Cailean Bailey

Manager, Global Talent Acquisition
Design Pickle

Cailean Bailey is a TA leader with expertise in global recruiting, scaling startups, and onboarding, all done with a creative spin and an engaging hiring process. He leads Global Talent Acquisition at Design Pickle, a creative services platform with a built-in design workforce, recruiting across Technical, GTM, and Creative roles. Based in Scottsdale, AZ, Cailean transitioned from coaching Division I men's soccer into corporate talent acquisition.

Design Pickle

Cailean Bailey’s Session(s)


10:00–10:40 am PDT —

Crafting a Candidate Experience That Stands Out

Talent Acquisition leaders can ditch the cookie-cutter playbook and create experiences that candidates will remember as candidates but also as future brand advocates. This session is all about keeping hiring human — by balancing creativity and technology, transparency, a bit of creative flair, and aligning a creative and engaging candidate experience that mirrors your onboarding and employee experience — with the ultimate goal of increasing candidate and employee satisfaction.


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