Director of Global Benefits

San Francisco, CA

Company Description

Thank you for your interest in Dropbox careers. We are actively hiring for this position and look forward to reviewing your application. Dropbox is continuing to monitor the COVID-19 pandemic as the health and safety of our community, employees and candidates remain our number one priority. We appreciate your flexibility as we adapt our hiring processes during this evolving situation.

Dropbox is the world’s first smart workspace that helps people and teams focus on the work that matters. With more than 600 million registered users across 180 countries, we’re on a mission to design a more enlightened way of working. Dropbox is headquartered in San Francisco, CA, and has 12 offices around the world.

Team Description

Our Recruiting & People team grows and develops the Dropbox family. We find, hire, and support the people who will shape our product and our company. We believe people do their best work when they’re happy, so we work to make Dropbox a place where everyone can thrive.

Role Description

Dropbox is looking for a Global Benefits Leader to join our Total Rewards Team. You will be a key partner to the Global Head of Total Rewards, leading a team of talented benefits and wellness professionals and working closely with cross-functional partners, external vendors, and internal business leaders across Dropbox. As Head of Global Benefits, you will be joining at an opportune time to design, develop, and execute on strategic initiatives that will contribute towards Dropbox’s long-term mission and success while building creative and delightful programs for our employees.
The Benefits Team wants to help our employees take care of their holistic selves, so they can unleash their creative energy at work. To that end, we design and manage health and welfare insurance, retirement, wellness, time off and perk programs for Dropboxers worldwide.


  • Accountable for global benefit programs in accordance with market practice and statutory regulations. Programs include but are not limited to medical, dental, vision, life, disability, wellness (physical, mental, financial), leaves, time off, EAP, retirement, and (US-specific) FSA, HSA, Commuter and COBRA
  • Develop and drive Dropbox’s strategic benefits road map and budget using feedback from internal partners and knowledge of benefits market trends, best practices and regulatory updates
  • Manage a distributed team (US and International) and guide them through benefits design, administration, and experience
  • Partner with third-party brokers, health insurance vendors, leave administrators and benefits administration system providers to ensure plans operate smoothly and at scale.
  • Develop collaborative relationships with key benefit stakeholders across the organization (e.g. payroll, finance, legal, HRBPs) to design and implement global program changes or additions


  • BA/BS in related field preferred
  • 12+ years experience building global benefit and leave programs, including design, cost analysis, and implementation
  • Experienced at handling self-insured medical plans, 401k governance and administration, and M&A-driven benefits changes
  • Experienced in evaluating and handling vendors and running an RFP process
  • Well-versed in leave statutes and technology market best practices
  • Strong change management and project management skills
  • Experience using a wide range of HR technologies including Workday and Zendesk
  • Knowledge of pertinent federal, state and local regulations, filing and compliance requirements (current and pending) affecting employee benefit programs including ERISA, COBRA, ADA, FMLA, HIPAA and ACA
  • Ability to influence and develop strong working relationships with multiple partners, including executives, line management, peers in human resources, and the broader employee population
  • Excellent verbal and written communication skills
  • Able to package and present complex analysis and recommendations clearly and comfortably 

Benefits and Perks

  • 100% company paid individual medical, dental, & vision insurance coverage
  • 401k + company match
  • Market competitive total compensation package
  • Free Dropbox space for your friends and family
  • Wellness Reimbursement
  • Generous vacation policy
  • 10 company paid holidays
  • Volunteer time off 
  • Company sponsored tech talks (technology and other relevant professional topics)
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, Latinx, Pridebox (LGBTQ), Vets at Dropbox, Women at Dropbox, ATX Diversity (based in Austin, Texas) and the Dropbox Empowerment Network (based in Dublin, Ireland).