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Why you should switch from Transactional to Transitional Leadership

Cassy Aite
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“I know three unicorn companies where a HR leader was among their first fifteen hires. People thought they were crazy, but they did it anyway, and it paid off”

Cassy Aite

In this episode

Enjoying leadership from an early age, Cassy firmly believes that true happiness comes from enabling others to do their best work. Working with teams worldwide and experiencing different cultures, Cassy knows first-hand that HR has a direct impact on wellbeing and productivity, which is why businesses that invest here early, tend to do best. 

Tune into this inspiring conversation with Cassy by clicking PLAY above. 

Cassy Aite covers: 

  • The story behind Hoppier and how the company successfully evolved as organisations were propelled into remote work
  • How to unify a culturally diverse team
  • Why companies need to switch from transactional to transitional leadership
  • Ways in which companies can invest in their people to allow them to progress both personally and professionally 
  • The benefits of understanding the role of forward-thinking HR early on

. . .

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In this episode


Cassy's background in leadership


Managing a culturally diverse team


Enabling people to do their best work


The story of Hoppier and how the company has evolved


Company culture and being scrappy


How to develop teams


The benefits of investing in people and HR early


Quick-fire questions

Resources from this episode

Transcript of episode

Tom: In this episode of the Culture Builders podcast, we're actually turning the tables. My name is Tom and I am one of the producers of this podcast. We're joined by the normal host, Cassy Aite. We're going to be talking about culture at his own business, Hoppier. Cassy, welcome to the show.

Cassy: Thanks, Tom. It feels weird to be on the other side.

Tom: Yes, because at this point, you have actually interviewed a number of people leaders, right? I'm assuming the insights you've got from them are going to help you be an amazing guest.

Cassy: I hope so.

Tom: First question. I want to understand when you first got into leading people within an organization, whether that was at Hoppier or with previous experience.

Cassy: It was at a previous experience, but I think there are many opportunities in life where you lead people and you may not realize it. I think of the first times that I led people were when I played soccer as a kid and I was a team captain or I coached soccer at some point too, and I coached football at some point too. My first time leading in an organization was actually before Hoppier. I worked in business development at a consulting company that was based in Italy and I worked in the German and the Austrian office.

I did that for about two years. We had a team of about 20 or so people that were working out of the German and Austrian office. That was really my first experience. It was a great experience because it was a totally different culture. I didn't speak the languages, and I was working with all these people from different countries around the world.

Tom: You just mentioned quite an important word for us at this podcast, which is culture. I'd like to dig into that example first, where you mentioned that they have a totally different culture than you were part of. My question would be how did you then go into that group of people and then either inspire or make that culture work for you if that makes sense?

Cassy: I think it's like the culture changes over time in some ways. Not in big ways, but when you have the makeup of that culture being people within the organization being very different, then the culture ends up being some kind of mishmash of those groups of people. As an example of that, I worked with a group of Italians that were very personable, wanted to talk about their personal life and share different things about themselves. Then I worked with a group of German people who just wanted to focus on the work and get down to it. Then for me, I'm somewhere in the middle.

Just that example, where we saw ourselves finding ourselves somewhere in the middle is the perfect example to me of how culture ends up being some kind of derivative of the group of people that make up that culture.

Tom: We're going to jump much more into culture later in the interview. Before that, I want to ask you, you mentioned before you were leading even before you really knew that. What drives you to lead people? Why do you do that, and what do you get out of leading people?

Cassy: I think to me, and I heard this the other day, and it's like true happiness is helping other people. I think about the moments in my life where I was happiest and where I had the most joy. It's so cliché and stuff, but it's true. As much as you think that maybe other things like money and possessions, et cetera, would make you happy, really true happiness is number one having gratitude, but number two, giving to others.

I think if you can close your eyes and think about the moments where you're happiest, you're going to think back to that moment where you did something for your child, or that moment where you did something for your significant other, or for your parents, or a friend, or somebody else that you care about. That to me is true happiness. For me, my biggest joy in work is helping people to achieve the things that they want to achieve.

I think, as a CEO, founder of the company, my job is to focus on enabling others to do their best work. That's why I love leading because I feel like I'm like this enabler that can help people achieve and to see and to remove those barriers for themselves. That's why I love leading.

Tom: Got it. Now, I want to talk about specific leadership case study. For those people listening, you may be aware of Hoppier, which is Cassy’s business. Also, you may also be aware that Hoppier used to have a different name and actually used to have a different product. I personally was very impressed at the speed in which you guys tweet your strategy. Can we first understand the leadership challenges over that time period, which I think was probably just one to two months where you guys almost completely overhauled your business model? What was that like? How were the personnel? How did you manage the personnel challenges there?

Cassy: We started Hoppier three and a half years ago originally as Desk Nibbles. The whole idea was that we were going to help companies with the way that they manage food in the office. This is while Emil was working as a software developer at Shopify, and he saw the way that they were purchasing things. He thought that companies like that, that are growing very fast could use help and we could build software for that.

