Helen Shacklett (00:00)

To explore everything you need to know about making a first hire and building your company culture, I’m excited to sit down with Shawn Hewat. She’s the CEO and co-founder of Wavy. So welcome to the podcast, Shawn. How are you doing today?

Shawn Hewat (she/her) (00:14)

I’m so good, thank you for having me.

Helen Shacklett (00:16)

Likewise, definitely. Tell us a little bit about Wavy and your growth journey so far. 

Shawn Hewat (she/her) (00:22)

Yeah, absolutely. And so I’m the co-founder and CEO of Wavy. We actually started the company in 2019 right before a little thing called COVID. And we initially started it as a passion project. We wanted to help groups of people find great experiences to connect with. And that ultimately turned into corporate experiences. And as we dug into the world of team building and employee engagement, thought there was a lot that we could improve.

A couple months into that journey, COVID hit and the world of team building and just how we connect as people changed quite a bit. So we thought, let’s take all of that research and time and love we’ve put into great experiences and bring it into the online world. Teams are going to be distributed going forward. How do we help them still connect and get to know each other more than a face and a name on Slack? We still need to be connected to each other. So we launched a full marketplace of team building events that expanded into wellbeing and mental health focused events, leadership development, arts, cooking, DEI training, you name it.

All of a sudden we were working with hundreds of teams around the world. We used this to gain insights on where companies and leaders were struggling with engaging their teams. What started as fun team building events turned into us building tooling and features to help leaders run better employee programming and get a better pulse on what’s driving engagement and what’s not. So years later, heading into 2026, we actually now exist as a culture insights platform. Essentially, Wavy helps leaders centralize, automate, and measure the real impact that all their people programming is having.

Anything from a town hall to an onboarding session to leadership training and annual kickoff — sales kickoffs, socials, hub events and more. Anything that lives on the calendar, you sync to Wavy and we give you real time insights and data on: is this actually making an impact? Who’s engaging? Who’s not? Is all of this budget and time going to good use? And is there anything you can change now instead of waiting for your annual engagement survey?

So coming on here today to talk about culture and hiring and talent. This is the world I live and breathe, so it’s fitting. And that’s a little bit on how Wavy’s evolved over the years.

Helen Shacklett (02:56)

No, that’s fascinating. I will say that sounds like one of the good things that come out of COVID, right, is Wavy. And what you uniquely bring to the table, it’s really taking the fluffiness out of culture programming. I love that.

Shawn Hewat (she/her) (03:03)

Yeah, thank you.

Helen Shacklett (03:10)

So before we dive in, tell us the story about your first hire at Wavy. So how you knew you were ready, the role, how you chose the right candidate and how it worked out.

Shawn Hewat (she/her) (03:21)

Our first hire was because we had launched this team building offering and we kind of put it out there as a feeler. This was spring 2020, three co-founders were working on the business so we were really the first employees or first hires. But then we put these experiences out there and started getting bookings from corporate teams. And that led to a referral to another team and another booking from the one customer who referred us to another customer. All of a sudden we were getting referred across HR communities — not just in North America, around the world. And we were completely overwhelmed with demand, which I think is a really good trigger for looking at not just your first hire, but building out your initial team.

Is there something you really can’t meet from a capacity perspective? Or are we blocking ourselves from growth because we’re too strapped for resources? So the three of us were working on the business. Could we do way more in business and sales if we had more people in here? So our first hire was customer facing. We really needed help on managing our event bookings, our partnerships, making sure customers had a great experience with Wavy and were coming back for more.

We had someone who was ready to jump in and do project-based work with us. So that’s how we ended up bringing them on board. And after their first couple of months with us as a contractor, we thought, we can’t operate without you. We need to bring you on board now. Once we started working with hundreds of teams, that’s when we decided, all right, we’re gonna need another developer in here to help build out the technology and another customer person to make sure we’ve got a fantastic experience. We’ve always been very customer obsessed at Wavy.

Helen Shacklett (05:10)

That makes sense. I mean, you’re people obsessed, right?

Shawn Hewat (she/her) (05:12)

Exactly. And the funny part about building and just navigating the waters that is building a startup is a lot of our customers and advisors and investors are in the people and culture space as well. So there are so many people in the talent, HR, people and culture space that we can tap on to say, hey, we’re doing this, what do you think? Or what are your best practices for this? So I’ve gotten a lot of advice and resources along the way.

Helen Shacklett (05:47)

So speaking of that, what do you think is the most valuable piece of advice that you got in regard to your first hire?

