EP2: AI-First HR & Leading Through Crisis with Shirley Baumer

Now to Next with Jason Averbook

A place to sit down with trailblazers, truth-tellers, and builders who are actively reshaping our world.

EP2: AI-First HR & Leading Through Crisis with Shirley Baumer

E2 • Aug 21, 2025 • 50 mins

In this powerful episode of Now to Next, Jason Averbook sits down with Shirley Baumer—co-founder and Chief Product Officer of DreamTeam—for a raw and insightful conversation about building a company amidst war, reimagining HR tech from the ground up, and what true leadership looks like in 2025. From her early days as a journalist to scaling monday.com into a billion-dollar company, Shirley’s journey is anything but ordinary. She shares how DreamTeam was built as an AI-native, product-led people platform—not just to digitize outdated HR processes, but to rethink them entirely. You’ll hear firsthand how she and her team launched features while sheltering from missile attacks, why she believes presence is the ultimate leadership trait, and how AI should be designed not just for power—but for trust and humanity.

Key Points

Startup in a war zone: Building a tech company while navigating missile threats in Israel
From monday.com to DreamTeam: Lessons from helping scale one of the world’s most successful IPOs
AI-native vs AI-added: Why building with AI from scratch is a game-changer for HR systems
Zero admin, full flexibility: How DreamTeam empowers teams to build and adapt workflows in minutes
Human skills in the AI age: Why empathy, presence, and critical thinking matter more than ever
Trust and ethics in AI: Shirley’s 3-layer framework for stewarding AI responsibly

Guest Bio:

Shirley Baumer is the Co-founder and Chief Product Officer of DreamTeam, an AI-native people management platform designed to replace outdated HR systems with agile, intuitive, and fully customizable workflows.

Previously, she was the first product manager at monday.com, where she helped scale the company from 30 to over 2,000 employees and from $6M to $1B in ARR—culminating in one of the most successful IPOs of 2021. Shirley is a second-time entrepreneur with a background in journalism and behavioral economics. Based in Israel, she brings a rare blend of grit, product leadership, and human-centered thinking to the future of work.

Follow Jason Averbook:

Substack: https://substack.com/@jasonaverbook X: https://x.com/jasonaverbook LinkedIn: https://www.linkedin.com/in/jasonaverbook Instagram: https://www.instagram.com/jasonaverbook YouTube: https://www.youtube.com/@nowtonextwithjasonaverbook Facebook: https://facebook.com/jasonaverbook

Follow Shirley Baumer:

Linkedin: https://www.linkedin.com/in/shirleyjb/?originalSubdomain=il

Speakers

Jason Averbook

Host • 43%

Shirley Baumer

Guest • 57%

Chapters

0:00	Introduction and guest welcome
1:28	Shirley Baumer's career journey and lessons from entrepreneurship
3:41	The impact of the current conflict on business in Israel
6:44	Building a company during wartime and HR technology evolution
10:14	Breaking old school HR processes with a product-led approach
19:23	Concept of a people OS, AI native platforms, and integration with apps
24:01	Reducing friction for employee HR tasks through AI
31:14	Simplifying complex tasks and changing skill requirements in HR
38:14	Balancing AI with human skills and the importance of leadership
44:32	Vision for Dream Team's future and maintaining organizational identity
47:29	Learning through experience, action, and closing remarks

Transcript

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