It ended up expanding. We rebranded in 2019 to Hoppier to be able to support with the procurement in the office for not just snacks, but also coffee, equipment, office supplies, and we built this marketplace around that. As a result of COVID-19, people are now working remotely. In a very short period of time, we started to see revenue first in San Francisco then in New York, then in Toronto just fell off a cliff. We had to come up with a solution because we realized this remote work thing is here to stay.

Even before the pandemic, we knew that remote work was a wave that was coming but slowly, and this just accelerated that 10 years. We ended up realizing after testing a bunch of different things that the thing that really stuck was this concept of supporting the management of fringe benefits. It's what we already managed in a way before as equipment, food in the office, etcetera, is a fringe benefit.

We effectively built on top of that idea, and we built the software that enables HR leaders to easily manage their budgets and to manage their allowances and stipends in a very simple way that's tax compliant, that's easy to manage, and easy to set up and remove for employees around the world. That's stuck and now we're seeing huge amounts of growth, growing faster than we ever did before because we're seeing companies that are finding new ways to support their employees. Either with a lunch program for remote employees, or a work from home stipend that allows employees to buy equipment, desks, monitors, keyboards, etcetera, and so many other interesting and unique things that companies are doing.

It was challenging, but I think it goes to our culture, which is being very flexible and scrappy. Scrappy in the way that we do things and just testing things, and we're able to move really fast and come up with a solution.

Tom: I'm glad you started to mention your culture because my next question on that is this scrappiness. Is that something that you actively wanted to see your people have or how did you bring that into the culture?

Cassy: It's a good question. We've always been very cognizant of how valuable culture is to us. It's funny because I thought that- -company culture, or whatever, this was corporate speak for brainwashing your employees. That's what I used to think. Now I realize that communication is probably the most important thing as a company grows. I think you can get away with not having strong communication early on and having total team alignment.

But as a company grows, you need to go from being a transactional leader, where I'm just telling people what to do, to a transitional leader where I give people the framework or we build the framework together, then my team goes out, and they execute. I don't need to tell everyone what to do. Otherwise, it's impossible to actually scale a company or any organization for that matter.

For us, we were cognizant of that really early on. We said, "We need to come up with a culture framework so that people make decisions according to the culture that we have currently, and that we want to continue to reinforce." Part of that culture, we broke it down into an acronym to keep it simple. It's really a makeup of just seven things. The acronym is W.E.I.G.H.T.S. The whole idea is that there are no shortcuts, everything is reps, so we have to exercise those aspects of our culture on a daily basis.

Those aspects are, you've got to create wow moments internally and externally, you have to have empathy, we are infinitely curious, we're genuine, we're high achievers, we are transparent, and we're scrappy. We developed that culture code or that culture framework around the types of people that we had in the company at a certain point, and what we realized what we wanted to build. I think it's done really well for us and it's allowed us to move fast. It's helped the team immensely, so something I'm really proud of that we've done early on.

Tom: When you did that culture exercise, the strategy for coming up with that, was it by looking at the current team members, choosing the best characteristics, the most effective characteristics that they had and then formalizing those? Or did you also think, "Yes, actually, we need to be scrappy and therefore we should add this in?” Or was it a combination of those two approaches?

Cassy: Yes, it was a combination. It was really looking at, "Who are we today? Who are the people that we are?" because if there's certain aspects about the people today, it's going to be hard to change them. We did it early enough where that wouldn't be difficult. Then there were, like you said, the other things that we recognize that maybe we don't reinforce this enough. Maybe we are not genuine and quirky, and we need to have more of that.

That's the exercise we went through and as a team. It probably took us two or three months, so it wasn't easy. Now what we're doing is we're reviewing them every year. We're making sure that all leaders are hiring and firing, making key decisions according to that framework.

Tom: That's now ingrained into the process and I assume you’re even, when you look to hire or fire, you're almost screening people against W.E.I.G.H.T.S?

Cassy: Yes, totally.

Tom: Got it. Makes sense. I want to pick out one of the parts of the W.E.I.G.H.T.S, which is H, high performer. What are you doing to actively develop the people within the business to ensure that they can live to that value?

Cassy: Yes. It's a great question. Of course, we use our own product, we use Hoppier in our own company. We've done both training internally and externally. Part of that external support that we give to employees is we do give employees the ability to spend on training or workshops or coaching, or something that's going to help them advance in their personal and professional career. That's really important to us. Even if it's for that employee that wants to advance in some other aspect of their career. As an example, if we had someone who was working in sales who wanted to be a UX designer, totally cool. We're going to support that. I think that that'd be really interesting if you had someone who has a sales background and going into UX design.

Those are the kinds of things that we're doing to support them externally, but also internally. Everything from, you've got one-on-one coaching with your lead, you've got 360-degree review with your entire team. You're not just reporting on the people that might be reporting to you, but you're also getting feedback on the person that you might be reporting to. That person gets that 360-degree review, and we do that on a biannual basis. Then we'll do “lunch and learn” and all kinds of other things.

We've got a team Audible account. We've got a library channel in Slack where people are posting all kinds of interesting things that they learn. Then we do a weekly show and tell as a part of our town hall every week. In that weekly show and tell, somebody will usually talk about something interesting that they worked on or they learned. We've had all kinds of things. One example was we had someone that talked about morning routines and all kinds of weird morning routines people do.

