What The Jacky Winter does

The Jacky Winter Group is a privately held, founder-led creative talent agency and production company headquartered in Collingwood, Melbourne, with additional offices in London (est. 2021) and New York (est. 2016). Founded in 2006 by Jeremy Wortsman, the company represents more than 100 illustrators, animators, makers and storyboarders globally and has delivered more than 12,000 commercial projects, including over 1,200 in 2024 alone. Its core service is end-to-end artist representation — sourcing talent, negotiating and contracting, producing, and delivering commercial illustration and animation for brand, agency and publisher clients across streaming, retail, apparel, beverage, entertainment, government and cultural sectors.

The company operates an ecosystem of interconnected sub-brands and proprietary technology products rather than a single unified SaaS platform. Core revenue streams include artist representation commissions, Companion on-demand production services for studios and brands, Spaces placemaking and physical commissions, Jacky Winter Academy course fees, The Play Group consumer product sales (including the viral 1000 Colours puzzle), Cobbler SaaS subscriptions to other commission-based talent agencies, PencilBooth artist newsletter tooling, Choreus on-demand support for unrepped artists, and Jacky Winter Places hospitality. The Group also supports Solid Lines, an independent First Nations-led creative agency, and has recently launched new verticals including Capital Virtues (creator-led agency, Feb 2026) and Gildlings (illustration-led literary agency, May 2025).

The business model is primarily relationship-driven B2B agency work — quote-based project fees for commissions, plus subscription revenue from Academy courses and Cobbler SaaS, plus consumer sales via The Play Group and Places hospitality. Distribution is direct and producer-agent-led across three continents on a 24-hour follow-the-sun workflow, supplemented by a self-serve artist search portal, content marketing through the Dear Jacky blog and Out of Commission newsletter, and community events (Open Tabs, Office Hours). No external funding rounds, institutional investors, or disclosed financials are referenced; the company is presented as self-sustaining and founder-led.

Name

The Jacky Winter

Legal name

The Jacky Winter Group

Website

https://jackywinter.com

Company type

Private

Founded year

2006

Operating status

Operating

Headcount range

11–50 employees

Short description

The Jacky Winter Group is a privately held, founder-led creative talent agency representing 100+ illustrators, animators and makers, delivering commercial illustration, animation and placemaking projects for global brands across three offices in Melbourne, London and New York.

Ownership category

akta.pro rank

Product category

Commercial Illustration & Animation Representation Agency

akta.pro primary industry

Full-Service Artist Management (MPAIAGAA)

Keywords

• Commercial illustration agency
• Artist representation services
• Animation production studio
• Creative talent management
• Placemaking and mural commissions

Headquarters

HQ city

Collingwood

HQ country

Australia

HQ region

Oceania

Offices8 records

Markets served

GTM type

B2B

Offering type

Services

Cost components

Personnel, Operations, Marketing or Sales, Technology or R&D, Infrastructure, Supply Chain

Revenue model

1. Artist representation commission: Core revenue stream: the agency represents more than 100 illustrators, makers, animators and storyboarders globally and earns commission on commercial projects facilitated on their behalf. Historical scale: more than 12,000 successful commercial projects delivered.
2. Companion on-demand production: Fee-for-service production and project management offering for studios, brands and independent artists that need help finding the right artist, producing a brief, or scaling the creative process.
3. Spaces placemaking & physical commissions: End-to-end physical-space art commissions (murals, sculptures, placemaking, live art) including fabrication, installation, permits and project management for built environments.
4. Jacky Winter Academy course fees: Paid cohort and on-demand replay of 'The Flight Path: An Introduction to Creative Project Management', a 4-week live cohort plus replay version for freelance artists.
5. The Play Group product sales: Direct-to-consumer product sales of puzzles, games, kites and sculptural objects designed by Jacky Winter artists (viral 1000 Colours puzzle with Clemens Habicht, etc.) via playgroup.design.
6. Cobbler SaaS subscriptions: External SaaS revenue from the proprietary back-of-house CRM/quoting/invoicing platform sold to other commission-based talent agencies.
7. Capital Virtues creator-led representation: Representation and partnership fees from the creator-led sub-agency that represents visual artists in online content creation and brand partnerships.
8. Jacky Winter Places hospitality: Revenue from short-stay hospitality properties (Gardens, Waters, Park) and exhibitions/gallery programming in Victoria, Australia.

