Ep. 196 - The SaaS Opportunity Hidden Inside Services

Guest: Dillon Okner, Founding Partner of The Oak Group / SiteRise  

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In this episode, we look at how a services business can become the proving ground for a SaaS opportunity.

Dillon Okner, founding partner of The Oak Group and creator of SiteRise, joins us to talk about building software from the inside of a professional services business. SiteRise was born from repeated problems Dillon saw while helping retail brands manage construction, store openings, document control, reporting, and cross-functional planning.

We dig into why Dillon chose to bootstrap the SaaS product through services revenue instead of raising venture capital, how his team identified product-market fit, and why messy spreadsheets, inconsistent file naming, and disconnected reports are often signs that a market is ready for software.

Dillon also shares what is working in SiteRise’s go-to-market motion, including outbound, conferences, relationship-based selling, LinkedIn Sales Navigator, and a creative “headshot-led growth” tactic that turned trade show engagement into product interaction.

Key takeaways:

• How services can reveal repeatable SaaS opportunities
• Why bootstrapping can protect product focus
• What breaks when teams scale with spreadsheets and disconnected reports
• How better construction and retail development data can support boardroom-level planning
• Why founder-led sales eventually needs operational support

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Transcript

Welcome to SaaS Backwards

SPEAKER_00 0:06

Welcome to the Stats Backwards Podcast, where we reverse engineer the success of fast-growing Stats firms and explore strategies CMOs and CEOs are using to drive their businesses forward.

SPEAKER_02 0:25

Welcome to SaaS Backwards, a podcast that helps SaaS and AI CEOs and go-to-market leaders accelerate growth and enhance profitability. Our guest today is Dylan Achner, founding partner of the Oak Group, a professional services firm in the retail construction space. And they've also created a SaaS application for this industry called Sightrise. Hey Dylan, welcome to the podcast.

SPEAKER_03 0:50

Hey, Ken, thanks for having me. I'm excited to be here this morning.

Dillon and Oak Group

SPEAKER_02 0:53

Yeah, I'm excited. I think we're going to have a lot of great stuff for our listeners. Just before we dig into this episode, could you please tell us a little bit about yourself and your company?

SPEAKER_03 1:03

Yeah, absolutely. So we started the Oak Group back in 2022. Prior to that, I spent my most of my career working in construction development from Apple to Tesla and enjoy technology, having the opportunity to build retail stores and spaces and warehouse alongside the building process, focusing heavily on how to reproduce and make things more efficient, opening your doors on time and really functioning under a you know a budgetary restrictions.

SPEAKER_02 1:29

Yeah, I imagine that the retail industry is very focused on meeting their deadline, meeting their budget, being able to start generating revenue as soon as possible from when they sign a lease.

SPEAKER_03 1:40

We hear this frequently. So a delayed project really has a lot of implications that we try to avoid and get the doors open as fast as possible.

SPEAKER_02 1:55

Yeah, and such a competitive business. So, you know, getting to revenue can't be any more important anywhere else.

SPEAKER_03 2:04

Isn't that why they have Black Friday?

SPEAKER_02 2:06

So when we did our prep session, you told me that you bootstrapped SiteRise and you funded it through your services business. And I want to know what that unlocked that venture capital wouldn't for you. You know, where did it make the journey easier or harder? And how should founders think about using services as a proving ground for an application versus a crutch for it?

SPEAKER_03 2:32

It's definitely a pretty long internal debate. And the biggest part of the debate is growth and how fast you want to do it. Right? Taking on debt allows for faster growth, but also allows for a lot of reporting nightmares and a lot of opinions inside the platform. And so we took the step back and strategy of, hey, let's go slow and grow. And as it continues to work, we can continue to grow it, as opposed to pouring gas on the fire right away and making sure we had something that was viable. And we really wanted to build a good foundation of a product to make sure it was a market fit and really ready to grow. So we went slow, we bootstrapped. We just brought on or the process of bringing on our first account executive on a you know, fully trained sales individual to really help accelerate the business. I think our biggest determination for us was really making sure we had a product that has a solid foundation and making sure that we've built this platform before several times that we could actually use the product that was a market fit for companies and not have an influence of PE firm wanting to run at a faster pace?

Services and SaaS Synergy

SPEAKER_02 3:30

Yeah, I mean, obviously, when you take investor money, it comes with a lot of responsibility, right, and expectations. And you already had a solid professional services business. And I'm wondering, what's the symbiosis there, though? So, like, does having your own application help on the professional services side? Or does having the app, you know, does the app benefit from, you know, a professional services kind of foundation? Is there some synergy there?

