About
Ryan Essmaker is a creative director and designer with 20+ years of experience helping companies—and the people behind them—communicate with clarity, depth, and soul.
His work spans brand, product, and storytelling. He’s led design across early-stage startups, scaled in-house teams, developed design systems rooted in clarity and expression, and produced expressive video campaigns. His approach blends emotional intelligence with creative leadership, balancing high standards with collaboration and trust.
Ryan began his career running an independent design practice during the early web, focused on standards and responsive design. He later co-founded The Great Discontent, a magazine and interview series known for its honest, artful storytelling. Among the 300+ creatives featured: Leon Bridges, Paloma Lanna, Sharon Van Etten, Reggie Watts, Roxane Gay, Michael Bierut, Stefan Sagmeister, Tavi Gevinson, Seth Godin, and Mara Hoffman. During that time, he also worked with agencies like Fictive Kin and Crush & Lovely, designing for clients including Kickstarter, NatGeo, Adobe, Mailchimp, NBCUniversal, and the City of New York.
More recently, Ryan led rebrands and served as lead product designer at Tellie and Simplecast. At Simplecast, his work across brand, product, and marketing helped position the company for acquisition by SiriusXM. At Tellie, he shaped the brand, led product design, and produced a video campaign that brought expressive, creator-focused energy to the platform. At Modern Treasury, he built the internal video practice from scratch, crafting human-centered storytelling for a complex B2B product suite.
He’s currently based in Austin, Texas, and available for freelance and contract work. He’s also open to the right full-time opportunity—particularly where creative direction, storytelling, and product design intersect.
In addition to his design work, Ryan co-runs Pretty Machine 🫦, a creative studio focused on photo and video for fashion, beauty, and boundary-pushing brands.
👉 Let’s connect
His work spans brand, product, and storytelling. He’s led design across early-stage startups, scaled in-house teams, developed design systems rooted in clarity and expression, and produced expressive video campaigns. His approach blends emotional intelligence with creative leadership, balancing high standards with collaboration and trust.
Ryan began his career running an independent design practice during the early web, focused on standards and responsive design. He later co-founded The Great Discontent, a magazine and interview series known for its honest, artful storytelling. Among the 300+ creatives featured: Leon Bridges, Paloma Lanna, Sharon Van Etten, Reggie Watts, Roxane Gay, Michael Bierut, Stefan Sagmeister, Tavi Gevinson, Seth Godin, and Mara Hoffman. During that time, he also worked with agencies like Fictive Kin and Crush & Lovely, designing for clients including Kickstarter, NatGeo, Adobe, Mailchimp, NBCUniversal, and the City of New York.
More recently, Ryan led rebrands and served as lead product designer at Tellie and Simplecast. At Simplecast, his work across brand, product, and marketing helped position the company for acquisition by SiriusXM. At Tellie, he shaped the brand, led product design, and produced a video campaign that brought expressive, creator-focused energy to the platform. At Modern Treasury, he built the internal video practice from scratch, crafting human-centered storytelling for a complex B2B product suite.
He’s currently based in Austin, Texas, and available for freelance and contract work. He’s also open to the right full-time opportunity—particularly where creative direction, storytelling, and product design intersect.
In addition to his design work, Ryan co-runs Pretty Machine 🫦, a creative studio focused on photo and video for fashion, beauty, and boundary-pushing brands.
👉 Let’s connect
CV
CURRENT
Creative Director & Designer
Freelance
Pretty Machine — Co-Founder
Photo & video for fashion, beauty, and boundary-pushing brands.
Freelance
Pretty Machine — Co-Founder
Photo & video for fashion, beauty, and boundary-pushing brands.
2022-2025
Modern Treasury — Principal Brand Designer
Built the in-house video function and produced campaign, product, and customer content for a complex B2B platform.
Built the in-house video function and produced campaign, product, and customer content for a complex B2B platform.
Tellie (now Astral) — Head of Design, Lead Product Designer
Led product and brand design through a rebrand and pivot; shipped core experiences and launched a video campaign.
Led product and brand design through a rebrand and pivot; shipped core experiences and launched a video campaign.
2018-2020
Simplecast — Head of Design, Lead Product Designer
Led creative and product design, including a full app redesign and rebrand prior to acquisition by SiriusXM.
Led creative and product design, including a full app redesign and rebrand prior to acquisition by SiriusXM.
2011-2019
The Great Discontent — Cofounder, Creative Director
Cofounded and directed the long-form interview magazine across digital, print, film, and live events.
Cofounded and directed the long-form interview magazine across digital, print, film, and live events.
2015-2018
Fictive Kin — Senior Designer, Product Designer
Designed internal products and client work for Kickstarter, NatGeo, and NYC; developed concepts, interfaces, and visual systems.
Designed internal products and client work for Kickstarter, NatGeo, and NYC; developed concepts, interfaces, and visual systems.
2011-2014
Crush & Lovely — Creative Director, Head of Product
Led design for clients including NBCUniversal and Adobe; helped scale the studio and open a new SoHo office.
Led design for clients including NBCUniversal and Adobe; helped scale the studio and open a new SoHo office.
2000-2011
Independent Work
Designed for small businesses and artists during the early web, with a focus on web standards and responsive design.
Designed for small businesses and artists during the early web, with a focus on web standards and responsive design.