Looks like you have JavaScript disabled. For the full Twine experience, you will need to re-enable it.

Hi, I’m Jason Castillo, an art director, designer, and illustrator with more than 20 years of experience across big-box giftware, Chicago retail, and cannabis brands. I’ve helped grow a home business into a popular retail destination in Chicago and built cannabis brands across multiple states, directing strategy and production from concept through print-ready files. I’m hands-on with sketching concepts, refining Pantone swatches, and ensuring every file is print-ready for packing and pickup. I thrive when turning ideas into scalable design systems. I can sketch concepts, build production-ready files, and collaborate across marketing, product, and executive teams to deliver cohesive visuals—from brand identity and packaging to environmental graphics and merchandise. My work is crafted to translate smoothly from screen to print and point-of-purchase, with a focus on clear storytelling and measurable impact.…Hi, I’m Jason Castillo, an art director, designer, and illustrator with more than 20 years of experience across big-box giftware, Chicago retail, and cannabis brands. I’ve helped grow a home business into a popular retail destination in Chicago and built cannabis brands across multiple states, directing strategy and production from concept through print-ready files. I’m hands-on with sketching concepts, refining Pantone swatches, and ensuring every file is print-ready for packing and pickup. I thrive when turning ideas into scalable design systems. I can sketch concepts, build production-ready files, and collaborate across marketing, product, and executive teams to deliver cohesive visuals—from brand identity and packaging to environmental graphics and merchandise. My work is crafted to translate smoothly from screen to print and point-of-purchase, with a focus on clear storytelling and measurable impact.

Jason Castillo





Hi, I’m Jason Castillo, an art director, designer, and illustrator with more than 20 years of experience across big-box giftware, Chicago retail, and cannabis brands. I’ve helped grow a home business into a popular retail destination in Chicago and built cannabis brands across multiple states, directing strategy and production from concept through print-ready files. I’m hands-on with sketching concepts, refining Pantone swatches, and ensuring every file is print-ready for packing and pickup. I thrive when turning ideas into scalable design systems. I can sketch concepts, build production-ready files, and collaborate across marketing, product, and executive teams to deliver cohesive visuals—from brand identity and packaging to environmental graphics and merchandise. My work is crafted to translate smoothly from screen to print and point-of-purchase, with a focus on clear storytelling and measurable impact.…Hi, I’m Jason Castillo, an art director, designer, and illustrator with more than 20 years of experience across big-box giftware, Chicago retail, and cannabis brands. I’ve helped grow a home business into a popular retail destination in Chicago and built cannabis brands across multiple states, directing strategy and production from concept through print-ready files. I’m hands-on with sketching concepts, refining Pantone swatches, and ensuring every file is print-ready for packing and pickup. I thrive when turning ideas into scalable design systems. I can sketch concepts, build production-ready files, and collaborate across marketing, product, and executive teams to deliver cohesive visuals—from brand identity and packaging to environmental graphics and merchandise. My work is crafted to translate smoothly from screen to print and point-of-purchase, with a focus on clear storytelling and measurable impact.

Available to hire

Hi, I’m Jason Castillo, an art director, designer, and illustrator with more than 20 years of experience across big-box giftware, Chicago retail, and cannabis brands. I’ve helped grow a home business into a popular retail destination in Chicago and built cannabis brands across multiple states, directing strategy and production from concept through print-ready files. I’m hands-on with sketching concepts, refining Pantone swatches, and ensuring every file is print-ready for packing and pickup.

I thrive when turning ideas into scalable design systems. I can sketch concepts, build production-ready files, and collaborate across marketing, product, and executive teams to deliver cohesive visuals—from brand identity and packaging to environmental graphics and merchandise. My work is crafted to translate smoothly from screen to print and point-of-purchase, with a focus on clear storytelling and measurable impact.

Skills

Illustration

Brand Identity

Logo

Experience Level

Illustration

Expert

Brand Identity

Expert

Logo

Expert

Work Experience

Creative Lead at CASTILLO CREATIVE CO.

January 1, 2025 - Present

Founded an independent creative studio partnering with multi-state cannabis operators, local businesses and start-ups. Designed daily email marketing campaigns for Trulieve Dispensaries in the Florida market. Art direction, design, and production for Grassroots 420 marketing campaign deployed across a dozen states. Built Second Chances Mfg. brand from the ground up, including visual identity, packaging, merchandise, and e-commerce site. Coordinated uniform and merchandise program and environmental graphics for a new dispensary in New Jersey.

Art Director (Full Time Contract) at Curaleaf

January 1, 2020 - January 1, 2025

Retained as a full-time creative contractor following Curaleaf’s acquisition of Grassroots. Developed brand identity, packaging, influencer kits, and campaign creative for Anthem, a multi-state product brand. Extended the Grassroots strain illustration system across new retail and merchandise in several state markets. Served as brand steward through merger; helped relaunch the brand across 14 states with a new visual identity. Collaborated on an enterprise-wide brand refresh, building scalable design systems and CRM templates adopted across 14 states. Produced retail, digital, environmental, and wholesale creative across multiple state markets for several established in-house brands.

Art Director at Grassroots

January 1, 2018 - January 1, 2020

First Art Director hired during a period of explosive growth, helping establish creative systems and product brands as Grassroots (product) and Herbology (retail) expanded into a 14-state cannabis platform. Art directed the first strain illustration system that became the brand’s visual signature across retail, social, and merchandise. Built the team’s project management system (Monday.com) and managed a junior designer; served as the go-to for creative decisions across the organization.

Art Director at Revolution Global

January 1, 2015 - January 1, 2018

Art Director for Illinois’ early legal cannabis brand, designing packaging across the full product portfolio including flowers, hash, concentrates, and vapes as regulatory framework evolved. Worked closely with the founder on daily brand decisions and launches. Built the brand’s retail marketing and dispensary presence from scratch in a market with no precedent.

Senior Designer (Contract) at Transit Tees

January 1, 2012 - January 1, 2015

Created original illustrations celebrating Chicago neighborhoods and culture for retail tees, prints, and gift goods. Designed event graphics, merchandise, and signage for major Chicago street festivals including Do Division, Wicker Park Fest, and West Fest.

Packaging Designer & Illustrator at DESIGNPAC GIFTS

January 1, 2007 - January 1, 2009

Designed packaging and point-of-purchase materials for large seasonal product lines spanning dozens of SKUs, creating private label and licensed products for retailers including Target, Sam’s Club, Costco, and Walgreens. Developed original character illustrations and packaging systems for seasonal consumer products, creating retail-ready artwork that balanced storytelling, merchandising, and production requirements. Translated product ideas into concept artwork for overseas manufacturing partners.

Packaging Designer & Illustrator at DESIGNPAC GIFTS

January 1, 2010 - January 1, 2012

Contract period focusing on packaging and point-of-purchase materials for seasonal product lines; private label and licensed products; packaging systems; illustrations for overseas manufacturing partners.