Founders' AI-Driven Executive Assistant - Remote

Pairs; United States; Remote; USD 65,000 - 95,000; Full time

Job summary

Pairs is seeking an Executive Assistant to the two founders who will own calendars, emails, travel, and follow-through. You will operate in an AI-first environment, protecting time, drafting in both founders' voices, and coordinating across time zones.

This is a trusted, ownership-focused role with direct reporting to both founders. The role demands discretion, strategic thinking, and systems-building, enabling the founders to focus on product, investors, and company growth.

Qualifications

• Experience supporting a founder or C-level executive at a fast-moving company.
• Experience managing calendars across three or more time zones and handling buffers and protected time.
• Excellent writing to draft in another person's voice and exercise sound judgment.
• End-to-end travel management including disruptions handled proactively.
• Ability to support two principals with aligned agendas.
• Discretion with confidential information is a reflex.
• Build systems with documented processes and automation.
• Operate with AI-enabled scheduling, briefings, and follow-ups.

Responsibilities

• Own calendars across time zones, manage conflicts, protect planning time, and maintain meeting rhythm.
• Triages both founders' inboxes and drafts replies in each voice.
• Plan, book, and brief travel; adapt in real time when plans change.
• Prepare meetings with right briefing and ensure actions are tracked afterward.
• Track commitments the founders have made to others, with deadlines.
• Build and maintain behind-the-scenes systems and AI tooling to reduce repetitive work.

Skills

Calendar management

Executive support

Travel planning

Voice drafting

Discretion

Systems thinking

AI tooling

Tools

Claude Code

Cursor

Top models

Job description

Pairs is seeking an Executive Assistant to the two founders who will own calendars, emails, travel, and follow-through. You will operate in an AI-first environment, protecting time, drafting in both founders' voices, and coordinating across time zones.

This is a trusted, ownership-focused role with direct reporting to both founders. The role demands discretion, strategic thinking, and systems-building, enabling the founders to focus on product, investors, and company growth.