SPEAKER_03 3:58

Absolutely. We wedge it back and forth both ways, maybe not to say it that way, but oftentimes as our customers are starting to grow with us on the professional services and construction side, they have no retention or no data synchronization, no nomenclature, and no structure to their file management. So we can then offer a platform that allows them to do that, that's customized to them, allowing the brand to have a single source of truths from the day we start with them. We just brought a brand on, uh, West Coast-based brand at one location, it's planning to expand. And our ability to give them a prototype is going to allow them to expand exponentially as they go from, you know, up north down to Southern California, Arizona, New Mexico, and having a place where their documents can be stored and transmitted back and forth is perfect for them. And so we run that both ways.

Aha Moment to Product

SPEAKER_02 4:44

That makes a lot of sense. And it's not the first time I've seen professional services, you know, give rise, if you will, to a software application. And I think for professional services listeners who have thought this might be a path. I mean, there's some clear evidence here with SiteRise, but also there's plenty of other evidence from small integrators to even global giants getting into the software business. So good for you. I think it's a great opportunity. I want to dial you back a little bit to kind of how this kind of came up for you. And you told me that you saw these kind of problems that Apple, Tesla, and others, I think, enjoy also before building SiteRise. I want you to kind of zero in on what was the aha moment that made you say this has to be a product, not just a workaround. And how will founders know when a repeated internal solution is actually an opportunity for a software product?

SPEAKER_03 5:38

Yeah, so it's kind of a two-part answer, Ken. When I first was at Apple in 2009, 2010 in the retail development team, I started using a product they had called Bento, which was like their family-sized version of FileMaker database structure. We quickly outgrew that, went to FileMaker, quickly outgrew that. And then a development team came in and built what Apple uses today as the retail tool. About the same time I left and went to Tesla with a director from Apple, and he said, Hey, we we need that database thing. We're about to start building all these stores. We want to catalog them. And right about then, it was synchronous that I was like, hey, we have the ability to build a tool that's going to give a company like Tesla a foundation for the rest of their career and growth path and allow them to expand. Well, when we repeated that same thing at Enjoy, I joined Enjoy. They had two locations and 1600 square feet in Northern California. When I left, we were in five countries with over two and a quarter million square feet. And we were able to do so by producing drawings, relationships, and allowing for users both internal and externally to play in the same sandbox, which brought us speed. And so as we started the professional services company, we found retailers that needed help building, but also had no central source of truth from reporting to document storage, you know, to everything we kind of offer today.

What Site Rise Does

SPEAKER_02 6:58

Yeah, this might be a good time for a little detour for you to describe the SiteRise app and what it does for retail.

SPEAKER_03 7:04

Yeah, absolutely. So SiteRise is the best in kind of three worlds: document storage. So it's an organized way to control your construction documents and file management, bringing in that DMS platform to life, right? Document management storage solutions out there. It's a source of truth. Where are my locations? You know, oftentimes we go in as a professional services team to companies and we ask their finance team for a list of locations. And I get a different list from their retail team, and I get a different list from their new store opening team. And they're synchronous, but they're all have a different nomenclature. And some people are talking about, you know, Third Street Promenade, and some people are talking about Santa Monica. And so, although it may be the same, the source of truth application starts to define those really critical points from the beginning. And then we were asking how you report on dates and opening. And every company I've ever worked at has a milestone report or a development status report or a construction weekly report. And so our ability to take all that location-based data along with planning and put a reporting level on top is what made SiteRise really come to life for us. So, kind of wrapping into a bow, Ken, SiteRise is an intelligent project management solution with a source of truth front end that allows it to be your kind of master database of retail or site selection as you grow.

Proving Market Fit

SPEAKER_02 8:18

Awesome. And now I want to bring you back to the question that I sort of segued out of. So, how were you certain that this was actually an opportunity worth investing in? Because it's it's not inexpensive to go build your own software.

SPEAKER_03 8:32

No, not at all. You know, and I had the joy of been backed by Apple or by Apple and Tesla previously as those ventures continued to enjoy. And so now to bring it on my own, I was working consulting for a PE firm and working through a lot of different vendors and trades and companies, realizing, wait a minute, we have six or seven retailers that we're building for as a consulting team. We need to start, you know, organizing this data. And so we started to bring SiteRest to light when we found that they had no cross-functional development reporting and name. And I was like, we have an application that's done this before, let's bring it to light. And then as it started to fit and started to sell it, we started to see market fit for it pretty quickly.

