Creating Space for Working Parents: Allison Whalen on Parental Leave, Planning, and Redefining Retention

What does it take to not only survive parental leave but to transform it into a strategic advantage, for employees and companies alike?

In this inspiring debut episode of The Balancing Act, Sarah Sheridan, Director of Sales and Executive Recruiting at Hirewell, sits down with Allison Whalen, CEO and co-founder of Parentaly, to discuss the future of parental leave, building systems for support, and why strategic planning makes all the difference.

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A Parental Leave Experience That Sparked a Business

Allison’s journey into entrepreneurship wasn’t planned. She began her career in enterprise sales, thriving in high-growth tech environments. But it was during her first maternity leave in 2017 that her world—and perspective—shifted.

“The leave was supposed to support my retention. Instead, it made me feel further away from my career than ever before.”

The disconnect between well-intentioned policies and poor implementation became a problem Allison couldn’t ignore. Her experience laid the foundation for Parentaly, launched in 2019 to help companies better support parental leave transitions, with coaching, planning, and re-onboarding programs.

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Redefining the Impact of Parental Leave

Contrary to assumptions, parental leave doesn’t just impact the parent going out. Allison walks us through data-backed insights into how leaves ripple across organizations:

• Managers often absorb the strain without support or goal adjustments.
• Colleagues are expected to cover work without having tasks removed.
• Direct reports lose momentum on professional development if leaders don’t plan ahead.

“Parental leave affects far more than just one person. A quarter of the year’s impact across multiple teams is significant.”

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From Disruption to Opportunity: Success Stories That Reframe the Narrative

Parental leave is often associated with stress and disruption. But with intention and structure, it can be transformative.

Allison shares a standout example of hiring a pregnant sales rep who used her limited time pre-leave to close deals faster, sharpen priorities, and overdeliver.

“A clear end date created focus. She pulled forward deals that would’ve taken a year.”

Others used their leave as a moment to transition into new, more fulfilling roles, emerging refreshed and re-energized, not stalled.

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Research That Challenges Assumptions

Parentaly’s groundbreaking survey revealed powerful truths:

• 94% of women with access to paid leave return to work, debunking the myth that most drop out.
• Three-fourths consider quitting within 18 months, often due to a lack of support upon return, not the leave itself.
• Career progression, not childcare, is the top concern for parents going on leave.

“These women want to stay. They just need systems that don’t push them out.”

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How Companies Can Take Action—Without Breaking the Bank

You don’t need an unlimited leave policy to make a meaningful difference. Allison suggests:

• Creating re-onboarding plans for every parent returning to work.
• Flexible return periods (e.g., part-time hours with full pay for the first month).
• Training managers to lead with empathy and structure.
• Open communication, like simply announcing a return date, can go a long way.

“Small systems signal that people matter. That alone improves retention.”

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Looking Ahead: The Future of Parental Leave

Allison predicts a decade of change:

• More companies adopting paid leave as the norm, possibly supported by federal or state funding.
• The rise of ‘floating’ teams or flexible contractors trained to cover parental leaves.
• A redefinition of fatherhood at work, with more men taking full leaves and becoming equal partners in caregiving.

“In 10 years, we’ll laugh at the idea of giving moms 12 weeks and dads just two.”

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Key Takeaways:

✔️ Paid leave isn’t just a benefit—it’s a retention strategy.
✔️ Coverage and re-onboarding plans help entire teams thrive.
✔️ Fathers must be included in the leave conversation.
✔️ Flexibility during the return period boosts engagement.
✔️ 94% of women return—but they need support to stay.

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🎧 Tune into Episode 1 of The Balancing Act to hear Allison Whalen’s full insights on leadership, leave, and why planning for real life leads to better business.

📩 Need help navigating talent strategy while supporting growing families? Reach out to Sarah Sheridan, Director of Sales & Executive Recruiting at Hirewell.