In this episode of the Unlearn Podcast, I sit down with Cass Pratt, Chief Human Resources Officer at Progyny, to explore how HR transformation with AI is redefining the role of people leaders. From building bots to boost employee experience to reshaping how we think about roles in an automated world, Cass shares an honest look at how she’s bringing people along on a transformation journey—with curiosity, experimentation, and heart.
We discuss her pivotal decision to say yes to opportunities beyond her comfort zone, the strategic shifts she’s leading inside a fast-scaling company, and why the future of HR is about enhancing humanity, not replacing it. If you’re wondering what leadership looks like when AI meets empathy, this one’s for you.
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Key Takeaways
- Unlearning expertise-dependence: Cass shifted from relying on experts to co-creating solutions with AI tools before engaging others.
- AI as a force for elevation: At Progyny, AI is used to give employees time back, not take roles away—enabling deeper focus on human-centric work.
- Low-code leadership: Cass, a self-described non-technical leader, built HR bots and reimagined policies through practical AI applications.
- Scaling culture through consistency: AI chatbots improved response times, standardized answers, and gave insight into employee concerns.
- Embedding experimentation: Teams are encouraged to ask, “What should I stop doing?”—sparking a culture of reinvention and initiative.
Additional Insights
- Progyny’s “Super Fans” initiative reframes AI gains as an opportunity to deepen customer and employee relationships.
- Training is done in cohorts to build shared understanding and reduce AI anxiety.
- Cross-functional collaboration with junior team members—like the intern who built the HR bot—shows how innovation can come from any level.
- Cass uses AI to simplify and globalize complex frameworks like competency models, improving alignment across teams and geographies.
Episode Highlights
00:00 – Episode Recap
Cassandra Pratt shares how embracing discomfort led her to leap into healthcare, build a transformative HR function, and lead with AI, not to eliminate roles, but to elevate people and amplify their impact.
02:37 – Guest Introduction: Cassandra Pratt
Barry introduces Cass Pratt, Chief People Officer at Progyny, a fertility and family-building benefits company scaling rapidly with a human-first, tech-empowered culture.
04:48 – Saying Yes to Growth
Cass reflects on a missed opportunity that taught her the cost of saying no—and set her on a path to jump into unknowns with conviction.
08:04 – Startup Lessons and Leadership Growth
From 50 to 850 employees, Cass shares what it means to grow with a company and embrace mistakes as part of the journey.
11:00 – Diving into AI Without a Tech Background
Despite lacking technical skills, Cass threw herself into generative AI—learning by doing and discovering intuitive ways to drive value.
13:10 – Unlearning the Expert Reflex
Cass rethinks her default of turning to experts first—instead starting with AI to shape stronger ideas and bring others in as collaborators.
15:13 – Redesigning Processes, Not Just Tools
AI opened up opportunities to rethink workflows from scratch, not just automate existing inefficiencies.
20:35 – Making AI Safe and Human
Cass shares how transparent messaging, training, and cultural reinforcement helps ease AI anxieties and keep the focus on people.
25:00 – Building the HR Bot with an Intern
An intern-built benefits chatbot improved response times, consistency, and surfaced new insights—highlighting the power of junior talent and experimentation.
28:41 – Simplifying Competency Models with AI
Cass uses AI to refine complex frameworks, making them scalable across geographies and easier for leaders to apply.
30:00 – Rethinking Work Through Elimination
By asking what should be stopped—not added—Cass surfaces high-leverage opportunities to transform HR workflows.
34:33 – The Two Extremes of HR and AI Adoption
Cass observes a divide: HR teams either lead AI transformation or risk being the last to catch up.
40:45 – Cross-Functional Collaboration and Culture
AI transformation is a team sport—embedding HR into company-wide initiatives empowers better collaboration and outcomes.
43:38 – Freeing Up Time to Be Present
Cass highlights how AI helps reclaim time for the most human part of HR: being present, listening, and solving meaningful problems together.
FAQs
Q1: How is Progyny using AI in HR?
Cass explains that Progyny is not using AI to eliminate roles but to elevate them. AI helps give employees time back to focus on work that truly requires human connection, like building stronger relationships with customers.
Q2: What mindset did Cass have to unlearn to effectively use AI?
Cass shares that she had to unlearn her habit of going directly to experts. Instead, she began starting with AI tools to explore ideas, form better questions, and bring others in as collaborators rather than just information sources.
Q3: Can non-technical leaders apply AI in meaningful ways?
Yes. Cass openly says she is not technical and cannot code, yet she has built AI-driven HR solutions by being curious and willing to try. Her story shows that hands-on learning and experimentation are more important than technical skills.
Q4: What role did junior employees play in driving AI innovation?
Cass highlights that their intern built the HR benefits chatbot, which improved response times and answer consistency. This example shows how innovation can come from any level when people are given the space to contribute.
