Careers

Role: Personal Assistant
Location: Brooklyn, New York | Hybrid | Full-Time
In-Person: Approximately 2–3 days per week onsite, with flexibility based on the principals’ schedules, household needs, projects, and events

Compensation: $125K+ [Competitive and commensurate with experience]

The Opportunity

We are looking for an exceptional Personal Assistant to support a young, successful, hardworking couple based in Brooklyn. This is a wonderful opportunity for someone who genuinely loves the art of making life run well,  the person who notices what needs attention before anyone has to ask, can take a loose idea and turn it into a thoughtful plan, and finds real satisfaction in creating order, ease, and a little bit of magic behind the scenes. The scope is wonderfully varied. One day, you may be finalizing a weekend itinerary, coordinating contractors for a home renovation, and making sure the refrigerator is stocked before your principals return from a trip. Another day, you could be arranging a vet appointment, overseeing something at their Hudson Valley property, researching the perfect hotel, or helping bring their annual Halloween party to life!

There are big things and little things here - and both matter.

The right person has meaningful experience working inside a private home and understands the particular trust that comes with being welcomed into someone’s personal life. You know how to be present without being intrusive, warm without being overly familiar, and proactive without overstepping. You take ownership naturally, exercise excellent judgment, and make things better simply because you are paying attention.

Most importantly, this couple is looking for someone who wants to build something long-term with them: a trusted person who will learn their preferences, anticipate their needs, and become an invaluable part of how their lives operate.

The Role

At its heart, this role is about making life easier, more organized, and more enjoyable. You’ll become the go-to person for the moving pieces of the principals’ personal lives and homes - managing everything from travel and properties to appointments, vendors, events, household needs, and the countless details that otherwise take up real time and mental space.

Responsibilities will include:

• Personal & Lifestyle Support: Manage personal calendars, appointments, reservations, reminders, errands, gifting, research, purchases, returns, and the many miscellaneous requests that naturally come with a busy life.

• Travel Planning: Coordinate thoughtful, seamless personal travel from beginning to end, including flights, accommodations, transportation, reservations, itineraries, and all the details in between.

• Brooklyn Home Management: Help ensure the primary residence is consistently organized, stocked, maintained, and running smoothly. Coordinate household supplies, groceries, deliveries, repairs, service appointments, and ongoing home needs.

• Hudson Valley Property: Support the ongoing management and care of the couple’s Hudson Valley property, coordinating vendors, maintenance, projects, seasonal needs, and visits.

• Bay Area Rental Property: Remotely oversee needs related to a rental property in the Bay Area, serving as a reliable point person for vendors, maintenance, and other property-related matters.

• Renovations & Home Projects: Help manage home improvements and renovations - coordinating contractors and vendors, tracking timelines, sourcing options, scheduling access, following up on open items, and making sure projects continue moving forward.

• Vendors & Household Partners: Build strong relationships with dog walkers, veterinarians, cleaners, contractors, landscapers, repair professionals, delivery services, and other outside partners. Make sure the right people show up, the work gets done, and nothing quietly falls through the cracks.

• Entertaining & Events: Help plan dinners, gatherings, celebrations, and events at home - including a beloved annual Halloween party that deserves its own mention! Coordinate vendors, rentals, food, décor, guest logistics, setup, and all the little details that make hosting feel effortless.

• Proactive Household Planning: Stay ahead of what’s coming. Notice when something is running low, needs servicing, should be scheduled, could be improved, or simply hasn't been handled yet, and take care of it.

• Special Projects: Jump into research, organization, purchases, planning, or one-off projects as life evolves. There will always be something interesting to tackle.

Who You Are

You are an experienced Personal or Family Assistant or private household professional who understands that excellent personal support is equal parts organization, judgment, intuition, discretion, and follow-through. You don't need a detailed instruction manual for every task. If you see something that needs doing, you handle it. If you don't know the answer, you figure it out. If there is a better way to do something, you thoughtfully suggest it.

You are someone who:

• Has meaningful prior experience supporting a private individual, couple, family, or household; experience working within a private residence is required.

• Understands the boundaries, discretion, and sensitivity required when working inside someone's home and personal life.

• Is highly organized and excellent at managing many unrelated moving pieces without losing sight of the details.

