Tiffany Stevenson on fixing the most overlooked business continuity risk

Tiffany Stevenson has led HR at companies like WeightWatchers, Patreon, Box and Sephora - and is currently chief people officer at The RealReal. 

She’s known for her sharp people instincts, candid leadership style and ability to make real change inside complex organizations.

Now, she’s bringing that expertise to Parentaly as a member of our CHRO advisory board - and for her, this work is deeply personal.

Tiffany was raised by a single mom who built a meaningful career in academia. Watching her do both helped shape Tiffany’s belief that career and parenthood shouldn’t be in conflict - and that companies can help make both possible with the right systems in place.

In today’s episode, Tiffany shares what drew her to Parentaly’s mission - and why she sees parental leave as a solvable challenge that’s critical to both business success and employee wellbeing.

She also explains why parental leave should be treated as a business continuity issue - not just a benefit - and how to bring CFOs into the conversation to align on cost, risk and long-term talent strategy.

And for the Oprah fans: Make sure you listen to the entire interview … especially the end.

Allison: Tiffany, thank you so much for joining me here today.

Tiffany: Thank you. I'm so excited. Thanks for the invite.

Allison: I have been looking forward to this for many reasons, but two primarily. The first is I always feel fortunate when I get to talk to someone like you that brings so much experience across so many different companies. But the second reason is that I've had the pleasure to get to know you better over the past couple of months. And you tend, and this is gonna put a lot of pressure on you now, you tend to be a very eloquent speaker about these topics, not just parental leave, but also HR more broadly.

And so I'm just gonna start this by putting the pressure on you. No, I... Well, and I really, think that it's always such a fun opportunity for anyone to hear from somebody who is at the helm at so many different large, different types of organizations when it comes to people and culture. And I think that you just, you talk about these topics in such an interesting and eloquent way. So...

Tiffany: Good times. I hope I live up to it.

Allison: Let's dive into it. I'm going to start with the easiest question, which is why Parentaly? You just joined our CHRO advisory board. You could do anything under the sun. You could advise any type of company, large and small. What is it about Parentaly that made you think, yeah, I want to spend my time on?

Tiffany: Well, I am so excited to be a part of this advisory board and there are so many reasons, but if I had to dial it into one, I think it's really about the mission. Your mission deeply, deeply resonates with me. My opinion, supporting working parents is not just a worthy cause, it's a solvable challenge within our lifetime. I wanna see a world where parents don't have to choose between their career growth and their development and raising a family. And I think this work goes so much farther beyond just offering a benefit, but it really gets to the heart of sort of fundamentally what I think is just broken and how we think about leave and leave management and particularly in the US. So I'm really inspired by this opportunity and I'm really grateful for the opportunity to contribute in any way that I can.

Allison: It's funny when you use the phrase solvable problem. We talk, we spend a lot of time obviously internally, apparently over the years talking about what makes us unique and what are our superpowers and what is our brand about. And one of the things that we talk about a lot is solutions. That there are a lot of people or companies or individuals who... are very loud about the problems, which we are too. We talk a lot about what are the problems of being a working parent, of going on parental leave, but we really like to focus on the solutions and to make it like an actionable thing. And even if it's not the be all end all, how do we start chipping away at it? I'm curious if there's also a personal connection for you with this topic, whether it's seeing parental leave or working parenthood, whether it's a personal experience you've had that made you identify with this a little bit more as well when I originally reached out to you.

Tiffany: It's such a great question. When I think about this topic, I can't help but to think about my own mom when I reflect on just the criticality of supporting working parents. She was a single mom in this workforce, and she spent her entire career as a professor and a librarian focused on the African diaspora. 

And when I think about her contributions to her craft, her dedication to her students and the lives that she touched, it not only improved the folks that she had the opportunity to work with. But it really influenced me as a future leader coming behind her. Her career really showed me that even as a single parent that you can have a meaningful career and be an awesome mom. And she was an awesome mom. I really want to see that as a true statement for all working parents. 

And so this opportunity to contribute in some small way of thinking about how this process can be fixed in our lifetime for all working parents, I think is a nod to her and how amazing she was really making it all work and really being proud of her career and proud of being a mother.

