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Lessons Learned From 15 Years of Building Complex Ecommerce Sites
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In today’s episode host Robert Jacobi sits down with Matt Schwartz, founder of the Atlanta-based agency Inspry specializing in WooCommerce. Together, they dive into the winding paths that led both of them into the world of WordPress and WooCommerce, recalling early web dev memories, agency origin stories, and those unforgettable moments of anxiety watching sites survive–or not survive–massive traffic spikes.

Matt opens up about the lessons he’s learned over nearly 15 years in the digital agency space, from the nitty-gritty of choosing the right CMS and plugins, to the importance of process, performance, and reliable hosting.

You’ll hear Matt’s candid thoughts on what makes WooCommerce shine for agencies and their clients, how the Woo ecosystem stacks up against SaaS competitors like Shopify, and why he believes in educating clients so they understand both the power and the responsibility that comes with running a WooCommerce store.

Plus, they explore the evolving role of SaaS in the WordPress space, discuss strategies for scaling complex eCommerce sites, and even tackle the challenge of elevating the WooCommerce brand in today’s competitive market.

If you’re an agency owner, freelancer, or just passionate about the future of WooCommerce, this episode is packed with valuable takeaways, personal stories, and plenty of laughs about all things WordPress.

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Takeaways

  • Agency Origins and Growth
    Matt Schwartz, founder of Inspry (not “Inspire”), shared how his agency started as a side hustle before taking the leap to independence, emphasizing the importance of strong client relationships and teamwork through the transition.
  • Evolution Into WordPress and WooCommerce
    Matt recounted exploring various CMS platforms (HTML, Drupal, Joomla) before committing fully to WordPress and WooCommerce, realizing they were the best fit for scaling and meeting client demand.
  • Learning Curves & Platform Maturity
    Early frustrations with WooCommerce led to trying other platforms like Shopify and Magento, but as both Woo and his own expertise matured, he found Woo increasingly flexible and powerful for custom builds.
  • Technical Challenges & Scaling
    Matt described nerve-wracking experiences with traffic spikes on client sites, leading to improved processes, such as rigorous host selection, pre-launch checklists, and stack standardization to avoid “please don’t crash” moments.
  • Scaling Strategies
    The episode covered vertical and horizontal scaling, stressing the significance of picking the right hosting and infrastructure—especially with modern hosts offering better auto-scaling for WooCommerce.
  • Headless WordPress: Cautious Adoption
    INSPRE has only used headless WordPress where it truly made sense, considering added complexity and cost, and advises clients honestly when they only want “buzzword” solutions.
  • Open Source vs. SaaS Platforms
    Matt advocated for Woo’s open-source approach for flexibility and data ownership, while also acknowledging the compliance, reliability, and brand recognition advantages of established SaaS platforms.
  • Where Woo Excels for Agencies
    WooCommerce is especially strong for agencies needing bespoke, complex ecommerce solutions, giving complete control over checkout, integrations, and business logic that SaaS rivals limit.
  • Areas for Improvement
    WooCommerce’s brand still lacks broad enterprise recognition, and agencies bear more responsibility for site performance and security compared to SaaS competitors. More client education is also necessary.
  • Migrations & Client Onboarding
    Most of INSPRE’s projects are either new builds or they inherit existing Woo sites, often cleaning up plugin bloat and technical debt. Migrations from SaaS usually occur for reasons of ownership, cost, or flexibility.
  • Hybrid SaaS & WordPress
    Matt introduced their SaaS, CheckView, built for automated WordPress testing, saying the hybrid SaaS+WordPress model combines the strengths of both approaches for agencies and clients.
  • Future of WooCommerce: SMB and Enterprise
    There’s still an important space for Woo among both SMBs and enterprises if the onboarding, back-end experience, and performance keep improving. Hosting providers and agencies may develop more streamlined Woo setups for different audiences.
  • Community, Collaboration, and Branding
    WooCommerce’s reputation can be elevated by showcasing high-profile, complex projects and strengthening collaboration with the broader WordPress community and Automattic’s increased resource investments.
  • Final Thoughts & Invitation
    Matt is open to connecting with others in the community, encourages discussions about Woo and agency life, and looks forward to more conversations about overcoming challenges in WooCommerce projects.