• Has experience coordinating household vendors, maintenance, repairs, or residential projects.

• Is comfortable managing properties and projects both in person and remotely.

• Is an excellent planner and can turn “we should go somewhere in February” into thoughtful, beautifully organized options.

• Has strong written and verbal communication skills and represents the principals graciously with vendors, guests, and outside partners.

• Is resourceful and knows how to research, compare, troubleshoot, and get to an answer.

• Has excellent judgment and understands when to act independently, when to present options, and when something warrants a quick check-in.

• Is comfortable with the everyday realities of personal assistance. You are just as willing to coordinate a complicated renovation as you are to make sure the fridge is stocked, a return gets dropped off, or the dog's appointment gets booked.

• Is naturally proactive. You don't wait for someone to notice that something hasn't been done.

• Is warm, grounded, low-ego, and genuinely enjoys being helpful.

• Wants to become deeply trusted over time and is looking for a long-term professional home, not simply the next role.

This is a role for someone who genuinely enjoys being in the know and a few steps ahead — keeping track of what’s happening now, what’s coming next, and the little things that need attention before they become big things. You’ll be the person who knows when the contractor is arriving, whether everything is set for the weekend, what still needs to be ordered, and yes, whether the Halloween party details are actually buttoned up. The principals are a hardworking couple with successful careers and full lives, and they are looking for someone who can bring a real sense of ease to everything happening outside of work. Someone who takes ownership, learns how they like to live, and over time can anticipate what will make their days run just a little more smoothly.

There is so much opportunity to make this role your own - to create better systems, become the trusted keeper of the details, and grow alongside them for years to come. They are looking for a true long-term partner who will know their homes, their preferences, their rhythms, and what matters to them. If you love being able to say, “Already handled!” — and secretly get a little satisfaction when you thought of it before anyone even had to ask — you’ll probably feel very at home here.

Location: Rancho Santa Fe, California
Schedule: Full-Time | Private Family
Compensation DOE: $100-175K | PTO | Health insurance stipend.

OPEN TO ROTA: (7/7 - LIVE OUT)

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.

Role: Executive Personal Assistant
Location: San Francisco Bay Area, CA
Schedule: Hybrid | Full-Time

The Opportunity

We are partnering with a successful founder to find an exceptional Personal Assistant to provide thoughtful, high-level support across his personal life. This is a newly created role and a chance to build something meaningful from the ground up - developing a deep understanding of how he operates, bringing greater ease and intention to his day-to-day life, and becoming a highly trusted resource over time.

There is real room here to take ownership. He is looking for someone with great instincts, genuine warmth, sound judgment, and the confidence to operate independently. Someone who sees what needs to happen, thinks a few steps ahead, and takes pride in creating an incredible level of support without needing a roadmap.

The scope will be broad and will naturally evolve over time, spanning homes, health and wellness, travel, social life, family coordination, and a variety of personal projects. For someone who has intentionally built a career in personal support and enjoys becoming a true right hand to one person, this is an opportunity to build a trusted, long-term partnership and have a meaningful impact on his day-to-day life.

What You'll Do

You will serve as a trusted resource across the principal’s personal life, taking ownership of needs large and small, anticipating what may be coming next, and creating the infrastructure that allows an increasingly busy life to run smoothly.

• Oversee personal scheduling and logistics, coordinating appointments, activities, reservations, events, commitments, and the many details surrounding them.

• Plan and coordinate personal travel, from frequent domestic trips to more complex vacations, private travel, and experiences with friends and family, managing transportation, accommodations, itineraries, reservations, and special requests. 

• Support the principal’s health and wellness priorities, proactively coordinating physicians, preventative care, physical therapy, fitness and wellness professionals, athletic activities, and related appointments and logistics.

• Help manage current and future residences, coordinating household needs, vendors, service providers, maintenance, household staffing, furnishings, installations, and ongoing operations.

• Support new home purchases, moves, and household projects from initial research and planning through vendor coordination, setup, and completion. The principal currently has needs across San Francisco and the South Bay, with the possibility of additional residences over time.

• Ensure homes are thoughtfully maintained and well supplied, anticipating household and personal needs and handling purchasing, deliveries, replenishment, and other day-to-day details without requiring extensive direction.

