Senior Executive Assistant

Senior Executive Assistant

Job Summary
The Senior Executive Assistant & Operations Lead provides senior-level executive support to a technical leadership team, operating with Chief-of-Staff-level judgment and strong engineering and product fluency. This role carries significant ownership and decision latitude — managing complex, cross-org priorities and personally owning the AI-powered systems and automated workflows that keep the leadership team running. Given the volume of cross-org, executive-facing communication involved, exceptional written and verbal English is essential.

Responsibilities
• Executive & Organizational Support (elevated): Manage complex, high-ambiguity calendars and shifting priorities across multiple (2-3) VP-level technical executives; act as a trusted gatekeeper with real decision latitude, not just scheduling logistics.
• Engineering & Technical Fluency: Maintain working literacy in the engineering org's structure, sprint/roadmap cadence, and terminology (comfortable navigating Jira and Confluence); translate technical updates into clear, accurate briefs for non-technical stakeholders.
• AI & Automation Ownership: Design, build, and maintain automated workflows across the entire leadership team — not just personal tasks. Own the toolkit (Zapier or equivalent, AI assistants, meeting-intelligence tools) and proactively find and eliminate manual, repeatable work across the team.
• Operations & Vendor Management: Own budget and expense rigor at a leadership-team level; manage vendor relationships; run large-scale event logistics.
• External Relationship Ownership: Deep-dive into the executive's key external relationships with customers and partnerships to know which ones need proactive attention and when; partner closely with the CSM to make sure the exec walks into every external touchpoint fully briefed and ready — not caught off guard.
• Cross-Functional Communication & Escalation: Serve as a proxy voice for the executive(s) in cross-functional settings; draft high-stakes communications; manage sensitive situations with discretion and sound judgment. Operate fluidly across multiple orgs — Engineering, Product, cross functional — within a large, matrixed company, where clear, polished English is non-negotiable.
• Mentorship & Standards: Set the standard for tool adoption and workflow design across the broader admin/EA function; may directly guide junior or contract EA support.
• Special Projects: Lead research, coordination, and follow-through on strategic initiatives with minimal direction.
• CTO Coverage: Step in with full confidence to manage the CTO's calendar and day-to-day schedule when his primary EA is out of office — exercising the same judgment and prioritization he relies on day to day, not just holding the calendar steady until coverage ends.

Qualifications — Seniority Benchmark
This role sits meaningfully above a standard EA seat. Qualifications are written to reflect that.
• 7+ years of EA or Chief of Staff experience, including meaningful time supporting VP- or C-level technical/engineering executives.
• Demonstrated experience supporting an engineering, product, or technical organization — comfortable with sprint cycles, roadmaps, and cross-functional eng/product dynamics.
• Proven ownership — not just usage — of AI tools and automated workflows.
• Exceptional written and verbal English proficiency — executive-caliber, with zero ambiguity, for high-stakes and cross-org communication.
• Experience working across multiple orgs and functions, not just one team.
• Background in large, matrixed organizations with sizable engineering, product, and technology teams — comfortable operating at scale, not only in smaller or single-team environments.
• Bachelor's degree preferred; equivalent senior-level experience will be weighed at least as heavily.
• Advanced fluency in Google Workspace, Slack, and Zoom; working familiarity with the Atlassian suite (Jira/Confluence); hands-on experience with AI assistants (Claude, ChatGPT, Gemini).

Attributes
• Operates with high-level judgment and discretion in ambiguous, high-stakes situations.
• Systems thinker who builds the fix rather than just flagging the problem.
• Treats AI and automation ownership as core to the role, not a side skill.
 

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