Advisor Spotlight: Tiffany Stevenson, Former Chief People Officer, WeightWatchers

by
The Parentaly Team
Oct 20, 2025
Tiffany Stevenson, Chief People Officer, The RealReal

We’re excited to welcome Tiffany Stevenson to Parentaly’s CHRO Advisory Board. 

Tiffany is Chief People Officer at The RealReal. Before joining them at the end of 2025, she served as Chief People Officer at WeightWatchers, where she led global people strategy and drove initiatives at the intersection of culture, equity and performance. 

Previously at companies like Patreon, Box and Sephora, Tiffany has HR experience spanning high-growth companies and brings a deep understanding of how to align business outcomes with human impact.

“Parentaly addresses what many miss: treating parental leave as both a human milestone and a business issue. Their program reflects the kind of cultural architecture that drives real outcomes for people and business performance, and is exactly what companies need to retain top talent while operating with leaner teams.”

For Tiffany, supporting Parentaly’s mission is personal. She believes supporting working parents is a solvable challenge - one that can be addressed within our lifetime if organizations treat parental leave as a strategic opportunity rather than an administrative function.

Below, Tiffany shares why leave is a defining moment for both individuals and businesses, what’s broken in today’s approach, and Parentaly’s direct impact on business continuity, operational effectiveness and long-term talent strategy.

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What inspired you to join Parentaly’s CHRO Advisory Board?

“I’m excited about joining the board because the mission deeply resonates with me. Supporting working parents is not just a worthy cause, it's a solvable challenge within our lifetime. I believe we can build a world where parents don’t have to choose between career growth and family responsibilities. This work goes far beyond offering a benefit; it gets to the heart of what’s fundamentally broken in how we approach leave and work in this country. I’m inspired by the opportunity to help drive meaningful, systemic change.”

Why is parental leave such an important issue in today’s workplace?

“To engage and retain a high-performing workforce, companies must treat leave and reentry as a strategic business process - not a disruption. Research shows that inadequate support during parental leave contributes to turnover, disengagement and lost productivity. By designing systems that support smooth transitions - for both the parent and the team - we protect institutional knowledge, preserve business continuity and strengthen long-term talent retention.”

What’s broken about how companies handle parental leave today?

“We often focus too heavily on the administrative aspects of parental leave, rather than managing the broader set of outcomes that impact all stakeholders. For both the individual and the business to succeed, we must go beyond compliance and benefits administration. That means equipping managers and teams to effectively navigate the temporary absence of a colleague, while also ensuring that the employee on leave is set up for a successful departure and reentry. A well-managed leave experience drives stronger engagement, retention and organizational resilience.”

What excites you most about Parentaly’s mission and this moment in time?

“With the rise of AI and growing pressure to operate with a leaner cost structure, doubling down on retention has never been more critical. Holding on to top talent requires a long-term view - supporting their success both on and off the court. That includes being intentional and disciplined in how we approach key life moments, like parental leave. When we get this right, we’re not only supporting our people; we're also protecting performance, continuity and the broader mission.”

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To celebrate all we’ve accomplished, our team shared what they’re most proud of since joining the team:

I'm most proud of how much we have done to improve the single hardest moment for women's careers (going on parental leave) ... one that is often shrouded in insecurity and fear. We've been able to help advocate for so many women (and men!) in a way that is empowering and truly life-changing.

Allison Whalen, CEO & Founder

What am I most proud of? Growth! Growing a category of support that didn't exist before Parentaly. Growing from a one-woman bootstrapped operation to a global team of 25+ employees and coaches. Growing our overall impact for working parents, with companies investing in our parental leave programming to support employees all over the world. And growing as humans: new babies, new friends, new life experiences... all while tackling new and exciting work challenges together.

Rich Burke, Head of Growth

When I reflect on what I am personally most proud of during my time here, it's working alongside a team where we constantly evolve and optimize everything that we do in order to deliver the best possible experience for the folks going through our programs. It sounds cheesy, but there are processes that my team and I used to do 100% manually that are now completely automated and systems in place that have become second nature to how we operate. Working with such thoughtful, smart, and creative people is incredible.

Sara Ophoff, Senior Program Manager

I’m most proud about doing work that makes parents feel confident and empowered about their careers during a time that can be overwhelming and challenging – not only for our clients and users who go through Parentaly’s programs, but also with our advocacy work on LinkedIn, through our podcast and other big campaigns that make a difference. It’s been pretty rewarding to build a brand people know and love because what we’re doing resonates with so many employees’ experiences in the workforce.

Jenna Vassallo, Head of Brand & Marketing

I am so proud of the way we've approached growth with such care and intentionality - with every adjustment we've made to our offerings, we've never lost sight of our goal to provide the most supportive and valuable experience for our users. I love looking back on the early stages of conversations and building that have led us to the experience we offer today. Personally, I am extremely proud of the work I've done to scale and automate our backend!

Rachel Andes, Program Associate

I am most proud of the work we do every single day to make a positive impact on working parents! Everyday I get to work with an amazing group of people…we work hard but we also have fun.

Sarah Gruber, Client Partner

I'm proud of scaling an employee experience that consistently delivers positive outcomes for new parents and their organizations. Our north star has always been the user, and we never sacrifice our high quality bar!

Mansi Kothari, VP of Product & Experience

I feel a sense of pride that I get to work behind the scenes supporting everyone. I’m proud to see all of the collaboration between the team and how Parentaly positively impacts employees.

Leo Manalo, Executive Assistant

I'm most proud of going through the Parentaly program myself! I'm so proud to work for and promote this company in a time where parental leave and supportive policies are at the forefront of a national conversation. But beyond this, I'm most proud to call myself a participant.

Emmy Carragher, Enterprise Partnerships

I’m really proud of the work I did to expand our coaching bench globally at Parentaly. It was so rewarding, not to mention insightful, to connect with talented coaches from around the globe. This expansion not only enriched our coaching offerings but also strengthened our commitment to making a meaningful impact on families all over the world.

Nicole Hagemann-Bex, Senior Coaching Operations Manager

I have tremendous pride in the knowledge that what I am doing will change the career landscape for new parents, particularly mothers. This will make it more likely that my daughter can have a career AND a family without worrying about the unintentional negative impact of taking parental leave. Nothing makes me prouder than that.

Mindy Himmel-Brown, Strategic Partnerships

In my short time at Parentaly, I'm proudest of the work we're doing with our clients' ERG groups to elevate the stories and advice of actual working parents. It's such an impactful way to spread the word about Parentaly as an essential resource for all people growing their families, and the managers who support them!

Alex Diskin, Enterprise Account Manager

I'm most proud about using LinkedIn to connect with others. I was recently able to share a helpful return to work doc with 50+ new people looking to make a difference at their company. Was pretty cool that people from Chewy, McDonald's, Honda, Cisco, AWS, Walmart and more want to integrate just a piece of what we have to offer. Also...I'm so proud of the way I feel as an employee at Parentaly. For the first time in my career my personal interests align with my professional interests and I've never felt more motivated.

Jenny Hurwitz, Strategic Partnerships

I'm really proud of being able to help the Experience team by handling the supportive functions so they can focus on the bigger picture. It feels great to know that I’m making things easier for them and contributing to the team’s success.

James Mango, Executive Assistant
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Wondering what the ROI of parental leave support looks like at PwC?