How do you design a parental leave program that supports parents, protects performance, and earns buy-in from managers – all inside a fast-growing tech company?

In this episode of the Kundra Podcast, Theresa sits down with Cheryl Rubian – former Chief People Officer at Greenhouse, the innovative hiring and onboarding platform. Cheryl is the first HR leader to join the show and the architect behind Greenhouse’s parental leave program. She brings a rare insider perspective: what it takes to move from policy to practice, and how to operationalize people processes in a way that genuinely works for both parents and the business.

Inside this conversation, you’ll learn more on:

• Building While Scaling: How Cheryl designed Greenhouse’s first parental leave program at a time when the company grew from 40 to 180 employees in one year – and what she wishes she’d known earlier.
• The Missing Link in HR Policies: Why empathy is not enough, and how operational discipline (calendars, checklists, structured touchpoints) becomes the backbone of a successful leave experience.
• The Ask Gap: The surprising insight Cheryl uncovered when senior women shared what they didn’t feel comfortable asking for – and what HR can do to close that gap.
• Performance & People: How proactive leave design can reduce business disruption – and why companies that support parents ultimately strengthen retention, engagement, and long-term output.
• A Practical Playbook for HR: Cheryl’s one-page manager guide, the matching parent-facing version, and how leadership buy-in unlocks organizational alignment.

Whether you’re an HR leader, business manager, or executive thinking about parental leave as part of your people strategy, this episode breaks down the real systems and decisions that turn parental leave from an ad-hoc event into a scalable, high-impact practice.

In this episode we cover:

• 00:00 Introduction & Cheryl’s Career Background
• 05:24 Building Greenhouse’s First Parental Leave Program
• 08:27 Why Good People Practices Need Operations – Not Just Empathy
• 12:23 Importance of Highlighting Leave Options
• 17:41 The Business Case: Why Parental Leave Matters for Performance
• 25:14 Cheryl’s Playbook: One-Page Guides, Leadership Buy-In & Flexibility

About Kundra

Kundra is building the future of parental leave.

We believe ambition and parenthood can thrive together – and companies that embed equity into their foundations today will lead tomorrow.

This podcast is part of our journey: speaking with working parents, business leaders, and HR innovators to surface the truths of career and parenting and the tools that make it work.

We’re now opening up pilot programs for companies ready to rethink parental leave. If you’d like to see how Kundra can support your teams, email [email protected] for a demo.

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