Careers

Role: Executive Assistant

Schedule: Full-time, on-site; hybrid some Fridays as business needs allow.

Compensation: Competitive, commensurate with experience

Overview

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! 

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.

Note: Our client is only considering current Miami-area residents for this position. If you do not meet this requirement, please do not apply for this role. We encourage you to submit your resume through our Future Opportunities page to be considered for future openings.

Our client is seeking an exceptional Senior Personal Assistant to support a dynamic family based in Miami. This is a highly trusted, deeply integrated role for someone who thrives in a fast-paced private household environment and genuinely enjoys creating ease behind the scenes.

The Senior Personal Assistant will serve as the primary right hand to the Principals, overseeing the day-to-day coordination of an active household and family life while managing a wide range of personal, operational, and project-based responsibilities. The ideal candidate is proactive, polished, highly organized, emotionally intelligent, discreet, and capable of navigating shifting priorities with calmness and precision.

This is a long-term opportunity for someone who genuinely enjoys private service and takes pride in building thoughtful systems, anticipating needs, and helping a family operate seamlessly.

Key Responsibilities

• Manage complex personal and family calendars, appointments, schedules, and logistics.

• Coordinate errands, household operations, and day-to-day family support.

• Oversee communication and coordination with household staff and vendors, including close partnership with the Estate Manager.

• Support hiring, onboarding, scheduling, and coordination of household staff and service providers.

• Maintain organization, inventory, and operational flow within the residence.

• Source household items, gifts, décor, wardrobe needs, specialty purchases, and personal requests.

• Coordinate gifting, entertaining, events, guest logistics, and hosting support.

• Assist with family travel logistics, itineraries, packing coordination, arrivals, and departures.

• Manage special projects, recurring responsibilities, and evolving family priorities.

• Create systems, trackers, and organizational processes that improve household operations and communication.

• Utilize apps, spreadsheets, and organizational tools to maintain visibility and streamline workflows.

• Anticipate needs, troubleshoot issues proactively, and help create calm, efficiency, and ease for the family.

• Maintain absolute confidentiality, professionalism, discretion, and emotional intelligence at all times.

Qualifications

• Significant experience supporting UHNW individuals, family offices, or private households required.

• Experience working within homes and around families with young children strongly preferred.

• Exceptional organizational, multitasking, and follow-through skills.

• High emotional intelligence, professionalism, discretion, and sound judgment.

• Resourceful, proactive, adaptable, and solutions-oriented.

• Strong communication and coordination skills across multiple stakeholders.

• Tech-savvy and comfortable using systems, apps, and tools to manage operations efficiently.

• Valid driver’s license with a clean driving record and ability to travel domestically as needed.

• Ability to pass background checks, reference checks, and legally permitted pre-employment screenings.

• Ability to routinely lift and move items up to 25 pounds, navigate stairs and multi-level properties, and comfortably perform hands-on household tasks indoors and outdoors.

Who You Are

You are someone who genuinely enjoys creating order, anticipating needs, and making life easier for others. You operate with warmth, professionalism, humility, common sense, and strong critical thinking. You are calm under pressure, highly capable, deeply discreet, and excited by the opportunity to become a trusted long-term partner to a family.

Schedule

Typical schedule is Monday–Friday, generally between 9:00 AM–6:00 PM, with flexibility required based on household needs, travel, events, projects, and operations. Occasional early mornings, evenings, weekends, and holidays may be required.

Travel

Some regular travel between residences may be required, particularly to California.

Compensation & Benefits

• Competitive compensation based on experience

• Health, dental, and vision

• Performance bonus eligibility

• 3 weeks paid time off

• 10 paid holidays annually

Full-Time/Hybrid (Open to part-time if desired):

A warm, active family in Durham, North Carolina, is seeking an experienced Personal Assistant/|Household Manager to oversee household operations, personal logistics, and day-to-day support. This role combines household management, personal assistant support, and executive lifestyle coordination within a busy family environment. Prior experience supporting private households, executives, families, or similarly high-touch environments is strongly preferred. The ideal candidate demonstrates professionalism, sound judgment, strong organizational skills, and discretion in handling sensitive information. 

This is a long-term opportunity for someone seeking to become a trusted and valued member of a family’s support team.

Responsibilities

• Household Operations

• Manage the day-to-day organization, readiness, and smooth functioning of the home.

• Coordinate vendors, maintenance, repairs, cleaners, landscaping, and recurring home services.

• Track household records, invoices, warranties, appointments, and service schedules.

• Manage packages, deliveries, returns, exchanges, errands, and seasonal household preparation.

• Support organization projects and guest readiness.

Personal & Executive Support

• Manage calendars, scheduling, reminders, appointments, and family logistics.

• Support the executive/principal with daily operational, personal, and lifestyle needs.

• Prepare and pack meals, snacks, beverages, and daily essentials for the executive/principal as needed.

