Careers

Location: Chicago, IL (River North)
Schedule: Full-Time | In-Person
Reports To: Managing Partner

Compensation: $90-130K DOE

The Opportunity

We are partnering with a highly regarded professional services firm to find an exceptional Senior Executive Assistant to support its Managing Partner.

This is a high-trust, high-impact role for an experienced Executive Assistant who knows how to operate as a true extension of the executive they support. While there are, of course, calendars, meetings, correspondence, and the traditional fundamentals of executive support, this role goes meaningfully beyond task execution. The Managing Partner is looking for someone who can understand the bigger picture, anticipate what is coming, exercise excellent judgment, and take genuine ownership of keeping priorities moving forward.

The right person will naturally look for ways to make their executive—and the organization around them—more effective. You notice what needs attention before it becomes urgent, close loops without being chased, and are comfortable making decisions within your lane. You understand that exceptional executive support is often about removing friction: protecting time, creating structure, staying several steps ahead, and quietly making sure the details are handled.

This is an opportunity to become a trusted partner to a senior leader and an important member of a close-knit, high-performing organization.

What You’ll Do

• Own and thoughtfully manage a complex and evolving executive calendar, balancing competing priorities and ensuring time is aligned with the Managing Partner’s most important objectives.

• Serve as a thoughtful gatekeeper and connector, understanding what requires the Managing Partner’s attention, what can be delegated, and what you can independently resolve.

• Anticipate upcoming meetings, deadlines, commitments, and decisions and ensure the Managing Partner is consistently prepared.

• Prepare agendas, presentations, briefing materials, notes, and other meeting materials as needed.

• Track follow-ups, commitments, and action items through completion—ensuring important details do not fall through the cracks.

• Create systems and rhythms that make the Managing Partner’s day more organized, efficient, and intentional.

• Draft and manage thoughtful, polished correspondence on behalf of the Managing Partner, including internal communications, external emails, and client-facing materials.

• Serve as a trusted point of contact for Partners, senior leaders, clients, and other important external relationships.

• Communicate confidently and professionally across all levels of an organization, understanding when to move something forward independently and when to escalate.

• Handle highly sensitive information and conversations with exceptional discretion, maturity, and judgment.

• Take ownership of administrative and operational responsibilities that can be removed from the Managing Partner’s plate, allowing them to remain focused on leadership, client relationships, business development, and growth.

• Prepare and coordinate agreements, contracts, and related documentation, working with internal and external stakeholders as appropriate.

• Independently drive projects from beginning to end, keeping stakeholders informed and ensuring deadlines and deliverables remain on track.

• Support special projects and initiatives connected to leadership priorities, firm strategy, business development, and growth.

• Step into evolving needs as they arise. This is a role for someone who is comfortable with variety and understands that supporting a senior executive does not always fit neatly within a job description.

Who You Are

You are an experienced Executive Assistant who takes real pride in being excellent at your craft. You understand the difference between completing a task and truly owning an outcome, and you are at your best when you have the trust and autonomy to make things happen. You are proactive by nature. You anticipate rather than react, ask smart questions, and quickly develop an understanding of your executive’s priorities, preferences, relationships, and working style. Once you understand the objective, you do not need—or want—to be walked through every step.

You are also:

• Highly organized, detail-oriented, and exceptionally strong at prioritizing in a fast-moving environment.

• Resourceful and solutions-oriented; when something changes, your instinct is to figure out the next best move.

• Confident operating with autonomy while maintaining excellent judgment around when to involve your executive.

• Comfortable working closely with senior leaders and sophisticated external stakeholders.

• A clear, polished, and thoughtful written and verbal communicator.

• Emotionally intelligent, mature, and steady under pressure.

• Discreet and trustworthy, with an intuitive understanding of confidentiality.

• Flexible and adaptable, without being easily rattled by shifting priorities.

• Someone who follows through. When you say you will handle something, others can confidently consider it handled.

• Collaborative and low-ego, with a genuine willingness to jump in wherever you can be useful.

What You Bring

• 5+ years of experience providing high-level executive support, ideally to a C-suite executive, founder, Managing Partner, or similarly senior leader.

• A demonstrated track record of operating as a trusted executive partner—not simply an administrative resource.

• Exceptional calendar management, organization, prioritization, and follow-through.

• Experience preparing polished executive-level correspondence, presentations, and other materials.

• Strong proficiency with Microsoft Outlook and the broader Microsoft Office suite.

• Bachelor’s degree preferred.

• Prior exposure to contracts, agreements, legal documentation, or paralegal work is a plus.

• Authorization to work in the United States without sponsorship.

The Details

This is a full-time, exempt position based in Chicago, IL. The role is primarily performed in an office environment and requires the ability to carry out the normal physical and technical functions associated with an executive support position, including extended computer use and occasional lifting of up to approximately 30 pounds. As with any senior support role, responsibilities may evolve alongside the Managing Partner and the needs of the organization. The successful candidate will be comfortable operating with flexibility and taking on additional responsibilities that reasonably fall within the scope of the position. This employer is an equal opportunity and at-will employer. Employment is contingent upon authorization to work in the United States and the ability to perform the essential functions of the position, with or without reasonable accommodation.

