$500 million and counting


Bid Faster. Win More. Build Smarter.

Explore the digital transformation of construction with STACK Construction Technologies CEO, Phillip Ogilby. In this engaging interview, delve into the cutting-edge world of cloud-based software, AI-assisted estimation, and BIM integration. Discover how Stack’s preconstruction solutions are revolutionizing the industry by providing contractors with data-driven insights and a frictionless freemium experience, all while reshaping the future of construction technology.

Stack Construction Technologies, which is a cloud-based software that helps contractors from project evaluation to completion and also maximizes their profits.

Phillip Ogilby
CEO of Stack Construction Technologies

Hello, everyone, and welcome to another episode of Wytpod. My name is Harshit and I’m the Director of Business Alliances at Wytlabs. We are a digital agency specializing in SaaS and E-commerce business marketing. Today’s guest is the CEO of Stack Construction Technologies, which is a cloud-based software that helps contractors from project evaluation to completion and also maximizes their profits. A big welcome to you, and I’m so happy to have you with me today.

Thank you very much. I appreciate being invited.

Let’s start talking about your journey. I would love to know what you were like as a young child and how you got introduced to the construction industry altogether. Please.

Sure. Yeah, it’s been quite a journey. I remember well, I wasn’t a terrific high school student at all. I found it difficult to pay attention, as many young people do. I was probably a C student in high school looking back on it. But the one thing I remember from my very early days, I remember as a teenager, is my friend Todd invited me to have a summer job and helped him paint his brother’s nightclub. His brother was probably five or six years older than us, and he’d taken a couple of investors and built this big fancy nightclub in Springfield, Ohio. I was 15 and had the chance to work with Todd and we were laborers painting the building. But I remember that summer, it sunk into me that if Todd’s brother can do this, anybody can do this. I planted this kernel, if you will, a little seed of entrepreneurialism in the back of my mind, and I’ve been driven to build success on my own ever since. I remember well when I graduated high school sitting with my parents they didn’t have much money for college, but my father worked in the Sheep Metalworkers’ Union of Dayton, Ohio.

In the late ’70s, that was a pretty good opportunity. I took advantage of it. I was 19 years old, just out of high school and making, I don’t know, $10 or $12 an hour, which was a whole lot of money back in those days. I thought I’d struck a gold mine there for the first few years. But the economy took a dip, and along the way, I got laid off. I remember well, I bought a house and my then wife, we had, I think, two, one son and another one on the way. I remember collecting unemployment and I picked up one unemployment check and I told myself, I’m just not going to do this anymore. I bought a book on how to root your house, and I then went to the Yellow Pages, which was a big thing. That was the Google of its day, right? Your parents had big books on there, or maybe your grandparents had books on their counter where you looked through the book and found a phone number for somebody who wanted to provide a service. I put an ad in the Yellow Pages and spent more than I had, but took a risk and started my own roofing business.

And people started calling and I’d go out and convince them and give them a price to put a roof on their house. And one thing led to another. I hired some of my buddies and bought an old beat-up truck, and pretty soon I’m in the roofing business. A couple of years later, I had an opportunity to move up and do more commercial work. I took a partner in with Ken Schreber in Dayton, Ohio, and we created a new business called the Ogilby Corporation, and I started doing larger commercial projects. Shoot, by then, I was 23 or 24, and I had as many as 50 employees at the time. That’s really where I learned the commercial construction business.

Nice. You’re pretty established as a company and 23, 24 years of it, having so many employees. It’s a big achievement.


It is. Looking back on it, it was somewhat terrifying at the time. I remember that well. I’m sure young entrepreneurs listening to this, or entrepreneurs of any age will appreciate the terrifying comment, but there’s an aspect to that associated with starting your own business. But along the way, I remember coming home from work one day, and my oldest son, Justin, I had brought home a personal computer, and Justin was one of those computer kids. He was just drawn to the computer. He had built a game and had some stuff shooting at each other on the computer screen and was playing a game. This was in the late ’80s. I thought, Man, that’s the coolest thing I’ve ever seen. Before you know it, I bought Justin some more books and we started working on building our estimating software for our roofing business. It took longer than we thought. It took probably three or four years. But by that time Justin was, I think, 15 years old or 16, we had not only developed our estimating software, I’d sold it to a bunch of my buddies and we had a meaningful amount of revenue, I remember.