Shawn Hewat (she/her) (05:53)

For us, the first hire was a no-brainer. We literally could not meet this demand. And we were building our technology alongside our customer growth. So it’s not like we were out there building something and shopping it around for customers. It was, we were bombarded by customers and needed to build better systems to support them.

That’s how Wavy’s growth journey went. So when we built out our vision for this culture OS and analytics product and raised some seed funding, how do we navigate from there? And I think some of the really good advice that we got — maybe after making some mistakes where we hired a bit too quickly and didn’t yet have the demand or capacity for it post seed raise — was: what’s breaking in your business? Are there certain processes or areas that are completely broken because you’re under capacity? Can you bring people on that can start with a project or contract-based work before going full-time? And that’s ended up being a way that we’ve brought a lot of people on board. People who are still with us for over four years followed this path.

Helen Shacklett (07:49)

Generalizing this a bit for the audience — it was really obvious the trigger for you about when to hire, you had all this demand to deal with. But for other folks kind of considering ‘is it time yet,’ do you have any indicators, framework signs to know when you’re ready to hire — financially or otherwise?

Shawn Hewat (she/her) (07:58)

Well, if I’m going to go a bit higher level, I think something interesting has happened over the last five years in the tech ecosystem. In 2021, a big indicator of your success was how many people do you have? The bigger the better — it was the indicator of success. And now in the age of AI and tons of gen AI startups coming to life, it’s actually the opposite. We’re doing X million a year and actually only three people. You can do a lot more with less.

So when I used to give advice a few years ago about how do we know when we need to make our first hire, I’d be more forward about building out your team. And now I’m like, why do you need to hire them? Can’t you do this yourself? Have you tried automating this process first? What will the impact be to the business if you do bring them on board? Is it going to streamline things so you can take on more customers? Are they going to help us open up a new market? Are they building a feature set that’s going to increase account size or bring in additional revenue? Like, what’s the real business case for bringing that person on board?

Helen Shacklett (10:18)

Now it is kind of crazy that now the flex is I can do so much without the head count, right?

Shawn Hewat (she/her) (10:23)

Yeah!

Helen Shacklett (10:24)

You kind of covered the question of full-time employee, contractor, fractional, but how would you suggest setting the level of seniority for that first person and really just overall the type of role that you should hire for?

Shawn Hewat (she/her) (10:37)

It’s really going to depend on what does your founding team look like? Where are the gaps and what area of the business is it going to be? In general at Wavy, we have quite a lean team and we’ve been focused on bringing more intermediate-senior folks on board who have great experience. They’re still eager to grow, but have accomplished quite a bit because of the level of experience and grit that they have.

I think a lot of times founders will bring early employees on board and give them a head of or VP title, perhaps a bit too early. It’s better to go generalist and then as the company grows and the team grows and you need to bring more structure in, then to start to look at title promotions and general promotions. I’d go manager or lead level rather than head of or director of or VP of, even if it’s a one-person team. Just better to see how they grow and how they take ownership and leadership as the company grows. What’s great in a startup is if things progress quickly, leadership opportunities and growth opportunities also progress quickly, but you don’t want to start at the ceiling and then have nowhere to go from there.

Helen Shacklett (12:10)

That really provides more opportunities to that person as the company grows. So it really benefits them and you. And it sounds like that’s on the heels of that — what are some top mistakes that either you’ve made or you’ve seen other founders make in a first hire?

Shawn Hewat (she/her) (12:28)

Similar to what we just spoke to, I think our first hire was head of their division. Then as we grew to a team of 10, there were some growing pains and like, okay, what does our actual org structure look like? We’re not at the size that we need leveling in place, but it does create a bit of tension between the 10th hire versus the first hire. What I’d do going forward or what advice I’d give to other founders: there are other ways you can set that up for a first hire — equity, option pool, the level of transparency you give them, growth opportunity — rather than giving out that title right away.

I was also pretty green to the space and a first time building a company. I’d worked at startups previously, but never started one of my own. I think you kind of have to make some of these mistakes. And then the other big learning in the topic of hiring was we raised a pretty great pre-seed round in 2021. Every single investor and other founder we talked to said: congrats, how big is your team? So I thought, let’s go hire a full team. And we grew to about 15 people and we didn’t yet have the demand and product-market fit that we needed to warrant all of those roles.

So we did have to make some adjustments. And at the same time, the landscape was completely changing — political turmoil, changes in employee engagement and HR, lots of changes in tech. Shopify did the big round of layoffs in 2022 and all of technology continued to follow suit. So it wasn’t a great time to have tripled our team when our customer base was struggling. I wouldn’t say it was a mistake, but if I was to do it again, I would hire in a bit of a different way where we really validated the need for each role, knew exactly what the goal was, and took a bit more time. We went really quickly because you feel like you need to, but I think if we just paused and planned more intentionally, it would have happened a bit differently.