• Coordinate personal and family travel planning, itineraries, reservations, transportation, packing logistics, and trip preparation.

• Manage professional wardrobe needs, including clothing organization, tailoring, dry cleaning, alterations, shopping, sourcing, and wardrobe-related logistics.

• Research options, source purchases, and manage special requests, errands, and projects.

 Family & Event Support

• Assist with family gatherings, celebrations, entertaining, and special events.

• Coordinate birthdays, holidays, gifting, flowers, cards, and milestone occasions.

Project & Systems Management

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

• Manage projects from planning through completion.

• Identify needs, solve problems proactively, and adapt to changing priorities.

Qualifications

• 3-5+ years of experience in personal assistant, executive assistant, family assistant, household management, estate management, hospitality, or comparable high-touch support roles.

• Demonstrated success supporting busy households, executives, families, or complex personal operations.

• Strong organizational, communication, and multitasking abilities.

• Comfortable working in an active household environment with young children and a family dog, including occasional pet-related coordination or support as needed. A full-time nanny is in place; this is not a childcare role, though comfort around children and family life is important.

• Tech-savvy and confident using calendars, spreadsheets, and digital tools.

• Demonstrated professionalism, discretion, confidentiality, and sound judgment in prior roles.

• Service-oriented, proactive, adaptable, dependable, and solutions-focused.

• Valid driver's license and reliable transportation.

Schedule & Compensation

• Full-time, hourly, non-exempt role based in Durham, North Carolina. [Open to part-time if desired by candidate]

• Typical schedule is 30-40 hours per week, generally Monday-Friday, with flexibility for occasional travel preparation, events, entertaining, and evolving household needs.

• Compensation: $30-35/hour DOE.

• Benefits:PTO, paid holiday, overtime eligibility (as applicable), healthcare stipend (as applicable), mileage reimbursement.

• Candidates must successfully pass background checks, reference checks, driving record verification, and legally permitted pre-employment screenings, as applicable.

Note: Our client is only considering current Miami-area residents for this position. If you do not meet this requirement, please do not apply for this role. We encourage you to submit your resume through our Future Opportunities page to be considered for future openings.

Our client is seeking an experienced Estate Manager to oversee the operations, maintenance, staffing, and readiness of their private residences. Based primarily at the family’s Coral Gables home, this role will also support a multi-state property portfolio, including residences in California, Michigan, and Coconut Grove.

This is a high-trust, hands-on leadership role for someone who understands the standards, discretion, and complexity required to manage significant private homes. The Estate Manager will ensure each residence is impeccably maintained, fully operational, properly staffed, and prepared to the Principals’ standards at all times.

The ideal candidate is polished, proactive, detail-oriented, resourceful, and equally comfortable managing vendors, household staff, property systems, preventative maintenance, projects, and hands-on household needs. They bring strong judgment, emotional intelligence, discretion, and a true ownership mentality.

Key Responsibilities

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

• Conduct regular property walks, inspections, and preventative maintenance planning.

• Manage household systems, including HVAC, plumbing, electrical, lighting, AV, security, pools, generators, irrigation, appliances, and smart home technology.

• Maintain household manuals, checklists, vendor lists, service records, inventories, warranties, emergency protocols, and property documentation.

• Oversee household staff, vendors, contractors, tradespeople, and service providers.

• Partner with the Principals and Personal Assistant on staffing, scheduling, onboarding, training, and performance standards.

• Source, vet, negotiate with, and manage vendors, proposals, invoices, budgets, timelines, and quality control.

• Coordinate repairs, installations, inspections, deliveries, preventative maintenance, and capital improvement projects.

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

• Prepare homes for Principal arrivals, guest stays, travel, events, seasonal transitions, and storm/weather-related needs.

• Support household events, dinners, and gatherings, including setup, vendor coordination, staffing, logistics, and post-event reset.

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

Qualifications

• 10+ years of residential, estate, or private household management experience.

• Experience supporting sophisticated private homes, family offices, or UHNW environments.

• Proven ability to manage large residences and/or multiple properties.

• Strong knowledge of residential systems, preventative maintenance, vendors, climate considerations, storm preparation, landscaping, pest control, and seasonal upkeep.

• Experience supervising household staff, vendors, contractors, and service providers.

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

• Excellent communication, organization, judgment, discretion, and problem-solving skills.

• Tech-savvy and comfortable implementing systems for tracking and communication.

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

• Valid driver’s license, clean driving record, and ability to travel domestically as needed.

• Ability to pass background checks, reference checks, and legally permitted pre-employment screenings.

• Ability to lift/move items up to or exceeding 50 pounds, navigate stairs and multi-level properties, and perform hands-on household tasks indoors and outdoors.

