Ep. 288 – WishingUWell, Inc., Vice President of Operations, Jake Heeb

Our guest today is Jake Heeb, COO Alliance member and VP of Operations for WishingUWell Inc. Jake is dedicated to helping others grow and succeed, and supporting WishingUWell’s efforts to be a more collaborative and well-functioning team. He is the go-to person for taking on issues, troubleshooting, and driving results. His mission is simple: be the bulldozer that clears the path for his team to flourish. He previously held the title of Director of Warehouse Operations at WishingUWell, but was recently promoted to VP of Operations, allowing him to focus more on the company’s overall success through operational experience. Jake holds a Bachelor of Science degree in Outdoor Recreation and Resource Management from Indiana University. In today’s episode, they discuss Jake’s journey from imposter syndrome to self-care advocate and culture champion.

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In This Episode You’ll Learn:

  • Why understanding what makes your employees tick is the most impactful thing a leader can do.
  • Jake’s experiences shutting impostor syndrome and embracing self-care as crucial elements of effective leadership.
  • The power of employee-driven clubs at WishingUWell where teams collaborate on shared interests and hobbies.
  • The transformative changes created in WishingUWell’s company culture as they’ve grown from 10 to 70 employees.



Connect with Jake: Website | LinkedIn

Connect with Cameron: Website | LinkedIn

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Join us in this episode as we welcome Jake Heeb, the Dynamic VP of Operations at WishingUWell. Jake’s journey from Imposter Syndrome to a self-care advocate and culture champion is one you won’t want to miss. Jake will share his experiences on shedding Imposter Syndrome and embracing self-care as crucial elements of effective leadership. Discover how he’s harnessed these insights to drive personal and professional growth.

At WishingUWell, Jake emphasizes the importance of hiring for culture fit above all else and learns how this approach has contributed to the company’s success and created a harmonious work environment. Discover the power of employee-driven clubs at WishingUWell, where teams collaborate on shared interests and hobbies. These clubs promote comradery and productivity, adding an exciting dimension to the workplace.

As WishingUWell has grown from 10 to 70 employees, Jake will highlight the transformative changes in their company culture and gain valuable insights on navigating growth while preserving core values. Jake believes in the power of listening to employees for continuous improvement. Explore how WishingUWell maintains open lines of communication and leverages employee feedback to drive positive change.

Finally, we’ll delve into Jake’s integration efforts as he shares his experiences of successfully emerging and acquiring a company into WishingUWell’s operations, uncover his strategies for seamless integration and strengthen the overall organization. You won’t want to miss out on this wisdom and inspiration that Jake Heeb, the VP of Operations at WishingUWell, brings to our show. Tune in to discover the transformative power of shedding imposter syndrome, prioritizing self-care and fostering a thriving company culture. You’ll also want to check out this episode on our YouTube channel as well. Now, let’s dive into the episode.

Jake, welcome to the show.

Thank you so much, Cameron. I’m excited to be here.

I’m looking forward to chatting with you. It was great meeting you for the first time in person. We met at our COO Alliance, the COO Connect event in Scottsdale. It’s cool to be able to hang out with you and get to meet you a little bit there. Why don’t we start a little bit about what your growth has been with the COO Alliance? That was the first in-person event that you came to. Talk to me a little bit about some of the growth that you’ve had from being a member and what it was like being at that event and then we’ll dive into what WishingUWell does.

When I got into this position, it was a few years ago. My CEO has been coached by you for a couple of years prior to that. I was able to take part in some of those coaching sessions. When I took this position, we both knew immediately that the COO Alliance was for me. That was going to be the next step of personal and professional growth and development for me. What I’ve learned and you’ve said it before that you see this as a three-year program.

As I’m renewing year two, I’m starting to understand that and get the feeling of that. In year one, there was a level of Imposter Syndrome when you first got into the mix of these groups and meetings. Where I’m at now is I know that I’m no longer an imposter. I’m excited to join these group conversations and not be afraid or timid to speak my mind and share areas of strength with other people or experiences. It broke through that barrier for me, which has been wonderful. It’s created that next level of excitement for me.

