Welcome back to the FNDN Series, where we continue our deep dive into startup people and reward practices, with industry leaders from across the startup world.

In our conversation with Hallie Condon, VP of People at Chili Piper, we unpack what it actually looks like to build AI deep into a people function. We dive into how her small team decides what to automate and what to keep human, the "company brain" she built so institutional knowledge doesn't walk out the door when someone leaves, and the surprising shift in context she's losing now that employees go to AI before they come to the people team. We also get into her sharpest take of all: why the traditional promotion path expects people to do the job for free before anyone will pay them for it. Keep watching to hear how AI is reshaping people operations, performance reviews, and the employer-employee relationship.

Join Startup People Summit, a one-day virtual conference designed for startup People leaders who want practical insight, honest conversations and proven approaches to scaling their People function — get your ticket here: www.startuppeoplesummit.com 



Chapters:
00:46 Guest Introduction: Hallie Condon, VP of People at Chili Piper
01:58 Managing a Fully Remote Team Across 36 Countries
04:07 How AI Shows Up in the People Function Day-to-Day
05:19 Automating Separation Letters and Admin Work
06:56 Using AI to Cross-Check Budgets Fairly
08:31 No Clean Strategy: Automating as Problems Come Up
10:29 The Tiered System: What Should and Shouldn't Be Automated
13:53 Introducing "Company Brain": Chili Piper's AI Knowledge Repo
16:03 Skills Library and Role-Based Onboarding
17:56 How Decision Memos Get Documented and Indexed
19:37 Company Brain and Reducing Attrition Risk
21:47 Fewer Conversations: Are People Going to AI Instead of HR?
23:20 Balancing Context-Gathering with Employee Trust
26:14 What the Memory System Deliberately Doesn't Retain
28:14 More Time for Deep Work, Fewer Casual Check-Ins
29:43 What Companies Got Wrong with AI-Driven Layoffs
32:36 The Breaking of the Employee-Employer Bargain
36:07 Gen Z, Boundaries, and the "Do the Job for Free First" Problem
39:01 Rethinking How Companies Assess Impact and Potential
40:04 Chili Piper's Approach: Promoting Early, Pay Range Transparency
42:06 Why People Managers Don't Get Paid More at Chili Piper
45:43 Introducing the "Impact Intelligence" Tool
50:30 Building Performance Principles with AI's Help
51:33 Final Advice: Get Curious About AI and Rethink Reciprocity

Connect with Hallie

Visit: chilipiper.com
https://www.linkedin.com/in/hallie-condon-0b181325/ 

Resources Mentioned

Company Mentioned:

Chili Piper - B2B SaaS company where Hallie is VP of People, with ~150 employees across 36 countries
Oyster - Global employment/compliance platform Hallie credits for managing their distributed workforce
Claude - AI assistant used to power Chili Piper's "Company Brain" and impact intelligence tools
Granola - Meeting notes tool Hallie uses to capture context from conversations

More FNDN Episodes:
Spotify: https://open.spotify.com/show/4GeBIeZOKrFxG1oiiPxmiM
Apple Podcast: https://podcasts.apple.com/us/podcast/fndn-series/id1794263484