Senior Executive Assistant — Product & Design

DoorDash USA•Chicago, IL

7d•Remote

About The Position

The Product & Design organization builds experiences that define DoorDash. We are a global organization partnering across multiple regions and time zones; this role will occasionally require working global hours to support leaders and cross-regional events. As we scale, we’re hiring a Senior Executive Assistant to be a strategic, independent partner to two VP-level leaders — delivering reliable operations while improving how the organization works across teams. About the Role This senior EA role directly supports two VP-level leaders in Product & Design. The primary expectation is independent ownership: you’ll manage complex calendars, run cross-functional programs end-to-end, and proactively identify and close operational gaps between the two VP teams. At this level you’ll work autonomously, anticipate and presolve coordination challenges across teams and time zones, and continuously improve how the leaders operate. The role is remote within the United States and requires regular travel for offsites, leadership events, and in-person collaboration. You're excited about this opportunity because... Maximize leader impact. Lead calendar strategy and prioritization for both VP leaders; proactively create focus time and align daily rhythms to strategic priorities. Drive cross-team programs. Plan and run leadership offsites, recurring forums, and org initiatives with senior stakeholders. Fill gaps & preempt blockers. Proactively identify where work falls between the two VP teams, close operational gaps, coordinate handoffs, and presolve issues before they reach the leaders. Own complex logistics. Manage multi-city travel, large offsites, vendor relationships, and budgets to ensure smooth execution. Prepare leaders for decisions. Draft and coordinate executive communications, prepare concise briefings, and ensure both VPs have clear context and materials for meetings and decisions. Leverage AI & automation. Use AI-enabled and automation tools to generate concise briefings, summarize meetings, design scheduling automations, and surface insights; evaluate and implement practical AI solutions that increase leader and operational efficiency while protecting confidentiality. Exercise independent judgment. Make timely operational decisions within agreed boundaries, escalate appropriately, and represent the leaders with professional judgment. Improve systems & workflows. Recommend and implement tools, templates, or processes that measurably reduce operational overhead and increase effectiveness across both VP offices. Share practical best practices. When relevant, contribute playbook items or tactical tools that help other EAs work more effectively — focus is on practical, shareable solutions rather than people management.

Requirements

8+ years supporting senior leaders or equivalent experience in fast-moving organizations.
Proven track record of independent ownership, proactive problem-solving, and closing operational gaps across multiple stakeholders.
Demonstrated experience supporting VP-level leaders (supporting two or more senior leaders preferred).
Strong project and stakeholder management — able to work across teams and manage ambiguity.
Excellent written and verbal communication.
Demonstrated ability to handle confidential information with discretion.
Advanced technical proficiency with enterprise calendaring and collaboration systems (Google Workspace, Slack, Zoom, travel/expense and scheduling/automation tools); hands-on experience designing complex scheduling strategies and automations, managing delegated access and multi-timezone coordination, and optimizing executive tooling at scale.
AI-minded and solutions-oriented: practical experience applying AI or automation tools (e.g., generative assistants, scheduling automations, RPA) to streamline executive workflows; comfortable with prompt design, integrating AI into tooling, and assessing privacy/security tradeoffs.
Willingness to travel regularly for offsites, leadership events, and in-person collaboration.
Ability to work occasional global hours as needed to support leaders and cross-regional events.

Nice To Haves

Experience supporting multiple VP-level leaders or C-suite executives.
Experience in Product, Design, or technology organizations.
Experience designing and implementing operational improvements and playbooks for executive teams.
Experience implementing AI-based tools for executive support or scheduling automation/integration tools is a plus.

Responsibilities

Lead calendar strategy and prioritization for both VP leaders; proactively create focus time and align daily rhythms to strategic priorities.
Plan and run leadership offsites, recurring forums, and org initiatives with senior stakeholders.
Proactively identify where work falls between the two VP teams, close operational gaps, coordinate handoffs, and presolve issues before they reach the leaders.
Manage multi-city travel, large offsites, vendor relationships, and budgets to ensure smooth execution.
Draft and coordinate executive communications, prepare concise briefings, and ensure both VPs have clear context and materials for meetings and decisions.
Use AI-enabled and automation tools to generate concise briefings, summarize meetings, design scheduling automations, and surface insights; evaluate and implement practical AI solutions that increase leader and operational efficiency while protecting confidentiality.
Make timely operational decisions within agreed boundaries, escalate appropriately, and represent the leaders with professional judgment.
Recommend and implement tools, templates, or processes that measurably reduce operational overhead and increase effectiveness across both VP offices.
When relevant, contribute playbook items or tactical tools that help other EAs work more effectively — focus is on practical, shareable solutions rather than people management.

Benefits

a 401(k) plan with employer matching
16 weeks of paid parental leave
wellness benefits
commuter benefits match
paid time off and paid sick leave in compliance with applicable laws (e.g. Colorado Healthy Families and Workplaces Act)
medical, dental, and vision benefits
11 paid holidays
disability and basic life insurance
family-forming assistance
a mental health program