Allison: I love that. Let's talk a little bit more about the parental leave experience specifically within the context of working parenthood. You know, one of the things that we've talked a lot with our CHRO advisors about and you specifically about is oftentimes companies think of the parental leave experience as a benefit, but they don't think about it more broadly that it's part of this natural life cycle that any employee may go through. And I would even go so far as to say, yes, parental leave, but also other types of leaves. There are a lot of similarities there where it's not just a benefit. It's actually a critical part of the experience of being an employee. I'd love to hear in your words, like, why do you think that this goes far beyond a benefit? Why is parental leave a business critical component for any company?

Tiffany: Absolutely.

Tiffany: Right.

Tiffany: I think this is a question that I don't think that we spend enough time as organizations talking about. I mean, what it comes down to is if we really want to engage and retain a high performing workforce, companies have to treat leave and reentry as like a strategic business process and not just a benefit and not a disruption. And I think that there's plenty of research out there that just shows that the inadequate support that happens

whether you're talking parental leave or other types of leave, but particularly in our context of parental leave, it contributes to turnover and disengagement and lost productivity. And it's not just for that individual who might potentially not return back, but it's also the team around them. So whether you're talking about the institutional knowledge, the judgment, or the team not having the benefit of having this balanced perspective and contributions from everyone who was a part of it.

So I think companies need to take this a lot more seriously and really see it as sort of a business mandate and not just sort of a nice to have something that we offer, but something that really protects and supports the business itself.

Allison: One of the things that you mentioned a lot when we had our kickoff CHRO meeting was whether Parentaly exists to support the career success of the employees or to support the underlying business. Because our messaging is sometimes confusing, admittedly. Sometimes we focus on one or the other. And I think what was so helpful in you highlighting that is that it can be both, and they are intertwined, but we have maybe struggled a little bit to explain those differences. Given your experience, having been a chief people officer and having had very senior roles across different companies in HR, how do you think of Parentaly? Is it more, in your personal opinion, about the career success of the employee? Is it the bottom line for the business, or how would you untangle that?

Tiffany: It's so interesting and I certainly sit in these discussions, you see both sides to this. I think these two ideas are very true at the same time. I think an undersold aspect of this business proposition is really thinking about it as a form of business continuity. And in this role in the seats that we occupy, we are often sitting with the CFO, sometimes the CLO or CAO. Really talking about business continuity. I mean, we think about it from a tech stack perspective. We think about it from unmanned disasters. Like we think about just a variety of things that sort of risk the business continuity. And I don't think that we spend enough time thinking about the impact of talent beyond succession planning. And I think that this is another element of that. And I really do believe that effective companies are thinking about business continuity particularly during these transitions in a way where the team does feel supported and that they do know what to do when this person is out of the business for a defined point of time, whether it's the knowledge that goes with them or just literally like who is going to be taking on work and are they ready to do that? And so much of what excites me about your business model is some of the work that happens behind the scenes with the leadership team that's going to be supporting that team member and making sure that all of that is facilitated incredibly well.

I'd like to believe that we have those systems in place in all organizations, but I just don't think that that's true. And not consistently. And I think that your business model really aims to address that, in my opinion, I do think this is almost an under-discussed topic that I think that your company really helps to address.

Allison: One of the other things that you had mentioned when we spoke previously was what involvement would a CFO have in this? And today, the CFOs certainly at our client organizations see what we do because we typically work through benefits or DEI or talent development groups and they'll escalate and they'll talk to CFOs about what we do and the way that they then bring this proposition actually oftentimes looks different to a CFO because they're thinking of the business in maybe a different way. How do you think CFOs should be involved in this type of a program? And how would you talk about this to a CFO?

Tiffany: Yeah.

Tiffany: Yeah, the CFO plays a critical role in understanding where the expense lines fall and making sure that every dollar investment that we're putting into the business is yielding the outcomes that we expect and the measures that we expect. This to me is a continuation of that. 

