Careers

We’re seeking a proactive Executive Assistant to support the Chief People Officer and Chief Financial Officer at a dynamic organization. This role requires strong problem-solving skills, attention to detail, and the ability to anticipate needs. If you're a resourceful professional who values efficiency and collaboration, we want to hear from you!

Responsibilities:

• Manage multiple priorities, ensuring timely execution.

• Coordinate meetings, drive projects, and facilitate communication.

• Oversee complex calendars and travel arrangements.

• Prepare and proof documents, presentations, and reports.

• Plan special events and large-scale meetings.

• Handle confidential materials with discretion.

• Anticipate executive needs and propose solutions.

Qualifications:

• 8-10+ years of experience in executive support or project management.

• Bachelor’s degree or equivalent experience.

• Proficiency in Microsoft & Google Suite (Excel, Slides, Docs, etc.).

• Experience with Salesforce, Slack, Adobe Acrobat, DocuSign, Zoom, and Teams is a plus.

• Strong critical thinking, problem-solving, and organizational skills.

• Personable with executive presence and stakeholder management experience.

• Occasional travel required; 2-3 days per week in the NY office.

Benefits:

• Compensation depends on experience: $110-125K.

• Medical, Dental, Vision, Life & Disability Insurance.

• 401k with Employer Match.

• Unlimited PTO & 14 Paid Holidays.

• Paid Parental Leave.

We are seeking a poised, responsive, and solutions-focused Executive Personal Assistant (EPA) to provide high-level support to a dynamic Principal based in Los Angeles. The ideal candidate will serve as an extension of the Principal, enabling seamless personal and professional operations with discretion, care, and precision. This is a unique opportunity for a proactive and thoughtful individual to work alongside a visionary leader in the technology and finance space while managing day-to-day logistics, evolving priorities, and confidential matters across multiple domains.

This position blends both personal and business-adjacent support, best suited for a candidate who thrives in a fast-moving, high-performance environment and takes pride in delivering exceptional service behind the scenes.

Key Responsibilities

Executive & Personal Support

• Manage an ever-evolving calendar across personal and professional domains, ensuring all priorities are aligned and thoughtfully executed

• Act as a trusted liaison and gatekeeper for the Principal, communicating with warmth and professionalism across vendors, advisors, household staff, and key business contacts

• Plan and manage all aspects of complex domestic travel - including flights, accommodations, ground transportation, dining, and activities - while serving as the central point of coordination for seamless execution and real-time adjustments. Flexibility to support travel that may occur on evenings or weekends, with proactive communication and responsiveness, is essential.

• Provide proactive support across daily personal responsibilities, including gifting, reservations, appointments, and personal coordination

• Oversee household and property operations, researching vendors, service appointments, and maintenance schedules

• Support private event planning, philanthropic engagements, and special initiatives with attention to detail, logistics, and hospitality

• Track and manage a wide range of projects, ensuring timely execution and thoughtful follow-through

• Maintain the highest level of discretion, confidentiality, and trust across all matters - personal, financial, and professional

• Communicate promptly and clearly across channels, offering updates, summaries, and thoughtful solutions with minimal direction

• Anticipate needs and remain several steps ahead, offering seamless support and simplifying decisions before issues arise

Required Qualifications

• Highly responsive: ability to quickly address needs, whether through a brief text, call, or a detailed email.

• Trustworthy and discreet: confidentiality and sound judgment are essential.

• Strong communication skills: articulate and professional in both written and verbal interactions.

• Organized and detail-oriented: capable of managing multiple priorities and seeing tasks through to completion.

• Agile and adaptable: comfortable with blurred lines between personal and professional responsibilities, maintaining the same level of dedication to both.

• Service-oriented mindset: enthusiastic about providing high-quality support, with a genuine desire to "make it happen" for the Principal.

• Values-driven and empathetic: strong moral compass; integrity is critical.

• Strong written and verbal communication skills, polished and professional in tone

• Organized, detail-oriented, and capable of juggling multiple priorities and deadlines

• Calm and adaptable under pressure, with a natural ability to bring order to ambiguity

• Technologically fluent and familiar with modern productivity tools and digital communication platforms

• Service-minded, humble, and genuinely motivated to “make life easier” for those they support

• Able to travel and adjust schedule as needed, including weekend availability for time-sensitive matters (especially travel-related). 

• Minimum 8+ years supporting a high-performing executive, entrepreneur, or private individual in a personal/executive assistant capacity.

• Proven track record of discretion, emotional intelligence, and ability to operate gracefully under pressure.

• Excellent written and verbal communication skills, with mastery of modern productivity tools (Google Workspace, Apple/iOS, etc.).

• Meticulous attention to detail, time management, and organizational abilities.

• Comfort with ambiguity and fast-paced environments; thrives on building structure and order

• Driver’s license and the ability to travel domestically on occasion, with valid U.S. work authorization.

• Experience supporting a founder or high-growth entrepreneur, particularly in technology, investing, or high-performance leadership (preferred but not required).

• Prior experience working in a hybrid home-office setting with hands-on involvement (preferred but not required).