Boardroom Data and Forecasting

SPEAKER_02 9:10

Awesome. So it's a matter of just sort of being present in the business. And in this case, you had built something already for others or part of a team that had built something for itself. So correct. Yeah, exactly. Kind of moving on, I think that you know, retail build-outs probably often looked at as a cost center, right? And not necessarily a strategic function. But how does that mindset limit growth? And how can better data flip the conversation into a boardroom level discussion?

SPEAKER_03 9:43

We say the same thing. Like retail and retail development is definitely the biggest cost center that most companies are going to see besides manufacturing. And so, with the ability to give them quality reporting and data on top of that to say, hey, you know, because if you think about this, if you have a data engineer or a data scientist and you're running a sales organization, a marketing organization, and have a retail development team, you're going to put that person into sales quickly to help drive data. Well, where site rides can provide that value and bringing that data to light for you allows you to not be an additional cost center looking for a data engineering team or a tableau team or, you know, a BI team. We can actually bring that data to light and allow you to go into the boardroom and show value into your store, your timeline, and how that capital expense is really going to get allocated properly from, you know, when are we going to refer the cost of this? When did this start going into the black? And so having the data to analyze that from SiteRaz really brings your education and conversational knowledge of retail one step further.

SPEAKER_02 10:39

Is there a CEO message in here in terms of predictability of store opening? If you're opening a lot of stores, obviously that has a CapEx component and then it has a revenue generation component. Does this get you into helping them do a better job forecasting and communicating to investing publics for private and public companies?

SPEAKER_03 11:00

100% on the planning side. So SiteRise allows you to plan in the application and put your dots on the map as you get ready to plan and allocate person power, which is critical because if you're looking at your entire organization, you can't stress one region more than another, right? Because if you start to stress one more on new store openings or new clinical openings or new, you know, you know, new location openings, that sales is going to drop. You need to dedicate the time and experience across your entire portfolio. So SiteRise allows that person plan to happen. So you can evenly distribute your Affects, but also your manpower as well.

SPEAKER_02 11:33

Okay, great. And I want to just take a break for our listeners for a short sponsorship message, and we'll be right back with Dylan Achner.

SPEAKER_01 11:42

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SPEAKER_02 13:04

And welcome back, everybody, to SAS Backwards. I'm here with Dylan Achner of the Oak Group and Site Rise. Hey, Dylan, before the break, we were talking about CEO applications and the, you know, the impact on the C-suite. But I want to get a little down and dirty here in terms of the life of the people in real estate. And you told me that you're targeting retailers that are still in that kind of messy Google Sheets to scale phase. I'm wondering why this is like an important trigger for you, like an important moment. And what breaks if these folks don't modernize their systems?

When Markets Are Ready

SPEAKER_03 13:40

Yeah, I mean, process breaks quickly, but so does timeline. You know, the two things that we preach pretty frequently are if a real estate broker goes out and tours a site and gets a uh lease outline dimension from a landlord on the PDF, he or she marks it up, they email it over to an architect, the architect puts it into CAD format, they upload it to Google Drive or OneDrive or Box, and they send that link, we download it, if it's redlined, we upload it, then that whole version control and journey goes on and on as we continue to develop the drawings 60, 60 different times back and forth. Well, in SiteRise, you can do all that in one shot. I can take a picture of the PDF directly on my phone, upload it to my deliverable, I can redline it in the tool, I can tag my architect, they can then make their adjustments to their CAD drawing, put it on SiteRise as a new version. And so you start to see the sandbox getting very full of everyone playing in the same tool and the transparency really getting elevated. And so, you know, from the day the real estate broker tours a site, the project management team can get insight into the tool and start developing budgets, initial cost estimates, and really, like I talked about in the beginning, rolling that eight ball forward and allowing the planning to happen while the lease is being developed. So on day one, when you open your doors or your lease is signed, you're ready to start building and you're not ready to start planning. We bring that way back in the journey.

SPEAKER_02 14:59

I want to step out of the retail space just for a moment and ask you can you offer any advice to other founders? Like, how can they know if a market is ready to move from this kind of duct tape and paperclip environment, if you will, you know, the sort of unsystematized space to something where a solution is provided? Is there a way for you to know that this could be a market?

