Careers

Overview
Schedule: Full-time, ~80% in-office (with flexibility as needed; occasional evenings/weekends for events)

We are seeking a dynamic, hands-on Marketing Manager to lead brand presence, event execution, and day-to-day marketing efforts for a boutique, high-caliber wealth management firm in Chicago.

This is a highly visible, collaborative role for someone who understands both strategy and execution—equally comfortable planning a thoughtful marketing calendar as they are rolling up their sleeves to create a polished invitation in Canva the same afternoon.

The ideal candidate brings experience in local, relationship-driven marketing, as well as meaningful partnerships across regional publications, newsletters, and community networks, and understands how to build brand awareness in a nuanced, highly personal way. 

Working closely with the Founder, advisors, and Executive Assistant, this person will play a key role in shaping and executing a thoughtful brand experience across every client and prospect touchpoint.

Key Responsibilities

Marketing Strategy & Execution

• Develop and execute a thoughtful, cohesive marketing plan aligned with the firm’s brand and growth goals

• Manage and maintain a marketing calendar spanning campaigns, events, partnerships, and content

• Partner with leadership to identify opportunities for brand visibility and client engagement

• Execute both long-term initiatives and quick-turn projects with equal precision

Events & Brand Experiences

• Plan and execute client events, intimate gatherings, and brand-building experiences from concept through completion

• Manage all event logistics including venues, vendors, guest communications, budgets, and onsite execution

• Collaborate with internal stakeholders to ensure each event reflects the firm’s tone, audience, and objectives

• Support both large-scale and more informal, grassroots events that deepen relationships and expand reach

Content & Collateral Creation

• Create polished, on-brand marketing materials including presentations, invitations, email communications, and simple promotional assets

• Partner with external designers and agencies while also owning smaller, quick-turn creative needs internally

• Ensure consistency in tone, messaging, and visual identity across all materials

• Maintain and evolve brand standards over time

Local Marketing & Partnerships

• Build and manage relationships with local magazines, newsletters, and relevant community platforms

• Identify and execute opportunities for placements, partnerships, and collaborations that align with the firm’s audience

• Oversee outreach, submissions, and coordination for local marketing efforts

• Track effectiveness and refine approach over time

Budgeting & Operations

• Manage marketing and event budgets with a strong sense of ownership and accountability

• Evaluate ROI across campaigns, partnerships, and events

• Source and negotiate with vendors, ensuring high quality and cost efficiency

• Establish and refine processes to support a lean, effective marketing function

Qualifications

• 5–8+ years of experience in marketing, events, or brand management, ideally within financial services, luxury, or client-facing professional services

• Strong experience planning and executing events end-to-end, with exceptional attention to detail, clear ownership, and a high degree of logistical coordination

• Proven ability to manage budgets and prioritize effectively within a lean environment

• Experience with local or regional marketing channels (e.g., magazines, newsletters, partnerships, community engagement)

• Proficiency with tools like Canva and the ability to independently produce polished, client-ready marketing materials

• Excellent written and verbal communication skills with strong attention to tone and detail

• Highly organized with the ability to manage multiple priorities and deadlines simultaneously

• Collaborative, team-oriented mindset with the ability to work closely with senior stakeholders

Who You Are

• A doer—you’re as comfortable executing as you are strategizing

• Scrappy and resourceful, with a “figure it out” mentality

• Highly detail-oriented, with a strong eye for design and presentation

• Personable and relationship-driven, able to represent the firm with polish and professionalism

• Organized and proactive, with a natural ability to keep things moving forward

• Someone who takes pride in creating thoughtful, elevated experiences—whether for 10 guests or 100

Additional Details

• Primarily in-office role (approximately 80%) based in Chicago

• Flexibility is offered as needed, though a strong in-person presence is important for collaboration and seamless execution

• Occasional evenings and weekends will be required to support events

Why This Role

This is an opportunity to help shape and elevate the marketing function at a boutique firm where quality, relationships, and reputation matter deeply. You’ll have the autonomy to build, the support to execute, and the visibility to make a meaningful impact — bringing both creativity and precision to a brand that values thoughtful execution and getting every detail right.

Overview

Our client is seeking an exceptional Senior Executive Assistant to support the CEO and President of a boutique, highly regarded wealth management firm in Chicago. This is a pivotal, high-trust role for a seasoned professional who operates with precision, discretion, and an intuitive understanding of what it means to provide true white-glove support.