Title: Senior Executive Assistant 
Location: Los Angeles, CA (Van Nuys area)
Schedule: Full-time, In-Person
Classification: Exempt
Salary : $120-150,000 yearly

Overview

Our client is seeking an exceptional Senior Executive Assistant to support the CEO and CCO and directly manage at least one administrative professional. This role requires a highly skilled individual who thrives in a fast-paced, entrepreneurial environment and brings extensive experience supporting senior executives in high-demand settings.

The ideal candidate is an exceptionally quick thinker who processes information rapidly, anticipates needs, and translates direction into action with minimal oversight. They possess outstanding organizational and prioritization skills, sound judgment, and strong business acumen, with the ability to navigate competing demands while understanding the company's broader priorities. They are highly detail-oriented, exercise absolute discretion with confidential information, and demonstrate the leadership skills and strategic thinking necessary to operate as a trusted partner to executive leadership.

Essential Duties & Responsibilities

Executive Support

• Serve as trusted support to the CEO and CCO, managing complex calendars, inbox management/strategy, priorities, and sensitive communications.

• Anticipate needs and proactively address challenges before they arise, exercising independent judgment on matters of significance.

• Prepare the CEO and CCO for meetings with comprehensive briefing materials, agendas, and background research.

• Attend key meetings, taking exceptionally thorough and accurate notes, capturing decisions, action items, and ensuring timely follow-through.

• Quickly synthesize information, translating verbal direction into action with minimal need for clarification.

• Manage CEO and CCO correspondence, screening, and prioritizing communications while drafting responses on behalf of leadership.

• Exercise sound judgment in prioritizing competing requests, recognizing business-critical matters and ensuring executive attention is directed toward the highest-impact priorities.

• Developing a fluent and ongoing understanding of technology platforms across various functions (HR, Finance, Supply Chain, Operations).

• Coordinate domestic and international travel arrangements, including detailed itineraries and logistics.

• Handle confidential information with the utmost discretion and professionalism.

Management & Leadership

• Directly manage and mentor a team of at least one Administrative Assistant.

• Set performance objectives, conduct evaluations, and provide ongoing coaching and professional development.

• Delegate tasks effectively to optimize efficiency and workload balance, ensuring accountability, accuracy, and timely execution.

• Implement and refine administrative processes to improve efficiency, streamline workflows, and proactively address operational challenges.

• Develop a strong understanding of the company's business model, key revenue-driving functions, and operational priorities to effectively anticipate executive needs and prioritize work accordingly.

Strategic Operations

• Manage special projects and initiatives on behalf of executive leadership, coordinating cross-functional teams and ensuring projects move forward efficiently with minimal oversight.

• Prepare reports, presentations, and analyses to support executive decision-making.

• Serve as liaison between executives and internal/external stakeholders, representing leadership in meetings when appropriate.

• Plan and execute board meetings, leadership off-sites, and company-wide events.

• Monitor budget expenditures and manage expense reporting for the executive office.

Organizational Leadership

• Act as a gatekeeper and as an ambassador of company values, setting the tone for professionalism and excellence.

• Build relationships across all levels of the organization to facilitate collaboration and information flow.

• Identify opportunities for operational improvements and drive effective implementation.

Qualifications

Required

• 10+ years of experience supporting C-suite executives, ideally founders, CEOs, or other high-level executives in demanding, fast-paced, and creative environments.

• 3+ years of people management experience, with proven ability to develop high-performing teams.

• Bachelor's degree or equivalent professional experience.

• Expert-level proficiency in Google Workspace and project management tools.

• Exceptional written and verbal communication skills with impeccable attention to detail.

• Demonstrated ability to handle multiple priorities simultaneously while maintaining composure under pressure, quickly shifting between tasks, processing new information, and adapting to changing priorities without sacrificing accuracy or follow-through..

• Strong business acumen with an understanding of corporate operations and strategic planning, including the ability to recognize business-critical priorities and exercise sound judgment in allocating time and resources.

• Absolute discretion and ability to handle highly confidential information.

Preferred

• Experience in apparel, beauty, entertainment, or similar fast-paced creative environments.

• Advanced skills in data analysis, financial reporting, or presentation design.

• Experience managing executive communications during organizational change.

• Prior experience supporting high-profile executives, founders, or senior leaders in complex, high-pressure environments.
  

* Compensation will be determined based on experience and other factors permitted by law.

Title: Estate Manager
Location: Miami, FL
Status: Full-time

Overview

Our client is seeking an experienced Estate Manager to oversee the operations, maintenance, staffing, and readiness of their private Miami residences. Based primarily at the family’s new Coral Gables home, this role will also involve regular travel to and oversight of a significant multi-state property portfolio, including multiple residences in California, a large family home in Michigan, and an additional condo in Coconut Grove. The Estate Manager will serve as the primary operational lead responsible for ensuring each property is consistently maintained, fully operational, and prepared to the Principals’ standards while the family is traveling or away from the residences.

This is a high-trust, hands-on leadership role for someone who understands the complexity and discretion required to run significant private homes at the highest level. The Estate Manager will oversee household staff, vendors, preventative maintenance, property systems, inventories, schedules, and ongoing improvements, ensuring each residence is impeccably maintained, fully operational, and always prepared to the Principals’ standards.

