AI-forward Executive Assistant

About the Role

This is not a traditional Executive Assistant role.

We're looking for an AI-Forward Executive Assistant whose core responsibility is to multiply the Founder's leverage by automating, systematizing, and closing the loop on day-to-day execution.

Your job is to make sure ideas turn into action, conversations turn into outcomes, and nothing drops — without creating more manual work.

If you love building agentic workflows, automations, and systems that eliminate busywork, this role is for you.

Mission

Remove, automate, and systematize the Founder's operational, administrative, and relationship-management workload using AI-first workflows — so the Founder can stay focused on strategy, relationships, and high-impact decisions.

What You'll Own

Founder Operations & Loop-Closing

• Own follow-ups, reminders, and next steps from Founder meetings, messages, and conversations
• Ensure 95%+ of discussions result in clear owners, timelines, and closure
• Proactively nudge stakeholders to keep initiatives moving

AI & Automation Systems

• Build, maintain, and improve agentic workflows that:

• Automate follow-ups and scheduling

• Track initiatives and pacing

• Reduce manual coordination

• Continuously ask: "How do we never do this manually again?"

• Add new automations regularly as the Founder's workflow evolves

Initiative Momentum

• Push Founder-initiated ideas forward without waiting for prompts
• Track progress, surface blockers, and escalate only when necessary
• Provide a simple weekly snapshot of what moved, what's blocked, and what needs attention

Personal & Relationship Ops

• Help plan events, dinners, and logistics
• Systemize staying in touch with key relationships
• Manage gift purchasing, reminders, and important moments
• Ensure no missed follow-ups, birthdays, or relationship touchpoints

What Success Looks Like

• The Founder reclaims 10–15+ hours per week
• Ideas move forward without constant reminders
• Systems run in the background with minimal oversight
• Fewer dropped balls, fewer reactive tasks, more momentum

Required Qualifications (Non-Negotiable)

• Advanced AI fluency with real examples of:
• Agentic workflows
• Process automation

• AI-driven systems that replaced manual work

• Experience building automations using tools such as:

• LLMs (ChatGPT, Claude, Gemini, etc.)
• Automation platforms (Zapier, Make, n8n, or similar)
• Strong systems thinking — you design workflows, not task lists
• Exceptional judgment around prioritization and escalation
• Bias toward action and ownership — you close loops, you don't wait

"I use ChatGPT" without concrete automation examples is not sufficient.

Ideal Background

• Former operator, technical EA, or automation-focused ops role
• Experience supporting a founder or senior executive
• Comfortable working with ambiguity and incomplete information
• Obsessed with leverage, efficiency, and compounding systems

This Role Is NOT

• A traditional calendar-only EA
• A reactive task taker
• A note-taker waiting for instructions
• A role focused on manual execution over automation

Interview Process

To apply, write 'I love AI' in the first sentence of your cover letter and note your favorite automations you've built and the ROI of each one. Applications that fail to do so will be disqualified.

Finalists will complete a working session, where you'll be asked to:

• Review a snapshot of real Founder workflows
• Propose systems and automations to improve them
• Explain what you'd automate, what you'd ignore, and why

We're testing judgment, AI leverage, and systems thinking, not polish.

Why This Role Is Different

You'll have:

• High trust and autonomy
• Direct access to the Founder
• The opportunity to design systems that meaningfully change how work gets done