Pricing tiers

Go-to-market motion4 records

Distribution channels7 records

Marketing channels15 records

Core offering

The Jacky Winter Group is a creative production and representation studio that represents the commercial talents of contemporary applied artists — illustrators, animators, makers and storyboarders — and connects them with brands, agencies, publishers and studios. It manages end-to-end delivery of commercial illustration, animation, motion, and physical art commissions (including murals, sculptures and placemaking) via an in-house producer-agent team operating across Melbourne, London and New York on a 24-hour follow-the-sun workflow. Beyond representation, the group operates sub-brands for creator-led content, literary representation, education, consumer products, hospitality and proprietary agency software.

Product overview

The Jacky Winter Group is a creative talent agency plus ecosystem of interconnected products and ventures rather than a single unified SaaS product. At its core is the Artists roster — commercial illustration and animation talent representation — supported operationally by Companion (on-demand production and project management for studios, brands and independent artists, also delivered to freelance artists via Choreus) and by Spaces (environmental art, murals, sculptures and placemaking) and Places (residencies, hospitality and the Jacky Winter Gallery). Around this core, Jacky Winter operates a portfolio of ventures that extend its services into adjacent markets: Capital Virtues (a creator-led agency for online content creators), Gildlings (an illustration-led literary agency), Solid Lines (a First Nations-led creative agency it supports), The Play Group (consumer design products like the 1000 Colours puzzle), Jacky Winter Academy (creative project management education), Out of Commission (industry illustration/animation newsletter), PencilBooth (artist newsletter platform), Choreus (production support for unrepped artists), Cobbler (back-of-house agency operations software) and Replier (messaging utility), plus resources such as Office Hours, Field Guides, Open Tabs and the Dear Jacky editorial Q&A.

Differentiator

Problem solved

Functional benefit

Brands

• Capital Virtues: A creator-led agency representing visual artists in the world of online content creation and brand partnerships.
• Jacky Winter Academy
• Gildlings
• The Play Group
• Choreus
• Cobbler
• Out of Commission
• PencilBooth
• Replier
• Jacky Winter Places
• Jacky Winter Gallery
• Jacky Winter Spaces
• Solid Lines
• Companion

Products and services

• Artist Representation (Talent Roster) Curated representation of more than 100 commercial illustrators, animators, makers and storyboarders across Australia, the US and the UK, brokered to brands, agencies, publishers and studios. Covers Illustrators & Makers, Animation, Visualisers & Storyboarders and editorial/infographic categories.
• Companion On-demand production, project management and expert advisory service covering finding the right artist, producing a brief, scaling the creative process and managing delivery — offered to studios, brands and independent artists on a quote basis.
• Jacky Winter Spaces End-to-end physical-space art commissioning service covering placemaking, murals, sculptures, installations and live art for music festivals, office interiors, retail experiences, brand activations and 20-foot exteriors — including fabrication, installation, permits and project management globally.
• Jacky Winter Places (Gardens, Waters, Park) and Jacky Winter Gallery Short-stay hospitality properties and curated art gallery in Victoria, Australia — including Gardens (Dandenong Ranges), Waters (South Gippsland coastline), Park and the Jacky Winter Gallery in Collingwood — offering residencies, exhibitions and accommodation for creative respite.
• Capital Virtues Creator-led agency representing visual artists in the expanding world of online content creation and brand partnerships — facilitating collaborations between artists and brands that value craft and online audiences.
• Gildlings Illustration-led literary agency that grows illustrators', picture book creators' and graphic novelists' careers in publishing from cover to cover — providing literary representation for visual storytellers seeking long-term publishing careers.
• Jacky Winter Academy Online learning platform offering courses, training and resources to help commercial artists manage creative projects — flagship offering is 'The Flight Path: An Introduction to Creative Project Management' delivered as a 4-week live cohort and on-demand replay.
• The Play Group Design-led consumer products venture that turns Jacky Winter artists' work into puzzles, games, kites and sculptural objects — best known for the 1000 Colours puzzle with Clemens Habicht — sold direct-to-consumer via playgroup.design.
• Cobbler All-in-one back-of-house operations platform for commission-based talent agencies, handling quotes, invoices and everything in between; built internally over 17 years and now offered as a subscription SaaS to other agencies.
• Choreus Dedicated support platform for unrepped freelance artists offering flexible on-demand production, quoting, project management and contract negotiation services using Jacky Winter's producer-agent expertise.
• PencilBooth Micro-newsletter platform made specifically for artists, providing an image-led template for artists to send a visual snapshot of their work to subscribers — positioned as an alternative to the 'Evil Algorithm Overlord' of mainstream social platforms.
• Replier Web utility for quickly responding to questions buried in long messages by selecting the important parts and removing the rest while preserving critical information.
• Out of Commission (newsletter) Weekly curated newsletter from Jacky Winter aggregating a fresh selection of commissioned illustration and animation from across the industry.
• Solid Lines First Nations-led creative agency dedicated to representing and nurturing indigenous artists with a constant connection to identity, culture and Country — supported and worked with by Jacky Winter as an independent partner agency.