I got completely out of the construction business and started selling the technology to help contractors to find success. I’m one of those guys who’s seen the ugly bottom of starting from scratch and clawed my way up. Then once I realized the impact that technology could have on my success, I wanted to share that with others. My relationship with my son Justin is that he’s our chief product officer today. Justin’s 41 years old now, and we’ve all gotten older, but we’ve built a successful business in the construction technology world.

That’s brilliant. And even Justin started pretty young.

Yeah, he did. I started a business. He and I started a company called I Square Foot during the dot com boom. I am one of those entrepreneurs who ended up selling that business for $85 million and I got about that much out of that deal. We had some very ugly deals with investors and I made some mistakes along the way, hiring a CEO that I shouldn’t have done. But long story short, I’ve seen a lot of this road have been in the technology space for a long time. And once that went the way it went with Ice per foot, I had to do it all over again. And so we started Stack. Today we serve thousands and thousands of customers, literally most of them in North America. We have customers all around the world, mostly in English-speaking countries, but it’s been quite a journey.

I would love to know where the idea of Stack came to you. How were the initial days with the company?

Yeah, it’s funny. Stack came from the idea behind Buildware. Buildware was what we called our original estimating software. With the Iceware boot business, we don’t spend too much time talking about that, but the concept there was we created a business that sold opportunities. We sold bidding opportunities. We helped change the way blueprints were distributed. When I first started that business, everybody was shipping big, fat rolls of blueprints around the country. When the internet took hold, it just occurred to me, Why don’t we create a solution that would allow a general contractor to invite his subs to bid, and then the subs could log into this website and download electronic drawings? Originally, the idea was it would create a bigger market for buildware, but then that grew on its own. The ice-for-foot thing, selling electronic leads online, and finding new opportunities for work for contractors was very popular. That became a business in and of itself. When that went the way it went, I left and moved on by pulling Justin out of there a year or two later and we just said, Let’s take Buildware and move it into the cloud and change the world again.

That’s really what we’ve done.

You’re one of the OGs of estimating and quoting our launch.

Yeah. I saw Elton John had come to our number of years ago, and one of the first things he said if people were cheering, was, If you live long enough and you stay in the game long enough, they call you a legend. I guess I got an upgrade here that I’m now

The legend.

Now that’s a little strong, but you get the point.

Let’s talk about Stack, Phillip, I had scored expertise. I see three solutions on your websites: take-off estimate, field productivity, and project management. Can you please explain a bit more in-depth about these three solutions?


Yeah, sure. You heard my journey. One of the things I’ve learned firsthand is that construction is enormously risky from a business standpoint. Because you don’t tend to find people coming out of business school and starting a construction company. They tend to get into construction like I did. It’s what they know. Maybe their dad was in it, their uncle was in it, their grandfather was in it, whatever it is. That’s how people end up getting into the building trades. It’s a blue-collar business up to the owner. In many cases, it becomes very difficult as a result for these folks to find success. I told you a little bit about the journey with technology. Technology changes the game for contractors, and so it’s become a passion of mine. We started with take-off. Take-off is the act of measuring the blueprint and determining quantities. I need to measure this area. I need so many cubic yards of concrete or so much dry, whatever it is. That’s called take-off. That was our very first business with Stack. We created the first-ever take-off solution in the cloud. There was some risk associated with that because, in those days, we were competing with software that was all desktop-based.

