Pennyworth Projects, LLC

What Pennyworth Projects, LLC does

Pennyworth Projects, LLC is a privately-held, bootstrapped boutique staffing and search firm co-founded by Julia Hudson (CEO) and Lisa Casson (COO), both former Executive Assistants in the Office of the CEO at Yahoo. The company operates three primary service lines: Personal Placements (domestic support staff such as nannies, house managers, and personal assistants for high-net-worth households), Professional Placements (executive assistants and project management roles for corporate environments), and Part-Time & Virtual Executive Support sold on hourly billing. The firm also operates a direct-to-consumer merchandise sub-brand called Pennyworth Goodies.

The business generates revenue through three distinct streams: a percentage-of-first-year-salary placement fee on full-time placements, hourly billing for ongoing support services, and direct-to-consumer e-commerce sales of branded merchandise. Distribution relies on direct sales consultation (booked via Calendly) and inbound demand from a closed network of former Yahoo, Fortune 500, and high-net-worth contacts. Marketing operations are executed through LinkedIn, Instagram, an email newsletter, and blog content.

The firm operates with no proprietary technology platform, no AI/ML systems, and no external funding — operations depend entirely on the founders' domain expertise, personal networks, and matchmaking methodology. The company is privately held as an LLC with two U.S. operational nodes (Chicago and Minneapolis). Headcount, revenue, and growth metrics are not publicly disclosed, and the firm appears to be a lifestyle-scale operation rather than a venture-scale business.

Name

Pennyworth Projects, LLC

Legal name

Pennyworth Projects, LLC

Website

https://pennyworthprojects.com

Company type

Private

Operating status

Operating

Headcount range

1–10 employees

Short description

Pennyworth Projects is a privately-held, bootstrapped boutique staffing and search firm co-founded by former Yahoo Executive Assistants. It places domestic and corporate support professionals for high-net-worth households and executives, and sells branded merchandise under its Pennyworth Goodies sub-brand.

Ownership category

akta.pro rank

Headquarters

HQ city

San Francisco

HQ country

United States

HQ region

North America

Offices2 records

Markets served

GTM type

B2B

Offering type

Services

Cost components

Personnel, Operations, Marketing or Sales, Others

Revenue model

1. Full-time Placement Search: Search agreement for fulfilling full-time roles based on a percentage of the candidate's first year's salary. Non-exclusive arrangement where clients are not obligated to hire presented candidates.
2. Ongoing Support Services: Hourly rate arrangement for part-time, virtual executive support and project-based administrative work. Includes minimum per week commitment with mutually at-will terms. Covers project management, events, relocations, and continuing administrative or operational efforts.
3. Merchandise (Pennyworth Goodies): E-commerce sales of branded merchandise including journals ($30), mugs ($25), tote bags ($28), crewnecks ($65), and caps ($32). Direct-to-consumer online sales.

Pricing tiers

Go-to-market motion2 records

Distribution channels3 records

Marketing channels6 records

Core offering

Pennyworth Projects is a boutique executive search and support firm that runs customized, closed-network placements for Executive Assistants, Personal Assistants, Estate Managers, House Managers, Chiefs of Staff, and Project Managers serving executives, entrepreneurs, and high-net-worth households. In addition to full-time placements, it offers part-time and virtual executive support on an hourly basis, and sells branded merchandise (Pennyworth Goodies) directly to consumers.

Product overview

Pennyworth Projects is a boutique staffing and search firm offering two core service lines (Personal Placements and Professional Placements) along with Part-Time & Virtual Executive Support. The company also operates Pennyworth Goodies, a merchandise line selling branded journals, mugs, tote bags, caps, and crewnecks targeted at administrative professionals. The placement services focus on matching high-caliber candidates with support roles including Executive Assistants, Personal Assistants, Estate Managers, House Managers, Chief of Staff, and Project Managers.

