In this episode of the Unlearn Podcast, I sit down with Cass Pratt, Chief Human Resources Officer at Progyny, to explore how HR is evolving into a design discipline that blends human connection with AI-powered productivity. 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.

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.

Useful Resources

Progyny: https://www.progyny.com
Connect with Cassandra Pratt: LinkedIn
AI Executive Coaching by Barry: https://barryoreilly.com

Follow the Host

LinkedIn: linkedin.com/in/barryoreilly
Website: barryoreilly.com
Facebook: facebook.com/barryoreillyauthor
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The Human Side of AI: How HR Can Lead the Transformation with Cass Pratt