I was never fully sure in the very early days, how much would people adopt a mission-critical solution like this. It’s midday and I’ve got to submit my bid and I can’t let the internet go down and all that. Would people adopt the cloud-based solution? And so, sure enough, two years in, we had over 600 customers. We were still working out of our basement, and that’s when I decided to go raise some additional money. But we started with take-off. Once we added some additional capital from the Samout Investors, we used that to hire developers and we expanded into the estimating space. Typically, historically in our industry, there’s take-off software and then there’s estimating software, and they don’t talk to each other very well. Stack was the first to bring all those together. That’s what we’re doing today with take-off and estimating. We call it our preconstruction solution. Everything before the actual building of the building. About a year and a half, almost two years ago now, we raised some additional money from our investors. We said, Look, we want to create and expand this into a platform. We want the contractor to be able to work with us in the very early days before the project bids, all the way through bidding, and estimating.

Then when they take the project in the field, we want them to stay in Stack. We acquired two businesses. We acquired a product called SmartUse based out of Montreal, and it’s a terrific solution. It’s designed for Blueprints on the iPad. It works online or offline. It’s a fabulous solution. It’s much less expensive for our customers. Typically, people using competing software are at the general contractor’s office and they’re spending a lot of money on the software. With SmartUse, it’s much less expensive, it’s much easier to use, and it works directly with our Stack estimating product. They can now take the drawings and the estimates from the office into the field. We also acquired a company called K-Ops, also out of Montreal. K-ops is project management. We’re weaving together right now, K-Ops and SmartUse. We’re designing all of that to make the data flow easily between the field and the office. Our long-term goal here, really, for the subcontractor, who’s our primary customer, is to allow him to take it into the field, but then also feedback on the information. We want to create this feedback loop where the actual cost, the time it takes, and the actual amount of materials that are used in the field, all get fed back into the office.

Next time they’re bidding on a project, they’ll have real, live, active data that comes from their experience. We’re creating a platform here for the subcontractor, and that’s been our mission and our journey.

That’s brilliant. I think you’ve already mentioned quite a good reason like How Stack can basically satisfy contractors’ needs and bring them all together into one software. I think that’s a pretty good way to give and scale and reduce multiple touch point dependencies and help the organization. But apart from this, what are the other three main challenges I would say not even mistakes that you feel contractors make in the construction business. Those three mistakes or challenges could be the reason that drives people to subscribe to Stack. Can you please tell us a bit more about that?

Sure. Step one, we talked about the failure rate being so high. A big part of that can be helped just by adopting technology. A lot of folks, when they think about adopting technology for their construction business, the first thing they want to buy is accounting software. That makes sense, and it’s probably not a bad idea, but the revenue that you’re counting, the bean counting that you’re doing, the dollars and cents you’re counting, that begins with an estimate, and it begins even more with a take-off. You want to be sure you’re adopting the preconstruction software, much like Stack. There are other solutions too. Stack happens to be the best. But you want to automate to the extent you can automate. You want to digitize that, we call it. You want that to be done electronically now. It’s much faster. It’s much more accurate. You get a paper trail. You can see what’s included, and what’s not, and then take that directly into your estimate. So you want to adopt technology before you ask for the revenue. That’s the way I always say it because if you and I are doing business and you want me to come to paint your house and I give you a price of $4,000, I don’t get another chance to ask for that money.

Many people will look at a house and say, Okay, it’s going to be $4,000. Most of our customers are commercial contractors, so this is a simple example. But most folks will eyeball it. When they come to Stack, they’ll eyeball it. They’ll look at a project, Oh, we’ve done five of those and I’ll do it for this amount of money. But that’s where you get into trouble when material prices start to increase like everything’s been increasing like crazy the last several years, from fuel to labor to material. You want to know what your costs are first. I’d encourage you to adopt the technology on the preconstruction side right before. Then you want to be able to seamlessly move that into the field as well, which goes to what we’re doing. You want to be able to take it into the field and you want to be able to see feedback in real time from the field. Again, that’s what Stack’s about. But it’s also driven by my experience and looking back on my contracting days. Many times, I had no idea what my costs were until the job was done and you sat down and you looked and you see you add everything up and you crush your fingers and you’re hoping you’re scratching your teeth and hopefully there’s something left.

