Inside Out Hiring

Role overview

About the client

The client is a dynamic multi-entity family office and serial entrepreneur operating across four distinct market sectors:

1. Real Estate Investment & Development: A portfolio of cash-investment residential properties across multiple regions, managed under individual entity structures alongside property management for outside owners.
2. Boutique Interior Design & Contracting: A boutique interior design practice specializing in high-end residential projects, turnkey furnishing, and property contracting.
3. Boutique Fitness & Wellness: A fast-growing infrared fitness studio brand with locations across key markets undergoing strategic expansion, corporate structuring, and location rollouts.
4. Personal & Family Office: Family office administration, executive scheduling, and personal household logistics.

The business operates with a small, high-touch core team—including licensed brokers, property accountants, bookkeepers, and studio managers. The Managing Partner requires a central partner to maintain cross-business oversight, streamline administrative follow-through, and bridge operational gaps across all four sectors.

About the role

As the Chief of Staff, you will serve as the primary point of organizational accountability and central connective tissue across all four business entities and personal operations.

You are the "layer above and between" the Managing Partner, external accountants, bookkeepers, studio managers, contractors, and clients—ensuring information is gathered, organized, updated, and dispatches to the right people on time. You will manage executive priorities, oversee property management logistics, support back-office design procurement, monitor fitness expansion deliverables, and handle high-level executive and personal administration.

As you demonstrate capability, the role will expand to include light marketing, client outreach, and broader operational management to drive business growth and client retention.

Key responsibilities

1. Real Estate Investment & Property Management Coordination 

• Master Property Registry: Maintain a current master database across all properties (holding entities, tenant details, rent schedules, security deposit holdings, lease expiration alerts at 120/90/60 days, insurance policies, tax appeal timelines, and utility logins). 
• Monthly Utility Close: Download, review, flag variance (>20% spikes), and reconcile monthly statements across all owner-paid utilities by the 7th of every month for the bookkeeper. 
• Standard Operating Procedures (SOPs): Write and execute SOPs for acquisitions, tenant move-in/move-out workflows, utility transfers, lease renewals, and maintenance requests. 
• Property Administration: Field tenant and vendor requests, coordinate property access, manage insurance/permit renewals, and log property maintenance/markup fees. 

2. Boutique Interior Design Practice Support 

• Project Back-Office: Set up and maintain project files, scope sheets, vendor contracts, and decision logs for all active interior design jobs. 
• Purchasing & Logistics Tracker: Track all orders from procurement to delivery (SKUs, deposits, delivery dates, damage reports, and storage logistics). 
• Budget & Invoicing Control: Perform weekly updates on budget vs. committed spend; draft client invoices, reconcile vendor receipts, and pass coded records to the financial team. 
• Marketing & Client Outreach: Compile project photos, maintain the CRM database, draft client check-ins, coordinate project photography, and manage digital portfolio updates during lull periods. 

3. Fitness & Wellness Business Operations Support 

• Investment & Capital Tracking: Maintain a clear ledger of capital contributions, member loans, and business expenses; ensure all brand-related spend is executed on dedicated business cards. 
• Corporate & Compliance Records: Track studio LLC entities, lease terms/options, insurance renewals, and legal agreements. 
• Expansion & Build-Out Logistics: Maintain project timelines, site evaluation files, contractor schedules, and grand-opening checklists for new studio locations. 
• Agency & Marketing Follow-Up: Monitor external marketing, PR, and ad agencies against agreed deliverables, timelines, and scope. 

4. Executive & Personal Administration 

• Calendar Management: Triage, structure, and protect the Managing Partner’s calendar; confirm daily appointments, resolve conflicts proactive of client meetings, and block focus time. 
• Family Logistics & Personal Admin: Coordinate recurring family appointments, school calendars, travel itineraries, household vendors, and personal renewals with absolute discretion. 
• Inbox & Triage Management: Monitor primary inboxes, flag priority action items, and draft responses to maintain timely follow-up. 

Operating Cadence & AI Tooling 

• Daily Morning Brief: Deliver a daily summary detailing priorities, required approvals, and daily schedules before Eastern business hours begin. 
• Daily Close-Out Note: Provide an end-of-shift update on completed tasks and pending items. 
• Weekly Syncs: Conduct a weekly strategy review with the Managing Partner and structured handoffs with the financial team. 
• AI-Enabled Execution: Utilize modern AI productivity tools (such as Claude/Claude Design) to quickly generate project spec sheets, floor plans, draft communications, summarize documents, and prepare client-facing materials. 

Qualifications & skills (Non-Negotiable)

• 5+ Years Experience: Proven track record in a high-level support role—such as Chief of Staff, Operations Manager, or Senior Executive Assistant—directly supporting a Founder or Senior Executive across multiple business entities. 
• Real Estate / Property Management Background: Direct experience handling property back-office operations, leases, utility setups, tenant transitions, and vendor coordination. 
• Financial & Numerical Aptitude: Proficient in spreadsheet management, budget tracking, invoice reconciliation, and preparing clean reporting packages for bookkeepers/accountants. 
• Systems Builder Mindset: Proven ability to create, implement, and maintain SOPs, CRM databases, project trackers, and checklists independently. 
• AI & Tech Proficiency: Comfortable utilizing modern software and AI tools (Claude/Claude Design, CRM platforms, project management tools, shared password managers) to drive operational efficiency. 
• Communication Skills: Flawless written and verbal English communication skills with a professional, warm, and collaborative tone suitable for high-touch clients and external partners. 
• Proven Tenure: Demonstrated history of long-term reliability and stability in previous positions. 
• Availability & Reliability: Available full-time (40 hours/week) during US Eastern business hours, with a reliable remote work setup (including backup power/internet solutions where applicable). 

Qualifications & skills (Non-Negotiable)

• Spanish language proficiency is a plus. 
• Prior familiarity with property tracking tools, password manager security vaults, and modern financial reporting tools (e.g., Ramp, QuickBooks read-access). 

Key Performance Indicators (KPIs) 

• 100% On-Time Monthly Financial Packages: Utility closes, invoices, and expense logs delivered cleanly to the financial team by designated monthly deadlines. 
• Zero Lapsed Obligations: Zero missed lease renewal deadlines, insurance renewals, or permit expirations. 
• Seamless Transitions: Zero gaps in utility service during property turnover events. 
• Budget Accuracy: Design and expansion budgets updated weekly with proactive flags on budget variances. 
• Operational Autonomy: Founder’s direct administrative workload demonstrably reduced within the first 90 days.