The cost of backfilling talent who don't return sometimes shifts your payroll costs in ways that become untenable. Or if you're thinking about temporary backfills, it's like the cost of doing that is something that becomes an additional expense. So I think that getting a CFO in this conversation to think about how from that perspective, are we really making sure that the investments that we're making in our talent are delivering the outcomes that we want to see happen and making sure that business continuity is being maintained. So having them a part of this conversation moves the conversation beyond just the administrative aspects of parental leave, which I'm sure for many CFOs, it's like, no, thank you. I don't want to be involved in those discussions. But really thinking about it from a business continuity and getting a return on every dollar that we're putting into our business with people being our greatest expense. Really making sure for every dollar that we're putting in that we're getting the investment that we want to see coming out of that. So I absolutely think that them being a part of that conversation is critical. Again, bringing everyone into this idea from a business continuity perspective.

‍Allison: I'm going to throw a question at you that I just thought of. So it's totally fine if you don't have any initial thoughts on this. How often are these types of challenges with business continuity being escalated to a CHRO? Because one of the things that we think a lot about is how when an employee goes on parental leave and they struggle and their manager really struggles to figure out how do I deliver on my goals if I'm gonna be down one or two people, you're overworking the teammates and whatnot, I think a big part of what we struggle with is there's a lot of silence around that. There's a lot of shame almost in complaining about something. We want to be supportive to our coworkers that are going on parental leave. And so we don't maybe escalate this. I'm curious if you've seen this? Have you seen helpful ways that people have escalated this type of challenge? I'm just curious if you have any thoughts about this.

Tiffany: I think if you were to talk to an HR business partner or someone who is providing more direct support to particular parts of the business, I think that you see a lot more color around the implication when someone goes out on leave. Some of the signs that you see would be missed deadlines, dissatisfaction, or turmoil within a particular team. Sometimes you see in extreme cases where

Allison: Hmm.

Tiffany: The resourcing isn't fairly distributed, but someone quits. You see it certainly in performance appraisal time when someone wants a promotion for getting something done because they were able to provide additional work. So I think that you sometimes see leading indicators and lagging indicators that something's working well or maybe not so well. But I think that that business partner, if you were to ask them, I think that what they see at a lower altitude in that organization is when it's going well, everyone's really clear on what they're delivering. People feel prepared to take on the additional work and the deadlines are met. You're able to see performance and things go. And then on the opposite side, you see the turmoil, you see the missed deadlines. And those sometimes are indicators that you might see later at the end of a quarter or at the end of a year when a metric is either hit or missed. So sometimes in those recaps, so we've all been in that quarterly business review where it's like, we missed that one. And why did we miss it? well, because we had someone who was newer who was having to take this on. They weren't ready. And you kind of see those kinds of things where we can get it, but we'll probably need one more quarter to get there. So those are some of the things that you see that just kind of let you know that maybe continuity planning wasn't addressing all the potential variables, and they actually weren't ready.

‍Allison: Do you think ERGs can play in this?

Tiffany: ERGs play such a critical role in the organization because I think that they are a good way of sort of aggregating concerns that might be unaddressed in what you offer today. And also positive indicators when things are really working well. The ERGs that I've worked with, I can draw on a few, but particularly like any of the ones that are centered around families, for example, they provide a wonderful sounding board on what's working, where are their potential concerns, and what's needed and what feels missed in that transition process or that leave process when they exit both and when they return. So I think that it's really valuable to really bring the ERGs together and really make sure that maybe we're asking them some very specific questions or having focus groups where you're kind of putting out there, their assessment of what they feel like works and maybe doesn't work as well. And I think that balance is between maybe one person who is incredibly vocal and lots of opinion versus in general, do I have a good snapshot of what it's like being a family led caregiver working for this company? So I think that those kinds of opportunities shouldn't be missed and I think they provide wonderful feedback.

Allison: Yeah, we've had really positive experiences partnering with ERGs once we become a vendor at a client company, as well as even before. And it's something that I've seen actually improve a lot over the past five years, that the infrastructure around ERGs is getting more and more sophisticated, where it is structured, organized, oftentimes with the budget, with an executive sponsor, in addition to working really closely with HR. And I think it's Such a powerful way to solve for a lot of the challenges that maybe people don't feel comfortable raising on their own.