The ideal candidate thrives in a fast-paced, high-expectation environment and brings a calm, proactive presence to every interaction. You are not only highly organized and detail-oriented, but also deeply attuned to the nuances of executive support at this level - anticipating needs, managing complexity, and ensuring nothing falls through the cracks.

This individual will act as a trusted strategic partner to both the CEO and President, while also managing day-to-day office operations, partnering closely with the broader team, and ensuring the firm runs with a high level of polish, efficiency, and cohesion.

Key Responsibilities

• Provide comprehensive, high-touch support to the CEO and President, managing a complex and ever-evolving calendar with precision and foresight.

• Coordinating travel, including detailed itineraries, logistics, and contingencies.

• Serve as a trusted gatekeeper and liaison, managing communications with internal and external stakeholders with professionalism and discretion.

• Anticipate needs and proactively solve problems before they arise.

• Lead the planning and execution of high-end client events, executive gatherings, and internal meetings.

• Partner with venues, vendors, and service providers to deliver polished, seamless experiences.

• Oversee event logistics including guest lists, communications, budgets, run-of-show, and onsite execution.

• Ensure every touchpoint reflects the firm’s brand and high standards.

• Partner closely with current—and as the company grows, future—support professionals across the firm, offering guidance, structure, and support to foster a collaborative, team-driven culture and consistent, aligned ways of working.

• Help establish and refine systems, processes, and best practices to optimize efficiency.

• Assist in managing office operations to ensure a smooth, professional, and elevated environment.

• Support special projects and firm initiatives with strong follow-through and attention to detail.

• Create and maintain systems that improve organization, communication, and execution.

• Track priorities, deadlines, and deliverables to ensure alignment and completion.

Qualifications

• 7+ years of experience supporting senior leaders or C-suite executives, ideally within wealth management, finance, consulting or UHNW environments.

• Proven experience planning and executing high-touch events with exceptional attention to detail (aligned with the level of ownership and logistics outlined in similar event-driven roles).

• Exceptional communication skills—clear, polished, and thoughtful in both written and verbal interactions.

• Highly organized with a natural ability to manage multiple priorities simultaneously.

• Strong interpersonal skills with a high level of emotional intelligence and discretion (consistent with relationship-driven roles requiring nuance and confidentiality).

• Proactive, resourceful, and solutions-oriented mindset.

• Comfortable working in a fully in-office environment with flexibility as needed.

Who You Are

• A true right hand - intuitive, reliable, and always one step ahead.

• A natural problem-solver who thrives in complexity and ambiguity.

• Polished, professional, and confident interacting with high-level stakeholders and clients.

• Detail-obsessed, yet able to see the bigger picture.

• A team player who leads with kindness, discretion, and integrity.

• Someone who takes immense pride in delivering excellence at every level.

This is a unique opportunity to support a highly respected leadership team within a boutique firm that values excellence, discretion, and thoughtful execution. You will play an integral role in shaping the day-to-day flow, elevating operations, and ensuring a seamless experience at every touchpoint.

Overview:
Full-Time | In-Person

Our client, a highly regarded and fast-moving organization, is seeking a top-tier Senior Executive Assistant to support a key C-suite leader. This is a rare opportunity to partner directly with senior leadership at the highest level, playing a critical role in shaping the executive’s efficiency and impact.

The right candidate will act as a true strategic partner — managing complex schedules, serving as a gatekeeper for priorities, and ensuring seamless communication across the organization and with external stakeholders. The right candidate is detail-obsessed, unflappable under pressure, and thrives in a fast-paced, high-stakes environment where confidentiality is paramount.

Responsibilities:

• Provide sophisticated calendar and schedule management, skillfully balancing competing priorities and ensuring the executive’s time is optimized for maximum impact.

• Act as a trusted liaison and point of contact between the executive, board members, investors, senior leadership, and key external stakeholders.

• Anticipate needs, identify potential challenges, and proactively develop solutions to keep operations running seamlessly in a fast-paced, ever-changing environment.

• Coordinate and oversee complex domestic and international travel, delivering flawlessly organized itineraries and agendas. Proactive contingency planning. 

• Lead meeting preparation and execution, including agendas, briefing materials, logistics, and detailed follow-up on action items to ensure accountability.

• Handle highly sensitive and confidential information with discretion, judgment, and the utmost professionalism.

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

• Plan and manage executive offsites, leadership team meetings, and company events with precision and creativity.