SPEAKER_03 15:26

When you start looking at kind of duct tape and paperclipping everything together and linking sheets together and really having a non-consistent source of data, the one thing we found that breaks first is nomenclature and the naming of files and certainty. And so I think, you know, we forced as much organization on teams as much as we can to allow them to not only see an optimized process, but to see tools that are successful. And in doing so, when we can all start speaking the same language from you know real estate design, construction all the way through to new store opening and the C-suite, we've been successful. When that starts to break is when people start to silo and make their own reports. And when you have reports feeding off of different reports, you start to be very complicated. And so I would say my best advice is really to drive it simple, live with one stack and organize your files from a nomenclature and a consistency standpoint as much as possible.

SPEAKER_02 16:18

Fair enough. So that the symptoms are people managing their own data sets, their own reporting. And as you had something really interesting in there that I just want to highlight, making reports from other reports seems like there's an opportunity for things to get out of sync and maybe not mean the same things.

SPEAKER_03 16:38

Without selling us here, one of the things we focused on last year was building one reporting table called our projects tab that allows every dependency or every kind of role in construction to slice and dice the same data. And so you can see a master data view of all the deliverables and dates, or you can cut down to what's important for you, can I? So for us, it's not a report on top of a report. It's just a different view of the same report.

SPEAKER_02 17:01

Awesome. I want to talk go to market now, because I think there's probably nowhere software people are more stressed than revenue generation now. Not only traditional revenue generation, but also what is the impact of AI on how they're going to go to market. But when we did our prep, you told me that, you know, it's pretty heavily based on outbound and relationships. You go to conferences, you're watching LinkedIn for when people move from one company to another, doing a lot of direct outreach. And I'd like you to reveal, if you would, what's working for you and where do you think others might underestimate the value of some of these tactics?

SPEAKER_03 17:44

You know, Ken, in the early days, what worked really well is people who had been on our platforms, right? And hey, you worked on Wink at Enjoy, you worked on TRT at Tesla. This is the same product, but more advanced. And so finding the internal expert and champion is really the biggest key. And anyone in sales is going to tell you the same thing. How to find that person is really the discovery. We focused a lot now on pain points. Is it data organization like we talked about? Is it reporting like we talked about? Is it schedule management? And so the hardest part for us is finding the internal pain points in the company, showing them how we can strengthen that and bring to light something that's going to be a much easier process. Now, the the next thing that's natural in any SaaS application that gets to introduce to any company is change management. And I always tell people, you can build a store on a Honda with a broken window and no HVAC and a donut on the tire, right? But I could put you in a Lexus that's going to drive. You're getting from A to B for sure. I don't need a Lamborghini. I don't want to pay out the nose for it, but I think so it's definitely a happy medium to integrate, process, and allow for something to be streamlined that's going to bring everyone to the same sandbox and play faster, which ultimately opens your doors faster.

Conference ROI and Headshots

SPEAKER_02 18:51

So let's dig a little into things like conferences. Not every founder or CEO is supportive of in-person events, trade shows. Tell us a little bit about your experience there.

SPEAKER_03 19:02

The hardest thing in platform to measure an ROI. And anything we do in this business, the quick question is you know, what's the ROI on this? Well, it's impossible to measure the ROI of a conference unless you can come out of there and say you booked 16 deals directly from here, which is very hard to do. I'd say it's hard to do. I think the biggest benefit of conferences for us is really the visibility, the FaceTime with customers, and getting their name out there. Someone who walks by and then gets an email from us a week, two weeks, three weeks later. Oh, I saw that booth site rise. I remember getting my headshot there. Or, you know, everyone's got their gimmicks at a trade show. We really want to interact with it. And we did something actually kind of unique this year. I'll I'll share this. But this idea of giving away free headshots. Everyone loves a new headshot. We brought a photographer in, he gave away headshots. You walk in the booths, very interactive and very bubbly. But to get your headshot, you signed up for SiteRise. And then when you logged into SiteRise, 24 hours later, when you got your headshots ready email, you were walked through the platform and then ultimately ended up at the download button. And so it's kind of a give and take. You get your headshot for sure. We I think we gave away three or four headshots per individual, but you also got a tour of the platform and we can see how you interact in it, how long you spent in the tool, and start to measure engagement. And so for us, the biggest ROI audible conference is the list of contacts we get out of it and the interaction we have with our current and future customers.