Important Links and Resources

Timestamped Overview

  • 00:00 Smooth Agency Transition Experience
  • 06:01 “Lessons on CMS Selection”
  • 10:03 Switching from Adobe to WooCommerce
  • 12:01 Optimizing Hosting and WooCommerce Stack
  • 15:45 Optimizing Websites for Scalability
  • 18:10 “Headless CMS: Necessity or Buzzword?”
  • 21:32 WooCommerce Transparency and Hybrid Approach
  • 25:09 “Benefits of WooCommerce for Agencies”
  • 29:16 Migrating Limitations and WooCommerce Audits
  • 31:42 Platform Agnosticism and Client Concerns
  • 36:07 “Agile Agency Decisions in CRM”
  • 40:22 Optimizing WooCommerce for Complex E-commerce
  • 43:24 Woo’s SMB Customization Strategy
  • 45:35 “Woo Communication Channels”
Episode Transcript

Robert Jacobi:
Hello and welcome to another wonderful Woo Agency Chat. I’m Robert Jacobi, Chief Experience Officer for Blackwall and your host for today. We’re missing some of our other crew because it’s Monday. Crazy Monday, May crazy travel month. But I’m thrilled to have Matt Schwartz here from Inspire Media sales and growth super lead. I’m just going to go with that. Matt, tell us a couple of things about yourself.

Matt Schwartz:
Yeah, thanks Robert for having me on the show. Definitely appreciate it. Yeah. So I run Inspry. We’re an agency focused on complex WordPress sites and WooCommerce and we’ve been around almost 15 years now. We’re based out of Atlanta and I also run Check View, an automated testing platform for WordPress as well.

Robert Jacobi:
Awesome. And yes, Inspry, not inspire.

Matt Schwartz:
It’s a problem. It. Well, to be honest, it was back in the day, you know, 2010 when domains kind of mattered. So inspir.com was available. But some people say Inspry, which is grammatically I feel like the right way to say it. It drives me crazy. But more on my end, I like the InspryInspry.

Robert Jacobi:
That means you’re agile, ready to move with your customers and clients.

Matt Schwartz:
Yeah, that’s actually what I was originally going to lean into was that. But then I don’t know, INSPRE just stuck and so we just have this multi definition now for the company. But it is what it is. Right.

Robert Jacobi:
So it’s free. Started in 2010.

Matt Schwartz:
Yep.

Robert Jacobi:
Out of a real office.

Matt Schwartz:
So it really didn’t. I was actually doing the good old moonlighting at while I worked at a. A full time job. Right. Started the agency in 2010. Then I thought I was going to stay with that. I closed down the agency that year and then restarted in 2011. Quit my job. One year on the mark. The day I hit 12, like literally I told them I was going to but they’re still a client to this day so obviously they were cool with it. And then it was like an immediate pay raise. Right. As a contractor. So I was very lucky with them. But yeah. So technically started in office, just not my office.

Robert Jacobi:
I love that story. My agency literally started the same way. Gave them a date which Was like nine months out. Said, you know, this won’t impact anything day to day, but stuff will be going on and here’s your fair warning. And, you know, when you have the right kind of team around you, works surprisingly.

Matt Schwartz:
Yeah, Definitely on. At least you gave them, like, a good notice. I would like to say I did the same. I did. Not as far as the transition, but, you know, definitely if you’ve got, like a good team and you’ve got good clients to kind of kick off your agency, I think the process was, at least for me, a lot smoother than I thought it would be.

Robert Jacobi:
Yeah. That’s great to hear. Love it. And your previous employer was in WordPress or how’d you wind up in WordPress? WooCommerce. That realm of the universe.

Matt Schwartz:
Yeah, all the things. So I started like a lot of people, you know, building HTML sites back in the day, you know, like playing around with template monster. Remember that thing? And I remember playing in like, you know, middle school and high school and be like, oh, man, like, these are so pretty. Right.

