Executive & Personal Assistant to Founder & CEO

Location: Remote (strong U.S. time-zone overlap required PST) Employment Type: Full-time, dedicated — 40 hours/week Compensation: Per month USD, commensurate with experience and capability Reports To: Founder & CEO, directly

About the Company

We are a growing portfolio of U.S.-based companies across the health, fitness, and wellness industries. The portfolio includes multi-location fitness businesses in multiple U.S. markets — including one expanding from four to six locations — alongside specialized wellness businesses.

The founder leads each business hands-on and invests deeply in his people; several key team members have been with him for eight-plus years. This is a high-trust, high-standards environment built on ownership, initiative, accountability, and genuine care for the work.

About the Role

This is a newly created role: the founder's first fully integrated professional-and-personal right hand. This is more than a traditional Executive Assistant position. It combines executive and personal support with project coordination, cross-functional execution, and AI-enabled systems building.

Running several companies at once, the founder needs one trusted person who can reduce the day-to-day noise, organize priorities, coordinate across his businesses and personal life, and take delegated outcomes through to the finish line.

You will work closely with the founder's existing executives, partners, employees, advisors, vendors, and other resources. Your job is not to personally do everything. It is to understand the desired outcome, determine who and what is needed, coordinate execution, follow up, remove bottlenecks, and close the loop without requiring the founder to remain in the middle.

The goal is not to add another person to manage. It is to create leverage and build structure that progressively reduces how much the founder has to manage.

Key Responsibilities

Executive Support & Prioritization

Own the founder's inbox and calendar, protecting his time and keeping him ahead of what matters
Turn a busy, multi-business week into clear priorities, with decisions, deadlines, and red-flag items surfaced first
Prepare meeting briefs, capture action items, track commitments, and ensure follow-through
Organize information so the founder can make decisions quickly without having to find the information himself

Cross-Functional Execution

Coordinate across multiple businesses and serve as a trusted liaison to executives, partners, employees, advisors, vendors, and other key personnel
Learn who owns what across the founder's existing ecosystem and activate the right people and resources to accomplish objectives
Turn delegated outcomes into clear owners, next steps, deadlines, and follow-up
Identify stalled initiatives, missing information, and bottlenecks, and drive them toward resolution
Escalate to the founder when his input is genuinely required — not simply because the next step is unclear
Own the loop until the desired outcome is completed

Personal & Life Management

Coordinate personal appointments, travel, transportation, reservations, and logistics
Manage personal administration, household/property matters, bills, documents, vendors, research, and remote errands
Coordinate with local or in-person resources when something cannot be completed remotely
Bring the same organization, discretion, and follow-through to the founder's personal life as you do to his businesses

AI, Automation & Systems

AI capability is a core expectation of this role, not a bonus.

Identify and build AI-enabled workflows and automations that reduce manual work and executive involvement
Use AI for research, communication, meeting preparation, reporting, project management, documentation, and decision support
Help build and maintain the founder's AI operating system — including reusable prompts, frameworks, custom GPTs/agents, knowledge bases, SOPs, automations, and workflows
Capture the founder's recurring processes, communication preferences, and decision frameworks so they become increasingly repeatable and scalable
Document systems so they are durable, transferable, and maintained within founder/company-controlled accounts wherever possible
Continually ask: Can this be automated, delegated, templated, systemized, or eliminated?

Knowing how to use ChatGPT or Claude is not enough. We are looking for someone who understands how to combine AI + automation + systems + people to create real leverage.

Required Qualifications

3+ years supporting a founder, CEO, entrepreneur, or senior executive as an Executive Assistant, Personal Assistant, Executive Business Partner, or Chief-of-Staff-style right hand
Near-native written and verbal English with clear, professional, confident communication
Demonstrated AI and automation fluency beyond basic prompting; be prepared to walk through systems or workflows you have actually built
Strong project-management and organizational skills, with the ability to coordinate multiple people without formal authority over them
Highly proactive and self-directed, with the judgment to determine what needs doing and move it forward
Comfortable with ambiguity and a fast-moving, founder-led environment
Absolute discretion and trustworthiness with confidential personal and business matters
Full-time availability, dedicated to this role, with strong overlap with U.S. business hours
Typing speed of 40+ WPM at 95%+ accuracy

Preferred Qualifications

Experience supporting a founder with multiple businesses or operating in a multi-entity environment
Exposure to health, fitness, wellness, medical practices, private equity, real estate, or other entrepreneurial businesses
Project or operations management experience, including process documentation
Light bookkeeping or financial coordination
CRM, lead-management, social media, or personal-brand coordination experience
Experience building AI agents, custom GPTs, knowledge systems, or no-code/low-code automations
A track record of long tenure with prior employers

Ideal Candidate Profile

You are:

Highly organized and proactive — you anticipate needs rather than waiting for instructions
High ownership, low ego — no reasonable task is beneath you, but you are capable of operating well above basic task execution
A closer — assigning a task or sending an email is not completion; you follow through until the outcome is achieved
A resourceful coordinator — you know how to work through other people and existing resources rather than trying to do everything yourself
A systems-builder — you turn recurring work into documented, repeatable processes
AI-native — you naturally look for ways AI and automation can improve how work gets done
A strong communicator — comfortable interacting with executives, partners, employees, vendors, and personal contacts on the founder's behalf
Discreet and dependable — someone the founder can trust with both his businesses and his personal life
Interested in the long term — motivated to learn how the founder thinks and become increasingly valuable over time

You understand the difference between delegation and abdication. When the founder says, "Take care of this," your instinct is to determine the desired outcome, identify the right people and resources, coordinate the work, follow up, solve what you can, surface what genuinely requires his decision, and take it through the finish line.

Why Join Us

Work directly with a successful entrepreneur across multiple growing businesses
Become a trusted right hand rather than simply an administrative support function
Build AI and operating systems from the ground up
Gain significant autonomy as trust develops
Work with a founder who invests in and develops key people
Grow your responsibility as the portfolio expands
Build a long-term partnership in a highly trusted role

Success in this position is not measured by how busy you are. It is measured by how much friction, mental load, coordination, and follow-up you remove from the founder's life — and how reliably the things delegated to you reach the finish line.

Executive & Personal Assistant to Founder & CEO - 21491