Chief of Staff

Role Type: Full-time W2 position supporting a CEO/founder and his family across executive operations, personal administration, household systems, and special projects.

Location: Must live within approximately one hour of Port St. Lucie, Florida. Regular in-person work at the family home and/or Stuart office; Executive Week in West Palm Beach.

Schedule: Standard Monday-Friday business hours, generally 9:00 AM-5:00 PM, with required flexibility during high-pressure moments.

Hybrid Structure: Up to three days per week remote; two days per week in person. Executive Week (once per month) requires in-person support Tuesday-Thursday in West Palm Beach.

Emergency Coverage: Must be capable and willing to step into a two-week household-manager rotation, 8:00 AM-9:00 PM with a one-hour daily break, if household coverage is lost.

Benefits: PTO, health benefits, and travel reimbursement except ordinary commute to the office or family home. No guaranteed bonus.

About the Role

This is a rare hybrid role for a highly capable operator who can help run the executive and personal life of a CEO/founder. The role combines business operating support, calendar and meeting discipline, AI-enabled documentation, project visibility, household systems, vendor management, personal administration, travel/logistics, and occasional hands-on household execution. The right person will be equally comfortable sitting in an executive meeting, using AI to turn messy inputs into a clean operating system, checking Asana for project risk, managing a vendor, building a household SOP, coordinating staff coverage, and helping physically with household tasks when needed. This is not a conventional Executive Assistant role, a traditional corporate Chief of Staff role, a nanny-only role, or a household-manager-only role. It is a high-trust, high-discretion role for someone who can operate across both business and private household environments without ego, drama, or excessive direction.

Core Mission

Create calm, order, visibility, and follow-through across the CEO’s personal life, household, and business commitments by owning operational details, building durable systems, managing staff and vendors, and protecting the CEO’s focus. Success means the CEO is more productive, the household is more stable, open loops close faster, staff perform better, business risks are visible earlier, and the family experiences the role as support rather than added management work.

What Makes This Role Different

• It requires both business and household experience.
• It is hands-on and strategic.
• It requires AI fluency.
• It requires unusual communication range. The person must handle direct feedback from the CEO without defensiveness while communicating softly and low-pressure in the household.
• It requires operational ownership.

Primary Responsibilities

1. Executive and Business Operating Support

• Manage the CEO’s calendar with excellent judgment and near-zero scheduling errors.
• Once per month, attend Executive Week in person in West Palm Beach, Florida, Tuesday-Thursday, and support meeting flow, minutes, action items, follow-up, and executive summaries.
• Use AI-assisted workflows to produce clear, concise, action-oriented meeting minutes.
• Track business projects through Asana and identify which projects are moving, stalled, unclear, late, or at risk.
• Follow up with project owners and apply light-to-moderate pressure when appropriate.
• Determine whether an issue requires CEO involvement or can be solved below the CEO level.
• Produce a weekly command brief covering calendar, household, business project status, risks, required conversations, open decisions, and relevant industry/AI items worth attention.
• Develop enough credibility over time to become a trusted member of the senior leadership operating rhythm, though not necessarily the executive leadership team.

2. Personal Administration and Life Operations

• Own personal administration as existing support transitions to another role.
• Organize passwords, accounts, financial files, vendor files, recurring bills, subscriptions, invoices, receipts, healthcare documents, EOBs, tax documents, and household records.
• Coordinate key appointments including medical, dental, dermatology, haircuts, and other personal or family logistics.
• Review invoices and unusual charges, flag variance or risk, and bring recommended solutions rather than unresolved problems.
• Support household budgeting, points/travel-program tracking, and recurring administrative routines.
• Maintain absolute confidentiality across family, financial, medical, business, and staff-related information.

