Jobs at The Calendar Group

Provides proactive, high-level administrative support to a CEO and VP of Operations across multiple businesses. Responsibilities include calendar and communication management, domestic and international travel coordination, meeting and presentation support, follow-up tracking, project administration, gatekeeping, and anticipating executive needs. The role requires discretion, adaptability, strong technology skills, independent judgment, and flexibility for occasional travel and communication outside traditional business hours.

Lead day-to-day operations as the Founder’s execution partner, translating priorities into plans, systems, workflows, KPIs, and accountability structures. Build and develop teams, oversee recruiting and employee development, maintain visibility across production, manage budgets and forecasting, coordinate vendors and advisers, and support new business and revenue initiatives. The role is responsible for scalable organizational growth while reducing the Founder’s operational involvement.

Support a CEO by managing personal calendars, appointments, travel, reservations, errands, events, and daily logistics. Coordinate closely with the Household Manager, adapt to changing priorities, handle sensitive information discreetly, and respond to time-sensitive requests outside standard hours. The role includes occasional domestic and international travel and requires exceptional organization, communication, judgment, follow-through, and flexibility.

Leads corporate finance for a multi-entity operating business, overseeing financial close, consolidated reporting, audits, tax posture, FP&A, payroll, banking, finance systems, internal controls, budgeting, forecasting, and process improvement. Partners with executive leadership to translate financial information into recommendations supporting growth, profitability, and enterprise value. Builds and manages a high-performing finance team and oversees external CPA relationships.

Provides full-time household support for a private Georgetown family, including detailed housekeeping, laundry, tidying, errands, coordination with housekeeping staff, backup childcare, school pickups, activities, and pet care. The role requires reliability, discretion, organization, independent judgment, and a valid driver’s license with a clean driving record.

Oversee a complex portfolio of operating companies, investments, finances, properties, and personal interests. Review financial performance, capital allocation, liquidity, and transactions; coordinate executives, investors, advisors, and professional service providers; evaluate investments; manage due diligence; mitigate risks; oversee property projects; produce decision-oriented reporting; and lead strategic special projects using AI and automation.

Provide high-level personal and executive support including Google Suite, calendar and inbox management, full travel coordination, personal and business errands, property and vendor oversight across multiple residences, frequent short-notice travel, and ad hoc tasks. Must be organized, resourceful, comfortable around children, able to drive manual and exotic vehicles, and maintain a clean driving record.

The Managing Director will oversee the personal financial ecosystem of a private equity CEO, managing liquidity and financial operations while ensuring efficiency in financial administration.

The Personal Assistant will support a private family with travel arrangements, calendar management, personal errands, and household tasks while maintaining flexibility and discretion.

Provide hands-on lifestyle support to a high-profile principal in Greenwich, CT: manage daily scheduling, oversee household staff, liaise with security, drive the principal, handle errands, retrieve mail/packages, and coordinate meals and logistics while working alongside a second assistant.

Provide full-time personal assistant and household manager support to a principal: manage schedules, errands, vendor coordination, property projects, travel logistics, event preparation, bill organization, and occasional travel. Act as a trusted, discreet, proactive resource to anticipate needs and ensure household operations run smoothly.

Live-in nanny to care for three children (ages 4–6): plan age-appropriate activities, maintain routines and boundaries, prepare meals, manage schedules and travel logistics, drive children to activities, keep play and sleeping areas organized, and coordinate with weekend nanny.

Provide executive and household administrative support including calendar and email management, travel coordination, vendor and project follow-up, errands, household logistics, deliveries and inventory, and daily care for pets and farm animals including overnight support during employer travel.

Manage daily operations and maintenance of two private residences, supervise household staff and vendors, coordinate projects and events, handle minor repairs and errands, track expenses and budgets, and maintain confidentiality and professionalism.

Provide comprehensive professional and personal support to a business owner: manage calendars, prioritize tasks, coordinate household and family logistics, oversee vendors and pet care, run errands, and deliver executive-level administrative assistance with discretion and professionalism.

Manage daily operations for two private residences, including calendars, travel, vendors, maintenance, errands, grocery and kitchen tasks, vehicle upkeep, record-keeping, and routine administrative support while maintaining confidentiality and coordinating seasonal relocation between New Jersey and Florida.

Lead and manage daily operations of two private residences, including maintenance, vendor coordination, household logistics, travel arrangements, budgeting, scheduling, event planning, and systems development. Ensure residences are prepared for principals, maintain discretion, implement organizational tools, and oversee staff and vendors to deliver seamless household service.