Schedule

Typical schedule is Monday–Friday, generally 8:00 AM–5:00 PM, with flexibility required for household needs, travel, events, vendors, projects, and property operations. Occasional early mornings, evenings, weekends, and holidays may be required.

Travel

Regular domestic travel between residences is required, particularly to California, averaging approximately 8–12 trips annually.

Compensation & Benefits

• Competitive compensation based on experience

• Health, dental, and vision

• Performance bonus eligibility

• 3 weeks paid time off

• 10 paid holidays annually

• $175-210K DOE

Our client, a highly respected, digitally-led fashion and lifestyle brand, is seeking a Senior Executive Assistant to serve as a strategic partner to senior leadership. This is a high-trust, high-impact role supporting two top executives in a fast-paced, growth-oriented environment. The ideal candidate brings exceptional judgment, discretion, and a proactive mindset—someone who operates ten steps ahead, elevates executive operations, and thrives in a dynamic, entrepreneurial setting.

In this role, you will oversee complex executive support while driving operational excellence and leading administrative functions across the organization.

Key responsibilities include:

• Managing executive calendars, priorities, communications, and travel (domestic & international)

• Preparing briefing materials, reports, presentations, and supporting strategic decision-making

• Leading and mentoring at least one Executive Assistant; setting goals and developing team performance

• Acting as a liaison across internal and external stakeholders; representing leadership when needed

• Planning board meetings, offsites, and company-wide events; overseeing budgets and expenses

• Driving process improvements, optimizing workflows, and leading special projects

Qualifications:

• 10+ years supporting C-suite executives, ideally in creative or high-growth environments

• Experience supporting leaders through growth, change, or transformation

• 3+ years of people management experience with a track record of building strong teams

• Bachelor’s degree or equivalent experience

• Expert proficiency in Google Workspace and project management tools

• Exceptional communication, attention to detail, and ability to manage multiple priorities

• Strong business acumen, professionalism, and discretion with sensitive information

• Experience in fashion, beauty, entertainment, or similar industries preferred
  
  Salary: $140-150,000 annually (commensurate with experience)
  Schedule: In-office, Monday–Friday.

A highly experienced Family Assistant/Nanny is sought to support a young child within a bi-coastal household based in Los Angeles, with seasonal travel to Upstate New York. This role blends attentive, developmentally focused childcare with hands-on family support, requiring a calm, structured, and adaptable professional who thrives in a high-functioning private home. The ideal candidate is warm, dependable, and intuitive—able to create a nurturing environment while seamlessly adjusting to shifting schedules and travel. Compensation ranges from $100–150K annually (non-exempt), with flexibility required for travel and a minimum of 18 weekends per year (weekday time off provided).

Key Responsibilities & Requirements:

• Provide attentive, full-spectrum care for an infant/toddler, supporting emotional, physical, and developmental needs

• Plan and lead age-appropriate activities (reading, sensory play, outdoor time, creative exploration)

• Manage daily routines including feeding, bottles/meals, sleep schedules, and developmental transitions

• Maintain all child-related organization: laundry, nursery upkeep, supplies, and toy rotation

• Ensure a safe, clean, and nurturing environment at all times

• Communicate proactively with parents on development, schedules, and observations

• Support general family assistant needs with a proactive, hands-on approach

• Maintain discretion and strict confidentiality in all aspects of the role

• CPR certified, TrustLine registered, clean background check, and excellent verifiable references required

• Strong infant/toddler experience and flexibility for travel between LA, NY, and additional destinations

Timezone Requirement: Must be ET or CT.

We’re looking for a part-time, remote Executive Assistant to join as an independent contractor. This role is ideal for a self-employed/freelance Executive Assistant with a proven track record supporting high-level executives with precision, discretion, and grace under pressure.

*NOTE: This role will begin at approximately 15 hours per week, with the expectation of gradually increasing to 30–35 hours over the next 6–10 months. This progression in hours should align with your availability and work goals. The position is scheduled to begin in mid-June. Long-term mindset is ideal

About the Role

You’ll provide seamless support ranging from inbox and calendar management to travel coordination, research, and project management. You must be self-motivated, tech-savvy, and confident in navigating shifting priorities and demanding standards.

Key Qualifications

• 5+ years of experience supporting senior-level executives.

• Exceptional organizational and communication skills.

• Proactive problem-solver with excellent judgment.

• Comfortable with tools like Google Workspace, Zoom, Slack, etc.

• Self-employed and available for as-needed, contract work.

• Must not be fully employed by or subcontracting through another business (freelancers or independent contractors only).

Role Details

• Remote (U.S.-based preferred).

• Contractor position. Part-time; some travel required throughout the year.

• Must be able to work during regular business hours Monday-Friday (that does not conflict or interfere with other commitments such as full-time employment).

• If located within a state that restricts ‘gig’ work (example: California), you must operate as a sole proprietor or as your own LLC. Pennyworth is not a staffing agency or an agency of record.

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.