Robert Jacobi:
Front page or that before your time?

Matt Schwartz:
No, yeah, front page. Dreamweaver. The whole templates within, I think Dreamweaver, you could update all the pages at once. Remember that? And it would have little variables, that whole thing. Yeah. So did that when tables were a thing. You know, you’d create custom Photoshop files and they’d be all tables and all of that. Good times. Yes. Yeah, we forget, right, how complex it is now compared to then, but. Yeah, so I already kind of was building websites. And then when I went to college, my first web dev job was working with Drupal at the University of Georgia. That was. That was a lot for me, to be honest, to start with my first CMS, like, true CMS, I played with like, Net Nuke and something like that. But this was definitely a learning curve. So did Drupal, did an internship at Disney for a while, and they were looking at their internal CMS at Animal Kingdom at the time and they were having layoffs. So they’re like, let’s let the intern make the decision on the cms. So. And I feel like, you know, I can say all this now, it’s been a long time, but so we looked at the time, we looked at Drupal, WordPress and Joomla, you know, kind of the big three. And at the time they decided to stick with Joomla. WordPress didn’t have, like, custom menus yet. Right.

Robert Jacobi:
Hey, I’m the Joomla Guy in this site.

Matt Schwartz:
Oh, I remember I saw you at some Joomla. Conferences. So yeah, we stuck with that. And then yeah, WordPress at least wasn’t quite there in that sense, like because it wasn’t even 2010 yet. And then I still started building a little bit on WordPress on the side. But it really wasn’t until probably 2012 or 13 that I really started to dive into WordPress where it was becoming one of my primary CMSS and WOO themes. You know, when it was a separate company, we built some WooCommerce sites pretty early on. It was again a little bit of a learning curve and there were some pain points because I was also learning E commerce at the time. I’d done like open cart Magento wine. But figuring out Woo took a while and I actually vowed in 2015 or 14 I would never use Woo again. And then look at me now. But I think it was partly just growing pains on my side. Right. Learning the platform and I think also Woo has just improved a lot in that period. So that, that’s kind of how we ended up back here.

Robert Jacobi:
What made WordPress and WooCommerce that choice, as you know. Yeah, obviously you’ve played with all the CMSs, which a lot of people can’t say. So you know, I’m liking that you’ve, I going to guess made an informed decision.

Matt Schwartz:
I mean I did, but I think it was more of the age old. You don’t really create processes and so I would always try to tailor the right cms for the right project, which sounds good in theory, but then you have to learn like 5 CMSs and then you aren’t thinking long term about scaling. So that was a lesson that took me what a decade and a half to figure out, I feel like. But you know, I eventually got there. Maybe if I just read a Freelancers for Dummies book, you know, in 2010. But it was, it did allow me to get exposed to a lot of different CMSs. And within that space WordPress really became the standard for a couple reasons. One, you know, our developers, including myself, really just enjoyed building on it faster, especially for small businesses. We could just build on it really quick like Joomla. You know, you can hate it, but I actually still really like it in a lot of ways. I missed certain things about it, but there was a lot of like over engineering for small businesses as far as how the framework worked. It was MVC and all that for like developers, which is great, but took a lot more money and time to build on it. Same thing with Drupal and just a lot of our clients weren’t hitting that. So we start to realize WordPress made sense. And at the same time WordPress was growing as a household name, so people started asking for it. So between those two, that’s when we were like, okay, we just need to transition entirely. Which honestly we didn’t do until a couple years ago. We were still using Joomla on some sites, but we hadn’t really built new ones in years. But it wasn’t really intentional. We had like 80, 90% WordPress, but we hadn’t really branded ourselves that way until more recently.

Robert Jacobi:
Seems like a pretty typical path for a lot of folks who’ve used non WordPress CMSs for a while. Definitely seen that both in the Drupal and Drupal communities, where the ecosystem and sort of the opportunities are much greater for all sorts of things.

