Parentaly CEO, Allison Whalen, on Navigating Career Uncertainty Before, During & After Parental Leave

Welcome back to The Grey Areas Podcast! This week, we’re diving deep into the often-overlooked transition back to work after parental leave—and what employers are missing when it comes to retention, career progression, and leadership accountability.

We’re joined by Allison Whalen, co-founder and CEO of Parentaly, a platform reshaping how companies support employees during leave. Allison shares her raw and empowering journey through infertility, parental leave at a high-growth startup, and the career cliff so many new parents unknowingly face. From building a business while pregnant to surveying thousands of working parents, Allison brings unmatched insight on how to keep ambitious employees thriving without forcing them to choose between career and caregiving.

Highlights include:
 • 7:52 – The origin story of Parently: How two friends from different industries realized leave failures were systemic, not personal.
 • 13:43 – The early days of Parently, from a Google Doc pilot, to signing Fortune 100 clients.
 • 21:32 – 2024 Parently survey findings: Only 4% of parents who quit post-leave left the workforce entirely, so why are companies still losing top talent?
 • 27:45 – The most powerful, and simple, indicator of a positive leave experience? A written re-onboarding plan.
 • 30:23 – Why the danger zone isn’t just the return to work, but the 6–18 month stretch when confidence rebounds and resignation letters follow.
 • 38:12 – The #1 thing HR teams can do right now: Study the problem before selling the solution.

Whether you’re a founder, people leader, or a parent navigating your own return-to-work journey, this episode is packed with actionable insights to rethink support and build cultures that retain talent through every season of life.

Allison’s Links
Website
LinkedIn:
Allison Whalen  
Parentaly