• Partner with staffing agencies as needed to research, vet, hire, and coordinate exceptional personal and household resources, including chefs, security providers, wellness professionals, coaches, drivers, household staff, and other specialists as needs evolve.

• Proactively support the Principal's social and personal life, creating opportunities and ideas rather than simply responding to requests. Establish regular planning cadences to stay ahead of upcoming weekends, events, travel, and priorities, and coordinate everything from dinners and reservations to hosted gatherings, outings, sporting activities, and memorable trips or experiences with friends and family.

• Own thoughtful, highly personalized gifting and personal purchasing, thinking ahead to important dates, milestones, celebrations, and opportunities to make something special. Keep an ear to the ground for the preferences, interests, likes, and dislikes of the people important to the principal; maintain visibility into upcoming occasions; and proactively source, personalize, procure, and coordinate gifts and gestures that feel considered rather than last-minute.

• Support personal interests and pursuits, researching and coordinating lessons, memberships, equipment, activities, and other resources that make it easier for the principal to invest time in the things he enjoys.

• Provide thoughtful coordination around the principal’s partner and immediate family where their needs naturally intersect with his, including travel, logistics, household matters, and occasional projects, while helping establish outside resources or dedicated support where broader ongoing assistance is needed.

• Coordinate closely with the principal’s Executive Assistant when personal commitments intersect with the workday, travel, or professional calendar.

• Take ownership of special projects that may sit outside traditional Personal Assistant responsibilities, bringing structure to something unfamiliar, identifying the right people and resources, and driving it from idea through completion.

• Build simple systems and processes that make recurring personal needs easier, more organized, and increasingly proactive over time.

• Above all, notice what needs attention and take care of it. Think ahead, anticipate what may be coming, and be agile enough to shift as priorities change. The scope of the role will continue to evolve and grow over time, and the right person will be energized by that evolution - quickly learning new areas, taking on greater ownership, and continually finding new ways to provide exceptional support as needs, priorities, and opportunities emerge.

Who You Are

You are an experienced Personal or Executive Assistant who loves this work. You genuinely enjoy creating order, solving problems, managing logistics, and being the trusted person who makes things happen behind the scenes.

You have significant agency and are comfortable operating without a detailed roadmap. You ask smart questions when you need to, but you don't need constant direction or approval to move something forward. If you're asked to find a great chef, coordinate a home project, solve a travel issue, or figure out how to get something done, your instinct is to research, assess, execute, and close the loop. You are equally comfortable managing a meaningful household project and stocking a refrigerator. There is no task that feels too big or too small. You understand that exceptional personal support can mean coordinating an interior designer one hour and picking up dry cleaning the next, and you approach both with the same level of care.

Personally, you are warm, approachable, calm, polished, and incredibly discreet. You are not easily rattled, you don't create unnecessary urgency or drama, and you know how to read a room. You understand the level of confidentiality that comes with working inside someone's personal life and private home and treat that access with tremendous care.

Most importantly, you are adaptable. You understand that personal support isn't perfectly predictable. Some weeks will be busy and highly in-person; others will offer considerably more breathing room. You are comfortable going with the flow, leaning in when things are demanding, and appreciating the flexibility when they are not.

What We're Looking For

• 6+ years of overall executive, personal, family office, household, or similarly high-touch support experience.

• At least 2+ years of dedicated Personal Assistant (or similar) experience supporting an executive, founder, principal, private family, or similar individual.

• Demonstrated experience managing personal logistics and private household needs - not solely corporate executive support.

• Experience coordinating vendors, household service providers, personal travel, appointments, reservations, errands, and projects.

• Strong understanding of the discretion and judgment required when supporting private individuals and working within personal residences.

• Exceptional organizational skills with the ability to manage details across three principals without losing sight of priorities.

• Highly self-directed, resourceful, and comfortable making judgment calls independently.

• Exceptionally tech-savvy and able to quickly learn and leverage new tools, platforms, and systems.

• Excellent written and verbal communication skills.

• Strong research skills and an ability to quickly identify, vet, and recommend high-quality options.

• Willingness and ability to regularly work in person throughout San Francisco and travel to Palo Alto as needed. Valid driver's license and reliable transportation.