Quantifiable outcome

• More than 12,000 successful commercial projects delivered since inception
• +2 more outcomes

Named customers30 records

Segments9 records

Ideal customer profiles6 records

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Feature6 records

Partnerships

20 partnerships are on record, tiered flagship ally / strategic — supported venture, flagship venture — wholly owned sub-brand, core venture, side venture, industry body membership, minor — community partnership, minor — co-programming partner, minor — co-production partner, minor — brand and content partner, minor — agency partner, minor — brand identity partner and minor — typography partner.

• Solid Linesflagship ally / strategic — supported ventureStrategic or Co-development PartnerFirst Nations-led creative agency dedicated to representing and nurturing indigenous artists with a constant connection to identity, culture and Country. Jacky Winter is 'privileged to support and work with' the independent agency, which sits alongside the JW roster. JW also produced the Solid Yarns podcast with Solid Lines and RMIT, and the relationship is referenced on the homepage, projects page and about page.
• Capital Virtuesflagship venture — wholly owned sub-brandStrategic or Co-development PartnerCreator-led agency by The Jacky Winter Group representing visual artists in the expanding world of online content creation and brand partnerships. Prioritises the artist and their practice over metrics, facilitating collaborations with brands that value craft and online audiences. Launched February 2026.
• Gildlingsflagship venture — wholly owned sub-brandStrategic or Co-development PartnerIllustration-led literary agency by Jacky Winter, built to champion visual storytellers. Dedicated to growing illustrators', picture book creators' and graphic novelists' careers in publishing, from cover to cover. Launched May 2025.
• Choreuscore ventureTechnology or IntegrationDedicated support platform for unrepped, freelance artists using Jacky Winter's expertise. Offers flexible, on-demand production, quoting, project management and contract negotiation so independent artists get paid what they deserve. Referred from Companion and the artists page.
• Cobblercore ventureTechnology or IntegrationProprietary (almost) all-in-one back-of-house SaaS for commission-based talent agencies — quotes, invoices and everything in between. Built over 17 years of internal use and now offered externally.
• PencilBoothcore ventureTechnology or IntegrationProprietary micro-newsletter platform made specifically for artists as an alternative to the 'Evil Algorithm Overlord'. Jacky Winter itself runs the pencilbooth.com/jackywinter newsletter for its community.
• Replierside ventureTechnology or IntegrationMessaging utility developed internally to help respond to long messages quickly, then shared publicly at replier.app.
• Jacky Winter Academycore ventureStrategic or Co-development PartnerEducation platform from The Jacky Winter Group offering courses, training and resources for commercial artists on creative project management. Flagship course 'The Flight Path' is offered as a live cohort and on-demand replay. Branding by Timba Smits.
• The Play Groupcore ventureStrategic or Co-development PartnerSub-brand that turns Jacky Winter artists' work into puzzles, games, kites and other objects (viral CMYK Gradient puzzle with Clemens Habicht since 2014). Operates own e-commerce site playgroup.design.
• Out of Commissionside ventureGTM or Marketing PartnerWeekly curated newsletter from Jacky Winter highlighting recent commissioned illustration and animation industry-wide; functions as both a community resource and a brand-building channel for JW.
• Association of Illustrators (AOI)industry body membershipOthersJacky Winter Group is a member of the AOI and abides by the relevant code of practice for artist agents (footer of homepage).
• AMA (Australian music/illustration agency body referenced on footer)industry body membershipOthersJacky Winter Group is a member of the AMA and abides by the relevant code of practice for artist agents (footer of homepage).
• Agents for Changeminor — community partnershipGTM or Marketing PartnerAn assembly of illustration agencies working to foster a more diverse industry. JW provides pro bono folio reviews to diverse creative talent throughout the UK and EU.
• Lamington Driveminor — co-programming partnerStrategic or Co-development PartnerGallery space within the Jacky Winter Collingwood HQ used for curated exhibitions by JW-represented and external artists (Dryads by Kat Macleod, Motif by Shelley, Best Before by Karan Singh, etc.).
• RMIT (Royal Melbourne Institute of Technology)minor — co-production partnerStrategic or Co-development PartnerCo-production partner with Solid Lines on the Solid Yarns podcast featuring in-depth conversations with First Nations artists and industry clients.
• Timba Smitsminor — brand and content partnerStrategic or Co-development PartnerJW artist credited with logo and branding for both Jacky Winter Academy and JW'25 seasonal update; recurring co-branding collaborator.
• Super Keen (SuperKeen Studio)minor — agency partnerImplementation/ SI/ Consulting PartnerBrand strategy and web design partner credited in the website footer.
• Formworkminor — agency partnerImplementation/ SI/ Consulting PartnerWeb development partner credited in the website footer.
• Dave Foster (Fostertype)minor — brand identity partnerStrategic or Co-development PartnerDesigner of the Jacky Winter wordmark/logo, credited on the About page.
• Extrasetminor — typography partnerStrategic or Co-development PartnerDesigner of the Rebond Grotesque typeface used across the JW website, credited in the About page footer.