This role offers the opportunity to make a meaningful impact in the life of a highly accomplished Principal, enabling both professional focus and personal ease. If you take pride in being the person who makes everything run smoothly, we would be delighted to hear from you.

Compensation: $150k+ (all-in)

We are currently seeking an administrative assistant to support the Asset Manager of a UHNW family. The ideal person for the job will be a proactive problem solver with exceptional communication skills, a meticulous attention to detail, and the ability to liaise effectively among family members, staff, and advisors. They will have previous experience working independently, performing administrative duties on a Mac platform, and providing support to C-level executives. This individual must maintain the strictest of confidences and respect boundaries between employer and employee.

Key Responsibilities

• Provide high-level administrative assistance to the Asset Manager, family members, and household team.

• Manage calendars, correspondence (email, mail), meeting logistics, and document organization.

• Maintain digital and physical filing systems, contact databases, and secure password systems (e.g., 1Password).

• Provide basic IT troubleshooting and tech coordination for the household team and family.

• Process and track shipments, orders, and deliveries across multiple properties and vendors.

• Prepare travel itineraries including flights, hotels, grooming, meals, and ground transportation.

• Generate reports, spreadsheets, and inventories across household categories (office supplies, crystal, silver, etc.).

Lifestyle, Household & Property Management

• Liaise between the family, household staff, vendors, and external advisors to ensure seamless operations.

• Coordinate private and family events, including guest lists, menus, venue logistics, and expenses.

• Oversee residential property maintenance, renovations, compliance, and capital project execution.

• Manage vendor relationships across categories like art, design, real estate, and security.

• Supervise vendor visits: schedule, onboard, track insurance and compliance documents, and summarize outcomes.

• Maintain records such as NDAs, COIs, tax forms, and service agreements.

• Oversee family vehicles: service, registration, acquisition/sales.

• Manage seasonal events and holiday coordination (décor, gifts, wrapping, thank-you notes, tip tracking, etc.).

Finance, Tax & Compliance

• Reconcile household and studio billing statements and credit card accounts weekly.

• Process payments and reimbursements, confirming ACH/wire instructions with vendors.

• Track recurring autopayments and expenses; update or cancel accounts as needed.

• Coordinate with external accountants and advisors on tax documentation and planning.

• Organize submissions related to charitable giving, K-1s, and registrations.

• Track financial activity across personal and family entities.

Project & Operational Oversight

• Support strategic goals across family trusts, entities, and businesses through task tracking and coordination.

• Provide project management support across capital upgrades, renovations, and vendor projects.

• Manage timelines, proposals, invoices, and change orders with general contractors and stakeholders.

• Coordinate household special projects, including onboarding tools and optimization of systems or culture.

Human Resources & Team Coordination

• Assist with HR tasks: interview scheduling, pre-employment paperwork, onboarding/offboarding, and OSHA-compliant form maintenance.

• Track PTO, sick leave, and staff schedules; maintain seasonal travel calendars.

• Serve as a daily point of contact for household staff regarding updates, vendor visits, and project timelines.

Health, Wellness & Security Coordination

• Support administration of family insurance plans and healthcare concierge services.

• Act as a point of contact for emergent and ongoing personal security needs in partnership with outside advisors.

Skills & Qualifications

• Bachelor’s degree required; advanced degree a plus.

• 5–10+ years of experience in family office, private service, operations, or executive support.

• Excellent written and verbal communication skills.

• High emotional intelligence, discretion, and a deep commitment to confidentiality.

• Proven track record in project coordination, financial management, and vendor oversight.

• Strong organizational skills with the ability to multitask, anticipate needs, and solve problems independently.

• Tech-savvy: proficient with Mac OS, Microsoft Office 365, Adobe, CRMs (e.g., Salesforce), Box.com, SharePoint, and common household tools.

Comfortable managing a wide range of responsibilities in a fast-paced and high-touch environment.

Compensation: 80k-100k/year, based on experience.

We’re looking for a warm, organized, and service-oriented Administrative & Events Manager to support the smooth day-to-day functioning of our Chicago office. This individual will be a critical part of the workplace experience—ensuring our space is polished, our people are supported, and our operations run with quiet efficiency.

This is a fantastic opportunity for someone who takes pride in “being the glue”—anticipating needs, keeping things orderly, and making sure the details never slip. You’ll support our internal team across a wide range of administrative functions while also playing a key role in maintaining a thoughtful, professional, and welcoming office environment.

This role reports to the Chief Administrative Officer with direction, collaboration, and mentorship from the Office Manager.

Key Responsibilities:

• Greet visitors and guests with professionalism and warmth; serve as a thoughtful first impression of the firm.

• Assist with scheduling across multiple calendars—setting up internal meetings, managing availability, and proactively resolving conflicts or overlaps.

• Coordinate domestic travel arrangements for team members, including flights, accommodations, ground transportation, and related itineraries; ensure confirmations, preferences, and backup plans are in place.

• Support meeting preparation from start to finish: coordinate room setup, prepare agendas, order catering, and ensure tech is functional and ready.