• Oversee all aspects of meeting guest and meeting management for the executive, ensuring a seamless and professional experience.

• Execute essential administrative functions including expenses, correspondence, and document management with accuracy and timeliness.

• Provide project management support on key business priorities, tracking deliverables and ensuring follow-through across teams for the executive. 

• Serve as a thought partner, offering perspective, prioritization support, and operational insight to enhance the executive’s decision-making and leadership effectiveness.

• Build and optimize systems, processes, and tools to streamline workflows, improve communication, and increase efficiency across the executive’s office.

The Ideal Candidate

• Minimum 10 years of experience supporting senior executives or founders.

• Experience in tech or similarly fast-paced, high-growth environments strongly preferred.

• A type-A operator: sharp, succinct communicator, hyper-organized, and adept at juggling shifting priorities.

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

• Adept at handling confidential matters, including board-level communication and sensitive business initiatives.

• Thrives in a fast-paced environment where precision and proactivity are everything.

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

Overview:
Schedule: Monday-Friday (9-6 or 10-7) OR ROTA (7 days on, 7 days off)/Candidates with long-term intent only

We are seeking a warm, positive, and dedicated Family Assistant to join our client’s (amazingly kind, warm, gracious, lovely…) bustling household in Rancho Santa Fe. This role is perfect for a go-getter with a heart of gold, someone who takes pride in being a “doer” and effortlessly handles a variety of tasks with a smile. If you are an efficient, smart decision-maker with a knack for providing seamless support, we would love to meet you!

The ideal candidate will be adept at jumping into various tasks and ask, seamlessly transitioning from one need to another, and providing loving care for a toddler, engaging in play, teaching, and entertaining activities whenever needed. You should be versatile, able to wear many hats, and handle a diverse range of responsibilities with grace and enthusiasm. This includes various responsibilities for the residences or family with young children.

Taking initiative is crucial, as is the ability to stay organized and maintain order in a dynamic environment. We value someone who approaches both mundane and exciting tasks with equal zeal and dedication, ensuring that all aspects of the role are attended to with the same level of care. You will need to oversee the day-to-day activities of a young child whenever needed, and other responsibilities, not limited to, handle scheduling, making appointments, family/children related errands, projects and ensure the household's operational needs are met.

Adaptability and a positive, can-do attitude are key, as you will need to navigate the ever-changing needs of a busy and expanding household, handling last-minute changes and urgent requests with ease. If you thrive in a fast-paced environment, love working with and attending to young children, and have a passion for providing top-notch support to a private household, this position offers an exciting opportunity to be an integral part of a wonderful home and home office! Travel from time-to-time will be required. 

Qualifications:

• Proven experience working in a private home and with a private family, especially with young children. Ideally 5+ years experience. (Experience with infants and toddlers is a must). 

• Excellent references reflecting a history of reliability, trustworthiness, and professionalism.

• Proficiency in Google Suite and general tech-savviness.

• Clean driving record and ability to run errands efficiently.

• Background check.

• High energy, positive attitude, and a genuine innate passion for helping others.

• Exceptional organizational skills and attention to detail.

• Experience as a professional nanny, trained/certified educator or related experience is preferred.

• Experience with administrative and project management duties is strongly preferred. 

• CRP certified, Trustline, other certifications/expertise regarding child development a plus 

Who You Are:

• A natural problem-solver who is proactive and resourceful.

• A natural “kid person” who is easy to be around and play with for young children. A great role model.

• A compassionate individual with a strong sense of responsibility and integrity.

• A friendly, approachable, outgoing person who gets along well with others. A team player who enjoys working with others to get things done. 

• A smart and efficient worker who takes pride in their role and always strives for excellence.

• Looking for your next role with long-term intent and a strong sense of commitment.

If you’re looking to make a positive impact in a supportive and dynamic household, this will be a great next chapter. Join our client in creating a harmonious, well-managed home where your skills and positive energy will be valued and appreciated. 

NOTE: In a ROTA position, holidays may fall during your scheduled weeks on. While the family is kind and generous, candidates must understand and accept that this arrangement often will require availability during certain holidays every other year per the schedule. Travel and other needs may occasionally disrupt the 7/7 schedule, so flexibility and adaptability are essential. However, essentially the position is a ROTA live-out role with stability and longevity.

Our client, a highly respected, digitally-led fashion and lifestyle brand, is seeking a Senior Executive Assistant / Director of Executive Operations 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

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.

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-April. 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.

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.