Careers

Note: Generally 1-day per week remote. Some nights and weekends are required for events.

Our client, a highly regarded entertainment organization, is seeking a stellar Executive Assistant to join the team. This role is designed for an experienced executive assistant who operates with precision, foresight, and sound judgment - someone who understands how to partner closely with a senior leader and help drive momentum across a fast-moving revenue organization.

This opportunity plays a central role in ensuring the executive’s time, priorities, and initiatives are supported with care and intention. Beyond administrative execution, this role requires strong business awareness, the ability to anticipate needs, and the confidence to operate independently while remaining closely aligned with leadership. Discretion, trust, and professionalism are foundational. The right candidate will bring calm, clarity, and structure to complex days, allowing the executive and broader team to stay focused on strategic outcomes.

How This Team Operates

This organization values people who are deeply organized, highly reliable, and thoughtful in how they show up. The pace is steady and demanding, and success comes from those who anticipate rather than react, who notice details others might miss, and who can move work forward without constant direction. Clear communication and strong judgment are essential. Leaders rely on partners who understand context, protect focus, and handle sensitive information with maturity and discretion. The team operates primarily in person, valuing close collaboration and presence, with occasional flexibility for one remote day per week depending on the flow and demands of the week. There is an expectation of professionalism paired with adaptability, the ability to remain composed under pressure, and to adjust quickly as priorities evolve. Trust is earned through consistency, follow-through, and independent problem-solving. Those who thrive here take ownership, think strategically, and see their role as a long-term partnership rather than a transactional support function.

Key Responsibilities

• Provide proactive, high-level administrative support to the executive, including complex calendar management, meeting coordination, correspondence, document organization, and preparation of agendas, presentations, and briefing materials for internal and external engagements.

• Anticipate scheduling conflicts, prioritize commitments, and actively protect the executive time and focus while managing sensitive and confidential information with the highest level of discretion.

• Serve as a trusted point of contact between the executive, internal leadership, department teams, and external stakeholders, ensuring clear, timely communication and alignment with organizational priorities and revenue objectives.

• Coordinate logistics and execution of meetings, presentations, and events involving sponsors, partners, and league contacts, while supporting the planning and execution of partnership and revenue-focused initiatives.

• Manage special projects assigned by the Executive, tracking timelines, deliverables, and follow-through with precision and accountability.

• Process expense reports, invoices, and purchase orders, and coordinate comprehensive travel logistics — including flights, accommodations, ground transportation, and detailed itineraries — proactively resolving issues to ensure seamless experiences.

• Manage VIP access requests, credentials, and premium guest accommodations for hosted events, coordinating closely with internal partners to ensure precision and follow-through.

• Maintain organized digital and physical filing systems, support office logistics and supply coordination, and contribute to ongoing internal process improvements and information flow.

• Represent the organization with professionalism, discretion, and confidence, supporting relationship-building efforts with sponsors, community partners, and league representatives.

• Remain flexible, responsive, and service-oriented, demonstrating a strong work ethic and willingness to support leadership and staff as business needs evolve.

Who You Are

You’re a get-it-done kind of person. When something needs to move forward, you don’t wait to be asked - you roll up your sleeves, figure out what’s needed, and make it happen. You’re highly organized, deeply detail-oriented, and you genuinely enjoy bringing structure to complex, fast-moving work.

You think ahead, anticipate needs, and take pride in staying a few steps in front of the day. You communicate clearly and thoughtfully, know how to read a room, and exercise strong judgment - especially when handling sensitive information. Discretion comes naturally to you.

You’re comfortable working side-by-side with senior leaders and external partners, and you know how to build trust quickly. You enjoy creating strong relationships and acting as a bridge between people, teams, and priorities to keep everything moving smoothly. You’re confident operating independently, tech-savvy enough to streamline processes without friction, and calm under pressure when plans change or the pace picks up. Most importantly, you see this role as a true partnership — someone who protects executive time, supports strategic priorities, and contributes meaningfully to the success of the business every single day.

Required Skills & Experience

• Minimum of three years of experience supporting senior executives in an executive assistant or similar role.

• Advanced proficiency in Microsoft Office (Outlook, Word, Excel, PowerPoint).

• Exceptional organizational, communication, and time-management skills.

• Strong business judgment with the ability to assess priorities and make informed decisions.

• Demonstrated ability to manage confidential information with professionalism and discretion.

• Calm, adaptable, and resilient under pressure.

• Tech-savvy and operationally efficient, with the ability to quickly learn new tools and systems.

• Team-oriented, service-driven, and results-focused.

• Willingness to adjust schedule as needed, including evenings and weekends, to support key initiatives and hosted engagements.

Additional Information

This is a full-time, benefit-eligible position. The organization is committed to fostering an inclusive and welcoming environment and offers competitive benefits and time-off policies to support healthy, balanced lives. The organization is an equal opportunity employer and does not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. Reasonable accommodations for medical or religious needs will be considered.

Compensation is $75-90K based on experience, level, skills, and other qualifications.

This is a full-time, senior-level Estate Manager opportunity for an established UHNW family in West Hollywood. The household operates at exceptionally high standards and is known for a positive culture and long-term staff retention.

The ideal candidate is a true team player with a polished, professional presence, strong judgment, and the ability to remain agile in a dynamic environment. Prior experience managing UHNW estates is required, with a demonstrated track record of stability in previous roles. A background in 5-star hospitality or an equivalent service-driven environment is strongly preferred.

This is an excellent opportunity for an experienced Estate Manager seeking a long-term role with a respectful, well-run household.