Helen Shacklett (15:20)

As long as you learn, that’s what matters. I mean, you could do everything right and then some circumstance changes and suddenly things are not going how you thought. And what’s interesting is other guests that I’ve had on the podcast have hit on the same theme — that you have to decide for yourself what success looks like. You can’t listen to what someone else tells you what scaling or being a great business looks like.

Shawn Hewat (she/her) (15:31)

Yeah. And hiring has kind of been the wild, wild west as businesses have gone distributed and remote friendly. A lot of my networks in the talent and HR space are dealing with scams and identity checking and making sure that people really are who they say they are. How do we know if they’re working at three other organizations? It’s been a huge learning for all companies. We’ve dealt with it a couple times. One time someone wasn’t who they said they were and we had to quickly action and let them go.

Helen Shacklett (16:45)

So, I’m so curious — can you tell us a little bit about what happened with that employee who was working at a bunch of places?

Shawn Hewat (she/her) (16:55)

We just onboarded them and pretty quickly realized that a few things weren’t as honest as we thought they were. There was some fishy behavior happening. And we work with an HR advisor and kind of brought the situation to them. Based on a series of check-ins that we did and trying to communicate with them and the advice from our HR advisor, we just shut it down pretty quickly. We ended up having to shut down all of their accounts, send them a termination notice, process the last payroll. It wasn’t like they were with us for a long time, but we followed that checklist that our advisor helped us with and communicated very clearly. It was disappointing for sure. But I’m not the only one who’s had this story and for bigger tech companies getting thousands of applicants, this is a huge issue they’re working on today.

Helen Shacklett (18:09)

Shawn, I think you’re reading my mind because that really is a great segue into something I was wondering about — just handling the HR side of things. So verification, employment contracts, payroll providers, what’s your advice for handling all of that?

Shawn Hewat (she/her) (18:24)

You definitely want to have your legal side of things in order before starting to hire a team. And if you’re an early stage founder listening to this, that means for you too. You need all of your incorporation docs and your founder agreement, your shareholders agreement, directors. You need your own separate employment agreements. That has to be organized before you’re ready to make your first hire. Making sure you’ve got a great either contract employment agreement or full-time employment agreement ready to go, and that you’ve had someone in HR or someone in legal help to create that. Because if you don’t have good agreements in place, you’re just putting yourself at risk. And believe me, legal action and issues happen way more often than you think. Don’t hire unless you’ve spent the time to get those things organized.

There are some good templates, especially for a contract employment agreement. It’s a little less risky. But yeah, I would have that in place. If you’re hiring someone full time, you also need to have some of these HR things in order. Like you need to have a payroll provider. Typically your fractional accounting person handles this. Ours still does today. But if you’re doing complete independent contractor agreements and you’re just going to send via e-transfer and have an invoice in your inbox each month, that’s pretty simple. But as soon as you want someone to be a full-time employee, you have to have a few other things in place.

Helen Shacklett (19:52)

What advice do you have for successfully onboarding someone once you’ve made the hire and really setting them up for long-term success?

Shawn Hewat (she/her) (20:00)

At Wavy we are very transparent — radically transparent. So if you’re working with us, we’re gonna treat you like an adult, we’re gonna be an open book all the way down to the bank account. Everything we communicate with our board and investors, if you’re working for us, you’re gonna get that information. Especially being a smaller team or an earlier stage startup, I think the more you can bring people in on the vision, mission, direction, be as clear as possible on where you’re heading, what challenges you’re facing, what’s going well — really help them be part of the inner circle, they’ll have so much more ownership and they’ll care so much more about their day-to-day work.

People need three things to be super high performing. They need to feel connected to the vision and mission of the company. They need to be connected to the purpose of their day-to-day work. Why does my work matter? What is it leading towards? And then they need to be connected to each other. Like, Helen, if we were working together, I’d need you to be more than a face and a name on Slack, otherwise I’m not gonna do good work with you. And if you can enable those three C’s, those three connection points, you’re gonna have a high-performing team.

It’s funny, because this is what we help our clients do, too. So we have to practice it internally and there’s certainly always been a high standard for how we build our own culture. And I think one thing on the transparency front that I’ve always said to my team and our wider ecosystem is: I’m learning this for the first time too. Not that our team doesn’t take leadership and set the vision and direction, but I’ve certainly done certain things well and certain things not well and have evolved over time. But I think the style in which we work today — a few of our team members have worked with us for over four years and that’s a lifetime in the world of startups.

