Ep. 91 – Bite Squad COO, Kyle Hale

Although cooking your own meals or going out to eat will always be the ideal way to eat, they’ve now been considered as luxuries for those with time and energy after a long day at work. Enter food delivery. From apps that deliver food to food delivery services that allow us to enjoy fresh, hearty meals from the comfort of our own home, the food delivery industry is booming. Cameron Herold’s guest today is Bite Squad’s Chief Operating Officer, Kyle Hale. Bite Squad is a restaurant delivery service prominent for providing excellent service, whether delivery or take-out. Partnering with local restaurants, they bring fresh food from the restaurant straight to the customer, quickly and hassle-free! Kyle Hale is an entrepreneur and technology executive who built his sales and operations career with both B2B and B2C high growth technology companies.


Connect with Cameron: Website | LinkedIn

Get Cameron’s latest book: The Second in Command – Unleash the Power of Your COO

Subscribe to our YouTube channel – Second in Command Podcast on YouTube

Get Cameron’s online course – Invest In Your Leaders

Kyle Hale is an Entrepreneur and Technology Executive, who built the foundation of his career in sales and operations with both B2B and B2C high growth technology companies. His roles span the fitness industry, multiunit operations in QSR, eCommerce, selling software to the enterprise and as a partner and COO of Bite Squad, a restaurant delivery service, which was acquired for $321 million in January of 2019. As COO, Kyle led the customer support, dispatch field operations and cross matrix managed sales, marketing and product with the CEOs.

A unique generalist with expansive domain knowledge in sales, marketing automation, product software development, full cycle recruiting, leadership and strategy execution. More of a creative than an executive, he has a non-egotistical approach with a focus on developing the psychology and performance of his team through one-to-one mentoring. After building two companies to acquisition in the last several years, he’s now consulting with startups in the Midwest and serving as the chief dad officer to his two-year-old son, Sky. That’s probably the coolest thing that’s been happening. Kyle, welcome to the show.

Thanks, Cameron. It’s great to meet you.

I’m looking forward to this. Before we started up, you said that you do have a bit of a unique background that not a lot of CEOs come out of the sales zone. The COO is such a misunderstood role that they can almost come out with so many different areas. Some run finance, some run engineering and some run sales. Why don’t you give us some of your background and maybe tell us a little bit about Bite Squad, who they were and dive in from there.

I’ll start with my background and pipe that into Bite Squad. I started my career in sales. My first job out of college was selling, super hardcore cold calling for a job board. It’s similar to Monster CareerBuilder, but it was a local brand. The founder did something smart where he had job boards that appeared local, jobs in Minneapolis or jobs in Vancouver, but he had them all over the country. No one was doing that hyper-local flare yet, but it was a from-scratch brand. What I learned there in my first job was building a brand and selling against CareerBuilder Monster and people were still doing a lot of postings in the paper at that time.

The tenacity it takes and the value you have to communicate in a very condensed way to be able to get a brand off the ground through cold calling. It was a great experience. That led me into the fitness industry where I also led sales for Life Time Fitness, which was publicly traded for a while and then went back private. It was purchased by Equinox. From there, I went into a specialty food for a company that ended up folding, but it was called HomeMade Pizza. It was an organic, all-natural bacon home pizza brand out of Chicago. I launched in several different cities and markets for them across the country and then that led me into the daily deal space. When Groupon was getting hot and LivingSocial, we’d started a brand called Crowd Cut.

I’ve met the founders, who would be the co-CEOs of Bite Squad as well later on. We’ve been working together for a while. I joined about a month after they started Crowd Cut. I was VP of Sales and Operations for the daily deal site. We were successful for a scrappy single market site. We earned about $1 million a month at the time. We ended up selling to a competitor. This leads us into Bite Squad. The origin story of Bite Squad was as the daily deal world started to get saturated and everyone started selling good so there are Groupon goods. We did the same thing and that was successful for us, but it was still saturated and declining as far as the daily deals space itself.