The ideal candidate is polished, proactive, highly resourceful, and exceptionally detail-oriented - someone who can seamlessly operate at both a strategic and hands-on level. They are equally comfortable interfacing with Principals, family office representatives, architects, designers, contractors, and senior service providers as they are stepping in personally to ensure the home is running flawlessly day-to-day. This person understands that exceptional estate management lives in the details. They are the type to notice when lighting feels off before a dinner party, catch an issue with climate control before the family arrives, ensure guest rooms are perfectly prepared, troubleshoot a smart home system, restock household essentials, or step in to handle whatever is needed in the moment to maintain the highest standards of readiness and care.

The ideal candidate brings at least 10+ years of residential or estate management experience, ideally within sophisticated private homes or UHNW environments, along with a strong understanding of the unique operational needs of coastal properties, including climate, humidity, storm preparation, landscaping, preventative maintenance, and seasonal upkeep. An established network of trusted local vendors and service providers is highly valued.

Above all, this person takes genuine pride in creating homes that feel effortless, elevated, warm, and impeccably maintained at all times. They are proactive rather than reactive, solutions-oriented rather than rigid, and possess the kind of quiet ownership mentality that defines exceptional private service. They understand that no task is too small when the goal is excellence.

Property Operations & Standards

• Oversee the daily operations, maintenance, and readiness of the Miami residence.

• Ensure all homes in the portfolio are maintained to the highest standards of cleanliness, functionality, beauty, safety, and preparedness.

• Conduct regular property walks and detailed inspections, identifying issues before they become problems.

• Maintain a deep understanding of all household systems, including HVAC, electrical, plumbing, lighting, AV, security, pool, landscaping, appliances, generators, irrigation, smart home technology, and climate-control systems.

• Develop and manage preventative maintenance schedules across all properties.

• Ensure seasonal, storm, humidity, pest, and climate-related maintenance needs are proactively addressed.

• Prepare homes for Principal arrivals, guest stays, family travel, events, and seasonal transitions.

• Track repairs, warranties, manuals, vendor contacts, service records, and property documentation.

• Create and maintain household manuals, operating procedures, checklists, vendor lists, emergency protocols, and property-specific systems.

• Maintain household inventories, supplies, equipment, tools, keys, access codes, vehicles, and property assets as appropriate.

Staff Leadership & Household Team Management / Vendor & Contractor Management

• Oversee all household operations personnel and external service providers, including housekeepers, groundskeepers, maintenance teams, vendors, contractors, tradespeople, and specialty service providers across the residences.

• Partner closely with the Principals and Personal Assistant on hiring, onboarding, training, scheduling, staffing coverage, and performance management to ensure the homes consistently operate at the highest standards.

• Establish and maintain clear household systems, service standards, routines, checklists, and expectations to support seamless day-to-day operations and an elevated household environment alongside full-time and outsourced staff and vendors. 

• Ensure homes are appropriately staffed and fully prepared for Principal arrivals, guest stays, travel schedules, events, and seasonal transitions.

• Serve as a steady, calm, solutions-oriented leader for household staff and vendors, fostering a professional, discreet, respectful, and service-minded culture throughout the properties.

• Build and maintain strong relationships with trusted vendors and develop reliable support networks for additional residences and projects. 

• Source, vet, negotiate with, and oversee vendors and contractors while managing proposals, budgets, invoices, scheduling, timelines, and quality control.

• Supervise maintenance, repairs, installations, inspections, deliveries, preventative maintenance, and capital improvement projects to ensure all work is completed to exceptional standards.

• Coordinate closely with architects, designers, builders, landscapers, security teams, project managers, and specialty contractors as needed while ensuring all external partners operate with professionalism, discretion, and respect for the private household environment.

Multi-Property Oversight

• Travel regularly to additional residences, especially California, to inspect properties, coordinate projects, prepare homes, and ensure consistent standards.

• Develop property-specific systems, schedules, and readiness protocols for each residence.

• Coordinate seasonal openings, closings, deep cleans, maintenance visits, vendor walkthroughs, and arrival/departure preparations.

• Ensure each property reflects the same level of care, consistency, and operational excellence.

• Provide updates to Principals, the Senior Personal Assistant, and/or family office regarding property status, priorities, projects, and concerns.

Events, Projects & Systems

• Partner with the Senior Personal Assistant to support family hosting, events, dinners, and gatherings as needed. 

• Ensure the home is physically prepared for events, including staffing, cleaning, setup, vendor access, parking/logistics, deliveries, rentals, lighting, climate, and post-event reset.

• Coordinate with chefs, florists, rental companies, valets, security, housekeeping, and event vendors as needed.

• Anticipate household needs before, during, and after events. Step in wherever needed to ensure seamless execution and an elevated guest experience.

• Manage household projects from start to finish, ensuring timelines, budgets, and quality standards are met.

• Create systems that make the homes easier to run, track, maintain, and scale.

• Use technology, apps, spreadsheets, databases, or estate management platforms to track maintenance, inventories, tasks, vendors, warranties, budgets, and household documentation.

• Provide clear updates on open items, repairs, vendor status, project progress, and upcoming needs.

• Identify opportunities to improve operations, reduce friction, and increase efficiency.