Matt Schwartz:
Definitely, yeah, it was exactly, just every part of it. You know, clients are more comfortable, there’s the community behind it which provides a lot more, I think, just opportunity for people. But also obviously the plugins ecosystem is huge, which Joomla Actually had a pretty good one, but it just wasn’t even nearly what obviously WordPress is just based on market share and all of that for sure.

Robert Jacobi:
So obviously diving into WordPress you want to do stores. WooCommerce. How did that struggle though, after you swore you’d never use it?

Matt Schwartz:
Yeah, so what kind of happened is early on when we used Woo, like I said, I was still even learning some things about WordPress. And as you kind of know, learning woo also means you have to learn WordPress and kind of the WordPress way, not just in the backend, but also just in how the code’s written. Certain things are definitely very WordPress specific, even if you know PHP. So that took a little bit to figure things out. And so early on we did some really cool sites actually. We had some sites that got some national coverage. Those were really cool and I had no idea what I was doing on the hosting side at the time. I don’t know how those sites stayed up. I will say woot to Siteground at the time because their dedicated servers somehow kept it up. When we were on multiple national comedy shows with bands that we worked with, it was crazy. I remember sitting there watching the Google Analytics in real time being like, oh, please don’t crash, please don’t crash. And somehow it worked. But in hindsight, still didn’t prepare enough for it. I just had no idea what I was doing. Right. And that kind of goes into where we Kind of landed. We started to get a lot of complexities and I didn’t know enough best practices. So it was the good old. The Woo site is built with duct tape and band aids. Right. If you just don’t design it properly. So we kind of vowed off of it. We ventured into some other platforms like Shopify, which there’s definitely some good things about those platforms. We tried Magento too, which was rough. I’m just going to say it.

Robert Jacobi:
I think that’s the nicest thing anyone’s ever said about Magento too.

Matt Schwartz:
Yeah, it was rough. I was like, clearly Adobe does not want our business. I can tell we are not even on their radar the way this is going. But. So we lost pretty major client. Nothing like blew up but you know, it was just a lot of money and effort for them. And we started to look at Woo again and for a lot of the custom tailored work we were doing, which is kind of how we ended up in Magento before Woo made sense as a good alternative because you can really build a custom experience for companies that need something more specific than I just sell widgets and they’re all the same. And I think that’s where Woo really shined for us and why we ended up back at it. And we just knew a lot more about WordPress because the whole time we were also still building in WordPress, just not as much in Woo. So that’s how we really ended up back in Wu land was. And by that point, I think like I said, Woo had grown up quite a bit. There’s a lot more around that obviously Automatic had purchased it and put some resource towards it, that sort of thing. Yeah. And it’s been really good since then. There’s still definitely struggles with certain things, but we feel like we can build almost anything in it, which is great.

Robert Jacobi:
So I love. Because I’m sure every agency and freelancers had that moment. Please don’t crash, please don’t crash, please don’t crash.

Matt Schwartz:
Yeah, definitely. Fingers crossed.

Robert Jacobi:
What are some of the workflows and processes you’ve put in over the last 15 years to not have that terrifying feeling?

Matt Schwartz:
Yeah. So we’ve done a couple things and I’m still not going to say it’s perfect, but definitely like sticking obviously to a more standard stack of customizations and plugins that we know really well. That kind of goes off what I was saying. I tried every cms, I tried every plugin. Obviously I have like shiny toy object syndrome for sure. So that’s been like a growth thing to try. To get out of that over the years and just focus on the tools that work for us, because then you really know how lightweight they are, how they’re going to scale. You just have a lot more experience with them. So definitely fine tuning our stack. Improving like our P’s, right, has been huge. Like we have pre launch checklist, that whole thing, especially for like a standard Woo site. And then really just working on from the hosting perspective, you know, trying different hosts, et cetera. Recently, I think it was maybe a year and a half ago, we did a lot of load testing with a application called Loadster and we ran it, we ran like maybe 10 hosts through it, doing the same test to see how each of the hosts did. It was way too much money to test all that, but I had to know. And of course it was also anecdotal to the client side we were working on, so keep that in mind. But everything was basically the same. And so we spent a lot of time and effort just figuring out what hosts could truly scale when clients were on things like TV spots. And so that was a really good exercise in just what works for us specific to our types of clients.

