Heather Cassar

▶0:01HostWelcome to the Built by People podcast, where we share the stories and insights of the world's top HR leaders. Join us as we dive deep into the minds of HR executives, uncovering their strategies, challenges, and triumphs in shaping today's workforce. I'm excited to welcome Heather to the Built by People podcast. Heather, thank you so much for joining us. And as a starting question, I always love to ask if you could share a little bit more about your career journey.

▶0:53GuestYeah, for sure. First, thank you so much for having me. Big fan of the show and super, super honored to be here. I think like most great HR people, I fell into it completely by accident. So, I was working full-time in event planning to put myself through college and like the very smart 21-year-old I was, accepted a full-time offer without actually asking how much they were going to pay me. So, I got my offer letter a few weeks later, saw the number, panicked, and then immediately called a temp agency and told them I didn't care what I did. I just needed enough money to pay my bills until I could find my quote unquote real job. Um, and they asked me if I wanted to be a recruiting coordinator at Thermo Fisher Scientific. And I said, I'll sweep the floors at Thermo Fisher. I just need to be able to pay my bills. So, I started there and 3 weeks in, they offered me a full-time job. And I remember calling my dad and saying, I don't know if I want to work out in HR and deal with people's problems all day. So, spoiler, it's been 14 years since then, and I do, in fact, deal with people's problems a lot of my day. I made it through, and from there, spent some time at Thermo Fisher in sort of various HR generalist roles and landed at Uber in 2016 as one of the first HRBPs for the engineering function. We grew from 6,000 people to more than double that in just over a year, which was exactly as chaotic as it sounds. And after that, I joined Square, which is now Block, and moved into various leadership roles in HR, and in 2020, became the first dedicated HRBP for Cash App. And over the last 4-ish years, I built out the HR function, the L&D function, and organizational development function. To over a 30-person organization, and it was the most fun and most I've ever learned in a job. And after I left there last year, took some time off, and by the time this airs, I'll be jumping into a new gig as a VP of people.

▶2:40HostHeather, you've obviously experienced hypergrowth at both Uber and Cash App, growing from 6,000 to 13,000 people in 13 months and at Uber and 25 to 4,000 people at Cash App. What were some of the biggest challenges and lessons learned during those rapid scaling periods?

▶2:58GuestYeah, at Uber, I think the biggest lesson learned for me was being able to make a decision with 10% of the information I needed at any given time. In hypergrowth companies and situations, you just can't wait for perfect data. There's no time for that analysis paralysis. You just have to use all your resources and piece it together to find that other 90%. So, from— I leaned on my peers, on customers, people who used Uber, mentors, people inside and outside of the company. And at Cash App, I think the biggest challenge was not over-engineering our programs. Cash App, when I was there, was a business unit within Block, and Block is a 13,000-person company, even though Cash App was much smaller. So, it really felt like a startup within a bigger organization, but one of the challenges was being able to move really quickly as a startup while still staying accountable to the larger organization at Block. So, I think there the key lesson and takeaway was to build just enough structure to keep up with the pace, no more and no less.

▶3:57HostHeather, can you walk us through the decision to eliminate the annual review cycle at Cash App and what led to that transformation and also elaborate on some key insights from transitioning to a continuous feedback model?

▶4:10GuestTotally. So, for anyone listening and is hoping for a quick solve to moving to a continuous feedback model, This was a marathon and not a sprint. It took over 4 years to get to this place. Why did we start with continuous feedback? When I first joined Cash App, I traveled to all of our offices and I met with every manager and I asked them 2 questions. I said, what makes you come into work every day with joy and with passion? And what makes it hard to do that? And the biggest frustration overwhelmingly was the annual review cycle. The engineers that I met with called January a no-service month because reviews took over everything. And that was terrifying to hear, right, as an HR leader, that a program that we owned was causing us to be detrimental to the product that we were producing. So, we knew that we had to change. And so, the first thing that we did was try to address some of the how. So, we rolled out Lattice for continuous feedback. And really interestingly, we didn't mandate it. We didn't require it, but we had an over 90% adoption rate. Really signaled to me that people were hungry for this and excited for more. So, from there, we tried to define really clear behaviors not just what we did at work, but how we did it, right? Talking about our values and our behaviors and, and how we show up. We built out a rating system, um, to help understand how people are performing in comparison to their peers and really get good calibration there. And then we started to work on ways to link that feedback to compensation. So I think one of the proudest moments in my career after I left Cash App was seeing that Jack Dorsey announced that they were going to scale this model across all of Block and starting from this little sort of grain of a thought that we have from feedback from our managers into this thing that incredible company is using was really a proud moment.