3. Household Systems and Staff Management

• Create and maintain the household operating system: checklists, routines, inventory standards, vendor maps, maintenance schedules, staff instructions, accountability tools, and escalation rules.
• Build systems that provide structure without making the household feel rigid or overmanaged.
• Manage household managers and vendors, including expectations, routines, performance visibility, accountability, and recommendations on staffing changes.
• Maintain a warm pipeline of potential household-manager candidates, so the family is never exposed by an unexpected staffing gap.
• Own vendor selection and accountability for both Florida and New Jersey homes, including quotes, comparison, scheduling, oversight, invoice review, and completion verification.
• Coordinate annual setup and close-down of the New Jersey home, so it is stocked, organized, vendor-mapped, and operational before the family arrives.

4. Hands-On Household Execution and Backup Coverage

• Regularly perform hands-on household work when needed, including laundry, food prep, stocking, errands, resets, organization, and other tasks where starting and stopping creates risk or inefficiency. May delegate these tasks to household staff if the household system is durable and efficient enough to allow.
• Own food and inventory reliability, so mission-critical household and meal items do not stock out.
• Be capable and willing to step into emergency household-manager coverage if the family loses a household manager.
• During emergency coverage, work a two-week rotational schedule of 8:00 AM-9:00 PM with a one-hour daily break while also leading the replacement search.
• Have prior experience independently managing children, even though solo childcare should not be a routine part of the role when the household is fully staffed.

5. AI-Enabled Systems and Documentation

• Use AI daily to solve real operational problems, not merely to draft simple text.
• Convert messy notes, transcripts, instructions, and preferences into usable SOPs, checklists, manuals, trackers, summaries, and decision aids.
• Draft policies and procedures with AI, then edit for accuracy, tone, and fit.
• Use AI to structure Asana work, summarize meetings, compare vendors, write staff instructions, create checklists, and produce executive briefings.
• Require minimal translation from the CEO; the standard is independent AI-assisted problem-solving.

Required Experience and Qualifications

• Business-side experience is required. The candidate must have meaningful prior experience in business, executive operations, project management, operations, leadership support, founder/CEO support, or a comparable organizational role.
• Household/private-family exposure is required. The candidate must also have meaningful exposure to private household operations, family support, household management, personal assistance, estate/family office work, nanny/household-manager work, or similar high-discretion personal operations.
• AI competence is required. The candidate should already be using AI tools to solve real problems in work or personal life.
• Asana or project-management-system aptitude is required. Prior Asana experience is preferred; strong ability to learn and use project-management tools is required.
• Childcare judgment is required. The candidate must have experience independently managing children and must be comfortable with a parent-led discipline approach.
• Local presence is required. The candidate must live within approximately one hour of Port St. Lucie and be able to work in person at the home, Stuart office, and West Palm Beach executive office as needed.
• Discretion is required. The role involves access to confidential family, financial, medical, business, staff, and household information.

Required Traits

• High agency and strong follow-through.
• Low ego and no title entitlement.
• Emotionally low-maintenance and able to handle direct feedback.
• Warm, calm, and non-triggering in a private household environment.
• Firm, organized, and fact-based with vendors, staff, and business stakeholders.
• Comfortable moving between executive work and hands-on household work.
• Able to create structure without creating rigidity.
• Fast learner who generalizes feedback and does not repeat avoidable mistakes.
• Highly discreet, trustworthy, and professionally bounded.
• Respectful of a conservative Christian family environment, even if not personally aligned with every belief.

Strong Nice-to-Haves

• Prior Chief of Staff, Executive Assistant, founder support, operations, or project-management experience.
• Prior household manager, family office, estate manager, personal assistant, or nanny/household-manager experience.
• Experience managing household staff or vendors.
• Experience with household budgets, healthcare invoices, insurance/EOBs, vendor files, or personal finance administration.
• Experience creating SOPs, manuals, checklists, onboarding materials, or accountability systems.
• Experience with travel logistics, packing systems, loyalty points, seasonal home setup, or multi-home operations.
• Prior experience with Asana or similar tools.
• Experience in healthcare, behavioral health, addiction treatment, or another regulated service business.