Chief of Staff / Executive Operations Manager

About the Business

The client is a second-generation luxury lighting company based in Maui, Hawaii — undergoing a powerful pivot. They’re transforming from a traditional showroom into a lean, remote-first, tech-enabled, service-driven powerhouse. They serve high-end residential and commercial clients through their curated Signature Lighting Package, managing every project from design and quoting to delivery and warranty. They’re also managing a portfolio of vacation rentals, commercial real estate, and other entrepreneurial ventures.

This is a chance to build something lasting, meaningful, and legacy-driven — alongside a founder who blends operational excellence, vision, and deep personal integrity.

About This Role

As the Chief of Staff/Executive Operations Manager, you are the calm in the chaos, the systems brain behind the visionary, and the operator who turns ideas into action. You’re not just keeping the trains running — you’re building the track. Your goal is to take things off the founder’s plate while keeping the company operating smoothly and profitably.

This is not a typical assistant role. This is your opportunity to grow into the integrator / COO seat of a multi-entity operation. We want someone who is committed to excellence, ownership, and long-term growth.

Responsibilities

Executive Support

• Act as a trusted partner to the founder — manage calendar, meetings, communications, and travel
• Triage inboxes and correspondence with clients, vendors, and team members
• Prepare for meetings, flag decisions, and follow up on outcomes
• Maintain confidentiality and act with discretion at all times

Systems & Ops Leadership

• Implement, manage, and optimize Monday.com for team task management and project tracking
• Document and maintain SOPs across all business units
• Lead internal weekly pulse meetings, ensuring deadlines and priorities are aligned
• Proactively identify bottlenecks and improve systems

Financial & Vendor Oversight

• Manage bookkeeping for multiple entities using QuickBooks Online and Odoo
• Handle payment tracking, invoice follow-ups, and expense categorization
• Track project budgets, profit margins, and cash flow trends
• Coordinate with vendors and contractors to ensure smooth operations

Travel & On-Site Support

• Willing to travel to the U.S. up to once per quarter
• Visits may range from 6 weeks to 3 months for in-person systems or projects

Traits That Make You a Fit

• You love organizing chaos — and are calm under pressure
• You think in dashboards, not to-do lists
• You don’t just manage — you lead outcomes
• You care about aesthetics, presentation, and polish
• You are a protector of time, energy, and momentum
• You are loyal, proactive, growth-minded, and you’re looking for a long-term home

Tools You’ll Use

• Monday.com (automations, workflows, dashboards)
• QuickBooks Online, Odoo
• Microsoft Teams, Outlook, Google Workspace
• Shared Drives, Dropbox, WhatsApp, Zoom
• Canva, Adobe (optional but a plus)

How We Work

We are not a corporate environment. We’re entrepreneurial, fast-moving, heart-centered, and intentional. We value:

• Ownership over excuses
• Clarity over complexity
• Peace and precision over chaos
• Family, legacy, and loyalty over hustle for hustle’s sake

Requirements

Qualifications

• 3+ years of experience as an Executive Assistant, Chief of Staff, Ops Manager, or equivalent
• Exceptional English (written and verbal)
• Comfortable managing remote teams
• Familiar with project-based and product-based businesses (bonus if you understand the construction or real estate world)
• Tech-savvy and able to self-learn new tools quickly
• Must be able to independently and willingly travel to the US for periods of up to 3 months

Bonus Points If You…

• Have worked in a design, architectural, or real estate environment
• Are a systems builder at heart
• Are process-obsessed but people-oriented
• Have experience managing multiple LLCs, properties, or cash flows
• Have aspirations to grow into a leadership position (integrator, COO, etc.)

Benefits

• Client Relationship : You will be directly working with the client. This means that you will communicate with the client, provide services, and address any client-related matters independently.
• Payments : All payments for your services will be handled by the client. Elevate and Delegate is not involved in processing your payroll. Your salary will directly go to you. 
• Vacation Leaves and Holidays : While we may have recommendations or guidelines regarding vacation leaves and holidays, the decision is entirely at the discretion of the client. You are expected to align your schedule with the client’s business needs and any specific policies or preferences they may have in this regard.

Salary: $1,600-2,000 per month

Schedule: HST

Role-type: Full-time