• Maintain discretion and professionalism in all documentation and communications.

Qualifications

• Minimum 10+ years of residential and/or estate management or private household management experience supporting sophisticated private homes, family offices, or similarly high-touch environments.

• Proven track record of long-term tenure in private service or high-trust household roles.

• Significant experience managing large private residences and/or multiple properties.

• Strong knowledge of area-specific vendors, service providers, climate considerations, seasonal preparedness,  landscaping, pest control, and maintenance needs.

• Experience supervising housekeepers, maintenance staff, grounds teams, vendors, contractors, and specialty service providers.

• Experience overseeing boats, jet skis, marine vendors, or recreational watercraft maintenance is strongly preferred.

• Strong general knowledge of residential systems, including HVAC, AV, smart home systems, plumbing, electrical, lighting, pools, irrigation, generators, security, and general maintenance.

• Able to manage both high-level operations and hands-on tasks with equal professionalism.

• Excellent judgment, discretion, confidentiality, and emotional intelligence.

• Highly organized, detail-oriented, proactive, and solutions-driven.

• Comfortable working around families with young children and in active, dynamic households.

• Tech-savvy and able to implement systems for tracking, communication, maintenance, inventories, and documentation.

• Calm under pressure and able to adapt to shifting priorities.

• Excellent communication skills and a polished, service-minded presence.

• Valid driver’s license with a clean driving record and the ability to travel regularly between residences, including domestic travel as needed. Candidates must be able to successfully pass an extensive background check, reference checks, and any legally permitted pre-employment screenings. This role requires the ability to routinely lift and move items up to or exceeding 50 pounds, navigate stairs and multi-level properties, and comfortably perform hands-on household tasks associated with maintaining and preparing private residences. Candidates should be comfortable working in both indoor and outdoor environments.

Who You are: 

You are a seasoned estate professional who understands the immense trust and discretion required to support a highly active private family environment. You know how to operate quietly and professionally behind the scenes while keeping countless moving parts running seamlessly—from household operations and vendors to staffing, travel preparation, maintenance, and the evolving needs of a busy family with young children.

You are someone who naturally notices what others miss. You catch the details before they become problems, anticipate needs before they are voiced, and understand how to create homes that feel calm, organized, welcoming, and effortlessly cared for at all times. Whether preparing a residence for a family arrival, coordinating multiple vendors and schedules, managing shifting priorities, or stepping in to solve an issue personally, you approach everything with ownership, professionalism, and care. You are highly capable, deeply discreet, emotionally intelligent, and service-minded. Confidentiality is second nature to you, and you understand the importance of protecting the privacy, routines, relationships, and trust of the family you support. You are calm under pressure, adaptable, resourceful, and comfortable navigating the pace and unpredictability that naturally comes with an active household and multiple residences.

You can operate strategically and independently, but you are never above handling the hands-on details that keep a home running beautifully. You understand the standards and rhythm required in a high-touch private service environment and take genuine pride in creating ease for others. Most importantly, you are looking for a long-term opportunity where you can become a trusted, consistent presence within a family’s life and grow alongside them for years to come.

Schedule:
Typical schedule is Monday–Friday, generally between 8:00 AM–5:00 PM, with flexibility required based on the needs of the household, family travel, events, projects, vendor coordination, and property operations. This role requires a service-minded, adaptable approach, including availability for occasional early mornings, evenings, weekends, and holidays as needed.

Travel:
Regular domestic travel between residences is required, particularly to California properties, averaging approximately 8–12 trips annually depending on family schedules and household needs.

Compensation & Benefits:

• Competitive compensation package commensurate with experience

• Health, dental and vision

• Performance bonus eligibility 

• 3 weeks paid time off

• 10 paid holidays annually, including:

  • New Year’s Day

  • Martin Luther King Jr. Day

  • Memorial Day

  • Independence Day

  • Labor Day

  • Thanksgiving Day

  • Day After Thanksgiving

  • Christmas Eve

  • Christmas Day

  • Employee Birthday

Please note that due to the nature of private service and household operations, occasional work on weekends and holidays may be required depending on Principal travel, events, household schedules, or operational needs. Flexibility and a team-oriented mindset are essential to success in this role.

Location: Rancho Santa Fe, California
Schedule: Full-Time | Private Family
Compensation DOE: $100-150K all-in DOE / PTO | Health insurance stipend.

This is a career-level professional nanny position requiring significant, dedicated experience caring for children in private homes. Candidates must demonstrate substantial professional nanny experience, excellent tenure with prior families, and a strong foundation in child development, and age-appropriate care. Formal education, certifications, and/or specialized training related to children, early childhood development, or education are strongly valued, with Montessori and/or Waldorf experience or training a particular plus. This family is seeking a highly experienced professional who has intentionally built a career working with children and can bring maturity, sound judgment, and a thoughtful, developmentally informed approach to the role.

The Opportunity

A warm, hands-on private family in Rancho Santa Fe is seeking an exceptional Family Assistant / Nanny to join their household and become a trusted, long-term part of their family team.

The family has three children in a blended household. This role will primarily center around the youngest children, with responsibilities naturally evolving as the children grow.