Scale indicators9 records

Recent moves11 records

Expansion highlights6 records

Broad incumbents

• Buck: Large independent design and motion studio with an in-house animation and illustration practice serving global brands. Comparable on the animation / motion side of JW's roster and a useful benchmark for senior creative talent and rates.
• Stink Studios: Global creative production studio with a strong animation and experiential practice. Comparable as a producer-led creative agency selling integrated storytelling, animation and placemaking to enterprise brands.
• Mother Design: Design arm of the Mother network, working at the intersection of brand, illustration and design for global clients. A useful benchmark for how JW's roster-plus-production model competes against integrated brand design networks.
• Nexus Studios: Established global animation and moving-image studio with representation and production capabilities that overlap with JW's animation and visualiser offering for enterprise brands.

Others

• Creative Review: Long-running industry publication and awards programme covering commercial illustration, design and advertising. Adjacent rather than competitive, but useful as a peer for the community/trend-report function JW performs for the illustration industry via Dear Jacky, Field Guides and Out of Commission.
• WeTransfer / WePresent: Creative platform with a large artist-discovery and editorial footprint (WePresent, Paper Planes). Adjacent rather than directly competitive, but a comparable ecosystem builder around illustration and creative talent that JW's Dear Jacky / Out of Commission / Field Guides programmes overlap with.

Direct peers

• IllustrationX: Online illustration agency and licensing platform with a global roster and self-serve search portal. Comparable to JW's artist-representation business and its public search portal / shuffle mode discovery experience.
• Handsome Frank: UK boutique illustration agency representing a roster of illustrators and animators for commercial work, with a strong publishing and editorial book of clients. Directly comparable to Jacky Winter's roster-plus-production model and its UK overlap.
• The Bright Agency: London-based illustration and animation agency representing a curated roster of commercial artists and supplying them to brands and publishers. Highly comparable in model (roster + producer-agent service) and overlap with JW on publishing and editorial illustration.
• Dutch Uncle: Independent creative agency representing commercial illustrators, animators and makers with global client work. Comparable scope and 'one-roof' producer-agent model, though typically stronger on animation direction.

Market position

Strengths4 records

Weaknesses4 records

Competitive moat6 records

Key risks6 records

Key highlights7 records

Customer concentration

• LinkedInlinkedin.com/company/the-jacky-winter-group
• Instagraminstagram.com/jackywinter
• Xx.com/jackywinter

Revenue estimate

Valuation estimate

Number of profiles

Profiles12 records

Subsidiaries14 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 The Jacky Winter