• Flexibility to occasionally accommodate travel, changing schedules, and needs across time zones.

Schedule + Location

This is a full-time, hybrid role based in the San Francisco Bay Area. General working hours will be approximately 9:00 AM–6:00 PM, with an understanding that personal support requires flexibility rather than a rigid clock. The principal travels regularly, including frequent time in New York, so there will occasionally be needs outside of standard Pacific Time business hours. Responsiveness, flexibility, and good judgment around what is truly time-sensitive are important. The role will be a thoughtful mix of in-person and remote support, with in-person time primarily centered around the principal’s San Francisco residence and, over time, a home in the Palo Alto area. Rather than following a prescribed weekly schedule, the balance will flex naturally based on travel, household activity, appointments, projects, vendors, events, and the priorities of any given week. The ideal candidate lives within a reasonable commute of San Francisco and is comfortable moving between San Francisco and the South Bay as needed.

The Right Fit

This role is best suited for someone who finds real satisfaction in making complicated lives feel simple. You anticipate, organize, research, troubleshoot, and execute. You know when to ask, when to act, and when to simply handle something without creating another decision for the person you're supporting.

This is a hands-on, physically active role, and candidates must be able to perform its essential functions, with or without reasonable accommodation. This includes regularly walking and moving throughout residences and around the city; standing for extended periods, including more than an hour at a time; walking longer distances while completing errands; frequently climbing stairs, bending, reaching, and carrying items; and lifting and moving 30+ pounds as needed. The role also requires regular local driving and the ability to safely and confidently navigate, drive, and park in a busy city environment.

For the right person, this is an opportunity to build a trusted, long-term working relationship with a principal who genuinely values exceptional support - taking meaningful ownership of his personal world, thoughtfully interacting and coordinating with his family as needs intersect, and becoming an invaluable resource as his life and priorities continue to evolve.

Compensation & Benefits

• Paid Time Off: Three weeks of PTO annually

• Paid Holidays

• Overtime: This is an hourly, non-exempt position eligible for overtime, double time, and other applicable wage protections in accordance with California law

• Work Tools & Technology: Necessary tools and technology will be provided or reimbursed as appropriate for the role, including a laptop, iPad, and cell phone expenses

• Guaranteed Annual Compensation: $150,000–$200,000, depending on experience. This is an hourly, non-exempt position, with the hourly rate structured to provide guaranteed annual base compensation within this range based on the role’s regular schedule in accordance with California law. 

• Bonus: The position is also eligible for a discretionary annual performance bonus.

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.

Role: Executive Assistant
Schedule: Full-time, on-site; hybrid Fridays.
Compensation: 80-90K DOE. Full benefits.

The Opportunity

Our client, a well-established and highly respected organization is seeking an exceptional Executive Assistant to become a trusted strategic partner supporting 2-3 senior executives. This is far more than a traditional administrative role, it is an opportunity to serve as an integral member of the executive leadership team, ensuring priorities move forward seamlessly while helping leaders remain focused on the organization's long-term vision.

The ideal candidate is highly organized, proactive, discreet, and thrives in a fast-paced environment where priorities shift and no two days look exactly alike. They naturally anticipate needs before they arise, communicate with professionalism and warmth, and enjoy bringing order, efficiency, and calm to complex situations.

This role offers the opportunity to build long-term relationships, work alongside accomplished leadership, and make a meaningful impact across a dynamic organization.

Responsibilities

Executive Partnership

• Serve as a trusted partner providing comprehensive administrative and operational support to two senior executives.

• Manage complex calendars, competing priorities, appointments, and executive commitments while proactively identifying and resolving scheduling conflicts.

• Coordinate domestic travel, itineraries, accommodations, transportation, and related logistics.

• Prepare executives for meetings through thoughtful briefing materials, agendas, reports, and supporting documentation.

• Track action items, deadlines, and follow-up to ensure priorities continue moving forward.

• Screen, prioritize, and coordinate incoming communications while exercising sound judgment and discretion.

• Draft, edit, and proofread executive correspondence, presentations, reports, and other high-level business communications.

• Prepare polished presentation materials for executive leadership, board meetings, and organizational initiatives.