▶5:50HostHeather, in your experience working with established companies going through hypergrowth, how does the HR approach differ from traditional startup scaling and what unique considerations come into play?

▶6:01GuestYeah, I'll use an analogy that I think a lot of people will understand. So scaling a hypergrowth company versus traditional startup is like the difference between assembling IKEA furniture with instructions versus doing it while the instructions are on fire. Both very difficult. So, in a traditional startup, I think you're really focused on building kind of the foundational HR structure, stuff like your hiring processes, your basic policies, figuring out if culture means free snacks and LaCroix or actual leadership values. And in those environments, it's methodical and it's still super fast-paced, but there's usually a little more time to be intentional. I think when you're working in a hypergrowth company, it's controlled chaos. So, you're hiring at lightning speed, you're trying to maintain your culture while doubling your headcount every few months, and you're onboarding people so quickly that you're wondering if that new person that just walked in is here by mistake or because they heard there were free snacks or if they're actually one of your employees. I think the biggest shift there is that when our function is HR, we have to operate like a business function, not just a support team. So, we're trying to align hiring with revenue goals. We're keeping leaders from burning out. We're making sure that we don't wake up one day and realize that we have 500 employees and no actual managers anywhere. And so, ultimately, it's about balancing speed and sustainability. I've heard a lot of startup founders have this sort of mentality of move fast and break things. I think in HR, our mentality can be more of move fast, but not so fast that we break everything all at once.

▶7:31HostHeather, having worked at companies like Uber and Block during different stages of growth, what are the most critical HR systems or processes that need to evolve as organizations scale?

▶7:43GuestYeah. One of my favorite phrases to use at work is to make exceptions for exceptional circumstances. So early stage companies, I think, often have inconsistencies in things like pay, bonuses, feedback, and that's totally normal, right? You're starting from a place where you have a founder or founders and they hire people they know, and those people trust them implicitly, and they're able to get a lot of the context on why decisions are being made. But as you start to scale and grow larger, those inconsistencies become pain points. People wanna know why decisions are being made. So I think the shift that has to happen is moving from gut feel decisions to things that are scalable, things that are transparent and have frameworks while still keeping some flexibility for unique cases. So in those situations, my litmus test has always been if I had to stand up at a town hall or in front of the company and explain why we made an exception to something that we said was part of a framework or that we weren't making exceptions to. Would people understand that? Not would they agree, but would they see the logic? Would they see the reasoning and say, okay, this makes sense to me?

▶8:47HostHeather, from your perspective, how has the role of HR leadership evolved in high-growth tech companies over the past decade?

▶8:56GuestHR follows the market. So when talent was in high demand, our function, HR, was about perks, about employer branding, about moving really quickly, doing new and exciting things. I think now with more supply than demand, the focus has really shifted to efficiency, accountability, and retention. I think the biggest change— touched on this before— is that HR is not just a support function. We're not a personnel department. We're a core business driver. I think the most important data set that I use every day, it's not retention rates. It's not employee engagement. It's the P&L. And if you don't understand how your business works and how you make money and the customers you serve, You won't succeed in the HR function today.

▶9:36HostHeather, what parting advice would you like to share with our community?

▶9:40GuestSo, I'm assuming that people are listening to this episode and maybe some of those people are considering roles at a startup, so I'll focus my advice there. Your actual job at a hypergrowth company is going to change really quickly, but the culture is going to evolve a lot more slowly. So, don't take the role just for the title, right? There's lots of companies where you have a sexy, flashy title. But really dig into the company's values, how they support people, how they handle change. And this is a hot take, but if those align with how you like to work, the role itself almost doesn't matter. In 6 months, it's going to be a different job anyway.

▶10:15HostHeather, thank you so much for joining us on the Built by People podcast. It was a pleasure to have you involved.

▶10:19GuestThanks, Dave.