Executive Assistant – Chief Business Officer

This is a fully remote position, open to applicants in Canada.

📋 Description

• Provide exceptional executive administration to Dropbox’s Chief Business Officer, utilizing strong judgment and follow-through.

• Take ownership of the CBO’s intricate calendar, effectively managing executive priorities alongside customer and revenue commitments, leadership forums, preparation time, focus time, travel arrangements, and personal obligations.

• Prepare for meetings by coordinating attendees, providing context, setting agendas, sharing pre-reads, decision points, and follow-up actions.

• Oversee comprehensive domestic and international travel arrangements, including itineraries, ground transportation, hotel bookings, meeting logistics, time zone considerations, contingency plans, and any necessary preparation or recovery time.

• Collaborate with the CBO’s Chief of Staff to ensure alignment on priorities, risks, requests, decisions, and follow-up actions.

• Work alongside executive admins, Chiefs of Staff, business partners, and cross-functional leaders to resolve scheduling and operational needs.

• Monitor communication drafts, deadlines, approvals, distribution lists, links, and ensure effective follow-through.

• Organize and execute executive meetings, offsites, and leadership events, emphasizing attendee experience, budget management, and contingency planning.

• Maintain administrative systems for expenses, contacts, recurring meeting structures, action-item tracking, and executive reference materials.

• Identify risks early, make informed recommendations, and manage issues through to resolution.

• Gain familiarity with existing systems, build trust, enhance pattern recognition, and optimize operational processes.

⛳️ Requirements

• Minimum of 8 years of experience supporting senior executives, preferably at the C-level or equivalent in a dynamic, complex organization.

• Proficiency in managing a highly complex executive calendar across various time zones, balancing competing priorities, recurring leadership forums, customer commitments, and protected personal or focus time.

• Experience in planning intricate domestic and international travel, including contingency strategies and coordination among various travelers, hosts, vendors, and time zones.

• Strong written and verbal communication capabilities, with the ability to convey information directly, concisely, and appropriately to senior leaders and cross-functional partners.

• Experience collaborating closely with a senior Chief of Staff, focusing on systems and process-based methods to navigate competing priorities.

• Demonstrated ability to prioritize independently, make informed decisions with incomplete information, and promptly escalate risks with recommendations.

• Proven track record of meticulous, detail-oriented execution in scheduling, events, communications, expenses, and follow-through.

• Experience as part of an administrative community, collaborating across executive offices rather than functioning as an isolated support partner.

• Comfort in a fast-paced environment where priorities can change rapidly, requiring the ability to continuously re-plan without overlooking critical details.

• High proficiency with workplace systems, including Slack, Gmail, Concur, Navan, Google Docs, Dropbox, and AI tools for enhancing efficiency through human-machine collaboration.

• Availability to primarily work on Eastern Time, with flexibility for occasional EMEA and APJ commitments and executive travel.

• Preferred: Experience supporting a Chief Business Officer, Chief Revenue Officer, Chief Marketing Officer, or any executive responsible for a broad, customer-facing organization.

• Preferred: Background in technology, SaaS, or similar fields with complex customer, revenue, and cross-functional operational rhythms.

• Preferred: Experience in supporting executive customer engagements, leadership offsites, board-related preparations, or S-team-level events.

• Preferred: Skill in using AI responsibly to enhance administrative workflows while ensuring accuracy, privacy, judgment, and final outputs.

• Preferred: Project or program management experience that complements, but does not substitute, strong executive administration fundamentals.

🏝️ Benefits

• Competitive salary and performance-based bonuses.

• Comprehensive health, dental, and vision insurance.

• Generous paid time off and flexible working arrangements.

• Opportunities for professional development and training.

• Collaborative and inclusive company culture.