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, 2 days per week typically, and 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

Location: Downtown Columbus

Full benefits, PTO, holidays, 401K and other perks.

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’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.