It’s interesting to see how many COOs, how many people that are in the second in command role have that Imposter Syndrome. I’ve certainly had it my whole career. It’s like every day, every month, and every year, whatever we’re building is now the biggest thing we’ve ever done. Everything keeps getting bigger and it always feels like, “I probably don’t have the skills to even be doing this,” but nobody has the skills to be doing what we’re doing.

We’re all figuring this crap out together. It’s awesome that you were able to shed some of that. Now you said that coming to the COO Alliance, the COO Connect event that we had, “I don’t want it to come off this the wrong way, but it was life-changing.” What do you think it did for you? What was it that opened up? One of the things that we said was the cracks where the light comes in. I’m curious where some of the light came in for you.

It was huge. It was the one thing that I needed that I didn’t realize that I needed. It came down to self-care. I realized that the type of person that I am and the type of position that I’m in, I am geared to helping others all the time. I want to go up to everyone else, take the burden off their shoulders, and put it onto mine. Carry that up the mountain and make things easier.

What happens is you get so wrapped up in helping other people you forget that the most important person is yourself. The more that you’re able to focus on yourself and help yourself, the better you’re able to help other people. The more that you can help other people. That was probably the most eye-opening experience for me at that event. It was slowing down and focusing on myself, first and foremost. That is going to be the ticket and the golden key to helping everyone else.

There’s a saying in Latin. I think it’s men’s sana in corpore sano, which means a healthy mind and a healthy body. We have to be able to, as leaders, take care of ourselves so that we show up with the right energy, show up with the right mindset and show up and we can respond to situations instead of reacting to them.

We also have to remember that we also need to be role models in our roles as COOs or as VP Ops, where we need other people in the company to look at the way we’re acting as leaders, the way that we’re showing up as leaders and be inspired by that. The only way we can be inspiring is to be showing up as our best selves. If we don’t practice that self-care, then that’s tough to do.

I’ve seen that firsthand since coming home from that event. You can call it meditation or whatever you want, but I make it a point to spend at least fifteen minutes quietly with myself every morning. That’s how I start my day. I want to make sure that I’m okay with myself, first and foremost. It has had dramatic effects on my mental state to where I’m not coming into the office every morning and stressed out and I’m like, “I’ve got X, Y, and Z to do on my calendar. I don’t have any time to do it.” I come in with a smile on my face every day and the first questions I ask are, “How are you doing today?” I genuinely care about the response.

That’s the ticket right there. “I genuinely care about the response.” I’ve seen so many leaders in the past and I experienced one many years ago. My old VP and I’m not going to say his name. We had our one-on-one like our weekly coaching meeting where he was coaching me. He started off the meeting by saying, “How was your weekend?” I stopped and I’m like, “Stop, you don’t give a crap. You don’t give a crap how my weekend was. You’ve asked me the same question for fifteen weeks in a row. Let’s stop on the BS. If you cared, then I’m going to answer, but you don’t.”

It frustrated me because he didn’t care. When we start showing up and caring about our people, they’re going to go through brick walls for us, but you’ve built that culture at WishingUWell. Talk about the culture that you guys have developed and you’ve been there for years. Talk to us about the culture, what it’s like now, and how you built that company culture that you’ve got.

It’s probably what excites me the most about WishingUWell and where I feel I’ve had the most impact on the company and other employees in the company. Starting out when I was warehouse manager, I started out with five people in the warehouse. I was directly responsible for building that team as we were scaling and growing.

At the time, over the course of about five years when I was in that position, we needed to double our warehouse workforce every year like clockwork. It went from five people where it was easy to manage five people, know what five people were doing, and still handle my day-to-day. As that team kept growing, I had to understand there was a point. Tyler helped me, my CEO, by teaching me the pizza method.

I remember him coaching me on that at first when I had about fourteen people under me and I’m like, “This is getting a little bit intense. I don’t know how I’m going to break through this and keep managing everyone on the same level.” He said, “Jake, you can only manage enough people to share a pizza with. Now is the time to start breaking things up and having supervisor-level positions and those kinds of things.”

Develop all of those positions. In developing those positions and hiring those particular types of people is one of the most important and insightful things I’ve learned. You learn very quickly when you’re dealing with those people on a day-to-day basis how to hire the correct people. Probably the number one thing that I learned was hiring for personality and attitude over hiring strictly because of the skillset, especially for a warehouse associate position. We can teach you what needs to happen in the warehouse. That’s easy to do.

