Latest / Beyond the Paycheck / What a Dime Jar Taught Me About Pay, Anxiety, and Employee Empathy
Transcript
- Kelsey Willock (00:01) Welcome Ann Watson, CPO at Covered Genius. We're so excited to have you on this Friday afternoon. To kick us off, I'd love for you to share a little bit more about your current role, background, and where you're calling in from today. Ann Watson (00:13) Thank you for having me. I'm really excited for the conversation. I'm Ann Watson. I'm the Chief People Officer at Cover Genius. I live in Berkeley, California. I work in San Francisco. Cover Genius is ⁓ a global company. we have about 700 employees across 23 countries. So I do spend a fair amount of time ⁓ of my time on the road. Luckily, right now I'm at home here in San Francisco. Unfortunately, the weather's not cooperating with that. So we're having a bit of a gloomy day here. Otherwise, it's lovely. ⁓ For my background, I ⁓ have been in HR for almost the entirety of my career and almost all of it has been spent in startups, tech startups. ⁓ I really do a lot of what I think of as 50 to 500s, that sort of ⁓ second growth phase after you've gathered your first group of people together and figured out that you have something and now maybe you have an investment or you're pivoting or you're kind of going to this next phase of growth where you... This kind of that tipping point where you need an HR person. ⁓ And then as I would say as probably over the last 10 years, as the role of HR has really expanded, especially when it comes to technology and the role we play, ⁓ those roles have gotten a lot bigger with a lot more in them. ⁓ And so that kind of time we spend ⁓ with an organization that's growing or time we spend with an organization that's growing. has really changed a lot ⁓ in terms of scope as well as ⁓ the interaction you have with everybody in that ⁓ change enabled period, just all the change all the time in those companies, which is really what I love. Kelsey Willock (01:58) And I certainly, I'm in your neck of the woods. I'm also in San Francisco and there are a lot of companies going through massive transformation in the Bay Area right now. So a very interesting time for you. So before we get into all the amazing work you do as a chief people officer, when you get to know you better, a bit more personally, and start with one of my favorite questions, which is what's your earliest memory of money? Ann Watson (02:06) That's right. Such a good question. I kind of want to steal this question, start asking everybody this question. ⁓ My earliest memory, so I was ⁓ raised Catholic. I was raised in Mesa, Arizona in the late 70s and early 80s, which was at the time of a fairly, ⁓ certainly not affluent and fairly rural, but also ⁓ very family centric, ⁓ lots of large families in the area. ⁓ I was raised Catholic, first, so as a young Catholic, I had to go to my first confession. And what I remember about my first confession was that I confessed to stealing dimes from our dime jar. And so in my family, in our house, we had a dime jar. My mom would go to the bank and get a roll of dimes every week or every couple of weeks and put them in the dime jar. And each one of us every day took a dime and took it to, this makes me sound like a really old, old timey person, but this was, this was Arizona in the eighties. We would take a dime with us to school to buy milk with our school lunch. ⁓ And so my first confession, I said as a young person, was that I had stolen dimes from the dime jar. And what's hilarious about this is that's not true. was so anxious about that moment that I made something up. So lying in first confession is hilarious. It actually is fairly on brand for me. But really that what when I thought about that story, because that you know, when you ask that question, that question, that's the first thing I think of ⁓ the things that that sort of shows for me is ⁓ anxiety around this, like, you know, there's there's the kind of anxiety in general, ⁓ and maybe a little guilt. ⁓ But ⁓ those kind of first early interactions for me ⁓ are not super comfortable or, or ⁓ Happy. Kelsey Willock (04:30) So as someone who also grew up Catholic, I am very hyper aware of the Catholic guilt that comes along with growing up in that faith. ⁓ But I love that you bring up the money anxiety component because I think that you often don't talk about how anxiety inducing money can be. It's significantly taboo topic. And so how that experience shows up in our early childhood actually impacts us the rest of our lives. And so. Ann Watson (04:57) Yeah. Kelsey Willock (04:58) We'll get into how that's affected, how you think about and show up for paying benefits. But before we get there, although I'm racing for that question because I'm already really interested, I'm really curious what your first job was. And if you remember what you did with your first paycheck. Ann Watson (05:14) So I babysat a lot, again, kind of where I grew up. ⁓ I think a lot of people now, if I said I was a nine and 10 year old who was put in charge of four or five kids for a night, that probably sounds. terrifying, ⁓ but you know, that was