We were saying like, “What else can we do?” I was using a service in town called Restaurant Connection, which was out of San Diego. That was a restaurant delivery service provider. They only had ten restaurants. The drivers weren’t that presentable. It wasn’t the marketplace that it is now. We said, “The tech’s not good. The drivers aren’t friendly and presentable. The daily deals to restaurants sell out fast. The restaurants don’t love them because they’re discounting a brand half off. They don’t believe the loyalty is there from the customer for repeat visits.” We said, “Let’s spin off another brand.” We started this restaurant platform. DoorDash wasn’t around yet. Postmates was around, but it wasn’t what they are now. They pivoted into that.

Grub was around, but not doing delivery themselves. They were more of a portal. Eat24 and Grub was around and that was about it. I took my daily deal sales team. We wire framed up what we thought Bite Squad was going to look like and we sold the first twenty restaurants. That was market fit for us as far as we were concerned on the restaurant side. We went and built the platform, came back 90 days later to the restaurants and said, “We’re ready to go live.” We use the daily deal site to sell deals for half off the delivery fee or free delivery. That was how we seeded our first several thousand customers. That worked for us and that was the beginning.

I love that you did proof of concept that you found twenty restaurants that said yes and you went and built the model afterwards. You didn’t build it first.

Yeah. I think we’ve always been good with going out and proving because we’ve done that in different ways. When you get that proof of concept, it gives you more confidence to build a product and allocate resources towards it.

I want to go back to the folding pizza business and find out what your lessons were in that because I think there’s always some lessons in those failures that we get along the way. Not failures, but working and building something. What were the big lessons out of that?

There are some good ones. I would say number one was that we primarily hired kids that were in high school. In Minnesota, it’s easy to find young talents that’s in high school that’s willing to work. When I opened up our stores on the East Coast, in the DC area, it’s different. They’re prepping to go to Ivy League school or go to college. It was hard to hire there. I learned about the different geographies and what hiring challenges can be. Lesson number two was that they had an amazing product. It was on Oprah. It was one of her favorite things. People I see still to this day say like, “That is the best pizza I’ve ever had.” That’s saying a lot for a bacon whole pizza especially, but the product was amazing. The presentation of the product was amazing. The stores were small. It had an Apple store feel to it. I understood the importance of packaging and product, but their business model is flawed in that they burnt a lot of money in bad real estate decisions. They also had these commissaries that were non-revenue generating. Those were the main lessons for me.

I love the employee lesson as well. I used to be involved in a company called College Pro Painters and they sold or closed College Pro after about 50 years in business. It was because they couldn’t find university students to run painting businesses anymore. It was easier for them to run other models.

I was laughing when I was listening to Sean Taher’s episode with you because you guys had talked about College Pro. I knew Sean back then. Sean also hustled spring break packages on college campuses and stuff. It was funny to listen to your interview.

It sounds like you had a similar upbringing too. You are always a bit of the hustle and savvy street smart. How did you meet your two founders originally? Is it when you did Crowd Cut?

A good friend of mine, who’s a chiropractor. His boss was a friend of Kian and Arash, the cofounders of Bite Squad. I was out with my friend’s boss at a happy hour locally here. I was expressing that I was planning on leaving the HomeMade pizza business because they wanted me to move to DC. I spent enough time out there that I didn’t want to be out there. We were talking about that. He said, “You should meet Kian. They started a daily deal site similar to Groupon. I met Kian a day later. I walked him into three businesses I thought would do daily deals where I knew the business owners and we like closed them there. He was like, “Do you want to come work for us?” I was like, “Cool.” He and I locked ourselves in a room and cold called for three weeks straight and sold a ton of deals together. It was a blast.

You got to like them and know these guys. You built that company up and you sold Crowd Cut then?

Out of the south, yeah.

How did that exit go?

That exit was fine because it was like part cash and then part earn-out over time. It was our very last payment we got, then that company ended up folding like a couple months later or half a year later. We didn’t have a ton of assets. We had a small team in Minnesota and we were able to transition a lot of them into the Bite Squad organization. That one was fine. That industry ran its course. You’ve seen Groupon sputter along overtime.

Did that industry run its course because Groupon grew too quickly? Did it run its course because people got bored of it or that market got saturated? What happened?

People get bored of it. When that first came out to be getting 50% off massages and resort packages and all these things, it was new and special. Over time that wears out and for the restaurants and the businesses, they got sick of the discounting too.

