Executive Operations Assistant for a Technology Executive

Role Overview
Title:
I am a technology executive with a complex, fast-moving schedule, multiple companies/initiatives, and several active inboxes and calendars. I’m looking for a sharp, proactive Executive Assistant who can fully own my digital workflow: emails, calendars, follow-ups, and operational coordination across my work and travel life.
You will manage multiple inboxes and multiple calendars for a single executive, using AI tools and structured systems to keep communication tight, priorities visible, and execution smooth. If you are detail-obsessed, thrive on organizing chaos, and enjoy working with AI tools instead of being threatened by them, this role is for you.
This is a full-time, long-term remote role with strong overlap required with US Eastern time.

Core Responsibilities
Multi-inbox email management
* Own end-to-end management of multiple Gmail/Google Workspace inboxes (business, personal-business, and project-specific).
* Triage all incoming emails: categorize, label, and prioritize based on context (investors, partners, vendors, internal, transactional, personal, etc.).
* Use AI tools (e.g., ChatGPT, Copilot, other assistants) to generate draft responses, then edit for accuracy, tone, and context before sending or surfacing for approval.
* Maintain a robust system of filters, labels, folders, and rules that works consistently across all inboxes.
* Ensure no important email goes unanswered or unnoticed; monitor SLAs (e.g., everything acknowledged within 24 hours unless explicitly deferred).
* Proactively unsubscribe, archive, and clean noise while protecting newsletters and sources I explicitly value.
Multi-calendar ownership
* Own multiple Google Calendars for a single executive (work, personal, portfolio/board, and travel-related calendars).
* Schedule, confirm, and reschedule meetings across all calendars so that time is used intentionally and conflicts are prevented.
* Coordinate across time zones with internal teams, external partners, investors, and travel-related contacts.
* Protect focus time and deep work blocks while balancing meetings, travel, and personal requirements.
* Prepare daily and weekly calendar briefs with context for each meeting (who they are, why we’re meeting, what outcome we want).
* Ensure that travel, buffer times, and recurring commitments are accurately represented across all calendars.
Travel, logistics, and preferences
* Support business travel planning: identify options, prepare shortlists, and finalize bookings for flights, hotels, and ground transportation in alignment with preferences.
* Build structured itineraries that align calendar events with bookings, confirmation numbers, time zones, and contact details.
* Track loyalty programs, common routes, preferred hotel brands, and seating preferences, and factor them into recommendations.
* Handle changes, delays, and last-minute adjustments with minimal disruption to the overall schedule.
AI, systems, and workflow optimization
* Use AI assistants to draft emails, summarize threads, prepare meeting notes, and create briefings for upcoming calls.
* Help design and maintain clear operating systems for email and calendar management across all accounts (e.g., labels, status tags, “for review,” “awaiting reply,” “archive by default”).
* Identify repetitive patterns and collaborate on automations (e.g., filters, templates, Zapier/Make workflows) that reduce manual work while preserving judgment and control.
* Keep simple documentation of workflows and decision rules so the system is repeatable and improvable over time.
Operational and executive support
* Track action items that emerge from emails and meetings and ensure follow-through, including nudging me and other stakeholders when needed.
* Perform targeted research (e.g., vendors, tools, travel options, prospect/company background before meetings) and synthesize into concise briefs.
* Maintain organized digital documents and links relevant to ongoing projects (e.g., in Google Docs/Drive, Notion, or similar).
* Support occasional personal-business tasks that intersect with my professional world (e.g., memberships, events, conferences).

You’re a great fit if you
* Have 2+ years supporting a senior executive remotely, with heavy emphasis on inbox and calendar management.
* Have demonstrable experience managing multiple inboxes and calendars for one decision-maker (not just a single account).
* Are highly organized, systems-oriented, and comfortable designing and following structured processes.
* Write clear, concise, professional English and can reliably refine AI-generated drafts so they sound human, thoughtful, and aligned with guidance.
* Are comfortable using Google Workspace (Gmail, Calendar, Drive) and modern SaaS/communication tools; familiarity with AI tools is a plus.
* Can understand enough technical context (APIs, cloud, SaaS, travel tech) to categorize and prioritize messages intelligently, even if you are not an engineer.
* Exercise strong judgment regarding what you can handle directly vs. what needs my input, and when to escalate something quickly.
* Are proactive and anticipatory — you are thinking one or two steps ahead on email, calendar, and logistics.
* Can reliably overlap with US Eastern business hours (at least 6–8 hours of overlap).

Bonus points
* Experience supporting a CTO, VP Engineering, or founder in technology, SaaS, or travel tech.
* Familiarity with tools like Jira/Confluence, Notion, Slack, or similar collaboration platforms.
* Experience with workflow automation tools (Zapier, Make, or similar).
* Exposure to travel booking workflows, GDS or OTA tools, or corporate travel management.

To apply, please include
* A brief summary of your experience managing multiple inboxes and multiple calendars for a single executive.
* Examples of AI or automation tools you’ve used to manage email, calendar, or workflows (ChatGPT, Copilot, Zapier, etc.).
* A short walkthrough of this scenario:?You log in at the start of your day and see 80+ new emails spread across three inboxes and multiple calendars with overlapping holds/requests. Describe step-by-step how you would triage the emails, clean up the calendars, and what you would surface to me in the first 30–60 minutes.