Helen Shacklett (22:07)

That is quite an accomplishment to have people sticking around for four plus years. They’re definitely happy.

Helen Shacklett (22:13)

So kind of building on that, you talked a little bit about the culture at Wavy, but are there any more aspects of the culture that you think are worth highlighting? And I would love to hear about how you think the culture you’ve built has influenced your growth trajectory.

Shawn Hewat (she/her) (22:27)

We’ve always described our brand identity and culture as “high quality goofs.” So we do have a little bit of silly, goofy fun during work. We’ve had the pleasure of being able to test out hundreds of those experiences — that’s been a nice perk for our culture. But we’ve also been intentional to do little things along the way. Cooking challenges where someone shares a recipe and we all have a week to cook it and then come to our next all-hands with a picture of our dish as the background and you have to present it as a chef.

But I’d say the rituals we always stick to: we start the week with our weekly wave, everyone getting together and aligning on what we want to accomplish. We’ve got different functional standups and syncs. We do an asynchronous update on Fridays, no internal meetings on Fridays so you can have a flow day. We’ve been very liberal on hours. We’re clear on what we have to accomplish and that’s our goalpost for success, not time spent at your computer.

And then the radical transparency part — I just had a board meeting this week and then after that in our weekly wave, walked everyone through the exact same slides I walked our board through. If anyone ever has questions, I’m an open door. I think that’s something that we really shifted as we had to reduce our team and operate in a leaner way and work towards our profitability goal, which we’ve now reached. And I encourage founders to follow that same level if they can.

Helen Shacklett (24:34)

Wavy is an example of a really thriving culture. So, if you had to synthesize your advice for building a culture that really brings out the best in people, what would that be?

Shawn Hewat (she/her) (24:45)

Yeah, I mean, I think as leaders we can influence culture, but my favorite definition of the word is that culture is the sum of your hundred most recent interactions with a company or organization. So it’s kind of just the way work and collaborating feels. If we’re a leadership team or a people team, the things you’re putting on or processes you’re setting in place are going to influence that.

There are some really great ways you can think about it. If your team is distributed, I think you have to think about a variety of rituals and practices that are gonna help people feel connected to each other, despite not always being in the same place. Maybe you bring the team together for a team week twice a year, but what’s happening in between that to make sure people feel connected to the company, the work they’re doing, and the people? Not having the same format all the time goes a long way. You’re going to have your monthly town hall — that’s important. But there are ways you can make it more engaging. Are there different opportunities for people to connect and learn together, to have fun together? Are there asynchronous rituals happening in Slack? Because one remote day can be pretty isolating. Five days a week can be even more so.

Helen Shacklett (26:32)

You described really well what a great company culture looks like. I’m kind of curious about ones you’ve seen that are not so great — and what was the effect on company performance?

Shawn Hewat (she/her) (26:44)

Yeah, I mean, especially looking across our clients. Sometimes we get ones that come to us in the middle of a huge restructure, a merger and acquisition, or a big leadership change. Morale feels off. I think change management has a big influence on how culture shifts. The big example over the last three years has been layoffs and restructurings. It kind of bursts the trust bubble. People are all working towards this vision and mission and they build connection with each other. There’s excitement. And then you go through a riff and that excitement and trust feels burst.

Often companies will go into, we’ve got to get people together and maybe we should do something team-building focused or celebratory with our next win. And that just may not feel right. People are struggling with psychological safety. They may feel guilty that they’re still there — it’s called survivor’s guilt. Maybe alumni they were close with haven’t been supported. Maybe there’s still not transparency coming from leadership on what the plan is from here.

Best thing to do is to prepare way ahead of the big change, knowing it’s going to have a negative impact on culture. Transparent communication goes the longest way. Making sure leadership is super transparent in the announcement and what happens after. Making sure people team and managers are going on listening tours, talking to both alumni and current employees. Making sure there’s additional mental health and wellbeing resources available. Add extra budget for counseling and therapy and your benefits. And then when ready, starting to establish some new rituals or programs that feel good for people. We often convince teams to lean more towards something creative, something wellbeing-focused.

Helen Shacklett (29:43)

Certainly. And I think a lot of folks kind of underestimate those things — at least from the outside, you’re the expert on this, but it seems like they don’t think about that as much and then they have to call someone like you to help them out.

Shawn Hewat (she/her) (29:57)

Yeah, or peer groups. I think something I’ve been so impressed with working in the people and culture space is how much HR leaders rely on their peers and community. Relying on your peers and making sure you’ve got experts on hand to help when you are going to be going through one of these things makes such a difference.