SIC 288 | WishingUWell

WishingUWell: It’s important to hire for personality and attitude instead of just hiring strictly for the skillset.


We can’t teach you and mold your attitude. We can’t teach your personality. Those are traits that are already with you. That’s what we started focusing on and hiring for as we started changing that and having that dramatic shift in how we hire. We found that the culture started building upon itself. It was an ideology that Tyler had from its inception.

Part of that was as we’re growing and developing these people, Tyler’s like, “This is what I want. How can we do more of this? How can we make these people happy?” He had a unique understanding that everyone has to come to work. This is not a glorified position. You have to stand on your feet. You’re working on monotonous, boring things all day long. How can we make this fun and make people get excited to wake up and come to work every day?

As we developed those teams and as our teams grew, we then started surveying people and understanding like, “What do you want to see at work? What are the things you want to be doing?” Now, we are at the point now where our culture has driven all of our people to create clubs. We have a garden club, hiking club, volunteer time off and we do an angel tree program.

It’s unique because everyone in the company starts developing all of these friendships. You find that there are all of these groups of friends that are doing things inside of work or outside of work. They’re hanging out on their break or going golfing after work together. It builds an amazing camaraderie for the team.

This is going across different functional areas too. You’ve got people in the gardening club from the warehouse, marketing and operations, or is it pretty much in one division that they’re all getting together?

It’s across the board. That was one of the things we try and do as well. In every one of these clubs, everyone has the ability to join, to participate, to be a part of it and that’s broken down some barriers as well between the office and the warehouse. It’s different levels of work. There are different mindsets around that work. There was almost an invisible barrier between the warehouse workers and office workers.

These developments of these clubs and some after-work activities, Friday fun days where we get together. We celebrated Cinco de Mayo and had a margarita party and did pinatas. It’s about finding those events and those things that people are interested in from all over the business so that they can get together and get to know each other.

Was there any stirring of the pot that had to happen to make those clubs get started or was that an organic thing?

There was a little bit of stirring the pot. I created the first club. It was a garden club. I had always been interested in gardening and found a couple of people that were interested in the same thing. I feel you almost have to encourage people and show them like, “It’s here at work, but it’s not a work function.” It’s not something like there’s not a piece to it that you’re responsible for or required to do.

This is just a fun thing where we get together and we learn more about how to plant vegetables. At the end of the summer, we’re able to eat all of those vegetables together and bring them into the office. We even share them with the community sometimes. We had like 300 or 400 cucumbers that came out of our garden, but it’s a lot of fun.

I like the fact that you identified all of the people inside of your company when you started hiring the right culture people, they almost become fire starters and sparks of the culture. That’s where the culture starts from, are the right people. Herb Kelleher from Southwest Airlines, when asked by them, “How do you get all your employees to smile like they do?” He said, “We hire smiley people.”

You can’t teach someone to be happy, so you hire happy people and those people will show up at work happy. Have you had to change the way that you’ve approached culture as the company has scaled? You’re now 70-plus employees. When you started, you were only ten. How has the company had to change and adapt from a cultural perspective with scale?

It’s had to change a lot. I believe you’ve said this before and I can attest to this as being true. Starting out as a small company, the CEO and the leaders are the ones that are responsible for creating that culture and embedding the culture into the people and developing that. We’re learning that we’re at the point now with our size where we need to start making some shifts so that the employees are calling the shots on what’s the next thing that we’re going to do to improve our culture.

SIC 288 | WishingUWell

WishingUWell: When starting out as a really small company, the leaders are really the ones that are responsible for creating culture and embedding that culture into the people.


Instead of having it come from the leadership down towards the people, the people are feeding us with all of that information. Once we started figuring out like, “We’ve got a group of people here and this is what they’re interested in.” Before, we would guess. I think it’s maybe these 2 or 3 things. Let’s get a food truck. I think they like tacos.” They come up to us and they’re like, “No, we want to do something outside of the box. We want to get a dunk tank.”

We’re like, “What in the world? Okay, let’s get a dunk tank if that’s what you folks want.” You get more participation in those things because people don’t see that as “Management or leadership is like pushing this on me or forcing me to do something.” It turns into, “Management or leadership is allowing us this opportunity.”