They love the idea or the model, but they couldn’t figure out the economics of it afterwards.

You got to deliver more value than a discount. They’ve tried to over time. I won’t call it a fad because it’s still around but it’s close to.

I used to be in the barter industry and it was similar. We used to do a lot with lines of credit for big hotel chains and stuff. They would sell those off at discount and then we’d flip them out. When you guys decided to do the business again, was there any second thoughts or wondering? I’ve always said that the role of the COO is powerful to be connected to the CEO. You guys already knew each other and had already done business together. Were there any second thoughts of should we do this again? Did you jump right in and go, “Yeah?”

We jump right in and we go “Yeah.” Once we got those twenty restaurants on board and I was using a service in Minneapolis. Arash, one of the co-CEOs, was using a service in Miami where he was located. We got the value. I had enough food background where I saw the value too. We felt like the opportunity was there. It was built off something that’s done for a long time. Restaurants have been doing delivery for a long time. It hadn’t been productized and commoditized the way that the services have done it now.

SIC 91 | Bite Squad

Bite Squad: Restaurants have been doing delivery for a long time. It just hadn’t been productized and commoditized the way that the services have done it now.


Did you self-funded initially?

We self-funded initially and did some small seed rounds in the first year or two. I don’t know if you caught this on my LinkedIn profile, but I left then and boomerang back. We started Bite Squad in 2012, I left in 2015 and came back in 2017.

Why did you leave? Why’d you come back?

I left because I was burnt out on selling to SMEs because daily deal was the Wild West. It was another one of those super high growth and fast, but Bite Squad was going to be selling to restaurants and they’re challenging to sell too. They get sold to more than anybody on the planet like credit card processing and loyalty programs, software and advertising agencies. These guys and gals, they’re troopers for how many calls they get. I’ll give them that for sure. I felt like I also was not learning anything anymore and I’m one of those types where when I stopped learning, I die on the inside. I felt like it’s time for me to move on and they weren’t at a point where they were giving out equity in Bite Squad. I was an employee of Crowd Cut and helped them start Bite Squad. When Bite Squad started, I wasn’t a partner yet. I felt like the ceiling was there from a learning and from an equity standpoint. I got a great opportunity to go be a VP of enterprise sales for a venture-backed software company in the Twin Cities called Leadpages. It’s a landing pages and marketing automation software.

You went over to Leadpages and then left Leadpages to come back?

I met Leadpages and Drip for a few years, which ends up being a wildly important part of the story because with Leadpages, all you talk about is funnels and conversion rate optimization. That’s all you talk about and that’s all you sell. That’s exploratory on the software side. I got to know the SaaS ecosystem probably better than most. We also acquired Drip, which was a marketing automation platform and a fantastic workflow builder built by engineers. It’s a solid platform. That taught me a lot about automation in general, which would lend itself well both through marketing for Bite Squad and product and other things. I ended up going back because I learned so much from Drip and Leadpages, but I didn’t feel like I was able to apply everything I was learning there.

I am a former client of Leadpages as well. How big were those companies?

Leadpages were the darling of tech in Minneapolis for several years. They’re still well-regarded, but they were probably around 150 employees when I joined.

I would’ve thought they were 3 or 4 times that. We had one of the COOs from Unbounce was a member of our COO Alliance. For some reason, I thought that Leadpages would have been like 300 or 400 employees at that point.

No, they are not that big. Unbounce is also a great company. We’ve sold against them and I learned that ecosystem well. We acquired Drip and Drip was out of Santa Fe, New Mexico. Apple hired them. They moved here and that company was small. They were 7, 8 employees. It was the founders, product people and some salespeople. That was great. Learning to sell that product was fantastic. It served me well later on.

Are there any big lessons that you took from Leadpages and from Drip then that you brought back with you?

Going back to Leadpages, you’re looking at everything as a funnel because everything’s about getting the lead to the page and convert it. After they convert, you show them something else in the funnel. You notice I made a comment to you when I was submitting something, a form on your webpage. I told you that it was broken. I’m now wired to like look at every little piece of the funnel. I would say where that served me well is like our driver hiring funnel at Bite Squad, for example, when I came back and I went through the process to apply as a driver, I was like, “This seems it’s way too hard, way too many steps.”