The parents are deeply engaged and genuinely love being with their children and are thoughtful and intentional about how they raise them. They both parents value a nurturing, developmentally informed approach to childhood influenced by philosophies such as Montessori and Waldorf: encouraging independence, creativity, imaginative play, time outdoors, practical life skills, curiosity, and meaningful connection.

They are not looking for someone to take parenting off their hands. Rather, they want a wonderful professional who can work alongside them - bringing expertise, initiative, warmth, flexibility, and another trusted set of hands to family life. There is already a longtime nanny primarily supporting the oldest child, as well as additional household support, so this person will be joining an established team rather than managing the household alone.

The Role

First and foremost, this person will be an exceptional caregiver: warm, loving, patient, engaged, knowledgeable, safety-conscious, and genuinely delighted by the baby, toddler, and younger-child years.

The role also has a natural family-assistant element.The family values someone who understands that private family life does not always fit neatly into a job description. The right person will be agile, observant, and happy to lend a hand with reasonable child and family-related needs as they arise. Some days may center around developmental activities, outdoor adventures, classes, outings, imaginative play, or establishing routines. Others may include reorganizing a playroom, rotating toys, handling children's laundry, packing for a family trip, installing or moving a car seat, picking up something the children need, or running a light family errand while Mom and Dad enjoy time with the kids.

There is no ego around the work. The family is looking for someone who notices what would make the day run more smoothly and is naturally inclined to help - while also communicating well and maintaining reasonable, healthy boundaries around the role.

What You'll Do

• Provide warm, attentive, developmentally appropriate care for the family's younger children.

• Create engaging days through play, reading, art, music, outdoor exploration, classes, outings, and age-appropriate activities.

• Support developmental milestones while encouraging independence, confidence, curiosity, emotional regulation, and practical life skills.

• Maintain thoughtful routines around naps, meals, bottles, feeding, hygiene, transitions, and daily schedules.

• Reinforce the parents' approach to boundaries, behavior, routines, and family expectations.

• Partner closely with highly involved parents, offering expertise and observations while respecting their preferences and parenting philosophy.

• Help maintain an organized, calm environment for the children, including playrooms, nurseries, closets, toys, books, and children's belongings.

• Handle children's laundry, tidying related to activities and meals, bottle or feeding-related cleanup, and other reasonable child-related household tasks.

• Keep children's clothing, gear, supplies, diapers, medications, and everyday necessities organized and stocked.

• Assist with occasional light family errands or logistical needs, such as picking up children's supplies, returning library books, preparing items for an activity, or coordinating something needed for the day.

• Help with practical family needs as appropriate, including packing children's suitcases, preparing for outings, organizing gear, and installing or transferring car seats.

• Communicate proactively with parents and other household staff about schedules, children's needs, supplies, appointments, activities, and anything requiring attention.

• Work collaboratively with the family's existing nanny and broader household team.

• Travel domestically and occasionally internationally with the family, helping prepare the children and their belongings and supporting routines while away.

• Pivot gracefully when family schedules change, children become sick, appointments move, travel plans shift, or the day simply unfolds differently than expected.

Who You Are

You are someone who genuinely loves children and has intentionally chosen this work as a career. You find the baby, toddler, and younger-child years especially rewarding and are energized by helping children learn, develop, and become increasingly confident and independent.

You bring strong childcare instincts and sound judgment, but you do not need to be the loudest expert in the room. You know how to partner with thoughtful, engaged parents - sharing ideas when useful, listening well, respecting their preferences, and ultimately supporting the way they want to raise their children. You are proactive without being intrusive, confident without being rigid, and professional without feeling overly formal. You can read the room. You recognize when a parent wants another set of hands and when they want uninterrupted family time.

You are also naturally flexible and agile. You understand that family life changes quickly and do not become rattled when the plan changes. If the children are happily spending the afternoon with Mom and Dad, you are comfortable shifting gears and finding something useful to accomplish rather than waiting to be directed. You are someone who can see that the playroom needs reorganizing, the diaper supply is running low, or tomorrow's car seats need to be switched - and simply take care of it or communicate what is needed.

Most importantly, you bring warmth, emotional intelligence, good judgment, discretion, and a genuine desire to become part of a family for many years.

What We're Looking For

The strongest candidates will bring:

• Significant professional nanny experience, particularly with babies, toddlers, and younger children.

• A demonstrated interest in child development and thoughtful, intentional caregiving.

• Familiarity with or appreciation for Montessori, Waldorf, child-led, play-based, or similarly developmentally informed approaches.

• Experience working successfully with hands-on, involved parents.

• A track record of longevity and a genuine desire for a long-term position. 

• Strong judgment, maturity, discretion, and emotional intelligence.

• Excellent communication and the ability to receive and incorporate feedback without defensiveness.

• A collaborative approach and comfort working alongside another nanny and household staff.

• A proactive mindset and willingness to pitch in with reasonable child and family-related needs.

• Strong organizational skills and attention to detail.

• Comfort with changing schedules and the unpredictability that naturally comes with children and family life.

• Previous family travel experience and comfort accompanying a family on trips.

• Excellent driving skills and comfort transporting children.

• Current CPR/First Aid certification or willingness to obtain it.

• The ability to swim and confidently supervise children around water.

• Authorization to work in the United States.