It’s very similar in many ways to the way that we teach kids how to ask Santa for gifts. If the kids write a letter to Santa Claus, then the parents read the letter and buy what the kids say they want. The kids are all like, “Santa read the letter.” It’s like, “No, your mom read the letter.” If we try to figure out what kids want, we always guess wrong. You ask the kids, what do you want? They tell us we do that and they’re happy. The same thing with culture. If you ask your employees, it sounds like that’s what you’re saying. If you ask the employees what they want, they’re telling you and you do those things. It’s easy to make a great culture because you’re listening to them. Is that your approach?

Absolutely. We’re in the process of doing that now. One of the struggles with that is because we’re starting that off. People aren’t as motivated to speak up just yet. We’ll ask a group of twenty people, “We want some exciting ideas. What do you guys want to do for the next Friday Fun Day?” You’ll get crickets for a little while. I’m like, “Do you folks want me to pick something? Seriously, what do you want?” “I think this would be a cool idea.” It starts to gain traction once everyone else sees that idea come to fruition, then the next time, they’re like, “The next time Jake’s asked me for this idea, I am going to speak up because he proved to me that he’s going to do this if I ask for it.”

When COVID hit, your company had to adapt as all companies did, but a good portion of your company’s employees had to come to work every day during COVID because you ran warehouses. Is that right?

That’s correct.

How did you operate that way when some people had to start coming to work and then another part of the company was working from home? How did you navigate that in terms of employees? It’s obvious, you have to do your job, you’re in an office or you’re in a warehouse. Were there any lasting effects from that and did you folks culturally go back to all employees being in the office afterward or now are you more of a hybrid organization? Where are you with respect to that?

COVID changed the world for everyone. For us, we had, like you were saying, this unique opportunity where we have warehouse people. They can’t work from home. We have to have them there producing. What we did was for a month, we had our office staff work from home and then we were considered an emergency company that was allowed to stay in operation. Myself and the entire warehouse staff would still come into the office every day.

Since we had the entire building, we were able to spread everyone out, do all of the PPE that needed to be done so everyone was safe. After those 30 days, what we saw was culture started shifting and started changing in a direction we didn’t want it to go in. We started seeing people starting to grow apart from each other, especially with that barrier of, like, it’s this invisible barrier between the warehouse and the office.

That started getting thick and started getting opaque instead of clear. We immediately started bringing people back to the office and started requiring that they come back to the office. We were like, “We’ll set you up with all the PPE. We’re going to make sure that you’re safe, but you’re going to be in the office with us because our culture is built around being together.” We’ve got an amazing facility, an amazing building. When no one is here to use that facility, that’s a level of the culture that’s not effective anymore.

Let’s say I put a gun to your head and said, “Jake, other than the warehouse, your company has to go remote for 24 months. Everybody’s going to be remote. Nobody comes into the office except the warehouse.” What would you have to do or change or adapt or what do you think your strengths would be culture-wise that would survive that?

What we would have to change is we’d have to get into the digital side of getting people together for group events and things like that and doing those jam sessions and things. We’re still able to get everyone together and have fun. We’re still able to meet, have huddles and understand where our goals and objectives are. I think the main thing that I would foresee happening is still being able to get people together digitally to still have fun. That’s the bread and butter of our culture. We want to have fun.

Let’s talk about your growth in the organization. You started in the company quite early. You started managing and leading the warehouse team. Now you’re running as VP of Operations. How have you had to adapt and grow as a leader over the years that you’ve been there? Have you had any specific areas that you’ve focused on?

In starting as that warehouse manager, I had been a warehouse manager prior to that back home in Indiana, but I managed facilities. I wasn’t managing people. This was my first position where I was directly responsible for managing people. I’ve always had a knack for management and leadership. I’ve always been the captain of every sporting team that I’ve been a part of.

I get excited to get other people excited about something and I understood that I have that enact. I took that and ran with it. What I mean is understanding people on a personal level is the most important thing that I learned. The more that you can get into the weeds of understanding what makes your employees tick is going to be the most important and impactful thing you can do.

It’s not just their work ethic, but it’s what are they worried about? What are they afraid of? What are they excited about? What are their goals outside of work? The more you know about those individuals, the better you can coach and develop them to be better person both inside of work and outside of work.

