Anna Smylie Caldwell



Brand Systems Design Lead
Block, Inc. (Dec. 2021—Present)

Communications Designer
Square, Inc. (2018–2021)

Graphic Designer
Wells Fargo (2015–2018)

Data Vis Design Intern
Pitch Interactive (Summer 2015)

Graphic Designer
FNewsmagazine (2014–2015)

Graphics Intern
Chicago Tribune (2014–2015)

Publication and Exhibits

Kazoo magazine
Quarterly print publication (Jan. 2022 – Present)

The Square Design Blog
Monthly digital publication (2020–2021)

Now Serving Coffee
Event for Square’s NYC Pop-up Shop (2018)

Big Talk
Exhibit at SF Design Week Hub (2017)

Exhibit with Voyeur Theatre Collective in Chicago (2015)

MFA Show 2015
Exhibit in The Sullivan Galleries in Chicago (2015)

The Design Show
Exhibit with The Chicago Art Dept. (2015)


MFA, Visual Communication Design
School of the Art Institute of Chicago (2015)

BJ, Journalism & Strategic Communication

University of Missouri (2012)

Technical Skills

Graphic design & data vis
Adobe CC, Figma, Google Suite, Microsoft Suite, Keynote

Digital design
Figma, HTML, CSS, WordPress, Contentful

Awards and Honors

Wells Fargo (2016 & 2017)

Designer of the Year and First, Second, and Honorable Mention in Illustration
The Student Society for News Design (2015)

Design for Best Newspaper Opinion Spread
College Media Association (2015)

Anna ︎ Caldwell (202︎)