pretty normal. ⁓ I don't remember, I couldn't possibly tell you what I spent my babysitting money on, although it was probably things like ⁓ candy and soda pop and. ⁓ frivolous kind of kid things. But what I really remember about working and getting a paycheck, ⁓ I worked for Starbucks. It was my part-time job when I was in college. I ended up staying after college. And Starbucks was essentially a startup at that point. It was still really small. There were just a handful of stores in Northern California. ⁓ It was not a super well-known brand. were, I think there were 200 stores. ⁓ It was just a really different place. But when I became an assistant store manager, I transitioned, this is a great story because it's also like a little into my career as well. ⁓ I went from being an hourly employee to being an employee on the salary. And my first full-time wage was 22,500. And I remember just thinking that was such an ⁓ absolutely... incredible amount of money and calling my parents and I remember my dad said that it had taken him, I think he said 10 years before he got to that level of working, which was, you know, it's both a little bit about poverty in my family, but also about sort of how, you know, how money changes over time and through generations. Kelsey Willock (07:03) I love how you bring that up and I am really curious. How do you think your relationship with money, whether it's those earliest memories of guilt or how you think about your parents' relationship with money and how it got passed down on to you, how does it help you think about paying benefits on behalf of the employees that you work with? Ann Watson (07:25) I think there's a couple of things for me that really influence in this job. And this is a unique job in that we walk around knowing what everybody makes. ⁓ we walk through our days in our organizations. We don't actually even think about the fact that we know that information and generally other people don't. ⁓ But also we end up with a pretty good idea of how much everybody makes. So if you're at a party and Americans love to talk about what they do for work, you kind of have a sense of like what this person's situation is ⁓ instinctively, just because you're exposed to that day in and out, especially if you're someone who's in survey data and if you're kind of building constructors, you see a lot of that information. ⁓ So I grew up ⁓ not well off. My parents were very young. But the interesting thing about my parents was they were in school the whole time I was growing up. My dad finished his bachelor's degree when I was, I think, nine or 11. My mom finished her PhD when I was 15. And so what I saw with my parents was, we didn't, we had, had a lovely, happy, like fun filled childhood, but we didn't have a lot of money. We didn't have a lot. ⁓ and the money we had went towards education and then seeing my parents get these, you know, these advanced degrees and take on new careers. And then we moved from Arizona to Northern California and my parents started to work for startups and started to work for companies that had equity programs and companies that had public, that were publicly traded and had equity programs. And there was this big, dramatic shift for them. And what that created for me was first this link that ⁓ education is a worthwhile reason to be in debt. ⁓ And that is, especially now that's become really complicated. I think that was really different in the 90s than it is certainly now. ⁓ And that also this idea that education is this path ⁓ out of poverty and out of ⁓ that cycle, which I find really interesting. I've always been interested in that. ⁓ When it comes to how that impacts ⁓ my relationships with employees, with pay and benefits. I think there's a big part of me that ⁓ is really ⁓ thoughtful and curious and tries really, I make a strong effort not to have assumption and judgment when it comes to people's lives and what their money stories are. There can sometimes be this idea of like, well, I know how much this person makes, so they must be well off or they must understand equity or they must, ⁓ you know, kind of know how to manage themselves. And that really isn't the case. And it's so easy in our roles to make those assumptions and make those judgments ⁓ about whether it's a senior executive or a really junior person. and remind you that work to remind yourself that actually you know nothing. That this very, very senior engineer who's worked at 15 phenomenal startups actually still would admit if they worked up the courage, would admit they actually don't understand how stock options work. ⁓ Or an employee who seems very well off and then they're... ⁓ you know, their lean or their, ⁓ you know, their, their ⁓ garnishment shows up and you're like, ⁓ I learned something about you. didn't know. Kelsey Willock (11:16) I think it's important too because we can so easily think, you just pay certain groups of people, you pay them more, and therefore their lives get easier. That doesn't include maybe they're a caregiver, maybe they're paying for other folks in their lives' education, maybe they have student loan debt themselves, which