Executive Assistant to the Chief Business Officer

Dropbox is a Virtual First company. For this role, we are currently only authorized to hire candidates from the following provinces: Alberta, British Columbia, Ontario, and Saskatchewan.

As the Executive Business Partner to Dropbox’s Chief Business Officer, you’ll create leverage through exceptional executive administration, judgment, and follow-through. You’ll own the details that help him and his team operate at its best: a strategic calendar, seamless travel, useful meetings, clear preparation, accurate communications, and thoughtful coordination across the Chief Business Officer’s team and the broader Dropbox leadership system. This is a high-impact executive administration role in a fast-moving and evolving business. You’ll work closely with the CBO, his Chief of Staff, the Office of the CBO team, other executive admins, Chiefs of Staff, business partners, and senior cross-functional leaders. You’ll often need to make decisions with incomplete information, surface risks early, and keep work moving without creating unnecessary noise or rework. This is an exceptional administration role where you’ll bring judgment and a point of view, but your primary responsibility is to make the executive and the operating system work better through accurate, proactive, collaborative execution. You’ll first learn the existing system, build trust, and develop pattern recognition — then you’ll bring best practices and your expertise to help reshape systems and make them work even better. If you’re highly organized, calm under pressure, direct in your communication, persistent about follow through, and energized by making complex executive work feel simple, then this role is for you.

Responsibilities

• Own a complex calendar as a strategic operating tool, balancing executive priorities, customer and revenue commitments, leadership forums, preparation time, focus time, travel, and personal commitments.
• Support meeting prep by ensuring the right attendees, context, agendas, pre-reads, links, decision points, and follow-up actions are in place.
• Coordinate domestic and international travel end-to-end, including itineraries, ground transportation, hotel and meeting logistics, time-zone planning, contingency plans, and preparation or recovery time.
• Partner with the CBO’s Chief of Staff to maintain shared visibility into priorities, risks, requests, decisions, and follow-ups.
• Collaborate with other executive admins, Chiefs of Staff, business partners, and cross-functional leaders to resolve scheduling and operating needs without creating parallel processes or confusion.
• Support communication by tracking drafts, deadlines, approvals, distribution lists, links, and follow-through, ensuring that important messages are accurate and do not stall.
• Plan and execute executive meetings, offsites, and leadership events with strong attention to detail and a crisp focus on attendee experience, budget, and contingency planning.
• Maintain accurate administrative systems, including expenses, contacts, recurring meeting structures, action-item tracking, and relevant executive reference materials.
• Surface risks early, make recommendations, and own issues through resolution rather than simply completing the first task requested.

Requirements

• 8+ years of experience supporting a senior executive, preferably a C-level executive or equivalent leader in a complex, fast-moving organization.
• Expertise managing a highly complex executive calendar across multiple time zones, competing priorities, recurring leadership forums, customer commitments, and protected personal or focus time.
• Experience planning complex domestic and international travel, including contingency planning and coordination across multiple travelers, hosts, vendors, and time zones.
• Strong written and verbal communication skills, including the ability to communicate directly, concisely, and appropriately with senior leaders and cross-functional partners.
• Experience working with and/or for a senior Chief of Staff in tight, trusted partnership on systems- and process-based approaches to make order out of competing priorities.
• Proven ability to prioritize independently, make sound decisions with incomplete information, and elevate risks early with a recommendation.
• Demonstrated track record of accurate, detail-oriented execution across scheduling, events, communications, expenses, and follow-through.
• Experience working as part of an admin community and collaborating across executive offices rather than operating as an isolated support partner.
• Comfort working in a high-change environment where priorities shift quickly and the person must continuously re-plan without losing important details.
• High competency with workplace systems, including Slack, Gmail, Concur, Navan, Google Docs (and of course Dropbox!), as well as AI tooling for efficiency through human-machine partnership.
• Ability to work primarily on Eastern Time, with flexibility for occasional EMEA and APJ commitments and executive travel.

Preferred Qualifications

• Experience supporting a Chief Business Officer, Chief Revenue Officer, Chief Marketing Officer, or another executive responsible for a broad, customer-facing organization.
• Experience working in technology, SaaS, or another business with complex customer, revenue, and cross-functional operating rhythms.
• Experience supporting executive customer engagements, leadership offsites, board-related preparation, or S-team-level events.
• Experience using AI responsibly to improve administrative workflows while personally validating accuracy, privacy, judgment, and final outputs.
• Project or program management experience that complements, but does not replace, strong executive administration fundamentals.

Durable Skills

• AI fluency means using these tools to amplify human judgment, not replace it.
• Awareness: Understand yourself and others.
• Judgment: Evaluate information and make decisions in complex situations.
• Adaptability: Learn, adjust, and stay effective through change.
• Connection: Communicate, collaborate, and build trust.

Compensation Canada Pay Range $118,200—$159,900 CAD. The range listed above is the expected annual salary/OTE (On-Target Earnings) for this role, subject to change. 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).

The Dropbox Admin team works magic behind the scenes to keep Dropbox teams around the world running smoothly. We support leaders across the company and help teams unlock their potential by prioritizing and anticipating needs even before they arise. We shine under pressure and create order from chaos. We serve as the backbone of the organization’s day-to-day functions—supporting the fast-paced, collaborative community that defines Dropbox’s culture with everything from scheduling and meeting agendas to event planning and travel arrangements. If you’re a resourceful doer who finds joy in making things happen, join our Admin team.

Dropbox’s Virtual First way of working is designed to help people do their best work with flexibility, autonomy, and connection. Day to day, teams work remotely with nonlinear schedules and core collaboration hours that support deep focus and individual working styles. We prioritize asynchronous communication to improve clarity, respect deep work time, and reduce unnecessary meetings. While remote work is the primary experience for our employees, we also prioritize intentional, in-person connection. We bring teams together through regular team gatherings, on-demand workspaces, and Dropbox Neighborhood events in order to strengthen team cohesion, foster creativity, and enhance momentum. Virtual First is built to provide the same access to opportunity, growth, and impact for everyone, regardless of location. This role requires travel to offsites and various other team gatherings (approximately 5-10% of the year or 2-3 days per quarter). We provide advance notice when possible and encourage candidates to discuss any accommodation needs during the interview process.

AI fluency is a core part of how we work and grow. It’s not about being an expert—it’s about using these tools thoughtfully and effectively to improve your work and support others.

Dropbox supports responsible use of AI for preparation, but misrepresentation of skills or experience is not permitted. To learn more, see our approach to AI in hiring. 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.