Recruiting is No Joke

Episode 96: Candidate Experience Is Broken, Here’s How to Fix It with Cailean Bailey of Design Pickle


Listen Later

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.

This episode is brought to you by Interactive EQ, the immersive talent assessment platform that goes beyond the resume. Experience first-person, real-life scenarios that reveal how candidates actually respond—not just what they say. See it in action at interactiveEQ.com and let them know Joel sent you.


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.


Resource Links

  • Design Pickle Linkedin
  • Design Pickle Official Website


  • 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.


    Recruiting is No Joke Social Media

    • LinkedIn
    • Website
    • Instagram
    • TikTok  
    • X (formerly Twitter

    • Learn more about your ad choices. Visit megaphone.fm/adchoices

      ...more
      View all episodesView all episodes
      Download on the App Store

      Recruiting is No JokeBy Joel Lalgee

      • 5
      • 5
      • 5
      • 5
      • 5

      5

      4 ratings


      More shows like Recruiting is No Joke

      View all
      Recruiting Future with Matt Alder - What's Next For Talent Acquisition, HR & Hiring? by Matt Alder

      Recruiting Future with Matt Alder - What's Next For Talent Acquisition, HR & Hiring?

      81 Listeners

      Bitch Bible by PodcastOne

      Bitch Bible

      14,602 Listeners

      Stassi by PodcastOne

      Stassi

      14,941 Listeners

      The Ben Shapiro Show by The Daily Wire

      The Ben Shapiro Show

      153,960 Listeners

      Science Vs by Spotify Studios

      Science Vs

      12,103 Listeners

      Spittin Chiclets by Barstool Sports

      Spittin Chiclets

      20,237 Listeners

      The Daily by The New York Times

      The Daily

      111,917 Listeners

      Up First from NPR by NPR

      Up First from NPR

      56,231 Listeners

      The Game with Alex Hormozi by Alex Hormozi

      The Game with Alex Hormozi

      4,370 Listeners

      The Toast by Dear Media

      The Toast

      33,020 Listeners

      The Resilient Recruiter by Recruitment Coach Mark Whitby

      The Resilient Recruiter

      59 Listeners

      All-In with Chamath, Jason, Sacks & Friedberg by All-In Podcast, LLC

      All-In with Chamath, Jason, Sacks & Friedberg

      9,207 Listeners

      The Elite Recruiter Podcast by Benjamin Mena

      The Elite Recruiter Podcast

      37 Listeners

      Politics By Faith w/Mike Slater by The First Digital Inc.

      Politics By Faith w/Mike Slater

      525 Listeners

      The AI Daily Brief (Formerly The AI Breakdown): Artificial Intelligence News and Analysis by Nathaniel Whittemore

      The AI Daily Brief (Formerly The AI Breakdown): Artificial Intelligence News and Analysis

      491 Listeners