• Review documents for accuracy, consistency, and professionalism.

• Serve as a liaison between executive leadership and internal and external stakeholders while maintaining excellent communication and responsiveness.

• Coordinate executive meetings, leadership sessions, strategic planning meetings, and company events.

• Prepare agendas, meeting materials, minutes, and follow-up action items.

• Manage meeting logistics including conference rooms, technology, catering, guest accommodations, and executive hospitality.

• Coordinate executive participation in community, industry, and organizational events.

• Support strategic initiatives through research, project coordination, data gathering, and administrative execution.

• Monitor project timelines, organizational priorities, and executive initiatives to help ensure successful completion.

• Assist with improving processes and systems that increase executive effectiveness and organizational efficiency.

• Manage special projects from planning through execution while balancing multiple competing priorities.

• Serve as a key point of contact for executive leadership across the organization.

• Build positive working relationships with leadership, board members, colleagues, vendors, business partners, and external stakeholders.

• Foster collaboration by ensuring timely communication and seamless coordination across departments.

• Represent leadership with professionalism, responsiveness, and exceptional service.

• Handle highly confidential business, financial, personnel, and organizational information with absolute discretion.

• Maintain the highest standards of confidentiality, professionalism, and integrity.

• Support additional administrative initiatives and projects as organizational priorities evolve.

Qualifications

The ideal candidate will bring:

• 5+ years supporting senior executives in an Executive Assistant or comparable strategic administrative role.

• Experience managing multiple executives, complex calendars, travel, and competing priorities.

• Outstanding organizational skills with exceptional attention to detail.

• Excellent written and verbal communication skills.

• Strong judgment, professionalism, and emotional intelligence.

• Proven ability to maintain confidentiality while handling sensitive information.

• A proactive, solutions-oriented mindset with the ability to anticipate needs before they arise.

• Flexibility and adaptability in a fast-paced environment with changing priorities.

• Strong proficiency with Microsoft Office, Outlook, virtual meeting platforms, and modern productivity tools.

• Valid driver's license with the ability to travel locally as needed.

Who You Are 

You are someone who genuinely loves making exceptional leaders even more successful. You thrive behind the scenes, finding fulfillment in creating order from complexity and ensuring that people, projects, and priorities move forward seamlessly. You are energized by being challenged and excited by the opportunity to continually grow alongside accomplished leaders and a high-performing team. You don't shy away from new responsibilities - in fact, you actively seek them. Whether you're coordinating a board meeting, solving an unexpected problem, or handling a last-minute administrative task, you approach every responsibility with the same level of care, urgency, and professionalism. You understand that the smallest details are often what make the biggest difference.

No task is beneath you, and no challenge feels too big. You have a "whatever it takes" mentality, balanced with excellent judgment and a calm, solutions-oriented approach. You are resourceful, adaptable, and naturally anticipate needs before they're voiced. You build trust easily and work well with people at every level of an organization. Whether interacting with executives, board members, colleagues, vendors, or guests, you are warm, polished, collaborative, and easy to work with. You leave people feeling confident that they're in capable hands.

You're highly tech-savvy and enjoy leveraging technology to improve organization, communication, and efficiency. You embrace new systems, continuously look for better ways to work, and aren't afraid to roll up your sleeves to make things happen.

Above all, you are someone who takes pride in becoming an indispensable partner—a trusted extension of the leadership team whose impact is felt every day, even when you're working quietly behind the scenes! 

Role: Executive Assistant to the Chair
Location: Washington, D.C. Area
Schedule: Full-Time, Monday–Friday; on-site
Travel: Regular domestic and international travel required (10-12 weeks per year)
Compensation: $100-125K/year DOE

The Opportunity

A prominent global sports organization is seeking an exceptional Executive Assistant to support its Chair. This is a high-level partnership for an experienced EA who is energized by complexity, operates with exceptional judgment and discretion, and naturally thinks several steps ahead.

The Chair maintains a fast-moving, highly visible schedule and works across a broad network of senior leaders and stakeholders around the world. The Executive Assistant will serve as a trusted extension of the Chair, ensuring her time, priorities, commitments, and relationships are managed thoughtfully and seamlessly.