That was on desktop and then I went to do it from my phone and I was like, “I can’t even complete this on my phone.” All these drivers are probably mostly applying from their phones. I had marketing tag, Google tag manager. Where’s the traffic coming from to this application page? Sure enough, 70% of the traffic’s coming from mobile. We have 70% of our applicants coming from mobile. It’s hard to apply on mobile and we’re having a service level problem at the time. That means you don’t have enough drivers. Your driver hiring is the most important funnel. I did this full audit and instincts from what I learned at Leadpages led to the audit and then ask about a little bit of data.

We overhauled that funnel. Anytime, I’ve overhauled a funnel like that, you almost always get a 30% increase in conversion rate. It took us about six months to overhaul it and had to bring some awareness to the issue and get it on roadmap and all that. We 2X our driver hires almost immediately afterwards. Our service level problems, they didn’t go away, but we had way less fire around hiring drivers. I was able to move on to other parts of the business as we continue to refine that.

Are you going to start a new company called Overhaul and take a percentage of the upside from all your clients?

I probably should. I’m consulting with a few groups and I use it a lot in product. I use it everywhere. On the Drip side where that’s all marketing automation, you’re looking at going down those work flows that helped me automate our customer support functions and getting some of that DNA on me. It was valuable and I don’t think I could have done what I did for Bite Squad had I not left for a couple of years and to come back as an equity partner for something I helped start and feel like a part of the original team come back and felt like a founder was special.

I said that tongue in cheek, but I almost mean it. I bumped into a couple of ad agencies over the last several months. One is called GiddyUp that does a lot of digital marketing, but they only do work for a percentage of revenue and some upside in the company. They’re turning companies away. They don’t charge you a fee. They take a pure percentage of revenue and a percentage of your company. They’re as good as they say they are. Whereas many agencies promise you the world, but then they can’t convert. It’s like, “If you’re that good, which you are.”

Performance-based monetization is always music to my ears if you can ever get it. It’s hard to find them.

Also, it’s a little bit of equity in the company as well. If you can get equity and options in some of these businesses too, that’s where your real kick comes. You leave there. You guys started up Bite Squad and you do your first two rounds of funding. How much were the seed rounds?

The seed round was like a couple million and I wasn’t around for the seed round. We took a bigger round. I don’t think they’ve ever made it public so I probably shouldn’t say exactly, but the second big round came from Bregal Sagemount Venture Capital out of New York. That was a pretty big round, especially for the Midwest, but all in all our funding was sub $40 million.

Enough in the first round though to get your technology up off the ground and get some salespeople. Was it all hardcore sales to get started? Was it hardcore sales to get all the restaurants? It’s a two-sided marketplace in a way, isn’t it?

It’s hardcore sales. What’s not represented well is that most of the sales are closed in person at the restaurant. It’s an outside sales team. It’s a field sales team. That’s a high cost and you have reps traveling. You send your best reps to your new market opening. There’s a definitely a cost center around sales because there’s a lot of travel involved. It takes a big group to achieve that growth. We had a sizable sales team.

What are good salespeople outside salespeople? What are you having to pay them to generate and keep them? What’s the lifespan of them? Is it 6 months, 6 years, 2 months, 2 years?

It depends. This was my first experience with outside sales reps. Daily deals sites were able to do inside sales with a little bit of out. Outside sales in our industry, you’re going to see salaries anywhere between 35 and 60. You’re going to see on-target earnings of around 100. You have your killers that might make 200-plus. We had some killers that were crushing it.

How long did they stay with you?

Some of them have been around for several years. The average sale cycle is probably more like a year. It’s pretty burnout. You’re traveling a lot. You’re moving around a lot.

Are they in a city for a month and then they move or in the city for a couple of weeks?

SIC 91 | Bite Squad

Bite Squad: One of the most important things that you can teach to your front lines team members is how to sell internally because they’re the ones that are closest to the market.


It could be either. It could be a couple of weeks. It could be a month. Sometimes we’re sending people to Hawaii and they’re there for a couple months. We were all over the country. It depends on what the market needed.

You’re looking for the fresh out of university kids that want to go and experience.

We generally found anyone who was too tenured, was stuck in their ways and that was harder to convert that person into a high performer.