• Bachelor’s degree from an accredited four-year college or university required.

The Family's Lifestyle

This is an active, health-conscious family that prioritizes quality time together. They value a screen-free childhood, outdoor play, movement, exploration, reading, creativity, and opportunities for their children to engage meaningfully with the world around them.

The family enjoys hiking, yoga, travel, and spending time outdoors. They are also very thoughtful about food and generally prioritize healthy, organic choices. The nanny does not need to live exactly the same lifestyle personally, but should genuinely respect these values and feel comfortable reinforcing them with the children.

Travel

The family travels periodically throughout the year, and flexibility to accompany them is an important part of the position. The ideal candidate understands that traveling as a nanny requires preparation, teamwork, patience, and adaptability - from packing children's belongings and navigating airports to helping maintain routines in unfamiliar environments.

Schedule & Location

This is a full-time, in-person position based in Rancho Santa Fe, California. The family is seeking someone who can offer dependable full-time coverage while maintaining reasonable flexibility around occasional travel, schedule adjustments, or changing family needs. Client is open to LIVE-OUT ROTA [7/7] OR regular Monday-Friday from 8am-5pm weekly.

The Long-Term Fit

This family is particularly interested in meeting someone who sees professional nannying as meaningful career work and who is looking for much more than their next position. They hope to find someone who will know these children through multiple stages of childhood, develop a deeply trusted partnership with Mom and Dad, collaborate beautifully with the family's existing team, and grow alongside the household for many years to come.

For the right person, this is an opportunity to join an exceptionally thoughtful family that values excellent childcare while also respecting the professional providing it - and to become an important part of a family's story as it continues to grow.

Job Title:   Executive Personal Assistant / Family Assistant
Location: San Diego (Travel required)
Schedule: Full-time, in-person
Compensation: $95-150K DOE

*DRAFT (may be updated):

Our client is seeking an exceptional Executive Personal Assistant to support their busy family and serve as a trusted extension of their day-to-day life. This is a unique opportunity for someone who enjoys variety, thrives in a fast-paced environment, and takes genuine pride in making things happen behind the scenes.

No two days will look exactly alike. One morning may involve coordinating contractors for an ongoing home renovation, reviewing design samples with the Principals and vendors, or creating a spreadsheet to help compare final options. That same afternoon could be spent organizing family travel, managing household purchases and returns, coordinating appointments, paying invoices, preparing for guests, or helping ensure every detail is in place for the week ahead.

The principals are looking for someone who is proactive, resourceful, and exceptionally organized, someone who naturally anticipates needs, exercises sound judgment, and enjoys solving problems before they become problems. They appreciate a true self-starter who is equally comfortable managing detailed administrative work, overseeing household operations, coordinating multiple vendors and projects, or rolling up their sleeves to handle whatever is needed that day.

They are seeking the person who helps connect all of the moving pieces in their life and home, ensuring nothing falls through the cracks and priorities continue moving forward. The family is warm, approachable, and very hands-on. They are looking for someone who will fit naturally into that environment - professional yet personable, positive, adaptable, and genuinely enjoys supporting a busy family. While this is not a full-time childcare role, there will be opportunities to lend a hand with the children, making comfort around family life an important part of the role.

This position is best suited for someone who thrives on variety, enjoys taking ownership, and finds satisfaction in creating thoughtful solutions, anticipating needs, and helping a busy household operate at its very best! 

Who You Are

You're someone who naturally takes ownership. You don't wait to be asked - you anticipate needs, solve problems, and take pride in following through. You're energized by variety and enjoy finding thoughtful solutions, whether you're coordinating a complex project or handling the smallest detail.

You exercise exceptional judgment, communicate with confidence and professionalism, and know how to navigate changing priorities with discretion and grace. You're equally comfortable working independently or collaborating with principals, household staff, vendors, designers, and trusted advisors.

You thrive in environments where no two days look the same and genuinely enjoy being the person others can count on. Most importantly, you understand that exceptional support isn't just about handling the big projects - it's about consistently getting the little things right, too.

Qualifications

• 7+ years supporting executives, principals, families, or private households in a high-touch environment.

• Previous experience as an Executive Assistant, Personal Assistant, Private Assistant, Household Manager, Estate Manager, or similar role.

• Exceptional organizational and project management skills with the ability to juggle multiple priorities simultaneously.

• Outstanding judgment, critical thinking, and problem-solving abilities.

• Strong financial and administrative aptitude, including comfort managing invoices, payments, spreadsheets, and household records.

• Tech savvy and highly proficient with Google Workspace, Microsoft Office, Apple products, and modern productivity tools.

• Excellent written and verbal communication skills.

• Professional, polished, discreet, and highly trustworthy.

• Comfortable working in a family home while maintaining the professionalism of an executive office.

• Valid driver's license with a clean driving record.

• Willingness to travel occasionally.

• Outstanding professional references and the ability to successfully pass comprehensive background screenings.

• Exceptionally proactive/resourceful, highly organized with remarkable attention to detail

• Positive, energetic, and solutions-oriented, calm under pressure

• Humble and willing to tackle tasks of every size, service-minded without ego

• Naturally accountable with outstanding follow-through

• Emotionally intelligent with excellent judgment

• Professional, polished, and discreet

If you are someone who thrives behind the scenes, enjoys bringing calm to busy lives, and takes genuine pride in making everything run seamlessly, we would love to hear from you.