This is not a traditional administrative support role. The right person will be a sophisticated operator who can quickly understand the bigger picture, anticipate needs before they arise, navigate competing priorities, and confidently make decisions within their lane. They will be calm under pressure, exceptionally organized, emotionally intelligent, and comfortable working at pace.

The Executive Assistant will be central to ensuring the Chair remains prepared, informed, and focused on the areas where her time and attention are most valuable.

The Role

• Executive Support & Calendar Management

• Own and strategically manage an exceptionally complex, frequently evolving global calendar.

• Serve as a thoughtful gatekeeper of the Chair’s time, balancing competing priorities, relationships, and organizational needs.

• Coordinate sophisticated domestic and international travel, including detailed itineraries, logistics, briefing materials, and contingency planning.

• Ensure the Chair is consistently prepared for meetings, events, speaking engagements, and other commitments.

• Draft correspondence and manage communications with a high degree of polish and discretion.

• Anticipate scheduling conflicts, logistical challenges, and shifting priorities before they become issues.

Executive Partnership

• Exercise excellent judgment around what requires the Chair’s attention and what can be handled independently.

• Develop a deep understanding of the Chair’s priorities, preferences, communication style, and ways of working.

• Act as a trusted extension of the Chair and represent her with professionalism and sound judgment.

• Look several steps ahead, identifying potential issues, dependencies, and opportunities proactively.

• Make thoughtful recommendations related to scheduling, prioritization, stakeholder engagement, and workflow.

• Bring solutions—not simply problems—and take ownership through resolution.

Stakeholder Management

• Serve as a key point of contact for senior internal and external stakeholders.

• Build trusted relationships across a global organization, navigating different markets, cultures, personalities, and time zones.

• Manage sensitive and high-level interactions with diplomacy, warmth, professionalism, and discretion.

• Navigate competing requests thoughtfully while protecting the Chair’s time and priorities.

• Communicate confidently and appropriately with senior executives, board members, partners, and other high-level stakeholders.

Executive Office & Operations

• Create and maintain systems and processes that improve organization, communication, and efficiency.

• Support preparation and logistics for Board meetings, leadership meetings, and major organizational events.

• Identify opportunities to improve how information, priorities, and workflows are managed around the Chair.

• Step into evolving needs with flexibility and a team-first mentality.

The Ideal Candidate

You are a seasoned Executive Assistant with 10+ years of experience supporting senior executives, including at least 2+ years directly supporting the leader of an organization—a CEO, President, Chair, Founder, or equivalent. You understand the pace, judgment, discretion, and level of ownership required to successfully support someone operating at this level.

You are a high-agency person. You see what needs to happen and take ownership of moving it forward. You are naturally proactive, resourceful, and solutions-oriented; you ask good questions, but you do not need to be given a roadmap for every task. You are comfortable making thoughtful decisions independently and know when something requires escalation.

There is also nothing too big or too small for you. You can move seamlessly from coordinating with senior global stakeholders or preparing for a Board meeting to handling a last-minute errand or small detail that simply needs to get done. You are not overly concerned with hierarchy or whose responsibility something technically is - you care about the outcome and about making the Chair and broader Executive Office more effective.

You are calm, grounded, and emotionally mature. You understand that priorities change, days can move quickly, and communication may sometimes be direct. You receive feedback well, adapt quickly, and remain focused on solving the problem rather than getting caught up in the pressure surrounding it.

You are also:

• Exceptionally organized, detail-oriented, and reliable.

• Proactive and anticipatory, naturally thinking several steps ahead.

• Confident and capable without ego.

• Comfortable operating with ambiguity and changing priorities.

• An excellent communicator with strong interpersonal instincts.

• Highly discreet and thoughtful with sensitive information and relationships.

• Someone who closes loops and follows through without needing reminders.

• Warm, polished, and able to build trust quickly across personalities and levels of seniority.

• A collaborative partner who enjoys working closely with a Chief of Staff and broader team.

• Someone who takes genuine pride in doing excellent work and making the people around them more effective.