What do you think were the big successes? How many employees before you guys sold?

We’ve got the contact center in Mexico City with over 200 team members that was outsourced so they weren’t employees. For one, this is great to be on the show because it’s such an operations heavy business. Let give you a feel for the structure, maybe in that’ll lead into the people. You’ve got field operations. You have about 1 to 2 people in every city that you operate in. They’re the ones that are hiring the drivers. Some markets you can manage virtually if you’re launching them from scratch to keep the cost level down. At some point, if they reach a certain order threshold, you’ve got to put a person there. You’ve got customer support in the US. You’ve got dispatch. You’ve got all the normal functions, HR marketing and legal. When I left, if I count the Bite Squad org or up to acquisition, let’s say we were pretty close to 500 people, not including drivers, which there are 10,000 plus.

Five hundred people plus the 10,000 drivers over a course of how many years did you build that up, 4 or 5?

Bite Squad started in 2012 and sold in 2019 so it’s seven years.

There’s got to be a pile like book after book, after book of lessons. When you outsource the call center in New Mexico, you didn’t by chance use a group called Listen Up Espanol, did you?

No, we didn’t.

I happened to have friends that run outsource call centers in Mexico. What was that like running with an outsource call center? How did you pick one?

Kian was the one who went down to Mexico City and he was one of the CEOs. He went down there and was the one that got the infrastructure up off the ground. I was the one that was responsible for getting the US and Mexico City team to work together and learn how to run shifts together, learn how to manipulate different channels if we’re seeing more calls or chats or tickets or whatever it is. Getting those teams to communicate well together took some time, but it was amazing what you can accomplish through Slack, video calls and on the fly coaching.

If they’re not in sync on something, if it is not paying attention to the right support issues that are coming in, they’re not looking at the right priority. Getting those two teams to understand what the priority is and why. It was honestly probably two weeks straight of relentless through dinner rush on Friday nights and through the weekends, having my laptop open at home and coaching them through how to work more efficiently together.

You mentioned coaching a couple of times here. It was mentioned in your bio that I started this with, what does coaching mean to you? Do you have a model or a framework that you use for coaching? How does that flow for you?

I love right on the job coaching, anytime you can do that. There are different formats for coaching, but the things that I look at, one of the most important things that I always teach from my sales background is how to sell internally, especially to your front lines team members because they’re the ones that are closest to market. They’re the ones talking to customers. They’re the ones talking to drivers and to restaurants. They know the trends and what’s going on. They know when there’s problems, but most people aren’t good at boiling that down to here’s the problem. Here’s how I’m quantifying it. Here’s what’s to gain. Here’s a path to fix it. I do a lot of coaching through teaching people how to send better emails and make them more digestible to the executive team.

I spent a ton of time doing that. I can leverage my sales background there. That’s something that I spend a lot of time on. The other thing I’m coaching is frameworks like giving people good framework. In support, it’s like, “Here’s your KPIs. You’ve got a monitor. Here’s your dashboard. Let’s build it out together. Here’s why we’re selecting certain things. Here’s your issue types that you’re getting inbound and tracking those. Here’s all the priority of the issues that you need to solve. Here’s how you hire and train people. Frameworks are effective because once they have that, then they can take it with them forever.

The frameworks that you’re doing are these SOPs or playbooks that you’re giving them that you’re training on that?

It’s stuff that we make together, but I’m usually doing the first framework for it and then helping working with them to fill it in because they’re going to have some knowledge that I may not have, but I need to help them. It’s a done with you project.

I hate to ask this question because I don’t want people to think it’s about the system or the tool, but it is more about there. You can write down the framework on a post-it-note and photocopied or send it out to people and you don’t need any special system. Did you use any special system or tool to automate or SOP everything to create your playbooks?

It’s just Google docs. We were super scrappy. Up until we got acquired, we still had the free instance of Slack, which is remarkable because we have 1,000 people on Slack and we were somehow still using the free version. There’s a line in Moneyball where Billy Beane was making fun of the fact that he charges the employees for the soda and the vending machines. I don’t know if you’ve seen that movie or not. Billy likes to keep the money on the field. We didn’t charge. I’m not saying that we did that, but we largely tried to save money where we could in software and everything else. We try to keep our money in our growth.

