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.

Location: Los Angeles, CA
Schedule: Full-Time | In-Person [Some flexibility]
Reports To: Top C-suite Executives 

Compensation: $125-150K DOE

About the Company

Our client is an exciting, growing consumer brand that has cultivated something special: a loyal and engaged community, a strong digital presence, and a business built around meaningful connections with its customers. With an entrepreneurial spirit at its core, the company has carved out a distinctive place in its market by combining creativity, thoughtful strategy, and a genuine commitment to doing things well.

This is a business with both momentum and ambition. Operating across multiple channels, the organization blends the energy and ingenuity of a modern consumer brand with the sophistication and discipline needed to build something enduring. There is a strong sense of purpose behind the work, an appreciation for fresh ideas, and an eagerness to continue evolving, innovating, and exploring what comes next.

Equally compelling is the culture. The team is collaborative, driven, and invested in one another's success. Initiative is welcomed, good ideas are valued, and individuals have the opportunity to make a visible impact. It's an environment where people are encouraged to think beyond their immediate responsibilities, take ownership, and contribute to the bigger picture.

For someone who loves the energy of an entrepreneurial business but also appreciates the substance of an established and successful organization, this is a particularly appealing opportunity. You'll have the chance to work closely with senior leadership, gain exposure to different facets of the business, and become an important part of a company with an exciting future ahead.

The Opportunity

Our client is looking for an exceptional Executive Assistant to become a trusted right hand to its C-suite leadership team, playing a central role in keeping a dynamic, growing business running seamlessly. This is an exciting opportunity for a polished, proactive, and highly capable professional who thrives at the intersection of executive partnership, strategic coordination, and operational excellence.

Far beyond traditional administrative support, this position calls for someone who can see the bigger picture while expertly managing the many moving pieces behind the scenes. From navigating complex calendars and coordinating travel to managing communications and ensuring executives are prepared for what's ahead, you'll be instrumental in creating the structure, efficiency, and breathing room that allow senior leadership to operate at their best.

The ideal candidate is someone who instinctively stays several steps ahead. You have exceptional judgment, a natural ability to prioritize, and the confidence to take ownership without needing constant direction. You know when to step in, when to make a decision, and when to bring something to an executive's attention. You are resourceful, solutions-oriented, and take pride in being the person others can count on to make things happen.

Adding another exciting dimension to the opportunity, this role also includes leadership and mentorship of at least one fellow Executive Assistant, along with involvement in executive meetings, cross-functional initiatives, special projects, and opportunities to refine and elevate administrative operations across the organization.

This is a wonderful fit for someone who loves being in the center of the action, enjoys building meaningful relationships with senior leaders, and finds satisfaction in making a tangible impact. You'll have the opportunity to become an invaluable partner to the executive team, help shape how leadership is supported, and grow alongside a business with tremendous energy and opportunity ahead.

Key Responsibilities

Executive Support and Calendar Management

• Manage complex executive calendars, balancing competing priorities and ensuring time is allocated effectively.

• Coordinate domestic and international travel, including flights, accommodations, ground transportation, and detailed itineraries.

• Monitor incoming communications, prioritize requests, and draft correspondence on behalf of executives as needed.

• Prepare executives for meetings with relevant background information, research, agendas, and supporting materials.

• Anticipate scheduling conflicts and logistical challenges, resolving issues proactively and with minimal disruption.

• Handle confidential information and sensitive matters with sound judgment and discretion.

Leadership Coordination and Operations

• Serve as a key point of contact between executive leadership and internal and external stakeholders.

• Coordinate leadership meetings, board meetings, offsites, and company events, ensuring logistics and follow-up are handled thoroughly.

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

• Track important priorities, outstanding action items, and deadlines to help ensure commitments stay on course.

• Oversee executive office budgets, expenses, and expense reporting.

• Represent executive leadership in meetings or other interactions when appropriate.

• Build productive working relationships across the organization and facilitate clear communication between teams.

• Maintain familiarity with internal systems and tools to support efficient day-to-day operations.

Team Management and Development

• Manage and mentor at least one executive assistant, providing guidance and support to ensure consistent, high-quality work.

• Establish performance expectations, conduct evaluations, and support ongoing professional development.

• Delegate responsibilities effectively and balance workloads across administrative support functions.

• Set clear expectations for the administrative team and encourage a collaborative, professional working environment.

Projects and Process Improvement

• Coordinate special projects and cross-functional initiatives on behalf of executive leadership.

• Identify opportunities to improve administrative workflows, internal processes, and executive support systems.

• Develop and maintain practical procedures that improve organization, efficiency, and consistency.

• Support strategic and operational initiatives by coordinating information, following up with stakeholders, and keeping projects moving forward.

• Prepare analyses and supporting materials to help leadership evaluate priorities and make informed decisions.

• Look for ways to strengthen the effectiveness of the executive office as the business continues to evolve.

Qualifications

• 10+ years of experience supporting C-suite executives or senior leadership, ideally within an entrepreneurial, consumer-focused, or high-growth organization.

• Experience managing executive priorities and providing support during periods of business growth or organizational change.

• At least 3 years of people management experience, including coaching, delegation, and performance management.

• Bachelor’s degree or equivalent professional experience.

• Advanced proficiency in Google Workspace and experience working with project management and collaboration tools.

• Excellent written and verbal communication skills, with strong attention to detail.

• Exceptional organizational skills and the ability to manage multiple competing priorities while maintaining accuracy and meeting deadlines.

• Strong judgment, initiative, and problem-solving skills, with the confidence to make decisions independently when appropriate.

• A high level of discretion and professionalism when handling confidential information.

• Strong business acumen and an understanding of how executive support contributes to broader organizational goals.

• Experience supporting senior leadership in a consumer-focused, digitally driven, or multichannel business is preferred.

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.

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.

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.

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.