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Episode 96: Candidate Experience Is Broken, Here’s How to Fix It with Cailean Bailey of Design Pickle
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What’s really happening behind the scenes when you hit “apply” on a job posting? Does candidate experience actually impact business results, or is it just a feel-good metric? Today’s episode will make you rethink how hiring really works, whether you’re a recruiter or a job seeker. Joel Lalgee sits down with Cailean Bailey, Head of Global Talent Acquisition at Design Pickle, a creative tech platform with over 550 employees in 15 countries. Cailean drops actionable insights on building candidate experiences that actually matter — and why most companies are getting it wrong.
You’ll hear Cailean break down the realities of startup life, including why hiring isn’t about ping-pong tables or equity dreams, but about handling chaos, bringing structure, and delivering business outcomes. She shares how her team uses behavioral competencies like curiosity and adaptability to make smarter hires, and reveals their secret weapon: tracking candidate Net Promoter Scores (NPS). If you’ve ever wondered how to measure real hiring success or get leadership buy-in for better processes, this episode is a goldmine.
Stick around as they explore what it really takes to stand out in today’s noisy job market — whether you’re building a team or trying to get hired. Cailean explains why providing feedback, setting expectations, and treating candidates like customers can make you an outlier in the best way possible. Plus, she shares how Design Pickle keeps candidates engaged from application to onboarding, and why companies of any size can implement “surprise and delight” moments without breaking the budget.
In this episode:
00:01:12 – Meet Cailean Bailey and Her Journey to Design Pickle
00:04:53 – Growing Design Pickle During COVID-19
00:10:41 – From Soccer Coach to Recruiter: Cailean's Career Pivot
00:24:07 – Agency vs. In-House Recruiting Realities
00:34:15 – The Hidden Truths About Working in Startups
00:39:47 – Measuring Curiosity and Drive in Interviews
00:50:25 – Startup Chaos and Proving Yourself on Day One
01:03:13 – Candidate NPS: A Game-Changer in Candidate Experience
01:15:32 – Why Great Candidate Experience Doesn’t Need Fancy Tools
01:25:58 – Connecting Hiring to Business Outcomes and ROI
01:39:12 – Why Candidate Experience Is a Marketing Play
01:51:47 – Setting Honest Expectations About High-Performance Cultures
02:02:17 – Final Thoughts and Where to Connect with Cailean Bailey
About Cailean Bailey
Cailean (pronounced Kay-lynn) is the Head of Global Talent Acquisition at Design Pickle, an AI-powered creative platform with a global design workforce. He leads a distributed team that manages 30,000+ applications annually across 14 countries, hiring for roles in Engineering, Product, Marketing, Sales, and Creative.
Before recruiting, Cailean was a Division I soccer coach, where he learned to build high-performing teams and guide people through pressure and growth. That mindset now fuels his approach to talent.
Outside of work, he’s into F45 workouts, strong coffee, globe-trotting (40+ countries), and waiting—sometimes patiently—for Manchester United’s return to glory.
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About Joel Lalgee
Joel Lalgee is an internationally known recruitment leader and coach who has helped thousands of recruiters build their brands online. In 2015, Joel started recruiting for a small start-up agency in Milwaukee. He quickly found his passion for recruitment. In 2019, he discovered content marketing, publishing his first posts on Linkedin. Since then, he has grown to over 400k followers, and his content has been seen over 1 billion times. In 2023, he started a business specializing in coaching recruiters, marketing consulting, and influencer partnerships.
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