Benefits & Perks

The organization offers a comprehensive benefits package for full-time employees, including:

• Medical, dental, and 100% employer-paid vision insurance

• Employer contribution to a Health Savings Account (HSA) for eligible medical plans

• Traditional and Roth 401(k) options with employer match up to 3%

• Generous paid time off, beginning at 15 days annually and increasing with tenure

• 18 paid holidays, including an end-of-year holiday shutdown and a paid day off for your birthday

• Generous paid parental leave

• Employer-paid long-term disability insurance

• Short-term disability and additional voluntary benefit options

• Medical and dependent care Flexible Spending Accounts (FSA)

• Comp days for qualifying business travel and weekend work

• Benefits eligibility beginning the first of the month following 30 days of employment

Additional Requirements

This position requires the ability to perform the essential functions of the role, with or without reasonable accommodation, including working at a computer for extended periods and occasionally standing, walking, bending, and lifting up to 50 pounds. The role may require domestic and international travel and flexibility outside of standard business hours as business needs arise. Candidates must be legally authorized to work in the United States and able to travel domestically and internationally as required. Reasonable accommodations will be provided in accordance with applicable law.

Location: Bel Air, California
Employment Type: Full-Time, On-Site
Compensation: Competitive salary with performance-based bonuses and a comprehensive benefits package - DOE [$200-300K]
Travel: Occasional travel to secondary properties as required​

The Opportunity

We are seeking an accomplished and discreet Director of Estates/Estate Manager to oversee the operations of a luxurious 10+ acre estate in Bel Air, California, and manage secondary properties and manicured grounds on site. The ideal candidate will possess extensive experience in managing high-end properties and staff for UHNW individuals, ensuring the highest standards of service, maintenance, and confidentiality.​

Key Responsibilities

Estate Operations Management

• Oversee day-to-day operations of the estate and residences, ensuring seamless functionality and presentation at all times.

• Implement existing Standard Operating Procedures (SOPs) and comprehensive House Manuals for each property.

• Demonstrate a strong understanding of how complex residential systems function—including HVAC, electrical, plumbing, water, sewage, pool, and technical systems—with the ability to diagnose issues, determine appropriate next steps, and engage trusted vendors from a well-established network of tradespeople.

• Coordinate and supervise maintenance schedules, renovations, and special projects with interior designers and vendors, ensuring minimal disruption to the principals.

• Manage household inventories, including art collections, wine cellars, and luxury vehicles, maintaining detailed records.​

• Provide concierge services for principals related to calendar management, scheduling and confirming appointments/reservations, research, and correspondence.

Staff Leadership & Development

• Recruit, train, and manage a diverse team of household staff, including but not limited to chefs, housekeepers, security personnel, and chauffeurs.

• Conduct regular performance evaluations and provide ongoing professional development opportunities.

• Foster a culture of excellence, discretion, and service-mindedness among all staff members.

• Work in conjunction with private flight department/pilots and yacht personnel.

Financial Oversight

• Develop and manage annual budgets for each property, ensuring cost-effective operations without compromising quality.

• Oversee all financial transactions, including payroll, vendor payments, and expense reporting, with meticulous attention to detail.

• Negotiate contracts with service providers and vendors, ensuring favorable terms and high-quality service delivery.​

Event Planning & Execution

• Plan and execute private events and gatherings, coordinating all aspects from concept to completion.

• Liaise with event planners, caterers, and other vendors to ensure events meet the principals' expectations and standards.​

Security & Confidentiality

• Implement and maintain advanced security protocols to ensure the safety and privacy of the principals and properties.

• Coordinate with onsite security team, third-party security vendors and personnel, and local authorities as necessary, maintaining a proactive approach to risk management.

• Uphold the highest levels of confidentiality and discretion in all matters concerning the principals and their assets.​

Qualifications

• Minimum of 10 years of experience in estate management for UHNW individuals or families.

• Proven track record of managing high-value properties and household staff.

• Exceptional organizational, leadership, and communication skills.

• Strong financial acumen with experience in budgeting and expense management.

• In-depth knowledge of luxury property maintenance, fine art, and high-end furnishings.

• Ability to handle sensitive information with the utmost confidentiality.

• Flexibility to travel and adapt to the dynamic needs of UHNW principals.

Role: Senior Executive Assistant
Location: Chicago, IL
Schedule: Full-Time | In-Person
Reports To: Managing Partner
Compensation: $95-130K 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.

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.