Tiffany: I agree. There's strength in numbers. And I think, again, it sort of takes the pressure off of one person's experience, even as a use case, because I think sometimes you might over pivot on one person's use case. But in aggregation, it's like, no, this is definitely a trend. And so how do we use these themes, to your point, just to make better decisions or better governance over the processes and policies that we have?

‍Allison: Right.

Allison: How does parental leave and the challenges that we've described today fit into the future of work?

Tiffany: It is such a critical part of the future of work. And every time I hear the future of work, I'm like, the future is now, but absolutely the future of work. If we aim to drive and deliver on our key objectives, it's going to come because we've engaged and retained a high performing workforce. so companies have to treat leave and just reentry as a strategic business process and not a disruption. 

And I think that as we said before, it just creates disruption when we don't think about these things. And I think you lose productivity, you lose sometimes tribal knowledge that is incredibly important, judgment, all of those things go out of the window when you aren't really thinking about doing and establishing these processes in a way that benefits both the talent who's coming in and out and showing their value and their commitment to the company and the organization's success. And it certainly doesn't hit the results and bottom line. So I think for both reasons, we have to be really, really intentional about making sure that we're engaging and retaining. And that means that we get better at these processes.

Allison: Yeah. And I think also there's an aspect like people are waiting later to start their families. They're going to be more senior when they go on parental leave or giving more leave. And so it is interesting to see how that progresses over time. 

Okay. Now I'm going to go to our rapid fire, which I know I'm making you sweat over this because we did not prep you with these questions. No, they're very easy, but I'm to ask you..let's see, five or six questions. And curious to get your initial gut feedback to that. These are not going to have, we're going to move off of the topic of parental leave. I'm basically taking advantage of having you here to ask you all the questions that I want to ask you. 

Tiffany: Good times!

Allison: So first up is what is the best leadership advice you ever received?

Tiffany: The best leadership advice I ever received was to run your own race and remember that you're just competing against yourself. I think that so much of what we do is always in comparison to others and sometimes it pushes us to do things that sort of operate outside of things that are naturally important to us, our own skills, talents, and capabilities, our own career paths and journeys. And I think that we were each put on this earth with a set of skills and experiences that were meant for us. And so we want to just harvest those, be open to the career experiences that match them, and keep doing those till we get to the destination that matters uniquely to us. So I think that was probably one of the better bits of leadership advice that I've gotten in my career.

Allison: You need to write a book. This is very well put. 

Tiffany: So kind.

Allison: Biggest myth about HR that you wish would just go away.

Tiffany: I think the biggest myth about HR that I wish would go away is that we only operate in the people vacuum. Like I think that people see this role as the place to go to for questions pertaining to ER issues, hiring and firing. And I think that there is so much that the HR organization offers to the business strategy overall. And organizations that truly understand that and think about people, strategy, mission and vision, and execution as one complete thought, truly understand the full potential and value that an HR organization has to offer.

Allison: What is one trait you would look for if you could only hire based on that one trait?

Tiffany: The trait that gets me the most excited is curiosity. Curiosity to me indicates openness to see potential, whether it's data coming from different resources, like we said. They're just as excited as an ERG, you know, what an ERG can add to that person's understanding as looking at financials, as looking at, you know, anything to help round out your decision making. So people who naturally bias towards curiosity are always exploring the fuller set of possibilities to try to make the right decision. So I think curiosity to me, if I only had one, I would match it with execution if I sneak one in, but curiosity to me, I think is the leading, the leading one.

Allison: Amazing policy or program that you were most proud to implement at Weight Watchers.

Tiffany: There are so many things I was super proud of. Goodness. One of the things that I was super excited to launch, because I would say value. So values would be the thing that I was really excited about. We updated our values. They feel very on brand to Weight Watchers and looking back at the founders. But if I had to go to one program that we implemented is that we implemented periodic days off for the company that we took together.