We had someone do a one-on-one on Photoshop, and how they learned how to use Photoshop, and they taught the team how to do basic Photoshop. We've had someone teach the team how to make the perfect espresso, so all kinds of cool things. I think that leads back to of course the culture value that we have, being curious.

Tom: Quickly to clarify on the external training part. Do you give each employee a specific budget that they have to spend on external training or how does that work? Do different employees get different budgets? What's the process?

Cassy: We don't force employees to spend on the budget, because we get that it's going to be ebbs and flows. Maybe one year you don't do any external training, but then the next year you're going to do, let's say 500 hours of external training. We're not going to force people to use it, but we do have it available for everyone to use, and it's the same amount for everyone. I've seen companies where they offer a greater amount and it depends on every organization. In some organizations, you may need to invest more in training for certain parts of your organization. In our case, we give a straight $5,000 per employee per year allowance for people to spend on different things that have to do with personal and professional development.

Tom: Got it. Now, I know you are [unintelligible 00:17:29], but just for the listeners benefit, because this is one of the first episodes in the podcast feed. The basic thesis behind this podcast is that for a business to grow, first we must develop the people, which is why I just asked those questions about developing people. As it seems you're doing at Hoppier, you're building this culture where one of your values is always being a high performer and therefore you're doing all these things around that. My final question in the middle of part of this interview is have you seen a direct business benefit from the efforts that you have been putting in to grow the team members?

Cassy: Yes, for sure. Totally. This is always the thing. I feel for HR leaders because it's an area of the business that can be hard to quantify. It's harder to quantify than a lot of other areas of the business. I think there's certainly ways to do that. You can look at retention, you can try to look at productivity but you just feel it. To me, you just feel it. You feel it, and then you see small examples of it, where you'll hear an employee that tells you, "Wow. I just wanted to let you know that I was going through a really rough period earlier this year. Because Hoppier supported me to be able to do this training, it gave me confidence and gave me the tools that I needed to do my job."

You're like, "Holy shit, I didn't even realize that, and I didn't realize you were going through that and you were thinking about leaving. This was able to uplift you and make you not just more productive, but also just a happier human being." That's so rewarding for everyone. Yes, these things just happen. It's like you feel them. You really just feel them. You can try to quantify them, and you can in some ways, like I said, but you'll just feel them and experience them. It's just become so clear that it's worth it to invest in your people.

Tom: Yes, that's the challenge for the HR leader. If you have let's say a CEO who maybe doesn't feel the same way as you do- -he or she may challenge the HR leader on the return they're getting on their employee training program. Then the HR leader would have to try and come up with those tangible or the numeric benefits. What you're saying there actually, it’s a feeling that you get, which I totally agree with.

Cassy: Yes. I think it's so much like when I look at larger organizations, and I talk to HR leaders in these larger organizations, the challenges they have to get budget approvals in comparison to other parts of the organization, is VP sales is going to be able to get their $300 million budget versus VP HR who's fighting for $50 million budget. Outside of their budget for hiring, is it going to be easier? For sure because I think ultimately, HR can be looked at as a cost center.

I think the way that people have to think about HR and these kinds of projects is to think about it as probabilities. To me, you have to think about probabilities and business is all about probabilities. You think about your outcome as the expected value. If you can increase your probability of success across the entire business by 15% to 20%, would you do that? Yes, 100%. Everybody would do it. I don't think there's any part of the company that can have a higher impact than on HR who's having a direct impact on the well-being and productivity of the people.

I think people have to remember and think about that impact and those probabilities. Just because something is harder to measure, doesn't mean you shouldn't do them. I know of three unicorn companies where within their first 15 hires, they hired an HR leader. People thought they were crazy and they did it anyway. I think what it did for them was it increased their probability of success by many multiples, because all of a sudden, they got better at hiring, all of a sudden, they got better at retaining those people in the early stages where it's very important to have your core team and if somebody leaves at that point, it's devastating. Again, it's like you got to think about those probabilities and how important those people are.

Tom: Turning HR into the profit center you could say. Awesome. Cassy, we now need to move on to a quick-fire round. My first question is, which people leader, whether you know them or not, would you most like to take for lunch?

Cassy: I think it’s Kim Scott, probably. She's amazing. She's the author of Radical Candor. She’s a leader at Google for many years and an entrepreneur and has tons of experience. Consulted for some of the largest companies in the world. I think she's awesome.

Tom: The single piece of advice you would give to a new people leader.

Cassy: Listen.

Tom: Awesome. Cassy, thank you so much for coming on. Probably my favorite part of the whole interview was the part where you said that yes, you can try to measure the impact of growing your people but the benefit can really be felt. I think that there's probably HR people leaders listening to this now nodding their heads. Even me, I can feel when people in my team are performing well. Then I look back and see that actually, the training session we did last week impacted that, or the budget we gave them impacted that so I totally agree. Thank you so much for coming on and I look forward to seeing you pull out more gems of wisdom for future guests on the show.

In this season

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