Now to Next with Jason Averbook

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 She shares how DreamTeam was built as an AI-native, product-led people platform—not just to digitize outdated HR processes, but to rethink them entirely.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. 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is the Co-founder and Chief Product Officer of DreamTeam, an AI-native people management platform designed to replace outdated HR systems with agile, intuitive, and fully customizable workflows.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 (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

In this candid first episode of Now to Next, Jason Averbook sits down with Jess Von Bank for a deeply human conversation on curiosity as a leadership superpower, why burnout is a design flaw of legacy work systems, the difference between optics and impact, a clear-eyed take on DEI and equity, and how AI’s value exchange should be measured in human impact. From growing up in rural North Dakota to building a global community, leading Diverse Daisies, raising three daughters, even racing for the “thrill of the hunt,” Jess shares how purpose, community, and reciprocity shape better systems—for people and for business. Guest Bio: Jess Von Bank is a Global Leader in HR Transformation & Technology Advisory, an industry analyst at Mercer and Now of Work Community leader, and President of Diverse Daisies. A prominent voice in HR and work tech, she is known for shaping industry dialogue, advising solution providers on product–market fit and storytelling, and leading Diverse Daisies, a non-profit dedicated to expanding opportunities for girls. A sought-after speaker and writer, Jess focuses on redesigning systems—work, technology, and policy—so people and business can thrive together. She brings a unique blend of strategic insight, community leadership, and human-centered vision to every stage she steps on and every organization she advises. 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 Jess Von Bank: Linkedin: https://www.linkedin.com/in/jessvonbank/ (0:00) Introduction and welcome (1:06) Jess Von Bank's background and storytelling in leadership (5:12) The role of curiosity in system design and burnout (11:49) Common threads in varied roles and the optics versus impact in leadership (20:19) Leadership challenges and DEI perspectives (27:03) Addressing gaps in DEI: Data, design, and understanding workforce needs (30:11) AI: Opportunities, challenges, and its future impact (37:53) Focusing on people over jobs and relearning in the AI era (46:53) Lightning round: Future of companies and skills for HR leaders (52:29) Defining the future of work and redefining reciprocity (54:35) Closing remarks

In this episode of Now to Next, Jason Averbook delves into the podcast's mission, emphasizing the urgency of speed in today's business environment and the importance of innovative communication channels. Drawing insights from conversations with leaders who are at the forefront of driving change, Jason explores the dynamics of transformation in the modern workplace. He also discusses the variety of content that listeners can expect, alongside notes on the publishing schedule. The episode concludes with a reflection on the journey ahead, setting the stage for future discussions that aim to reshape and redefine the business landscape. (0:12) Introduction and mission of Now to Next with Jason Averbook (0:35) The need for speed in business and innovative communication channels (0:47) Insights from leaders on driving change (1:19) Content variety and publishing schedule notes (1:59) Closing remarks