Updated will be made with final, formal job description in the coming week.

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.

Overview

We are seeking a highly connected, outgoing, and self-motivated Business Development & Sales Consultant to support client acquisition through strategic networking, outreach, and relationship-driven sales efforts. 

Key Responsibilities

• Proactively source, engage, and qualify prospective clients through:

  • Professional networking

  • Warm introductions

  • Strategic outreach

  • Relationship-based sales conversations

• Represent the company with professionalism, discretion, and integrity

• Clearly communicate service offerings, value propositions, and engagement models

• Support prospects through the sales cycle until contracts are signed and engagements are successfully initiated

• Maintain accurate tracking of outreach, conversations, and deal status

• Collaborate with internal stakeholders to ensure smooth handoff and fulfillment

Compensation Structure

• $300/month professional retainer

• Commission per successful client: typically $1,000–$3,500

  • Commission is earned when the consultant:

    1. Brings in the client

    2. The client signs a contract

    3. The contract is successfully fulfilled per the agreed terms

• No cap on commissions

• Strong performers bringing in ~1-3 clients per month can generate meaningful ongoing income

Ideal Candidate Profile

You are someone who:

• Is highly social, confident, and genuinely enjoys building relationships

• Has an established professional network and strong “network effect”

• Is a self-starter who does not need micromanagement

• Is exceptionally organized and reliable with follow-through

• Has a proven track record in:

  • Sales (minimum of 3 years)

  • Business development

  • Partnerships

  • Consulting or relationship-driven revenue roles

• Is comfortable representing a brand publicly and professionally; do not have a conflict of interest with other engagements such as a full-time role that will not allow for such a public secondary role. 

Contractor Requirements

• Must operate as an independent contractor

• Strong preference for candidates who file taxes as:

  • Sole Proprietor, or LLC

• Must supply and maintain own equipment, tools, and workspace

• Responsible for own taxes, insurance, and business expenses

• Able to manage workload independently without interfering with another full-time job, or other professional obligations that would not allow for this engagement long-term.

Conflict of Interest & Transparency

• This role must not conflict with any current employer or client agreements

• All outreach and business development must be conducted ethically and transparently

• Candidates must be comfortable with:

  • Publicly listing this role on LinkedIn

  • Working within overlapping professional networks

  • Clear disclosure of affiliations when appropriate

Why This Role

• Flexible, part-time structure with meaningful upside

• Unlimited earning potential per year

• Opportunity to leverage your existing network in a high-integrity, professional environment

Target Production: Ideally, 1-3 new clients per month, equating to $24K-126K in commission per year. Restrictions and terms apply. The contract will detail the final engagement and specifics.

Overview

A client is seeking a Manager of Content, Community & Monetization to take ownership of revenue generation across established digital platforms, including virtual programming, newsletter monetization, and social media channels.

This is a part-time, independent contractor engagement ideal for an experienced content or community manager looking to build a strong portfolio of monetized programs while maintaining autonomy. The role is not client-facing and does not involve sales, recruiting, or service delivery. Instead, the Manager will focus on content-led monetization, scalable programming, and brand-aligned partnerships.

This engagement is intended to be long-term, with opportunities to build durable revenue streams and demonstrate measurable impact over time.

Key Responsibilities

Virtual Programming & Events

• Concept, launch, and monetize virtual programming (webinars, workshops, panels, or short series)

• Oversee pricing, positioning, and promotion in collaboration with existing content strategy

• Prioritize high-margin, low-overhead offerings

• Own revenue performance and post-program analysis

Newsletter Monetization

• Manage and expand monetization of an existing newsletter with approximately 10,000 subscribers

• Secure sponsorships, partnerships, or paid placements aligned with brand values

• Collaborate on editorial strategy to support monetization objectives

Social Media Management & Monetization

• Take ownership of social media channels across agreed-upon platforms

• Develop monetization strategies including partnerships, sponsored content, and audience conversion

• Grow engagement and revenue while maintaining brand integrity and voice

Strategy & Execution

• Identify and test new monetization opportunities across owned channels

• Track performance metrics, iterate on initiatives, and refine strategies based on results

• Collaborate with client leadership to ensure alignment with standards, timelines, and goals

Compensation Structure

• Monthly Retainer

  • $200 per month base retainer to support continuity and ongoing ownership

• Commission-Based Earnings

  • Percentage-based commission on net profit generated from:

1. Virtual programming and events

2. Newsletter sponsorships and monetization

3. Social media partnerships and monetization

• Earning Potential

  • Compensation scales directly with performance and outcomes

  • Strong performers can build meaningful annual income through compounding revenue streams

  • No cap on commission-based earnings

Engagement Structure

This role is structured as an independent contractor engagement.

The Manager must:

• Operate as a sole proprietor, LLC, or other legal business entity

• Provide their own equipment, tools, and workspace

• Set and manage their own work hours and schedule

• Be responsible for their own taxes, insurance, and business expenses

While the role is part-time and highly autonomous, the Manager is expected to:

• Meet agreed-upon deadlines and deliverables

• Adhere to client standards, policies, and brand guidelines

• Communicate consistently and operate with professionalism and discretion

Qualifications

• Demonstrated experience monetizing digital audiences, content, or communities

• Experience with newsletters, virtual events, and/or social media monetization

• Manager-level experience owning programs from concept through execution

• Strong strategic thinking paired with hands-on implementation

• Comfortable working independently with accountability for results

• Interest in a long-term engagement with measurable portfolio outcomes

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 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.