SPEAKER_02 20:21

So I like that. We've found something brand new here, headshot-led growth. Forget PLG, forget the enterprise sales motion. It's headshot-led growth. I love it. And but I think you've you've touched on some important points. First of all, you can't expect one-for-one dollar in, dollar out for everything you do in go to market, right? That's just not realistic. And some things can't have a straight line to attribution. But I think any salesperson who's been around a while will tell you if somebody knows my brand, it's a lot easier for me to penetrate that organization than if they don't. I think the other is, and it's amazing, here we are six years after the pandemic. I think that people are just beginning to realize how important face-to-face is and how much events can actually drive opportunity. And love the headshot in the booth thing. I've done things similar to that in the past. You know, getting people into your booth for something of value to them. But I also really love this idea of you got to download it through a login to our application. That's a good one. So if you've listened this far, you probably feel pretty good about it as a SAS back as listener.

SPEAKER_03 21:34

Well, if you get nothing out of it, there you go.

Tracking Job Changes

SPEAKER_02 21:36

Is there any other stuff you're doing, like this monitoring of job changes? How are you guys actually managing that? Is that done by your people or do you have some tools that are helping you with that?

Hiring First Account Executive

SPEAKER_03 21:45

LinkedIn Sales Navigator does a great job of doing it off the bat. It does monitor people of interest and lists that we compile. And we have lists for different segments of retail or manufacturing or quick service. And we're simply just looking for job changes or where people highlight. New career or position change, we go through that route as well. But LinkedIn Sales Navigator does a great job of doing that.

SPEAKER_02 22:05

Last topic I want to talk about, you touched on it very briefly, but you were as an organization moving from founder-led sales to hiring this account executive for SiteRise. So what's changing for you operationally and culturally at this important moment in the company?

SPEAKER_03 22:23

You know, founder-led sales are great, right? People love to hear the story. People love to understand the platform, view my eyes, but technical sales is not something I'm trained in. And so bringing in a technical salesperson is going to really help operationalize that and allow me to focus more on developing a business to grow from feedback from our customers, interacting with the current customers, working on support, you know, anywhere I can really help grow the business, I'm going to sit on as quick as I can. I'm still going to sell. I'm still going to be on as many sales calls as I can. I personally love it. I, you know, the passion for our software, I think bleeds out of me day in or day out. And so I think for someone to hear about it from me is great. But for someone to do discovery with a client, understand the pain points, the solutions, we're going to let someone who can technically do that better than me bring that to light for us.

SPEAKER_02 23:09

Where do you see the biggest opportunity with the freed up time that you're going to have, which, you know, may or may not actually occur? Yeah. But the measuring that one yet. Where do you want to text?

SPEAKER_03 23:21

I would say a little bit of automation. And I don't want to say AI deeply because that's a big trigger word for people, but I think automating some of the tools we use internally to support some of our customers, but also measuring the quality of our support back to our customers to make sure they're getting what they need. A lot of the feature growth that we do, Ken, is by request of customer. You know, we're a boutique firm. And so if I can take your direct request and something you need and then measure it against other clients and say, is this something you need? I have a product fit right off the bat. And so a lot of my time is going to really be diving in deeper with our customers, you know, engaging with their teams to make sure the tool is productive for them, how we can enhance it for them and really build it on a way that's going to allow them to be more successful with what they have that we've offered.

SPEAKER_02 24:00

Hey, and that's a great place to land the episode. And I think a great focus for you as you build a sales function dedicated to SiteRise. If people want to reach out to you, learn more about the Oak Group or SiteRise, how can they do that?

SPEAKER_03 24:14

Yeah, Dylan at Sitrise.app or Dylan at the Oak Group.lc. Either one. Love to hear about it.

SPEAKER_02 24:20

That's awesome. Thanks so much for being here. Really appreciate your time on SAS Backwards.

SPEAKER_03 24:25

Likewise, Ken, thanks for having me.

SPEAKER_02 24:27

Yeah. And if people want to reach me, I'm on LinkedIn slash in slash Ken Lempit. My demand generation, advertising, and strategy agency for SaaS companies is AustinLawrence Group. We're at AustinLawrence.com. And if you haven't subscribed to the SAS Backwards podcast, would love to see you do so. It's available almost everywhere. Podcasts are distributed, and full video episodes are on YouTube. Hey Dylan, thanks again for being on SaaS Backwards.

SPEAKER_00 24:54

Thanks, Ken. Thanks for listening to the SAS Backwards Podcast, brought to you by Austin Lawrence Group. We're a growth marketing agency that helps SaaS firms reduce churn, accelerate sales, and generate demand. Learn more about us at www.austinlawrence.com. You can email Ken Lempett at kl ataustinlawrence.com about any stats marketing or customer retention subject. We hope you'll subscribe and thanks again for listening.