Hiring more women in tech isn’t enough if companies can’t retain them. In this episode, Gillian Emerson, Head of Talent & Partnerships at Toast, breaks down what actually drives equity, flexibility, and long-term retention in modern hiring.

Just a few things that we cover in this week's episode:

• Why diverse pipelines fail without retention-first systems
• How flexibility and choice impact women staying in tech
• What happens when company names and credentials are removed from candidate reviews
• How return-to-office mandates affect hiring and retention
• Where AI helps hiring—and where it quietly creates new risks

🍞 About This Week's Guest

Gillian Emerson is the Head of Talent & Partnerships at Toast, where she helps tech companies hire and retain more women by redesigning recruiting systems from the ground up. As one of Toast’s first employees, Gillian helped build its recruiting function while also growing a membership community that supports women in tech across North America.

📄 About Looks Good on Paper / Willo

Every week Looks Good on Paper explores how trends in hiring, talent, and work are going beyond what shows up on a résumé.

Episode Chapters

00:00 – Welcome & Gillian’s journey to Toast
01:40 – Building Toast’s recruiting function from scratch
03:50 – Why women leave tech—and why retention matters
04:50 – The biggest hiring mistake companies keep making
06:40 – Flexibility, choice, and return-to-office policies
09:00 – Rethinking how candidates are evaluated
11:00 – Why pedigree and big names can mislead hiring
13:30 – Hiring beyond resumes and “shiny” credentials
16:00 – How Toast experiments with different hiring approaches
17:30 – AI in hiring and its unintended consequences
19:00 – Hiring and recruiting trends for 2026

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Show Resources

• Willo: willo.video - The most cost-effective way to screen candidates at scale. Interview candidates anywhere & at any time
• CV Free Toolkit: cvfree.me/join - Break up with the CV and get everything you need to modernize your hiring approach with skills-based assessments
• Anita Chauhan: linkedin.com/in/anitachauhan - Connect with the host