I agree with all that as well. Too many people try to, in every case, whether building a dashboarding software or putting processes in place, it’s not about using something like Process Street or Basecamp. It’s understanding the methodology first. It’s not about the newest email tool. It’s having a system to manage your emails. People skip over the important stuff that you seem to wrap your head around early. On the growth and on the hiring, to get 500 internal people, at what point did you bring HR into the company?

For things like driver hiring, where you’re hiring thousands of drivers a month, you don’t bring them in because it’s such high volume that you need your city managers to process that. HR is helping with things like background checks. They’re helping with someone the behind the scenes stuff. Your local city manager in that city is going to be the best person to the best proxy for hiring the right people. When I came back, we didn’t have a marketing team. We didn’t have an HR team. We had one person in HR when I came back. We had 2 or 3 people in marketing. The finance wasn’t built out.

I spent 50% of my time, the first six months coming back. I had an Excel spreadsheet with every single hire that we needed to make and that’s where that sales background kicks in. I’m sourcing the ads myself from Indeed. I’m hiring a director of support, director of dispatch, managers, training managers and director of HR. I helped hire our first CMO. I’m hiring content people, marketing automation specialists and the list goes on. I was involved in that. I love hiring. It’s something I’ve done a lot of it. It’s something I enjoy. As I’ve heard a billion times on this show, getting the right people for the right stage of business that you’re in and what they’re charged with for in twelve months term is what does this person have to accomplish in the next twelve months?

If they can do that, that’s the high priority stuff. If they can at least make it a couple of years, 2, 3, 4 years, hopefully longer than that. It was partnering with whoever the department that needed to hire with. I was working with them. If it wasn’t something I oversaw, then I would at least come in and do the final interview. I safeguarded who we brought in. I was the presence in Minneapolis. Kian was in Mexico or in Las Vegas where his residence was and Arash was in Miami. I was the leader from the exact team in Minneapolis. I’m the only one that was visible every day.

What do you think your weaknesses were as a COO? You have a bunch of strengths. We all have to have some weaknesses and be okay with that, delegate them and get them off our plate. Were there a couple of areas that you got off your plate right away or try to avoid?

Where I’m weakest would be in finance and accounting, I don’t have a strong mathematical mind. It pisses me off because I want to. I have this thing that I struggle where when I’m not good at something, I’m in a room and I can’t quite comprehend exactly what people are saying. I have to ask a lot of questions and I get frustrated. I have this vicious loop where I’ll go buy a book about that subject and I’ll read it, struggle through with it and get angry about that. I’ve learned that if I can learn enough to be able to ask the right questions, to be able to still guide the overall objective or things about the business, then that’s good enough.

A lot of times that person in finance accounting or data analytics, they don’t always have the insight to the customer so that they can make some bad decisions without your insight. If I can have enough tools to be able to ask questions that at least get helped me get through that conversation with them, then we both come out better on the end. I’d say that’s a weakness of mine. Deep analytics and yeah, I’m not a chief analytics officer so that makes sense. I would say anything overly analytical and then financial models and accounting are not my jam.

I’m right there with you. The school system heard a lot of us because it told us that we had to be the smart person and memorize everything and be good at everything. You go to school for eighteen years and you’re told you suck at something because you’re getting 65% all the time. Like you pointed out, you can get the head of analytics and they would be terrible at sales, marketing and hiring too. You need to have those skills. How did you structure your leadership team and with the remote, how did you guys meet and how often do you meet?

SIC 91 | Bite Squad

Bite Squad: Getting the right people for the right stage of business that you’re in is really important.


Leadership team structure, as far as what roles we had or what type of roles we have?

Walk us through the top level of the org chart, who reported to who and in which business areas.

I’ll start with the CEO. They’ve different skillsets, both smart. Arash largely spent his time in growth strategy, engineering and tech infrastructure. Kian was much more at P&L driven and operations. He also did sales early on. He was sales ops and P&L with finance and accounting. I had customer support, dispatch, which is basically all the logistics around which driver gets what order from what restaurant, all the menus team and restaurant success team. You got to build a menu for the restaurant and get them onboarded. Field ops, which are the people in the city hiring the drivers and managing the business in the city. Those teams rolled up to me and then I cross managed marketing, mostly around marketing automation since I came from Drip and implement the Drip at Bite Squad. I had a lot of knowledge base there.

