The Grey Areas Podcast with Kelsey Donlon
The Grey Areas Podcast with Kelsey Donlon is ready to disrupt corporate America! This is a space for candid conversations and deep dives into the complexities of the workplace. The mission: to empower women with transparent, inspiring narratives and challenge the status quo in corporate culture.
Grey Areas is a safe, non-judgemental digital platform, podcast and community that inspires and empowers women to navigate the grey areas in the workplace. So what does that mean? Well, the ‘grey area’ is an ill-defined situation…or in other words, it’s murky AF. Kelsey is here to help make this vague situation, much clearer. This community and podcast will hold corporations, executives and Human Resources accountable by leveraging legal education, transparency, and shared stories to drive change.
Each episode will tackle aspects of the grey area; managing anxiety in the workplace, tension between coworkers or managers, understanding employer boundaries, working with HR in an appropriate and effective way, navigating job loss, and so much more. So tune in, to hear Kelsey and her guests share a wealth of information and to be part of a safe space for people who have a hard time navigating the toxic workplace.
Let’s navigate grey areas, together!
The Grey Areas Podcast with Kelsey Donlon
The Grey Areas of Parental Leave: Allison Whalen on Navigating Career Uncertainty Before, During & After 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 Parentaly: How two friends from different industries realized leave failures were systemic, not personal.
• 13:43 – The early days of Parentaly, from a Google Doc pilot, to signing Fortune 100 clients.
• 21:32 – 2024 Parentaly 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: https://www.parentaly.com/
LinkedIn: Allison Whalen Parentaly
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