Differentiator

Problem solved

Functional benefit

Brands

• Pennyworth Goodies: Branded merchandise including journals, mugs, tote bags, crewnecks, and caps featuring witty slogans for administrative and executive support professionals

Products and services

• Personal Placements Customized and closed-network searches matching high-net-worth households and families with candidates for domestic support roles including Estate Managers, House Managers, Housekeepers, Family Assistants, Personal Assistants, Private Chefs, and Family Concierges, with focus on worthy backgrounds, highly developed skills, and appropriate temperament.
• Professional Placements Tailored searches identifying high-level candidates from the start for corporate environments, including Executive Assistants, Chief of Staff, Coordinators, Project Managers, Office Managers, Events Managers, Administrative Assistants, and Directors of Executive Operations.
• Part-Time & Virtual Executive Support Part-time and remote assistance from seasoned professionals offering project management, executive travel coordination, public relations, security detail, and high-impact administrative work for a select handful of clients.
• Pennyworth Goodies E-commerce merchandise line selling branded journals ($30), mugs ($25), tote bags ($28), crewnecks ($65), and caps ($32) featuring witty phrases for administrative professionals and executive assistants directly to consumers.

Quantifiable outcome

• Efficient and streamlined search process with high-quality candidates delivered quickly

Named customers1 record

Segments3 records

Ideal customer profiles3 records

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Scale indicators2 records

Recent moves3 records

Expansion highlights4 records

Broad incumbents

• Adecco: Adecco is one of the world's largest staffing firms, with office-support and administrative placement divisions globally. Overlaps with Pennyworth's placement offerings but serves a mass-market segment rather than the HNW/executive niche.
• Insight Global: Insight Global is a large staffing firm placing professionals across IT, finance, accounting, and administrative support. Overlaps with Pennyworth's professional/executive placements, but with a much broader industry and role scope.
• Beacon Hill Staffing Group: Beacon Hill places administrative, executive-assistant, HR, and finance professionals across multiple US markets. Comparable to Pennyworth's professional placements, with a much broader geographic and functional footprint.
• Kelly Services: Kelly Services is a global staffing provider with administrative, executive-support, and professional placement capabilities. Comparable in the underlying placement services category, though positioned broadly across many skill verticals rather than boutique-niche.
• Robert Half International: Robert Half is a global staffing and recruiting firm with a dedicated administrative and executive-support practice. Overlaps with Pennyworth's placement services across the executive-assistant category, but operates at vastly greater scale and breadth.

Emerging players

• Wing: Wing provides dedicated virtual assistants with a tech-enabled matching and management layer for executives and entrepreneurs. Comparable in customer segment and virtual-support offering, with a more technology-forward delivery model than Pennyworth.

Direct peers

• The Execu|Search Group: The Execu|Search Group is a recruitment firm placing executive assistants, administrative professionals, and corporate support staff. Directly comparable to Pennyworth's Professional Placements line in role types served and high-end office-support focus.
• BELAY: BELAY matches clients with US-based virtual assistants, executive assistants, bookkeepers, and web specialists. Comparable to Pennyworth in serving executives and small business owners with vetted remote support professionals on an ongoing basis.
• Boldly: Boldly provides subscription-based virtual executive assistants to executives and entrepreneurs. Closely comparable to Pennyworth's Part-Time & Virtual Executive Support offering, with a similar target buyer (busy leaders needing high-caliber remote support) and recurring-revenue model.

Market position

Strengths5 records

Weaknesses5 records

Competitive moat3 records

Key risks6 records

Key highlights6 records

Customer concentration

• LinkedInlinkedin.com/company/pennyworthprojects
• Instagraminstagram.com/pennyworthprojects

Revenue estimate

Valuation estimate

Number of profiles

Profiles2 records

Funding overview

Funding rounds

Investors

Funding detail is available on the Subscription and Enterprise plan.Contact sales →

M&A

Investments

M&A and investment is available on the Subscription and Enterprise plan.Contact sales →

Frequently asked questions about Pennyworth Projects, LLC