You want to get ahead of that and you can do that with technology. The other thing is you want to surround yourself with people who are good at things that you’re not great at. I can’t stress that enough. Regardless of the business that you’re in. As an entrepreneur, entrepreneurs tend to be people like me who think, Let’s go charge. Let’s go take the hill. I’ve got an idea. I know it’ll work in the market, but maybe we’re not so good at following up on all the details that it’s going to take to feed and clothe and house the army on the way up the hill. So it’s very important and it’s been a big part of my success, is surrounding myself with people who are better at other areas than maybe on the weekend.

That’s nice. Let’s talk about the customer journey on Stack. Say, for example, I’m a contractor, I came maybe like Google searching, trying to figure out estimating software and I stumbled across Stack, and booked a demo. How exactly my journey is going to be on Stack? Please tell us.

Yeah, that’s a great question. This is a big part of the reason we’ve gone from zero to thousands and thousands of customers over the last seven, eight, nine years. We developed a freemium model. We want to eliminate the friction between you and us. We want to eliminate the friction. We want you to get in, and use the product. We allow you to use it for free. There are a few limitations along the way. You can’t put on a limited number of projects. We limit the number of projects you can put in there. We started with a free trial. A lot of people in the software business will start with a free trial. I did a delay for a foot. We did it in the early days of Stack. The problem with a free trial is, that it’s great if you get that person’s attention during that first seven or 14 or 30 days, whatever it is, but so often people are distracted, busy, they’re living their lives, they have other priorities. They forget all about it. Then maybe they’re interested six weeks later and the trial has expired. We said, Let’s fix that process. We developed this freemium model where people can come in, create an account, and use it for free forever, as long as they want.

Now, you’re not going to use it a ton. We’re going to put some limitations around it. But you’ll get in, you’ll use it, you’ll measure, you can create your estimate, and you can get a real sense of what the product can do for you. Once that happens, one of the big drivers of our success, especially competing with desktop software, is we have this little green button in the lower right corner that’s chat. A lot of times we’ll ask, Look, if you have trouble, just click there and chat, and we have people that are answering those chats real live during the work day. That enables us to engage with the user. He might have a question, How do I do this? How do I do that? If we see that he’s active on the product, we might even chat with him. Hey, how can I help? Would you like to see a demo? Once we get you into a demo and somebody professional shows you how to use the product, we close at a very high rate. 65% of the time we’ll get a credit card from you within the first seven days after we get you into a demo just because the product sells itself.

If you understand everything it can do for you.

We’re always looking to take friction out of the process. I think that’s very important. Far too few companies today are taking that approach. It frustrates me for the rest of my daily life to interact with other companies. It’s just, Oh, this is too hard. Why do I have to do this? Why do I have to do that? I think it’s important to always look at ways that it’s to eliminate that friction and make it easier to relate and communicate with your customer. Look, if you’re delivering real value, you’ve built a successful business. That’s all there is to it. If you’re not delivering real value, stop, take a deep breath, and go do something else. That’s been our approach.


That’s brilliant. What I’ve seen in the SaaS industry, especially Software, which sell it at a premium. The pricing is maybe 1,000 K or so. We can’t generalize it, but something we just premium. They don’t usually offer a free trial. There’s a demo and then the sales happen and then you can. If you want to maybe just have the demo account, you don’t have to raise a special request and get it done. It’s good to have some premium software out there. We are still offering premium products altogether, which people can use, be confident about, and then go ahead with the purchase. That’s right.


That’s a nice thing to do.

Yeah, that’s what we do.

I think, Phillip, even you would agree, that a lot of organizations now, for obvious reasons, are shifting towards artificial intelligence. So does Stack offer any such solution or is it something that is on the roadmap?

I would say it’s definitely on the roadmap. We’ve got a bit of a little Skunkworks project, we call it right now, mostly around symbol identification, where we’re training, we’re using models and we’re training it, using our customers’ data. It’s nothing intrusive at all, but we’re just trying to make the system smarter and more intelligent around finding symbols automatically. We will move towards adopting that for the take-off process as well, but it’s a misnomer to think, It’s interesting, we had this conversation in a leadership meeting yesterday afternoon. When I first started Stack, we offered take-off as a service. I had a small team of people, and you would send us your blueprints and we’d agree on a price, and I had people that would do the take-off for you. We would do it all, we’d send it back to you. That business didn’t succeed. It never really got off the ground. One of the big challenges was because all the risk was on the part of the contractor when he or she was submitting a price to their customer, they found it necessary to almost go back and do it over themselves. They were never fully comfortable taking numbers created by somebody else and submitting a number for which they’d be financially responsible.

