Chief of Staff to the CEO

Partner closely with Dropbox’s co-founder and CEO, Drew Houston, and the executive leadership team as a proactive and highly strategic Chief of Staff. This role offers a unique opportunity to significantly impact strategic decision-making and operational efficiency at the highest level. You will serve as a critical liaison, advisor, and facilitator, ensuring strategic priorities are clearly defined, communicated, and executed.

Role Description

You will drive strategic execution by managing CEO-driven initiatives, ensuring alignment and follow-through across the organization. Optimize and prioritize the CEO’s agenda, ensuring strategic utilization of executive time. Facilitate critical internal and external communications, executive meetings, board preparation, and high-level strategic planning sessions. Act as a primary point of contact and strategic advisor, supporting CEO decision-making with data-driven insights and analytics. Leverage advanced AI and automation tools to streamline executive processes, improve decision-making speed, and enhance strategic outcomes. Foster cross-functional collaboration, aligning diverse teams toward common strategic objectives. Provide cohesion for executive leadership team, ensuring priorities are balanced across CEO and other executive demands. Manage processes and rhythms for CEO in partnership with Executive Assistant and other members of Office of the CEO team. Regularly accompany the CEO on essential business travel, ensuring seamless execution of priorities on the road.

Requirements

• 5–7 years of experience (top-tier consulting firm or investment banking experience required. Ideally have additional experience in a strategy/product/business operations role at a tech company)
• Experience in strategic planning and other company operating rhythms
• Exceptional analytical and strategic thinking skills
• Strong communicator and collaborator with employees of all levels and departments
• Proven ability to manage complex stakeholder dynamics at executive levels
• Experience utilizing AI-driven tools to improve operational efficiency and strategic decision-making
• Ability to travel regularly with the CEO, sometimes on short notice
• Resides in California, Bay Area strongly preferred

Preferred Qualifications

• Experience in a product role at a tech company

Compensation

US Zone 1: $187,000—$253,000 USD
US Zone 2: $168,300—$227,700 USD US Zone 3: $149,600—$202,400 USD

The range(s) listed above is the expected annual salary/OTE (On-Target Earnings) for this role, subject to change.

Please note, OTE are for sales roles only.

Salary/OTE is just one component of Dropbox’s total rewards package. All regular employees are also eligible for the corporate bonus program or a sales incentive (target included in OTE) as well as stock in the form of Restricted Stock Units (RSUs).

Dropbox takes a number of factors into account when determining individual starting pay, including job and level they are hired into, location/metropolitan area, skillset, and peer compensation. We target most new hire offers between the minimum up to the middle of the range.

Dropbox uses the zip code of an employee’s remote work location to determine which metropolitan pay range we use. Current US Zone locations are as follows:

• US Zone 1: San Francisco metro, New York City metro, or Seattle metro
• US Zone 2: California (outside SF metro), Colorado, Connecticut (outside NYC metro), Delaware, Illinois (Chicago metro), Indiana (Chicago metro), Maryland, Massachusetts, Michigan (Chicago metro), New Hampshire, New Jersey (outside NYC metro), New York (outside NYC metro), Oregon, Pennsylvania (D.C. metro), Pennsylvania (outside NYC or DC metro), Texas (Austin metro) Virginia (DC metro), Washington (outside Seattle metro), Washington DC metro, West Virginia (DC metro), Wisconsin (Chicago metro)
• US Zone 3: All other US locations

Dropbox is a Virtual First company and is open to hiring candidates in all authorized locations.

Company Description

Dropbox isn’t just a workplace—it’s a living lab for more enlightened ways of working. We're a global community of bold visionaries and resourceful doers who are shaping the future of Dropbox—and with it the future of work. Our Virtual First model combines the autonomy of a distributed workplace with the power of human connection, making space for both meaningful work and meaningful relationships. With our start-up mindset and enterprise-level opportunities, you can be who you are and grow into who you’re meant to be. Here, you can own your impact to make work more intuitive, joyful, and human—for you as a Dropboxer and for hundreds of millions of people worldwide. If you're ready to push boundaries—and yourself— Dropbox is ready for you.

Benefits

Dropbox is committed to investing in the holistic health and wellbeing of all Dropboxers and their families. Our benefits and perks programs include, but are not limited to:

• Competitive medical, dental, and vision coverage
• 401(k) plan with a generous company match and immediate vesting
• Flexible PTO/Paid Time Off, paid holidays, Volunteer Time Off, and more, allowing you time to unplug, unwind, and refresh
• Income Protection Plans: Life and disability insurance
• Business Travel Protection: Travel medical and accident insurance
• Perks Allowance to be used on what matters most to you, whether that’s wellness, learning and development, food and groceries, and much more
• Parental benefits including: Parental Leave, Child and Adult Care, Day Care FSA, Fertility Benefits, Adoption and Surrogacy Support, and Lactation Support
• Access to over 10,000 global co-working spaces, making it easy to book flexible workspaces for collaboration or individual work
• Quarterly Cell phone and internet allowance
• Mental health and wellness benefits
• Disability and neurodivergence support benefits

Additional benefit details are available upon request.

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, enABLE, TODOS (Latinx), Pridebox (LGBTQ), Vets at Dropbox, and Women at Dropbox.