

Requirements

Significant experience leading Sales Enablement or Revenue Enablement within a high-growth B2B SaaS organization.
Proven success building global enablement strategies that improve seller productivity and measurable business outcomes.
Experience partnering with senior executives across Sales, Revenue Operations, Product, Marketing, and Technology to influence strategy and execution.
Demonstrated ability to use business performance data to diagnose sales challenges, prioritize investments, and measure program effectiveness.
Ability to operate with a transformation-mindset as a builder, willing to break through barriers and challenge the status quo to increase impact.
Experience identifying and driving adoption of AI-enabled capabilities within Sales or GTM organizations through enablement, training, and change management.
Strong leadership experience building, developing, and coaching high-performing teams through periods of growth and change.
Excellent executive communication, influence, and organizational leadership skills.

Preferred Qualifications

Experience leading enablement across enterprise, commercial, and product-led sales motions.
Experience building AI adoption programs and enablement strategies that accelerate responsible use of AI capabilities with proven results.
Deep familiarity with modern sales enablement technologies including CRM, content management, conversation intelligence, learning platforms, and emerging AI solutions.
Experience leading globally distributed teams across multiple regions.
Demonstrated ability to connect enablement investments to improvements in pipeline creation, conversion, ramp time, productivity, or revenue growth.

Compensation

Benefits & Perks

Health & Wellness

Health Insurance

Dropbox provides medical coverage through Anthem (PPO or HSA) or Kaiser HMO (CA and HI only) for employees and their families.

Dental Insurance

Dental coverage is provided through Guardian Dental for employees and dependents.

Vision Insurance

Vision coverage through Guardian VSP includes a $250 annual allowance for frames or lenses.

Mental Health Benefits

Mental health support is provided through Modern Health, which offers coaching and therapy for employees.

Life Insurance

Life insurance is provided at 2x base salary up to $1M, with AD&D coverage included.

Disability Insurance

Disability coverage is included in the benefits package.

Flexible Spending Account (FSA)

Pre-tax flexible spending accounts are available for healthcare and dependent care expenses.

Health Savings Account (HSA)

A health savings account is available to employees.

Pet Insurance

Dropbox offers pet insurance coverage for employee pets.

Gender Affirming Care

Health coverage includes transgender healthcare benefits supporting gender-affirming treatments.

Fitness Stipend

Dropbox provides a $100 per month gym and wellness reimbursement plus full free access to the Peloton Corporate Wellness Program.

Wellness Programs

A quarterly perks allowance of up to $5,000-$7,000 per year covers wellness, caregiver support, productivity, ergonomics, learning, and groceries.

Employee Assistance Program

Dropbox provides an Employee Assistance Program with confidential counseling and support resources.

Financial

401(k) / Retirement Plan

Dropbox offers a 401(k) retirement plan including a Mega Backdoor Roth feature allowing up to $23,000 per year in additional after-tax contributions ($30,500/yr for employees 50+).

401(k) Match

Dropbox matches employee 401(k) contributions dollar for dollar, up to $6,000 per calendar year.

Equity / RSUs

All regular employees receive Restricted Stock Units (RSUs) that vest over 4 years, quarterly at 6.25% per quarter, with no traditional 1-year cliff.

Time Off

Unlimited PTO

Dropbox offers an unlimited PTO policy for vacation and personal time.

Unlimited Sick Days

Dropbox provides unlimited sick leave separate from vacation PTO.

Paid Holidays

Dropbox provides paid holidays in addition to PTO.

Military Leave

Dropbox provides dedicated paid military leave for employees serving in the armed forces.

Remote & Equipment

Company Equipment

Dropbox provides a custom work station and company phone for employees.

Company Offsites / Retreats

Teams gather quarterly for in-person offsites lasting 2-3 days, supplemented by Dropbox Neighborhood community events and on-demand Studios for collaboration.

Coworking Allowance

Dropbox provides access to On-Demand workspaces and Studios at no cost to employees.

Family & Care

Parental Leave

Dropbox states that it "supports families with paid parental and family leave, assistance for adoption and surrogacy, and access to resources for both child and adult back-up care." The company does not publish a leave duration.

Adoption Leave

Adoption assistance reimburses up to $25,000 per child with a $50,000 lifetime maximum, alongside adoption and surrogacy support.

Fertility Benefits

Assistance for adoption and surrogacy for growing families.

Professional Growth

Learning & Development Budget

Dropbox provides a continuing education stipend, tuition reimbursement, online course subscriptions, Dropbox-sponsored tech talks, and Lunch and Learns; learning is also an eligible category under the quarterly perks allowance.

Mentorship Program

Dropbox runs a structured mentorship program for employees plus apprenticeship programs.

Defined Career Pathways

Dropbox publishes an Engineering Career Framework that defines expectations at each level and offers customized development tracks plus a promote-from-within practice.

Culture & Perks

Charity Matching

Dropbox matches employee charitable donations up to $2,000 per employee.

Employee Product Discount

Employees receive exclusive discounts with partnered companies and on Dropbox products.

Employee Resource Groups

Dropbox supports Employee Resource Groups (ERGs) and a Dropbox Neighborhood community program for connection across the global workforce.

Employee Recognition Awards

Dropbox runs a formal employee awards program to honor work and contributions, supported by quarterly engagement surveys.

Job Description

Role Description

Responsibilities

Requirements

Preferred Qualifications

Compensation

Benefits & Perks

Health & Wellness

Financial

Time Off

Remote & Equipment

Family & Care

Professional Growth

Culture & Perks

Tech Stack

JavaScript & Libraries

Frameworks

Frequently Asked Questions

Is Dropbox fully remote, or will I ever need to go to an office?

What does async by default look like day to day?

How does Dropbox set pay for remote roles?

Which benefits stand out for remote employees?

Do employees actually like the Virtual First model?

Interested in this role?

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