In learning that, that’s what’s got me excited in my personal development. It’s driving my professional development now, where I have learned. I get so excited to develop people and get into the weeds of what makes them tick so that I can be that coach to get them to the next level, whether personally or professionally. I go back and I read books. I look at webinars and do those things so that I know how to best coach people.

Another unique thing is starting out with a small team. I was coaching at the associate level. I was coaching the people that were doing the work. As that progressed, it turned into now I had to learn how to coach other managers and other supervisors on how to coach the people doing the work. That’s a different level of coaching and leadership that you have to do. When these people aren’t the ones doing the work anymore, they’re the ones that have to coach the next level of people. I found that interesting and one of the things that I enjoy most is it’s almost like coaching a coach.

It is very much like coaching a coach as well. Were there specific things you started to do differently to coach those more mid-level managers? Was there a specific approach? Walk us through the specific things you did differently.

I’d say two of the main things that I’ve done were sitting down and having meetings with people. At the time, I didn’t know that they were called skip-level meetings. Sitting down and meeting with people, going to lunch with people that are outside of the office and diving in. It was funny when I first started doing it. People were like, “Jake is asking me to lunch. What is this about?” I’m like, “I want to know more about you.”

I have a unique example of a person I was able to do that with and found out that they were struggling personally without telling anyone in the company that they had lost. Their mother had moved away, their wife had gotten divorced and don’t have any friends. They go home and they sit and sulk. This was somebody with a bad attitude but was the first person in the warehouse every day. They’re the last person to leave and was the go-getter all the time.

I sat down with him. I was like, “You’re angry all the time”, then he shared that information with me. He and I worked together on developing a plan for his personal life to get you some groups of like-minded individuals so that you know what you like. One of the things that he said that was so cool. He was like, “I love going to the dog park. One of my favorite things to do is sit on the bench at the dog park.”

I was like, “Tyler, my wife loves going to the dog park. I don’t necessarily care to go, but she loves to go. You and my wife should get together and go to the dog park together.” They do that now almost every single weekend. That little bit of change in his personal life dramatically affected his attitude inside our work facility.

It’s cool that you cared about people to that level. We’ve been trying to get people to see Alliance do that, but you’ve been doing it for years, which is amazing. You guys went through an interesting period in months when you acquired a company in Cincinnati. Can you walk us through what that acquisition was like and what it was like in the months post-acquisition and starting to integrate them into the organization? I’d love to be able to learn from you there.

We did acquire. It was like a piece of another company. Their warehouse operations and fulfillment operations are in Cincinnati, Ohio. In doing so, one of the main things we wanted to do was look at the team they had established, first and foremost, and understand how they hired those people and how that differed from how we hired people.

What we found out was most of their staff, about 75% of it, was temps. We have been through the run the muck with temps in and out of our warehouse. We have found out that that is not the way that we want to do things. That does not improve our culture and that’s not a positive way to do things. We want to hire people and hire the correct people to come in and do the job.

We went through and interviewed every single one of those candidates in those positions and found that there were only 3 people out of about 14 that we decided we wanted to keep. Those three people stayed on board with us and then we immediately depressed the accelerator and had to start filling those additional positions.

Luckily, I’m not as responsible for hiring people anymore. We have a VP of people. Heather has taken our culture to the next level and has been a rockstar in that position for us. She’s been able to hire people very quickly for us so that we didn’t lose out on a massive amount of lack of work being done out there because we decided to cut ties with everyone. I will say in cutting those ties, it was easy to do because it was temps.

It was a matter of contacting the temp agency and being like, “We’re done. We don’t need you anymore.” We start hiring for that. One of the unique things that we’re still actively working on is still embedding the culture as it is here in Colorado. It is only a warehouse out in Cincinnati, Ohio. We haven’t had the time yet to develop that facility in the same way we’ve developed our Colorado facility with a coffee bar and an in-house gym and all of these frills and exciting things. It’s back to square one.

When are you going to be layering those things in, then? When are you going to start layering in those parts of the business, then? The gyms and the coffee bars and that stuff, is that coming?

We’ve started a little bit of that process. They’ve got a pool table and a ping-pong table in there now. They’ve started doing their Friday Fun Days and getting a food truck or doing some barbecues and things like that. We’re starting to develop that culture and what we’re doing is we’re letting them start to call the shots. What is it that you want to do? We asked them about that because we’ve got a summer party coming up.

