Getting diverse candidates in the door is the easy part. Keeping them is where most companies quietly fail — and they usually don't notice until the people they worked hardest to recruit have already left.

Diversity hiring without a retention strategy isn't equity. It's a pipeline with a hole in it. And the cost — in team morale, employer brand, and actual dollars — compounds every time it happens.

Gillian Emerson, Head of Talent and Partnerships at Toast, knows what a retention strategy actually looks like versus what gets put in a deck. In this episode of Looks Good on Paper, she breaks down why equity has to be embedded in systems and not just hiring goals, what flexibility really means to employees versus what companies think it means, and how to build teams that don't just represent diversity on paper.

What you'll learn:

→  Why diversity hiring without retention strategy produces churn, not equity

→  What flexibility actually means to employees versus what companies think it means

→  How to embed equity into hiring systems rather than just hiring targets

GUEST

Gillian Emerson — Head of Talent & Partnerships, Toast

LinkedIn → https://www.linkedin.com/in/gillianemerson/

YOUR HOST

Anita Chauhan — Fractional CMO, host

LinkedIn → https://www.linkedin.com/in/anitachauhan/

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

LISTEN & FOLLOW

Spotify          →  https://open.spotify.com/show/0dbfz6y0tMq3crViHQD66H

Apple Podcasts   →  https://podcasts.apple.com/podcast/id1625835562

All episodes     →  https://looksgoodonpaper.buzzsprout.com

WATCH ON YOUTUBE - https://youtu.be/_w9ScoYMtCk

POWERED BY WILLO

Hire humans, not resumes  →  https://www.willo.video/looks-good-on-paper

CONNECT WITH US

LinkedIn  →  https://www.linkedin.com/company/10170893

If this episode changed how you think about hiring, share it with one person who needs to hear it. And subscribe — we're rewriting the rules of hiring, one episode at a time.

Diversity hiring without a retention strategy is a pipeline with a hole in it. Companies that focus on diverse recruitment but haven't examined their promotion criteria, pay equity, flexibility policies, and management culture will keep losing the people they worked hardest to hire.

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