Faces of HR

Words of Wisdom from an Employment Lawyer Turned HR Professional

In my line of work, I run into employment lawyers and HR professionals all the time. But I almost never run into people who are both. Today’s interviewee has that distinction, and it has given her a unique look at both worlds.

Jessica Pfisterer, Head of People, Lively

Meet Jessica Pfisterer, the Head of People at Lively, a company that provides health savings accounts to employers, individuals, and families.

How long have you been at Lively?

I’m actually pretty new here. I started at Lively about a month ago. I’m the first HR hire here. There’s a lot to do!

I bet! What got you started in HR?

I came upon it somewhat accidentally. I worked for a really tiny start-up in 2006 where I was the company’s jack-of-all-trades doing HR, payroll, and office work. At that time, I was already planning to go to law school—I’m also a lawyer. I worked there for a couple of years.

The company ended up losing funding, so I went to law school and focused on employment law. That’s what I was interested in and wanted to do. After graduating, I found that the legal work was not quite what I thought it was going to be.

I thought maybe I would use my skills to get back to the tasks I was doing before, and it worked out really well for me. I’m just on the flip side of what an employment attorney might usually do. I actually think my legal background has helped me a lot with my career since then, and I really like the part of HR that makes companies great places to work. That’s really the exciting part of it for me.

Much of your experience is at start-ups. Is that by design?

When I first got to MuleSoft, it wasn’t clear that that would be the trajectory. I liked it so much that I decided to go and do it again at Greenhouse and now here at Lively.

It’s certainly something that interests me. There are a lot of really unique and interesting problems to solve when building a company, especially when there’s so much change happening in HR fields, like what kinds of tools are available and how people are approaching everything from employee experience to forming its reviews. It keeps changing, and there’s some flexibility in scaling a company and helping it find what the right tools are.

You’ve had the unique distinction of being the first HR person at a company. A lot of our readers have fallen into being the first HR person at their company, and some of them probably don’t even have that title, but that’s what they’re doing. What advice would you have for someone like that?

When I think back to my time at MuleSoft, I was kind of doing the HR stuff but also other stuff. I was trying to make it all work and was sort of a one-person show. I had to make the case for why it was important for me to focus on just HR and retention.

The folks who are doing this kind of work can get really caught in the weeds of getting everything done. There’s compliance, there’s payroll, there’s benefits; you have to go do them. But, if you don’t focus on the other pieces—the complete employee experience, happiness, and retention—all that work goes to waste. I think people get stuck when they feel like they don’t have time to make the case for themselves.

The best thing people can do is make the business case for having an appropriately staffed HR or people team. It doesn’t mean things will be different; it doesn’t mean they’ll get it right away. But, they should at least understand their capacity and explain to folks that if someone isn’t hired to do this part, they won’t be able to do X or Y because they don’t have the bandwidth or the resources.

I think when you’re in the day-to-day grind of HR, it can be easy to forget to step back and look at what you might be capable of if you made the business case to upper management or the founders.

Do you have anything from your personal life that motivated you along your path?

I’ve always been very interested in justice and human rights and people being treated well. Those things matter to me. I feel like HR is just a microcosm of them. It’s part of why I was interested in employment law. It’s the idea that for the most part, we all have to work in jobs and interact with each other. Why not make our company the best-possible place to be? I think, over time, it became a focus that led me to HR. It’s been a narrowing down of something I’ve always believed in.

This is part of the reason I chose the companies I chose, first Greenhouse and now Lively—is for the interest they have in retaining a diverse workforce and making sure people are well-supported and able to be their best selves at work. I’ve chosen companies that line up with that.

What would you say is something from your time in HR that you’ll never forget?

I feel like there are so many things. One time, I was able to help an employee through the process of getting a green card. It was such a long process that I didn’t see it to completion because I wasn’t at the company long enough. But I was there for the bulk of the process.

He had already gone through the process once, and it had gone wrong. There were some errors, and the person had a bad experience with a prior employer before I got involved. A couple of years after I left, I got a message from him on LinkedIn saying, ‘Oh my gosh, it finally came through, and I can’t believe it; you’ve changed my life.’

I was just like, wow. I think that happens in other cases in smaller ways. I do think that HR folks have a big impact on employees, and that was one example of when I got the direction correct for that person, and it was really nice.

That must have felt good.

Yeah, I think it happens to a lesser extent in a lot of ways. But your readers are probably doing things every day that actually impact employees’ lives in real ways.

How about the other way? Has there been anything from your professional time that’s helped influence your personal life?

I’ve recently gotten more into business partnering and philosophies around feedback. I’ve also spent more time looking at the bigger picture, and I’ve learned the different kinds of strategies for feedback folks use. I personally like Radical Candor by Kim Scott—a lot of folks might be familiar with that. I actually try to use that in my personal life, as well. I trained employees on it, and then I realized that I should use it all the time because it’s a really great way to communicate. It’s proven to be fantastic.

Because my job is a people function, it’s really all about how people communicate with each other. Most of that also translates well to life outside of work. I tell employees when I’m training them, ‘Hey, you can use this in your regular life, and that can also be practice for when you use it at work with your manager or with a coworker.’

What is that burning thing you always wanted to say to the world?

I really think I would just double down on the idea that whether you’re calling it HR or People, the work is really important. It’s important to lift our heads up and make sure that we’re thinking ahead and that we’re being proactive. I think that’s the focus shift that will really help folks elevate what they’re doing at their company. No matter the size of the company, you are going to get something of value if you sit back and ask, “Where do we want to go, what do we want to do, and what are the resources we’re going to need?”

When I made that focus shift, it changed the way I approached HR, and it’s made it more enjoyable for me. It has also been more impactful for the companies where I work. That’s something I’m really excited about.