Creative leader with a track record of building standout brands, scaling design teams, and driving impact through strategic, insight-led design. I specialize in rebranding, design systems, and growth-stage execution from startup to IPO. Known for elevating creative standards, mentoring high-performing teams, and leading cross-functional work that gets results.

Experience

Head of Visual Design

OCTOBER 2023 – Present

Currently leading the creative function at Checkmate, where I spearheaded a full rebrand and website redesign that tripled daily sessions and elevated our industry position. I built scalable design systems, implemented agile workflows, and rolled out new stakeholder processes to improve collaboration and output. I also developed a mentorship program for the design team and helped establish a culture grounded in trust, ownership, and creative excellence.

Associate Director, Design

July 2023 – SEPTEMBER 2023

Brand Designer

September 2020 – JULY 2023

Led Olo’s brand evolution through IPO, scaling design operations to support 2M+ daily orders across 600+ restaurant brands. I directed brand execution across web, UX, and video, and designed high-impact experiences for our national customer conferences. I also implemented brand systems, mentored junior designers, and ensured cross-channel brand consistency across marketing, product, and internal communications.

UI and Visual Designer

FEBRUARY 2020 – SEPTEMBER 2020

Collaborated with cross-functional teams to design intuitive, on-brand digital experiences for a range of clients. My work included UI design, wireframes, and interactive prototypes, as well as establishing visual guidelines and scalable systems. I also supported product direction through market insights and user-centered thinking.

Sr. Designer and Brand Manager

SEPTEMBER 2010 – JanUARY 2018

Directed brand strategy and creative execution for mission-driven clients across education, poverty alleviation, and global development. My work contributed to measurable growth and funding increases for several nonprofits. I also ran a hands-on internship program, facilitated human-centered design workshops, and created scalable internal systems for design delivery.

Education

University of Arkansas at Little Rock

Fine & Studio art

Attended 2004 – 2006

Proficiencies

Figma

Adobe Creative Suite

Webflow

Framer

Hubspot

Guru

Notion

Asana

Jira/Confluence

HTML & CSS

Specialties

Brand strategy and positioning

Creative direction and team development

Messaging and narrative systems

Design systems and creative operations

Creative systems that scale teams and

strategy

Product positioning and storytelling

SaaS and emerging tech brand strategy

Website architecture and content strategy

Campaign and experiential creative

Executive and investor communications

Cross-functional collaboration and

influence

Internal brand adoption and culture

integration

Agile creative workflows

Talent mentorship and leadership

Agency and partner collaboration

Brand strategy and positioning

Creative direction and team development

Messaging and narrative systems

Design systems and creative operations

Creative systems that scale teams and

strategy

Product positioning and storytelling

SaaS and emerging tech brand strategy

Website architecture and content strategy

Campaign and experiential creative

Executive and investor communications

Cross-functional collaboration and

influence

Internal brand adoption and culture

integration

Agile creative workflows

Talent mentorship and leadership

Agency and partner collaboration

© Jenna Dixon 2025

© Jenna Dixon 2025

© Jenna Dixon 2025