can, I'll never forget I attended a conference a few years back where the woman speaking on the panel had shared her and her husband were in half a million dollars of student loan debt. Ann Watson (11:28) Yeah. Kelsey Willock (11:43) in a very high paying job, but that means that the high paying job isn't enough. You've got to think of all the other nuances and how life affects you. So I love how you have this approach of sincere empathy, recognizing your parents were in these situations. And it's not just your parents' situations, it's so many others, but you're in the mindset to be thinking about them. Ann Watson (11:51) That's right. Yeah. Kelsey Willock (12:08) Where do you think compensation and benefits are breaking down most often today? Ann Watson (12:16) So from a ⁓ US perspective, there's some amount of this, I think, about this in my job globally. ⁓ And certainly, globally, have a lot of different countries with just different philosophies and different standards and norms. ⁓ And I think one of the really difficult things is seeing other countries have much stronger ⁓ care programs, whether it be kind of traditional medical care ⁓ or support programs and you know the something like parental leave ⁓ in other ⁓ in other locations versus what we do here in the US. I think that that is really probably the hardest thing about being an employee in the US is that your employer really owns and controls your access to care, your ability to raise your family, your ability to recover from illness. There's just so much that is riding on your employer and this is already sometimes a difficult relationship. and one that controls your livelihood. And then you add to it, in this country, we add to it. This is now also my source of health insurance or of caring for my family, ⁓ of being able to, you know, deal with the uncertainty of life. I think that's probably where, especially in this country where ⁓ that breakdown is most apparent. Kelsey Willock (14:06) so important because, you know, I've talked to a lot of folks that, you know, we're always looking for what is the one solution that can solve for many markets and understanding that workforces can be so international, but many of the benefits that we offer only make sense within those markets. ⁓ But then again, employees talk to their colleagues, you know, an employee in the United Kingdom speaking to a colleague in the United States might be like, why do you have that? Ann Watson (14:24) Mm-hmm. Yeah, that's right. Kelsey Willock (14:36) But it doesn't necessarily make sense in both places. But how do you find this balance of making employees feel equitable across the country, knowing the countries they operate in are very different and individually have very different needs? Ann Watson (14:50) Yeah, and if you chase parity, if you try to keep everything the same globally, think it's so, I mean, maybe you have the luxury of working for the kind of employer where you could achieve something like that, but the different levels of different benefit in different. ⁓ different places in the globe are just so distinct. And Americans are, it's fun. One of the things I really love about working for global companies, which I have always loved is that as an American, that ability to kind of step outside of that and look inward at what it means to be an American, as opposed to the rest of this team is German or Australian or somewhere else. And you start to see, know, like, wow, we really don't like to take time off. It makes us deeply uncomfortable. ⁓ so if I'm, and yet there is often this, ⁓ gosh, you know, the team in Spain gets so much time off and, you know, we get our, you know, 10 holidays ⁓ and our unlimited time off. that we are too afraid to use and too uncomfortable to use. Why can't we be more like that? ⁓ And there's both the difference in the cultural difference ⁓ as well as the, even if I offered that, that might not be the right benefit for you. I might be kind of putting aside a bunch of money that you won't be able to utilize or won't. be interested in utilizing where I could do that. I could be more effective ⁓ with that benefit somewhere else. And so I think that that's always the challenge of not just, you know, paying attention and being curious to think through what your different groups need, but then also communicating that in a way that resonates, that doesn't start to feel like this, like, well, I got my stuff and you got your stuff and why do you have that and I don't have that sort of Trying to soothe that comparison instinct is a big part of the challenge. Kelsey Willock (17:11) So whether it is domestic, international, or coverage for the entire company, what's a benefit that you've introduced? Where you've seen go from just simply attracting talent or being a check the box solution to really transforming the lives of your employees. Ann Watson (17:30) So, so hilariously, I've tried a lot of, I'm always willing to try something different, especially if I, if I start to feel like, I think this is a gap for people. And I think I'd like to, I'd like to go talk about it, or I'd like to go see what we can do about