Robert Jacobi:
It’s important it down to you have a core group of hosts. I won’t ask for names that you’re just committed to. No, I mean, I think most.

Matt Schwartz:
No, no, I mean, it’s fine. There’ll be a Pressable case study coming out shortly, so you might see us in there. But yeah, we have essentially some core hosts that we know really well, that we trust and we work with, and that really helps us cater, depending on the project, what makes sense with that customer’s unique needs. And sometimes it’s scaling vertically, sometimes it’s more horizontally. Right. It just really depends on the project. So we try to figure all that out up front if we can, because I do think that’s something you have to think about with something like Woo. Right. When you have a more complex site.

Robert Jacobi:
So I like to always be the idiot in the room. I’m glad Bob’s not on the podcast because then he would say you actually are the idiot in the room for our audience. When you talk about scaling horizontally and vertically, what does that actually mean?

Matt Schwartz:
Yeah, yeah. So it really depends on what you’re trying to do. But for example, like you may split off your database into like a separate server, for example, and kind of split things off more across the board so it can handle different complexities going on. Or it may be more like you’re trying to scale up based on like the number of servers that are running to handle your traffic coming to a site. So like a lot of hosts will offer vertical scaling, but I think some hosts do a lot better job at that than others. I think horizontal scaling’s a little bit more complex, but some can handle that. But definitely vertically. Like you’ll see auto scale type features. Right. And that’s what we were really testing is like could they auto scale assuming it was all in the same database. And essentially we’re leaning on them entirely to do like the clustering around that.

Robert Jacobi:
But like the whole stack’s on one actually dedicated box or virtual server, virtual machine, whatnot. Yeah, I had a fun little question that just like totally popped out of my head because we’re talking about scaling and all that. So that’s the question. What awesome customers do you have that make those spikes happen?

Matt Schwartz:
Yeah, so it definitely tends to be like consumer based companies. So a lot of them like they’ll get, you know, know they’ll pay for, let’s say to be on a morning show. Right. And that’s, it’s not a long amount of time, 10 minutes, maybe 15 minutes where they’ll have a massive spike. Right. And those are the sort of things it’s like, how do you prepare for that? And this came out of, like I said a couple years ago we had a client that had a situation and we thought it would scale pretty well and it did not. Right. So, so that did not go well and they kind of kicked us off to be like, okay for our certain situation, let’s dig into it. So we were doing everything from you know, cutting down on the core stack, like I mentioned of like what plugins are being used, like even things like ripping out the page builder as much as possible. Right. Because a lot of times those don’t scale really well to, you know, to upgrading php, to using things like perfmatters, different tools. So we were doing all of that and then on the other side we were looking at the hosting situation. So a lot of those clients though, consumer based, you know, they pay a lot of money to get on these marketing campaigns and the last thing you want to be responsible for is them spending X amount of dollars and then they don’t really make anything and they lose money actually. So that’s why it’s I think really important with any consumer facing sites or any sites that are going to potentially go viral. But there are hosts out there that can handle those spikes better ahead of time than others. Like there’s definitely the age old like let’s stick on a cloud or shared host day to day and then you can transition to Dedicated for like a month or something or a period of time. Like that does work, but I think some hosts are getting to the point where the auto scaling is starting to work pretty well and you don’t necessarily have to worry about that. But that was, you know, definitely an education over the past couple of years on how we could improve that, especially getting back really hard into Woo and just what you have to do with those more complex sites.

Robert Jacobi:
I still see a lot of that’s, you know, hopping over to Dedicated for that Black Friday Cyber Monday Madness will try to hop back and forth or ramp up their plan for the, you know, for eight weeks, like that. But yeah, that’s not automatic and that requires you to be very vigilant about what’s going on.

Matt Schwartz:
Exactly.

Robert Jacobi:
Did you get caught up, Are you still caught up in the headless WordPress universe?

