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

Shanal Kazi breaks down why so many hiring decisions still optimize for comfort over capability — and what changes when you stop treating the CV as your strongest signal. We cover the hidden bias against non-linear careers, and what “better signal” could look like in 2026.

What you will learn:

• The real cost of hiring for polish and big brand names
• The hidden bias toward linear career paths (and what it screens out)
• How to assess capability, self-awareness, and growth without over-indexing on CVs
• Why role clarity and honesty matter more than “culture fit” clichés
• What 2026 hiring should prioritize as AI becomes embedded in the process

👓 About Our Guest
Shanal Kazi is an experienced Manager of Engagement & Inclusion and Talent Management, With more than 14 years of experience across organizational development, culture, and enterprise change in complex global environments.

She brings a global lens shaped by living across countries, rebuilding her career as an immigrant in Canada, and seeing first-hand how resumes can hide the attributes that actually predict success.

📄 About Looks Good on Paper / Willo
Looks Good on Paper is a podcast by Willo exploring how hiring, talent, and work are changing beyond the resume.

▶ Watch the full episode here: https://youtu.be/bU29ODKDmmQ

Chapters
00:00 — Welcome + why this episode starts 2026
00:54 — A career that “doesn’t make sense on paper”
01:45 — Early career barriers and bias in hiring
03:15 — What resumes fail to capture about candidates
04:28 — Biggest hiring mistake: comfort over capability
06:17 — Role clarity, honesty, and working across cultures at Samsung
08:09 — Hidden bias: linear careers (and why it’s flawed)
10:58 — If CVs disappeared: what replaces them
14:00 — 2026 trends: AI, transparency, and diversity of thought

If this episode was useful, follow the show and leave a quick rating or review — it helps more hiring teams find these conversations.

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

Most companies think growth means hiring more people. According to Mike Bettley (Senior Director of Talent, StackAdapt), that mindset is exactly what leads to wasted budgets, bloated teams, and stalled growth.

In this episode of Looks Good on Paper, Mike explains why hiring is the most expensive decision a company makes — and why adding headcount is often a lazy substitute for real strategy. Drawing on his experience at Google, Thomson Reuters, and OpenCare, Mike breaks down how high-growth companies decide who to hire, when to hire, and what problem each role is actually meant to solve.

This is a must-listen for founders, hiring managers, recruiters, and talent leaders navigating today’s volatile job market.

In this episode, we're covering

• Why “we need more people” is usually the wrong answer
• How to identify the real business bottleneck before hiring
• When scaling too early creates long-term damage
• Why company pedigree (Google, Meta, etc.) is a misleading hiring signal
• Whether CVs still matter in an AI-driven hiring market
• The skills talent leaders will need heading into 2026

👤 About Mike Bettley

Mike Bettley is Senior Director of Talent at StackAdapt, leading global hiring across a company that has grown from 800 to over 1,600 employees in just two years. His career spans Google, Thomson Reuters, and high-growth startups, giving him a rare perspective on what actually works at every stage of scale — from scrappy startups to global enterprises.

👉 https://www.linkedin.com/in/michaelbettley/

About Looks Good on Paper

Looks Good on Paper, powered by Willo, explores modern hiring, talent strategy, leadership, and how work is changing beyond what shows up on a résumé.

Episode Chapters

00:00 – Why hiring is more dangerous than people think
01:40 – From Google to startups to StackAdapt
03:10 – Why hiring is the most expensive business decision
04:15 – The biggest hiring mistake companies keep making
05:30 – Headcount vs solving real business problems
07:00 – CEOs, hiring strategy, and the 80/20 rule
08:25 – Why hiring too far ahead backfires
09:25 – The hidden bias of company pedigree
13:55 – Can hiring work without CVs?
15:50 – Writing, communication, and AI-era skills
19:45 – The skills talent leaders need in 2026
21:40 – Final thoughts

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