Careers

“The best way to get something done is to get started,” says our client, a dynamic entrepreneur who operates at full speed.

We are seeking an exceptionally capable and resourceful Executive Personal Assistant (EPA) to support a visionary business leader with wide-ranging global interests. The Principal oversees multiple companies, significant real estate holdings, and philanthropic endeavors—all while maintaining a rich family and personal life.

The ideal candidate is a proactive “air traffic controller” who thrives on managing complexity with calm precision. This role blends executive and personal support, requiring sound judgment, adaptability, and a solutions-oriented mindset.

The Principal is energetic, idea-driven, and deeply engaged in every aspect of life—business, culture, people, and experiences. They value thoughtful touches like handwritten notes as much as they do strategic execution. The right EPA will be trusted with sensitive financial information, oversee both the big picture and the finer details, and bring order, care, and momentum to an ever-evolving environment.

Key Responsibilities

• Serve as a trusted partner to the Principal, balancing professional, personal, and family priorities with discretion and foresight.

• Manage complex, multi-layered calendars across business, real estate, nonprofit, and family domains.

• Act as liaison and gatekeeper with leadership teams, advisors, staff, vendors, and service providers worldwide.

• Support travel logistics, events, and personal commitments with impeccable attention to detail.

• Anticipate needs and stay several steps ahead, providing seamless support and simplifying decisions.

• Coordinate with leadership, ensuring the Principal remains informed and priorities move forward.

• Assist with oversight of personal and investment real estate portfolios across the U.S. and abroad. 

• Support the Principal with their philanthropic initiatives and foundation work, including regenerative farm projects and nonprofit activities.

• Assist in orchestrating events, retreats, and celebrations with creativity and precision.

Required Qualifications

• Minimum 8+ years supporting a high-performing executive, entrepreneur, or principal in a hybrid executive/personal capacity.

• Exceptional organizational and project management skills; able to manage multiple priorities across domains.

• Highly responsive, self-motivated, and accountable, with strong follow-through and a bias toward action.

• Can travel up to 8-10 weeks per year as needed. 

• Outstanding written and verbal communication skills; polished, professional, and warm in interactions.

• Tech-savvy, fluent in modern productivity tools (Google Workspace, Apple/iOS, project management platforms).

• Proven discretion, emotional intelligence, and ability to operate with calm under pressure.

• Flexible and adaptable, comfortable with changing priorities, and occasional travel

• Experience supporting principals with complex portfolios (business, real estate, nonprofit, family office) strongly preferred.

• U.S. work authorization and valid driver’s license required.
  
  

This role offers the chance to partner with a visionary leader building a boutique “family office” environment that spans entrepreneurship, real estate, philanthropy, and joyful living. The right candidate will take pride in being the steady force behind the scenes, ensuring priorities are advanced, projects are completed, and life flows seamlessly.

If you thrive on juggling complexity with grace, value discretion, and find joy in making things run smoothly, we would love to hear from you.

Hybrid: Strong preference for someone located in the North Bay/Marin area of San Francisco Bay Area. Open to remote-forward candidates who can travel 1-2 times per month as needed, alternatively. Compensation depends on geo-location and experience: $100-215K per year.

Our client is seeking a resourceful, high-caliber Executive Assistant to partner closely with their CEO. This is a pivotal role for someone who thrives as the glue of an organization—equally comfortable orchestrating high-level priorities for a seasoned leader and stepping in to keep day-to-day details moving without being asked.

The ideal candidate enjoys being hands-on, balancing “big picture” initiatives with everyday logistics, and finds satisfaction in making it all run smoothly—no task too large, no detail too small.

We’re looking for a confident, unflappable professional who thrives in an in-office, collaborative culture but appreciates the flexibility to work remotely about 10–20% of the year (for example, around holidays or during quieter weeks). 

About the Client

Our client is a privately held organization that owns and operates a portfolio of businesses across a range of industries. They focus on building and guiding companies for long-term success—providing leadership, strategy, and resources that help these businesses grow sustainably while creating opportunities for their teams and communities. With a decades-long legacy of entrepreneurial spirit and thoughtful stewardship, they have cultivated a reputation for pairing capital with values-driven leadership. Their work blends strategic investment, operational insight, and a commitment to relationships—creating an environment where innovation and integrity thrive.

Their core values of Respect, Family, and Community guide everything they do, creating a workplace culture that values collaboration, trust, and meaningful impact.

What You’ll Do

• Serve as the right hand to the CEO, ensuring their time, priorities, and communications flow seamlessly.
  
  

• Manage complex, fast-moving calendars with an eye for alignment, preparation, and impact.

• While the role lightly supports three other senior executives, the primary focus is the CEO.

• Coordinate domestic travel—handling every detail from itinerary to contingency planning.

• Act as liaison with internal leaders, external partners, and the board with professionalism and discretion.

• Anticipate needs—looking ahead to remove obstacles and lighten the CEO’s load before being asked.

• Provide light-touch scheduling and coordination for the leadership team as needed, partnering with their assistants and teams to keep things moving.

• Assist in the planning and execution of leadership meetings, board sessions, offsites, and special events.

• Oversee key office rhythms such as vendor relationships, space planning, supply coordination, and event logistics—keeping the HQ organized without letting facilities work overshadow your focus on executive support.