Private Family Estate | Miami, Florida

Location: Miami, FL, with domestic travel to additional properties
Compensation: Approximately $150,000 annually, commensurate with experience
Schedule: Full-time, with flexibility based on household needs
Experience: Minimum 8 years in a comparable private household role

The Opportunity

We are seeking an experienced, polished, and exceptionally resourceful Houseman / Household Operations Specialist to support a private family based in Miami, Florida, with additional residences throughout the United States.

This is a highly hands-on, service-oriented position for someone who enjoys being in motion, solving problems, and making things happen. The ideal candidate brings the attentiveness and versatility to the table. This is a dynamic, roll-up-your-sleeves role for a capable professional who can move seamlessly between household support, errands, property projects, transportation, and whatever else the day may require.

One moment, you might be coordinating a delivery or resolving a minor household issue. The next, you could be helping prepare a residence for guests, transporting a principal, overseeing a small project, carrying heavy boxes, assisting the Chef in the kitchen or traveling to another property to ensure something gets done.

The right person will be comfortable operating in sophisticated private homes while remaining approachable, practical, discreet, and entirely unpretentious. No task should feel beneath them, and no reasonable challenge should feel outside their willingness to tackle.

Key Responsibilities

Hands-On Household & Property Support

• Provide daily, practical support to ensure the smooth operation and presentation of the family's primary Miami residence.

• Perform light household fixes and adjustments, such as tightening hardware, repairing a loose doorknob, assembling items, replacing basic fixtures, and addressing minor issues within one's capabilities. Troubleshooting around technical issues (Lutron, Apple TVs, etc.) required. 

• Assist with moving furniture, lifting and carrying deliveries, organizing storage areas, preparing spaces, and other physically active household tasks.

• Receive, inspect, unpack, and distribute deliveries, furnishings, equipment, and household purchases.

• Identify household needs proactively and take appropriate action without requiring extensive direction.

• Coordinate with outside tradespeople and vendors when a project requires licensed or specialized expertise.

Errands, Transportation & Personal Support

• Handle a wide variety of errands, purchases, pickups, returns, deliveries, and time-sensitive requests.

• Provide occasional transportation for principals or family members, as needed.

• Assist with luggage, vehicles, household equipment, and preparations for family travel.

• Support the family's changing daily priorities with a positive, solutions-oriented attitude.

• Anticipate practical needs and provide responsive assistance without creating unnecessary complexity or additional work for the family.

Projects & Multiple Properties

• Travel periodically to the family's additional residences to assist with household projects, installations, property preparations, deliveries, and other operational needs.

• Act as a trusted on-the-ground resource to ensure tasks and projects are completed properly and efficiently.

• Coordinate with contractors, vendors, and other household professionals when necessary.

• Assist with property openings, seasonal preparations, arrivals, departures, and special projects.

• Follow through on assignments from beginning to end, communicating progress and escalating concerns appropriately.

• Support construction, renovation, marine, or boating-related projects where relevant experience allows.

Family & Lifestyle Support

• Work comfortably within an active household with young children and evolving schedules.

• Understand that family priorities can shift quickly and respond with patience, adaptability, and good judgment.

• Maintain a professional but warm, approachable presence around principals, children, guests, and household staff.

• Respect the family's privacy, routines, preferences, and personal boundaries.

• Collaborate effectively with other household employees and external service providers without requiring a formal leadership role.

Qualifications & Experience

Required

• Minimum 8 years of relevant professional experience in a comparable hands-on private household, houseman, household operations, or hybrid personal/property support role.

• Previous experience working in sophisticated private residences with high standards of service, discretion, and presentation.

• Demonstrated employment stability, with strong tenure and a consistent history of successful long-term professional relationships.

• Exceptional resourcefulness, practical problem-solving skills, and a demonstrated ability to get things done independently.

• Comfort performing physically active work, including lifting, carrying, moving household items, and assisting with practical projects, with or without reasonable accommodation.

• Strong working knowledge of household operations, maintenance fundamentals, and when to engage qualified professionals.

• Excellent professional presentation, interpersonal skills, and communication.

• Valid driver's license and a driving record suitable for assigned transportation responsibilities.

• Ability and willingness to travel domestically, sometimes with changing timelines.

• Flexibility to accommodate evolving household schedules and occasional needs outside standard business hours.

• Ability to provide strong professional references and successfully complete applicable pre-employment screening.

This is an active, hands-on position requiring the ability to perform a variety of physical and practical household tasks, with or without reasonable accommodation. Essential responsibilities include:

• Lifting, carrying, pushing, pulling, and moving household items weighing up to or above 50 pounds.

• Walking, standing, bending, reaching, and navigating stairs throughout the workday.

• Climbing and working from step stools or ladders when necessary to complete routine household tasks safely.

• Loading and unloading vehicles, handling luggage, moving deliveries, and assisting with household furnishings and equipment.

• Operating a motor vehicle safely and maintaining a valid driver's license for assigned driving responsibilities.

• Traveling domestically by commercial aircraft, including to additional family residences, as required.