• Track and reconcile expenses and reimbursements in a timely and accurate manner.

• Provide general administrative support to internal team members: update shared documents, manage light data entry, format materials, file documents, etc.

• Help plan and execute internal events and team moments—ranging from client events, industry events, team lunches and birthday surprises to offsite gatherings and seasonal celebrations. This includes vendor outreach, sourcing venues, coordinating catering, managing RSVPs, and ensuring smooth event execution.

• Assist with onboarding logistics for new employees, including desk setup, welcome materials, technology requests, and access to internal systems.

• Serve as a liaison between cross-office teams for shared initiatives and operational needs.

• Receive, sort, and route mail and deliveries; manage shipping logistics as needed.

• Participate in special projects and provide cross-functional support based on team priorities—bringing a helpful, can-do mindset to whatever comes your way.

You Are:

• Exceptionally organized and detail-oriented, with strong time management and follow-through.

• Warm, personable, and someone who enjoys creating an inviting environment.

• Discreet, professional, and polished—someone who knows when to step in and when to step back.

• Comfortable with a fast-paced, high-standard environment.

• Proactive, reliable, and resourceful—able to figure things out without needing to be asked twice.

• A strong communicator with solid written and verbal skills.

• Tech-savvy and confident navigating tools like Microsoft Office, Zoom, MOXO and SF.

Qualifications:

• 2–4 years of relevant administrative, office operations, or hospitality-forward experience.

• Demonstrated ability to manage competing priorities and handle logistics or coordination across a team.

• Bachelor’s degree preferred.

• Authorized to work in the U.S.

Compensation & Perks:

• Salary range: $80,000+ commensurate with experience

• Health, dental, and vision insurance.

• Paid time off and company holidays.

• 401(k) with company match.

• A kind, collaborative, and mission-driven workplace culture.

• Hybrid work structure (average 80-90% in office per year).

More details coming soon.

We are thrilled to share a full-time opportunity (approximately 45 hours per week) to support a warm, welcoming family of four, including a toddler and a newborn. This role is ideal for a seasoned professional who brings confidence, calm, and care to a busy household with young children.

The ideal candidate will have a minimum of 5 years of full-time, hands-on experience in a similar role, with a strong background in caring for infants and toddlers. Current CPR certification is required, and all candidates must be willing to complete a comprehensive background and reference check as part of the process.

This is a long-term position for someone who is looking to build a lasting relationship with a truly wonderful family—thoughtful, kind, and deeply appreciative of the care and consistency a great candidate can bring to their home. If you're seeking a position where you can grow with a family and make a meaningful impact, we’d love to hear from you.

Submit your interest HERE, and we’ll follow up with the full job description once it’s available.

Late October/early November start date.

We’re seeking a seasoned and certified Independent Meeting Planner to join our preferred contractor network. This part-time, contract-based role is ideal for a high-performing professional running their own business, with deep expertise in corporate event planning and a commitment to white-glove client service.

About the Role

As a preferred contractor, you’ll be called upon as needed to lead or support high-end, detail-critical meetings and events for executive and corporate clients. You must operate independently, manage contracts with professionalism, and deliver seamless experiences from planning to execution.

You Are:

• A Certified Meeting Professional (CMP) or equivalent.

• A meeting planner business owner or sole proprietor (this is a strict requirement — no subcontracting or agency work permitted that would create a conflict of interest or availability).

• Experienced in corporate meetings/events with a proven track record.

• Skilled in contractor/vendor negotiation and logistics management.

• A master of white-glove client service, able to work with discretion, polish, and proactivity.

• Flexible and available to take on project-based work as needed.

• Adept at working remotely with exceptional communication and organizational skills.

Role Details

• Remote (U.S.-based preferred).

• Contractor position. Part-time, flexible hours, project-based. Hours are not always guaranteed and vary from 1-20 per week depending on client and role.

• 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 are seeking a highly experienced, self-employed Event Planner to join our preferred contractor network. This is a part-time, project-based contract role ideal for professionals who own and operate their own planning business and bring 6+ years of experience producing corporate and lifestyle events.

About the Role

As a contractor, you'll lead or support events that demand precision, discretion, and a white-glove client experience. From corporate gatherings to intimate brand events, you will be expected to handle end-to-end planning, vendor coordination, and on-site execution. Travel is required for select projects.

Key Qualifications

• 6+ years of experience planning corporate and lifestyle events.

• Strong background in vendor sourcing, logistics, and on-site management.

• Proven ability to provide white-glove service to high-level clients.

• Polished communicator with excellent attention to detail.

• Must be self-employed/independent contractor and operating as a freelancer (not employed by or subcontracting through another business).

• Available to travel as needed for event execution.

• Reliable, flexible, and confident working in dynamic, high-touch environments.

Role Details

• Remote (U.S.-based preferred).

• Contractor position. Part-time, flexible hours, project-based. Hours are not always guaranteed and vary from 1-20 per week depending on client and role.

• 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 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.

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, flexible hours, project-based. Hours are not always guaranteed and vary from 1-20 per week depending on client and role.

• 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.