• Help sustain a welcoming, well-run office environment where collaboration can thrive.
  
  

Who You Are

• Experience: 7+ years supporting senior executives (CEO or C-Suite preferred); experience in a multi-generation, family-owned or investment-driven business a plus but not required.

• Self-starter: Able to pivot easily between high-impact projects and everyday logistics without heavy direction.

• Glue mentality: A natural team player who finds joy in making others’ work lighter, in whatever way is needed.

• Communication: Poised and clear in both written and verbal communication; discreet with sensitive information.

• Operational edge: Highly organized with strong judgment, anticipating needs, and solving problems before they surface.

• Tech-savvy: Proficient in Microsoft Office Suite; adaptable to new platforms and tools.

• Collaborative energy: Enjoys working in person with colleagues and understands the importance of being present in an office community.
  
  

This is a rare chance to be at the center of a values-driven, entrepreneurial organization that balances legacy with innovation. You’ll partner with a CEO who values trust, partnership, and humor alongside operational excellence—helping to shape an environment where businesses grow thoughtfully and people thrive.

Compensation depends on experience: $80-100K

Note: This job is 4 days a week in-office (Monday–Thursday). Some Fridays are flexible depending on the executive’s schedule. General office hours are 8:45am–5:30pm.

Overview:
Our client, a high-growth and fast-moving organization, is seeking a top-tier Senior Executive Assistant to support a key C-suite leader. This role offers the chance to partner directly with senior leadership, enhancing executive efficiency and impact. The ideal candidate is detail-oriented, unflappable under pressure, and thrives in a fast-paced environment where confidentiality is essential.

Responsibilities:

• Manage complex calendars, balancing priorities and optimizing the executive’s time.

• Serve as a trusted liaison between the executive, board members, investors, senior leadership, and key external stakeholders.

• Anticipate needs, resolve challenges proactively, and ensure smooth operations.

• Coordinate domestic and international travel, including itineraries, agendas, and contingency planning.

• Prepare and execute meetings: agendas, briefing materials, logistics, and follow-up on action items.

• Handle sensitive and confidential information with discretion and professionalism.

• Collaborate with other Executive Assistants and cross-functional teams to maintain alignment on strategic initiatives.

• Plan and manage executive offsites, leadership meetings, and company events.

• Oversee meeting guest management to ensure a seamless professional experience.

• Execute administrative functions including expenses, correspondence, and document management.

• Provide project management support on key priorities, tracking deliverables and follow-through.

• Build and optimize systems and processes to improve workflows, communication, and efficiency.

The Ideal Candidate:

• Minimum 10 years supporting senior executives or founders.

• Experience in tech or high-growth environments strongly preferred.

• Sharp, succinct communicator, hyper-organized, and adept at juggling priorities.

• Highly tech-savvy, leveraging digital tools to drive efficiency.

• Skilled at handling confidential matters, including board-level communication.

• Thrives in a fast-paced environment requiring precision and proactivity.

This is an extraordinary opportunity for an elite Executive Assistant to step into a high-visibility, high-trust role supporting senior leadership at a leading organization.

Benefits:

Health Insurance, 401K program, salary $150-215K based on experience.

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: $150-200K (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 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.

Note: Non-typical work schedule. This is not your 9-5 role. Please read full JD.

We’re supporting the Founder & CEO of a high-growth Ed-Tech company in finding a discreet, resourceful, and highly self-directed Personal Assistant. This is a full-time remote role for someone who thrives on quietly keeping things in motion—behind the scenes—so the Founder can focus on leading the company.

The Role

Think of this as being the wizard behind the curtain: you’ll manage the personal and administrative side of the Founder’s life with a high degree of autonomy. While you’ll coordinate closely with the Executive Assistant who handles business-facing priorities, your focus will be on removing things from the CEO's plate otherwise.

This means: serving as a gatekeeper and point of contact for a wide range of people—from family members to outside vendors; handling paperwork and personal logistics; and managing requests that come up across time zones and outside of traditional business hours. The work isn’t driven by the CEO’s daily schedule but by the varied needs of the role itself.

What We’re Looking For

We’re seeking someone who is:

• Autonomous and decisive: able to make sound judgments and move things forward with minimal direction.

• Discreet and composed: you handle sensitive matters with absolute professionalism.

• Proactive and unflappable: you anticipate needs, respond to the unexpected, and keep things organized.

• A strong communicator and gatekeeper: clear and kind in representing the Founder to family, vendors, and other contacts.

• Organized yet adaptable: you can prioritize effectively in a shifting landscape.
  
  

The Essentials

• Full-time, fully remote role; hours will flex based on the needs of the week rather than a standard 9-to-5. On-call nights and weekends expected. You are not tied to a desk 8 hours a day but rather find the rhyme of the week based on the needs.

• Expected to be responsive during core working hours with the understanding that after-hours, evening, holiday, or weekend needs will arise regularly. Some weeks may be lighter than others; understanding of that flux.

• Day-to-day will include coordinating with outside vendors and service providers, managing personal paperwork and commitments, liaising with extended family, and ensuring logistical and administrative needs are handled seamlessly.
  

This role is ideal for someone who enjoys being quietly indispensable—steady, responsive, and always a step ahead, ensuring the Founder’s personal world runs as smoothly as their professional one.

Compensation: $100K/year