• Performing hands-on household projects and adapting to varying physical demands throughout the day.

Highly Preferred

• Experience working directly for a high-net-worth or ultra-high-net-worth family.

• Experience supporting multiple private residences.

• Familiarity with residential construction, renovation projects, or contractor coordination.

• Experience with recreational boats, yacht operations, marina logistics, or marine maintenance coordination.

• A background combining personal assistance, houseman duties, and hands-on property support.

• Previous experience working in a household with young children.

The Ideal Candidate

We are particularly interested in someone who possesses the following qualities:

• A natural doer: Someone who sees what needs to happen and takes ownership of making it happen.

• Agile and adaptable: Comfortable when the day's priorities change, sometimes several times.

• Hands-on and practical: Enjoys physical work, problem-solving, and being actively involved rather than sitting behind a desk.

• Polished but approachable: Understands the expectations of a sophisticated private household without being overly formal, rigid, or self-important.

• Resourceful: Can independently determine the next step, find a solution, or identify the right professional to handle an issue.

• Discreet and trustworthy: Respects confidentiality, personal boundaries, and the sensitive nature of private family life.

• Family-friendly: Enjoys working in an active environment with young children and understands that family needs come first.

• Reliable and committed: Takes pride in building long-term relationships and being someone the family can consistently depend upon.

• Low ego, high capability: Equally comfortable handling an important project and taking care of a simple errand.

Compensation & Employment Details

The anticipated base salary is approximately $150,000 annually, with flexibility depending on the candidate's experience, qualifications, and overall fit. This is a full-time position based primarily in Miami, Florida, with domestic travel to additional family properties as needed. The schedule requires flexibility and will be discussed in greater detail during the interview process.

Final compensation structure, benefits, and applicable overtime eligibility will be determined in accordance with the position's duties and applicable law.

Background Screening & References

Due to the private, sensitive, and high-trust nature of this position, candidates must be willing to undergo a comprehensive, legally compliant pre-employment screening process. This may include criminal history, employment and education verification, driving record review, financial background screening, and thorough professional reference checks, as applicable to the position and permitted by law.

Financial background screening may include a review of credit history and relevant public financial records, conducted with the candidate's written authorization and in accordance with applicable law. This screening is particularly relevant because the position may involve access to confidential financial information, household cash, credit cards, bank accounts, purchasing authority, and responsibility for handling or overseeing financial transactions on behalf of the family. The purpose is to assess job-related financial responsibility and potential risks associated with the stewardship of private household assets.

Any employment offer will be contingent upon satisfactory completion of the applicable screening process and verification of professional references. All findings will be evaluated individually, consistently, and in accordance with applicable federal, Florida, and local laws. Neither a criminal record nor adverse credit history will automatically disqualify an applicant.

Candidates who are unwilling to participate in the required background screening process, including financial screening, or who cannot provide verifiable professional references should not apply.

Equal Opportunity

The employer is committed to fair and equitable consideration of qualified candidates. Hiring decisions will be made based on relevant experience, qualifications, professional suitability, and applicable legal requirements.

Not every exceptional opportunity has a job posting.

Our clients regularly come to us looking for experienced, part-time Executive Assistants to step in and provide high-level support. These opportunities arise throughout the year and vary in scope, hours, industry - but are always meant to be long-term.

Rather than posting each opportunity individually, we maintain a carefully curated network of outstanding independent contractors we know and trust. When the right engagement comes along, this is the first group we call.

Executive Assistants who have a proven history of supporting senior executives, founders, entrepreneurs, family offices, or private principals with professionalism, discretion, and exceptional attention to detail.

Our clients typically need support with:

• Complex calendar and inbox management

• Domestic and international travel coordination

• Project management and special initiatives

• Research and vendor management

• Meeting preparation and follow-up

• Personal and business administrative support

• Keeping busy executives organized and operating at their best

Every client is different, so flexibility and adaptability are essential.

Ideal Qualifications

• 5+ years supporting senior executives, founders, or principals

• Exceptional organizational, communication, and follow-through skills

• Excellent judgment and the ability to anticipate needs before they arise

• Highly proficient with Google Workspace, Microsoft Office, Zoom, Slack, and modern productivity tools

• Comfortable working independently with minimal oversight

• Professional, polished, resourceful, and calm under pressure

Contractor Requirements/Preferences

• You are self-employed and actively working as an independent contractor or freelancer.

• You have availability to take on part-time client engagements during normal business hours (Monday-Friday).

• You are not seeking a traditional full-time employee position through this posting.

• You are not subcontracting through another company or staffing firm. You do not run your own support firm or agency.

• If you reside in a state with independent contractor regulations (such as California), you must operate as your own sole proprietorship or LLC. Pennyworth Projects is not an employer of record or staffing agency.

Every engagement is unique.

Typical opportunities may range from 10-30 hours per week. Some clients require occasional travel, while many are fully remote.

We'll reach out when an opportunity aligns with your experience, availability, and preferences.

If you're interested in joining our preferred contractor network, we'd love to hear from you.

We're constantly seeking talented candidates for our clients across various industries. If you’re interested in being considered for future roles, please upload your resume and contact information in the button below. We'll keep your details on file and reach out when a suitable opportunity arises.