I think the future certainly has a ton of AI in it. We’re bringing it to bear. We’re working on it behind the scenes. But I think ultimately there’s also a component with what we do because it’s so mission-critical. I think the days of somebody just injecting a series of PDF files and then taking the number and handing it to their customer, I think those are down the road little ways.

Any other construction business trend that’s impacting your product development?

What’s funny? Building information modeling has always been a thing. When you see three-dimensional models that architects create, those are called BIM models typically. We refer to them as building information modeling models. That’s always been a technology that people have said that’s going to eliminate the need for takeoff software. It’s going to eliminate the need for it. Candidly, it’s why we don’t have a lot of big national competitors in the takeoff space, to be honest. It’s a little-known secret, don’t tell anybody, but mostly there’s this general feeling of executives sitting around making decisions that somehow BIM is going to change the world and make takeoffs irrelevant. That’s not happening today. It hasn’t happened. Bim is a 20-year-old technology now, and it has its place, but it’s not in the estimating world. There’s BIM, there’s artificial intelligence is getting a ton of buzz, of course. There’s a lot of people in our space saying, Oh, pretty soon you’ll just stick your drawings in and out. We’ll come to the estimate. I just told you why that’s not going to be the case anytime soon. We’re trying to use it really as take-off accelerators to make things faster.

We think that the near-term future for that technology in our business is around accelerating what you’re doing. But you’re not going to be able to completely take your eyes off the wall because you’re not going to trust it.

Also, you do a lot of automation as well, under the various solutions that you have. I think that also helps people scale faster and have them quickly down around time.

Yeah, we do a lot of things too, and we’ve done it for years. We keyword search everything. If you want to find all the blocking on a project, you just type in blocking, boom, and we’re going to highlight it everywhere on the blueprints, everywhere on the specs. We’ve done a lot of things and we continue to look for ways to accelerate, just simple accelerators to take the information you’ve got and make it faster and easier to get the work done.

Got you. I think, Phillip we’re coming to an end and I would like to have a quick rapid-fire with you. Are you ready for that?

Sure, let’s go.

What was your last Google search?

My last Google search was I’m thinking about buying a new airplane, and so it was about buying a new airplane. That’s funny, but that’s what it is.

All right, Richie, Rich in the house. What has been your favorite age so far?

My favorite age? Yep. That’s a crazy question. That’s a crazy question. And I look back and people long for their youth. I’m having a pretty good time right now. I’m working hard to stay in shape. I’ve got more money than I’ve ever had, and it’s more comfortable. So I would say right now.

That’s brilliant. Okay. What is your hidden talent?

My hidden talent? My hidden talent. That’s a great question. I’m not even sure how to answer that one either. I learned how to fly airplanes, so that’s pretty cool, and I love doing that, as you can imagine. I think I’m pretty good at communicating, and I think I’m pretty good about solving problems and articulating how to solve those problems, and I think that’s gotten me a long way.


What never fails to make you laugh?

Never fails to make me laugh. That’s a good one too. I don’t know. A good joke, for sure.

Not sure how else to answer that. I will add to the last question, though, about my hidden talents. I think one of the things that helped to make me successful is my ability to get people to join me on my mission. I’m surrounded by amazing people at Stack from the leadership team down, and I couldn’t be more proud of the people. I would say my ability to influence people to come join me on the mission is a big hidden talent of mine.

I think people’s skills are vital anyway. When you have a leadership role altogether.

Thank you, Philip. Thank you so much for the time and all the wisdom that you’ve shared. I’m not hoping, but basically, I’m sure. And I doubt the viewers will enjoy this session. Thank you so much. Appreciate it.

I’ve enjoyed it. I appreciate the invitation. Thanks again.



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