It helps the CMO build out the marketing team, the content marketing automation specialist, and all that. Sales is the other. Marketing and sales were the two departments I cross manage and then internal product. I pretty much owned with the VP of product. We have all these tools and systems we got to use to run the business. That was on my end and CMOs are running marketing. Our chief legal ran HR and legal and then our CFO ran finance and accounting.

How did you guys meet? How often did you meet? What was the structure there?

We did weekly. The top exec team, the C-level met once every two weeks. On Thursdays, we had our bi-weekly meeting and then we all got together then with our director levels every Monday. Every Monday we had a kickoff meeting.

You guys are meeting remotely. A lot of your meetings were done then over Zoom as well?


I had the question related to your growth and culture. I can segue into the culture question. It’ll come back to me where I was going to ask them this, but why did you go back? Why did you end up going back from Leadpages and Drip to go back over?

I didn’t think I would go back not because we ended on bad terms or anything like that. I thought that cycle of my life was over. We stayed friendly while I was gone, Kian, Arash and I. I knew they were growing and they had asked me to come back probably six months prior to when I did. I said, “No, I’m good where I’m at. I’m happy I was making great money. I was learning a ton. I was working as a huge marketing team. I’m building out the sales team. It was a lot of fun.” After they got that round from Bregal Sagemount, they came back more seriously and were like, “We want you to come back as president and COO.”

At that point when I learned more about the growth, we hadn’t dived into that the last few times they’d approached me again. I saw their growth and I got excited because I knew that there was a big hole. A lot of the gaps that they had as CEOs were the ones that I was good at. I was so excited because I learned all this stuff at Drip and Leadpages that I felt like I had absorbed, but wasn’t able to put back out into the world. For me, this was “I can apply all this stuff, fix a ton of stuff, have a ton of fun and build a big team.” I like leading big teams.

It’s almost like you came back in at a different size. You’re first two or more startups with them. This is almost your third business with them when you came into a more mature business and took it up.

When I came back, we were around 25 million to 40 million in GFS. When I left, we were right around 300. It was 2.5 years of high growth. If you look at like second measure charts, we are a big hockey stick.

When you went back into the company, what did you have to relearn or unlearn as well?

I had to unlearn the old way that we used to work together. There was a lot of good DNA in how we work together but we had fewer financial parameters. I was so used to not spending and doing more with less. We still always do that. It’s part of our culture to do it that way. I had a little more wiggle room to play, to hire, to expand hiring in the right head counts, not head count for head count, but the right head count. I had to unlearn how we used to work together a little bit. There were some things that were slightly dysfunctional about how those two worked together. They were yin and yang. They made a lot of improvements there in their relationship. I had to unlearn that and know that’s much better than going away. Otherwise, it was a lot of the same problems that I knew were there when I left. Now, we’re at a much grander scale. The scale is there. It was exciting.

The company has got to be drastically different. Scale is different. The span of control for you is different. How long did it take you to hit the ground running or was it easy because you’d come out of Leadpages, which was a bigger company?

It was easy. I knew it was going to be intense. One thing was probably lost on a lot of people is that A, it’s operations, heavy business and B, you’re on all the time and it’s an intense business because it’s on demand. It’s like people are ordering and they want their food now. There is this natural, ASAP culture about that business that is fun and addicting almost in a way. You get back in and it was hit the ground running hard. The first big charge was the hiring. That was brutal hires I got to make. Also, this customer support department needed a lot of help. I put a ton of infrastructure there.

We implemented Zendesk. They needed a whole new tech stack and new training program. They need to do levels for people to be able to journey through in customer support to grow themselves. They needed performance management tools so we built that charts and snapshots. I worked with a team on that. It was like getting right into it. What was hard coming back was there was a lot of things to fix. It was like, where do you focus your time and prioritize? That was the bigger challenge coming back in because I got pulled in a lot of directions right away.

I’m curious what you learned with bringing in some of the senior talent? Some of the people that you were bringing in from the outside as you brought on your second round of funding. You were able to hire probably more senior people and more seasoned people. Are they any lessons in doing that? Things that went well or things that didn’t go well?