We’re like, “We’re not going to be able to fly everyone from Cincinnati to Colorado or vice versa. We’re going to have two separate parties. What do you guys want to do in Ohio? Here’s the budget. Tell us what you want to do.” We’re going to play volleyball, but that doesn’t mean that you folks can go golfing or go putting. Go do whatever it is that makes you happy.

You’ve been out there how many times since the acquisition?

I want to say like seven times.

You’ve been to Cincinnati 7 times in 7 months from this acquisition. Was that anticipated? Was that decided? What were you doing on most of those visits? Was it culture or observing? Can you walk us through what it was like?

Initially, we knew that I needed to be out there to visit a lot to set the team up for success and to make sure that we quickly turned that into a profitable function. The other piece of it was we knew we didn’t want temps. We knew we needed some people out there to help with the work that was actively happening. What we started doing was me, our warehouse manager in Colorado and then we’d bring a team of 3 to 4 associates with us. We’d go to Ohio on about a two-week cadence with additional helpers.

The 3 to 4 associates would go into the Ohio warehouse. They’d be teaching and coaching the staff in there on, “This is how we do things with WishingUWell now. This is how things are different.” They became the trainers for us. Myself and the warehouse manager, we’re on the observational level. We were observing, “How is everything set up in the warehouse? How is inventory flowing through here? How are you reviewing employees? How are you talking to employees and putting them on a pip and all of those kinds of things?”

We found that it needed a lot of work. After the first 1 to 2 visits, we were like, “We need to keep coming back until we feel confident.” After a while, we started feeling that confidence. We’ve got the team built up to where we don’t need to bring in additional help anymore. Now it’s to the point where Heather can go out there and start showcasing our benefits, highlighting our culture more, and getting people excited to be a part of WishingUWell.

In your role in the VP Ops role, I’m sure there’ve been some failures and some stressful, tough times. Can you walk us through a couple of things that you’ve done that were hard or that you struggled at or failed at? What are the lessons from those?

I talked about it before, but I was learning how to hire the right people. I learned very quickly how to hire the right people based on attitude and personality. The pitfalls there were when you had to deal with people with bad attitudes and crappy personalities. Every day, they’re coming in and causing more drama or more problems. You learn fast.

Some of the other areas, good example, is like I’ve learned that I’m weak at financials. I’ve never learned about financials other than in an accounting class one time in college. I don’t know how to budget correctly. What I do in those times is I see that as a learning opportunity and I’m like, “I am weak at financials. This is something I want to get better at.” I start setting myself up for success by learning more about that, both from our accounting team also going and falling back into the COO Alliance.

With all those areas of weakness that I have, I’m able to lean on this group of like-minded, wickedly smart people that have all been through similar situations before. Another thing is I’ve been new in this role. My degree is in Outdoor Recreation and Resource Management. I thought I wanted to be a park ranger for the rest of my life and stumbled into this role and then learned that I love getting to know people and developing and coaching people, but I don’t know what’s around the next corner. I don’t know what to expect next week or next month. The best thing I can do is set myself up for success by surrounding myself with like-minded people and ensuring that I’m always learning as much as possible.

SIC 288 | WishingUWell

WishingUWell: The best thing you can do is set yourself up for success by surrounding yourself with like-minded people and making sure that you’re always learning as much as you possibly can.


All right, let’s go back to the 22-year-old Jake Heeb. What advice would you give the 21-year-old or 22-year-old Jake that maybe you know to be true now but you wish you’d known back then?

Take care of yourself, first and foremost, and that’s going to be the best way that you can take care of everyone else around you. I’ve always known that I wanted to help other people, but I’ve learned that the best way to do that is to start by looking within.

It’s the golden thread. It’s how we started off at the beginning and how we’re wrapping up at the end. I’m glad that it’s still top of mind for you. Jake Heeb, the VP of Operations for WishingUWell. Thanks very much for sharing with us on the show.

Thank you so much, Cameron. It was awesome. I enjoyed every minute of it.

I appreciate it. For everybody reading, make sure you check us out on the YouTube channel as well and devour the episodes and share them with some friends.


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