Senior Executive Assistant – Product & Design

Executive AssistantExecutive AssistantFull TimeRemoteTeam 10,001+H1B SponsorCompany Site LinkedIn

Location

Illinois

Posted

34 days ago

Salary

$112.2K - $165K / year

Bachelor Degree8 yrs expEnglishRPA

Job Description

• Manage complex calendars for two VP-level leaders. • Run cross-functional programs end-to-end. • Proactively identify and close operational gaps between the two VP teams. • Plan and run leadership offsites, recurring forums, and org initiatives with senior stakeholders. • Draft and coordinate executive communications and prepare concise briefings. • Use AI-enabled and automation tools to enhance productivity. • Make timely operational decisions and represent the leaders with professional judgment. • Recommend and implement tools, templates, or processes that measurably reduce operational overhead.

Job 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.