We hired seasoned people in some areas that are critical like finance and accounting. We hired people that were a little greener in operations. When you look at the need of operations, the need was high from even a time commitment standpoint. Because our busiest periods are on the weekends and Friday nights, we were at the office on Friday nights still at 8:00, 9:00. That’s how it was in 2017, 2018, but it was fun. We have music out in the open. That greener and younger culture was more prominent in operations. We still were a company that operated with a mentality of like, “Let’s find people that are green and malleable. You can mentor them and coach them and you’re not going to pay like a senior level hire. We can only hire so many of those people with our cash burn as we’re growing.

You did some of the younger Jack of all trades, master of none in high-culture people.

Some of those people and a good example is my director of customer support. I hired her as a training manager to overhaul our training content, but she naturally started leading the group. I gave her the title and we worked so closely together. It was a great relationship. My director of dispatch had Air Force background. He came in from world. He had career and logistics experience. He was great. He was a little more tenured. Our team was junior but fantastic.

My guess is a bunch of them are going to follow you around in your career. Last couple of questions. When you’re getting ready to go through an acquisition, any lessons or words of advice for people to be careful of or to be cautious of or both around working with the acquiring company, but then also with your team that can get distracted through that whole process. I’m talking pre-acquisition lessons.

The CEOs of Bite Squad and the CEO of Waitr didn’t do their diligence in mapping out how the companies were going to work together. Our CEOs pretty much left after acquisition. They were ready to move on. The Waitr CEO was on the road a lot doing roadshows with analysts and all this other stuff and was doing that whole thing. We got outside of our identity very fast and that hurt us to a degree. Doing your diligence on how are we going to operate together, how are we culturally? We were different and still are different operating companies. Our CEOs didn’t pull us in for a lot of those types of conversations. By the time, it came around to that, it was like there are some problems with that.

You’ve gone through a ton of growth. You’ve got a kid who’s not quite two years old. He’s never going to listen to you when he gets older. I’m always curious as to what advice we would give ourselves. If you were to go back to the 22-year-old Kyle who’s getting ready to start off in his career, what advice you give yourself?

I got a couple ones for myself. One I hit on earlier where it’s like, “Young Kyle, this is future Kyle talking to you. You’re not good at math and that’s okay, but you can understand trends and a P&L and you need to do some learning so you know enough to be able to ask the right questions in those conversations, in those meetings, in those rooms so that you can take care of your business units and your business. At the end of the day, finance is there for that and that’s okay.” That’s one piece.

Two is I’m a builder. I love building teams. I love building companies. That’s where I’m happy and where I’m very energized and why I stopped doing that, I get depressed. If you’re a builder, follow that path. Where you’re weak, others are strong. Where you’re strong, others are weak. We all got to work together. Those would probably be three things. Maybe the last thing would be pay a little more attention to strategy along the way. You’re in the weeds. Even early on in your career, pay more attention to strategy. It’s something I’m trying to hone in more now and building more skillset around. I’ve had a lot more exposure to it these last few years. That’s another thing I tell myself to take notes on through time.

Kyle Hale, the COO for Bite Squad, thank you for sharing with us on this show.

Important Links:

About Kyle Hale

SIC 91 | Bite SquadKyle Hale is an entrepreneur and technology executive who built the foundation of his career in sales and operations with both B2B and B2C high growth technology companies. His roles span the fitness industry, multi-unit operations in QSR, e-commerce, selling software to the enterprise and most recently as partner and COO of Bite Squad, the restaurant delivery service which was acquired for $321M in January of 2019. 

As COO Kyle led customer support, dispatch, field operations, and cross matrix managed sales, marketing, and product with the CEOs. A unique generalist with expansive domain knowledge in sales, marketing automation, product/software development, full-cycle recruiting, leadership, and strategy execution. More creative than an executive, he has a non-egotistical approach with a focus on developing the psychology and performance of his team through 1-1 mentoring. 

After building two companies to acquisition in the last 7 years, he is now consulting with startups in the midwest and serving as Chief Dad Officer to his two-year-old son Sky!


Please Fill The Form Below To Apply: