Executive Assistant to CEO

Overview

In-Office: Primarily in-office, with flexibility as needed over time

Lumenai Investments LLC is an AI-powered quantitative investment manager serving family offices, advisors, and institutional investors. We specialize in absolute-return strategies designed to generate high alpha.

We are seeking a highly capable, grounded, and proactive Executive Assistant to work directly with Founder & CEO John Bailey. This is a high-trust, in-office role for someone who thrives in responsibility, anticipates needs before they arise, and wants to grow alongside a founder and firm in build mode.

This role is central to the CEO’s effectiveness and the firm’s daily operations. You will manage inboxes, calendars, scheduling, travel, and priorities with precision, while gradually taking on broader operational, analytical, and firm-building responsibilities.

The ideal candidate is calm under pressure, detail-obsessed, emotionally grounded, tech-savvy, and comfortable operating with autonomy and accountability.

The ideal candidate is excited about a long-term role and growing with the firm as responsibilities expand over time.

Executive & Administrative Support

• Own and manage the CEO’s inbox and calendar across all accounts
• Proactively review schedules daily and prepare the CEO for upcoming meetings
• Send a daily end-of-day summary (by ~5:00 PM) outlining the next day’s first meeting and priorities
• Anticipate conflicts, gaps, and follow-ups before they become issues
• Handle inbound inquiries from the website, mail, and general firm inboxes

Scheduling, Travel & Logistics

• Coordinate complex domestic and international travel
• Manage Calendly and other scheduling tools
• Support investor meetings, conferences, roadshows, and events
• Track follow-ups, materials, and post-meeting action items

Operations & Systems

• Pay bills and manage basic financial/admin workflows
• Assist with payroll, HR coordination, insurance, and operational setup over time
• Work closely with the firm’s tech stack (Calendly, Hub Spot, CRM systems)
• Maintain organized systems for documents, tasks, and communication

Writing, Tech & Tools

• Draft and edit professional emails, memos, and materials
• Use ChatGPT thoughtfully for drafting, summarization, and workflow efficiency
• Support light research, presentations, and reporting as needed
• Maintain a high standard of written communication

• Exceptionally organized with strong attention to detail
• Proactive, anticipatory, and able to “run with the ball” independently
• Calm, grounded, and effective under pressure
• Emotionally mature with thick skin; does not take feedback personally
• Confident, direct communicator who is comfortable picking up the phone and handling live conversations with clients, partners, and stakeholders when needed
• Trustworthy, loyal, and discreet
• Tech-savvy and quick to learn new systems
• Polished, professional, and client-facing in presentation and demeanor
• Comfortable interacting with and supporting high-net-worth and institutional clients

• Bachelor’s degree required
• 3–7+ years of relevant experience (flexible based on overall fit)
• Experience in finance, investing, consulting, or professional services preferred
• Proficiency with Microsoft Office, Google Workspace
• Familiarity with Hub Spot, CRM tools, Linked In, Twitter, and modern productivity tools

This role begins with core executive and administrative support and expands over time into broader operational, analytical, and firm-management responsibilities (payroll, HR, insurance, internal systems).

You will be part of the core team, working closely with the CEO to build the firm and grow together. The ideal candidate is excited by ownership, responsibility, and long-term opportunity, not just a job.

• Competitive salary + performance bonus
• Potential equity participation
• Unlimited paid time off
• Healthcare, dental, and vision benefits