it. And one of the things I've learned about that through failure is that sometimes, you know, that, that gap between what I, what I say I want, and my willingness to act. on that is really deep. And so like one of my favorite examples of failing at trying to go from attracting talent to like changing lives is deciding that a good initiative would be to see that we could, if everybody could have a will and an advanced healthcare directive in the United States. ⁓ Because that's a big deal. ⁓ it's from financially, it's a game changer if something happens to you. And so I talked to a bunch of people. was at one of our, I talked to a bunch of people. Do you guys want this? yes, that'd be great. So I went out and found someone who was willing to like come in and talk to the group and would be supportive of helping very simple, like here's a very simple will, here's a very simple advanced healthcare directive. We could have sort of like a death dinner only at lunch, at work, and everybody could leave with a will and ⁓ a healthcare directive. And ⁓ man, that was not good. I mean, it was fine. Like we did it. like, but that idea that, you know, we could, we could jump across, I could support them from desire to action was not true. That is, it's such a complicated topic. It's so uncomfortable. ⁓ Kind of like, I mean, the only thing we don't want, we want to talk about less than we want to talk about money is death. So if I want to talk about death and money, like good luck. ⁓ But what I, but on the flip side of that, what I, and this is maybe a ⁓ slightly unusual answer. ⁓ I was in an organization that really embraced remote work way before the pandemic. So this wasn't like as an outcome of that. This was, you know, very early on, you know, we, we realized that the people who knew the most about our product actually were actually our users and they weren't here in San Francisco. They were all over the country. And what we ended up this at the kind of as we pursued this, as we started to think about like, okay, well, let's most of this team will just not work here and we'll talk to, we won't, maybe we won't see them ever and we'll talk to them less frequently and how will that work? ⁓ And what was lovely about it was that we went from, ⁓ know, for this idea. ⁓ where we were trying to think of ways that we can improve the ⁓ quality of our talent and have, know, attract new people and people with great experience. And what I ended up, what we ended up having were these situations where, you know, the employer we were competing with was Walmart. So someone who's living in a rural small town, have... almost no employment opportunities. The largest employer in their town is Walmart, not trying to knock on Walmart, but there wasn't a lot of, there just wasn't any opportunity. There certainly wasn't opportunity to work in a tech company ⁓ and to change, that is life-changing to have, not only to have the opportunity to have, ⁓ you know, being part of a, you know, a pre-IPO company or having equity, having some sort of an event attached to that. ⁓ but also just being working for a different kind of employer, know, tech companies in general, as opposed to, again, no knocks, a Walmart, there's a difference in the level of benefit that are provided. There's a difference in the level of compensation. There's a difference in the amount of opportunity ⁓ and support that ⁓ some employers can provide that other employers either can't or don't. And for me, those moments where someone said, yeah, I was a... I was working at Walmart and now I work here ⁓ or some other kind of, or I was struggling to work and I'm a caregiver for an aging parent and now I have a job that I don't have to leave the house ⁓ and that's really changed my life financially. Kelsey Willock (22:08) The examples you gave are so interesting. I love that you bring up the trust and will example. And why I think it's so important is when you, like it reminds me of the example of, know, when you ask people, ⁓ when we had horses, what do you want? Everyone said a faster horse. We're not good at conveying what we really want or finding solutions that solve for the pain points we have. And vice versa. Sometimes we actually don't want what we say what we want. Our actions matter so much more. Ann Watson (22:14) Yes. Kelsey Willock (22:38) But I think that the hidden message behind everything you're saying is it can't hurt to you know, try and test different things in your populations, just, you know, uncovering data points and surveys or listening to what people say isn't enough. You've got to actually see what they show up for. Ann Watson (22:55) Mm-hmm. Kelsey Willock (22:57) And I think that, you know, a benefit of being a remote company or allowing work outside of the biggest cities in the United States means flexibility in the people that can actually work these jobs. think living myself in San Francisco, I know how expensive it is. And that means that probably a lot of talent that can't afford to live here. And so creating opportunities for them in unique places is absolutely a benefit in itself. Ann Watson (23:18) That's right. Yeah. And