The reason why we did this was that at the time, the company was in a massive turnaround. So this was a 62-year-old brand. And so there was a lot of work that was going into the turnaround. We had done an acquisition. We were integrating the acquisition. You couldn't imagine how much work was coming in all directions. And so by implementing these corporate days off, because what we were seeing in the data was that people weren't fully utilizing their PTO because they never had time or if they were in the feedback we were getting in our surveys, they would be like taking PTO, but still taking calls because they were just wanting to make sure that business continuity was happening. And so by us taking dedicated time off together, it helped to really reinforce the importance of taking a break. It honored the environment that we were in at the time, which was that it was very hard to take a break if all your, all your homies are still there working, you'd feel bad about that.

And it just kind of created an environment where people took true rest and we were able to really celebrate the rest that we were able to take. And you got to see glimpses of people's lives. And so we had places where you could share what you did with your time, whether I took my kid to the zoo finally to like, this is just me. Here's a picture of me painting my nails to like long weekend. So I was really excited that we kind of met the moment with a solution that felt very appropriate for where we were.

Allison: I have a hard-hitting question. Did you ever get to meet Oprah Winfrey when you were at Weight Watchers?

Tiffany: That's such a good question. I did get to meet Oprah. Okay, so here's a fun fact. I don't even know if this will show up, but here is me and yes, yes. So of course I should be right here, just to remember my brush with greatness. I did get a chance to meet Oprah. I mean, obviously she was a part of our board. So through her board service, we did have opportunities.

Allison: I love her, by the way.

Allison: My gosh, that's amazing.

Tiffany: To interact. I also was working on a couple of projects as I owned Social Impact as well. And some of that work was centered around causes that she cares very much about around access to weight health. And so I got to work with her one-on-one on some of the programming that we were working on, particularly in the city of Chicago, where we were experimenting with some just efforts around access around the South Side of Chicago for weight health and she is incredibly visionary. She gave me the best feedback and guidance. She never held back, but she always does it with love and appreciation. so yeah, it was such a blessing to have an opportunity to meet her and work with her and absorb as much as I could. She's an amazing and an exceptional person.

Allison: I can't believe I've never asked you this before. Just as we were thinking about Weight Watchers, was like, wait, used to be on the board and I wonder if she's met her. And you're like, I've met her. That's amazing.

Tiffany: The first time I met her, couldn't even say my name. So it was my first day of work. And as soon as I saw her on the Zoom square, couldn't remember. I couldn't get Stevenson out. I got Tiffany, but that was where I trailed off.

Allison: Well, back when I was in college, this is a total tangent, there was an opportunity, if you were in college, a woman in college to write an essay to win tickets into her audience. And she had like a 10 year wait list to get tickets, know, free tickets, because they had this movie, Mona Lisa Smile about women and, know, wealthy, I think. I got in the audience and then I convinced the producer to let me bring my mom.

Tiffany: Yeah, we're gonna have a movie.

Allison: And she flew in that same day and was like, I mean, I think it's the happiest I've ever seen my mom. Like more so than when any of us got married or had kids or anything. She was just like, I got to be in the audience at Oprah. So I'm a huge fan girl. I, we will have to talk about this more when we are not being recorded

Allison: Last question. What is one specific thing that you're looking for in your next professional opportunity?

Tiffany: I think I look for the same thing in my professional opportunities, and it's to really drive and have impact. And I think make true a world where your people results and your business results are seen as one giant opportunity. And it doesn't have to be one or the other, but they can both live together in harmony so that you have healthy business and healthy people outcomes.

That is what I want in every opportunity. I love to make impact. I love to be able to support businesses in their transitions, whatever the transition is, whatever the transformation is. But when those two things are true, I think that's really where the goodness comes. And I love being a part of that.

Allison: Tiffany, you passed this with flying colors. You were so, I'm almost like, did Jenna send you these questions in advance so that you could prepare? But in all seriousness, thank you so much for being with me here today. I thought this was so great and helpful. And thank you for all of your support that you've provided to us and all of your incredible advice that you're always giving us.

Tiffany: Yay! This is serious fun. Thank you. Thank you for doing what you're doing. Again, this is important work and I'm excited to watch it grow. So thank you.