Helen Shacklett (30:20)

By the way, Shawn, you mentioned some really fun, cool events like the picnic challenge and things like that. Do you have a favorite type of culture event or activity? I’m just curious.

Shawn Hewat (she/her) (30:32)

Wow. Yeah, I mean, I’ve done so many throughout the years. I think I’ve really grown to like the arts-based events. It’s such a nice something I can keep and use, or do that craft again in the future. And it is a wellbeing-focused event, if you think about it. You use the left side of the brain. Take a break from the typical work week. Our team did like hand-knit a scarf or blanket with really chunky wool. That was great. I loved that one and picked up a new skill along the way. And then some of the cooking ones, whether cooking together in person or virtually. I love experimenting in the kitchen and trying new recipes. Those are some of my personal favorites.

Helen Shacklett (31:23)

No, those are all great. It’s really hard to choose one, honestly.

Shawn Hewat (she/her) (31:28)

Yeah, I mean those are things I like to do outside of work too, so that’s where my personal preferences go.

Helen Shacklett (31:34)

All right, so one thing I kind of wanted to circle back to real quick. So when you’re assessing someone to be on your team, how do you assess whether they’re a good culture fit for Wavy?

Shawn Hewat (she/her) (31:48)

We more look at culture add — like, what are they going to bring that’s new to the table? Not just at Wavy, but with a lot of organizations we work with, it’s: the more diverse in thinking and people, the richer our culture will be. We certainly look for alignment with our values. I want this person to think very differently than me and bring completely new skills and interests to the table. That’s going to help to enrich that community.

But how do you know if someone’s gonna be a great hire? We get into scenario-based questions and understanding what it will be like to work together. Something that matters to us is being really solution-oriented. So if you’re going through a problem in an interview and their first action item on solving that problem is coming to me to ask me what we should do — that’s not a good sign. Ideally, you go to your leader and say, hey, this problem happened. I’ve already done this. Here’s a few ideas I have that I think could fix it. Do you have any others? We really like people to have autonomy on problem solving.

And because we’re high quality goofs, we like to test for some of that personality, too. Silly scenario-based questions like: you have an unlimited budget and you’re gonna make a documentary on one topic — what’s it gonna be and where’s the screening party happening and who are you bringing? Not everyone’s gonna thrive with improv, but you get a bit of a better sense of personality. And I’m big on the reference call. Even if I feel ecstatic about this person, those are opportunities to learn from the last person who managed them. Really dig into: where can they grow? What do they excel at? What can I help them improve? It’s awesome.

Helen Shacklett (34:18)

It’s an opportunity for you as a manager to learn about that person. It’s like a head starter. A cheat code, really.

Shawn Hewat (she/her) (34:23)

Yeah, yeah. And if it’s somebody you really want to bring on, like you want the real transparent information from their last manager on where can they grow? What do they excel at? Hey, I’m going to be working with them — what can I help them improve? It’s awesome.

Helen Shacklett (34:40)

All right, so wrapping up, Shawn, this was such a great conversation. Can you give me, if you had to sum up your key takeaways you think people should remember most, what do you think those would be?

Shawn Hewat (she/her) (34:51)

When building a company and thinking about making hires: don’t hire because it’s great to have a bigger team. Hire because you’ve proven that there is a need for another role on your team. And it doesn’t have to be full time. It could be part time or project based. But what exactly is that role going to do to help you reach your goals? I think rooting every hiring decision in that and having alignment between founders, between the leadership team, before you even put that job posting out or share that you’re bringing folks on is super important. And you don’t have to sprint towards that team growth. That’ll happen if you keep rooting yourself in: do we have the right demand for this? Do we have the right customer? Is our product meeting the needs and value that our customers need? I think all will come to life after that, and don’t rush into hiring for a vanity metric. You need to prove that there’s a real need to bring more folks on board.

Helen Shacklett (35:51)

You know what? I think that everything you’re describing really takes a lot of the uncertainty, maybe even the anxiety, out of it — and brings clarity to the situation so that founders can move forward confidently.

Shawn Hewat (she/her) (36:02)

Yeah, and you won’t get everything perfect. There will be lots of mistakes made along the way. So act quickly when you know you’ve made a mistake. Inaction is what kills us. Yeah, I’d recommend acting quickly too. But thanks for having me. This has been a really fun conversation.

Helen Shacklett (36:22)

No, I’m so glad that you came on. I appreciate the time.

Shawn Hewat (she/her) (36:26)

You too.