even the reverse of that, of having employees in San Francisco who come to you and say, hey, this is what's going on in my life. And I need to move somewhere. then ⁓ I remember a long time ago being part of a conversation about international expansion. And there were lots of people talking about these very data-driven reasons why they were expanding globally that were very business oriented. And all of my experiences and all of my stories were very human oriented. were ⁓ one of our founding engineers needed to go home. And so now we have an office in Poland or somebody needs to be somewhere else for a really ⁓ deeply personal reason. But as an employer, what I described earlier about like we've got this relationship that's somewhat tenuous. as you if you have a long tenured employee who is really important and special to your business, being able to have that flexibility for something like remote work or for international expansion can be just as life-changing as a salary increase is or some other kind of benefit you might offer. The other thing I would be compelled to add that I've learned through the years is there are a lot of really you know, again, in that vein of things that maybe people don't want to talk about or they're uncomfortable about, there are lot of benefits that you can provide. You can just decide that you're going to do this. It's a very sort of ⁓ authoritarian way to think about it maybe, but like I'm going to do this on your behalf. ⁓ And what I hope is that you never thank me later. And what I'm talking about are things like life insurance or things like ⁓ a long-term disability for salary support if someone has a catastrophic injury. Things like ⁓ automatic enrollment in a 401k, automatic increase in a 401k. It's happened twice to me that someone has reached out and said, hey, when I was 20, you automatically enrolled me in a 401k plan. And now I have a savings account that I had kind of forgotten I had, and it's valuable. thank you for that head start. ⁓ and that's, I don't think that's a, that's not necessarily a thing that happens very often, but it was super impactful. ⁓ and now it's a thing that, like I said, I would just decide to do that on someone's behalf because I hope you never need like the, the idea of like the difference between attracting talent and changing someone's life. There are a lot of things we provide for changes in people, like life changing events that are not positive or not, you know, happy and joyful. but we wanna be prepared for those as well, even more so because they are so impactful for someone ⁓ and can be ruinous, especially when it comes to a healthcare event that impacts your ability to hold a job and make a living. Kelsey Willock (26:37) And last question for you, is what benefits trends or trends overall in your world do you think are going to shape the employee experience most over the next year? Ann Watson (26:48) I mean, I couldn't possibly answer this question without saying AI, but I'm gonna set that, I'm just gonna like check, yes, we all know this. ⁓ I think I'm actually, maybe I'm really hopeful that ⁓ pay transparency changes things for the better. Maybe I'm a little bit of an outlier in that. I love pay transparency. I love the... ⁓ Rigor it requires. I love the conversations that inspires. I know it's really hard. I know it's really scary. I know it's distracting. All the things. overall, I think it's really good. And I encourage, know, I think the ⁓ new EU regulations are going to be really interesting. think the states that have these regulations, it's been really interesting. What we're learning about people's behavior when it comes to things like putting salary ranges and job postings. There's so much good in there and so much opportunity. I would love to see that continue. Kelsey Willock (27:55) I couldn't agree more with you. I think that, you know, with the regulatory changes, could probably spend another 30 minutes talking about pay transparency in general and how you're all organizing it. But I think it's a really important change that is really ultimately going to benefit us all. So thank you so much, Ann, for this wonderful conversation. I learned so much from you. And I sincerely appreciate all the candor, especially around sharing more about your childhood. Ann Watson (28:03) you Thank you. Kelsey Willock (28:23) and how that's infected how you show up for people. just carries through in the conversation how much you care for people. So I sincerely appreciate your time. Where can our listeners connect with you beyond this conversation? Ann Watson (28:37) You can find me on LinkedIn. ⁓ I am actually someone who doesn't participate in social media. So you can't find me on social media other than LinkedIn if you consider that. But also, know, my email is in my LinkedIn profile. You can always send me an email. ⁓ I would love to connect with anyone. I have a website at Zone2People. And if you want to look for that and connect with me there as well. Thank you. Thank you, you too. This was a great conversation. Kelsey Willock (28:59) Fabulous. Well, thank you so much again and have a wonderful weekend.