Matt Schwartz:
So I’ll be completely honest, we haven’t done a ton with it. Mostly it just didn’t. It just hasn’t made sense for a lot of our clients and maybe that will change. But you know, like, we’ve done some work more on a sub level like build a configurator that’s headless within Woo, but the whole site’s not headless. Right. So we’re using like the REST API to pull in product data and then make a really nice configurator in JavaScript so that it’s really flu fluid compared to if we just built that out with like jQuery. Right. And building out in WordPress itself. So like that has been interesting, but outside of that we haven’t done a ton just because I think it was hard to justify the cost and the complexities for a lot of our clients, you know, and I know you hear everything like, gotta do headless. And we do have clients that come to us and they’re like, can we do headless? And I’m like, why do you want headless? Do you need headless? So we try to have that conversation and figure out. And you know, sometimes I think clients, they just, they hear those buzzwords and they think they need to do it. And again, I’m not saying it doesn’t have its place, but I think where we are in the market, we have some, you know, enterprise clients, but we have a lot of small medium businesses and just for them, that sort of thing, 100% just, I don’t think makes sense for the larger ones. I think there can be an argument for it, but I think also sometimes it doesn’t make sense either. So.

Robert Jacobi:
Yeah, well, to your point, horizontal and vertical scaling has gotten increment hugely better over the last five years. You know, headless was a darling for a bit, but I always thought there was that. There are a ton of hidden costs to headless and like right from the get go, you know, some are a little less hidden than others, but when you start looking at maintenance and upkeep and all that, you really have to look. But you know, if we’re going to reference Joomla. Sort of that MVC day where you really have to look at multiple different types of code bases and really have an understanding deeply of the architecture that you put together and that’s expensive, that it takes smart people to do that.

Matt Schwartz:
Yeah. And you know, they won’t necessarily have the knowledge on the headless side. So you can’t just throw any of your team on it necessarily if they don’t have that knowledge. And then even things like, oh, we want to add this new feature, you know, you have to make sure it’s obviously compatible from the headless standpoint, whether that’s a custom plugin or a commercial plugin. Right. Like you have to have a way to route all of that. So like you said, I think there is a lot of hidden costs and you know, I’m not going to completely poo poo on it, but I just don’t know if it’s, you know, the right solution for a lot of our clients.

Robert Jacobi:
On WordPress.org WooCommerce is open source ish in that you can see all the code, but you know, getting a pull request submitted is probably close to impossible. Do you feel that’s a good balance versus something like Shopify or any of the big Commerce or whatnot?

Matt Schwartz:
Yeah, I Mean, I obviously love that, you know, WooCommerce itself is open source. You know, I think the fact that it is backed by Automatic for me, I think makes sense because having, you know, a basically those resources, I think is really important. I don’t think Woo would have gotten this far necessarily without backing from Automattic, but I do think, you know, being more transparent in how, you know, you’re building out Woo is really important. And I think at least what I’ve seen is Automattic’s been kind of waking up to that because we’ve seen a lot more transparency and just wanting to get feedback from agencies. You know, they have a lot more ways now that you can basically get a version, you know, of a pull request done and not just in code, but also just in overall feedback for the program. So I think from that perspective, the hybrid approach that we’re doing I think works and I think you have seen a lot of success in general with that. Obviously WordPress with Drupal, same thing. You know, having kind of that hybrid approach I think is good to have, but I think continuing to make things more transparent and make things more efficient in getting agencies and other developers involved is still something that, you know, the community’s improving on, I think. And Automatic as well.

Robert Jacobi:
No, I think you actually did. I think the most open source of the E commerce, major E commerce players was the original Magento, Right?

Matt Schwartz:
Yeah, until, you know, Adobe. So, yeah, that died a long time ago, unfortunately. Yeah. And I think this is, you know, there are some other open source options out there, like OpenCart for example, but you know, it’s not really. It’s at least. And again, I don’t know if I should say this, but last I heard, you know, it was basically ran by like one guy. And to me, you know, that was a little uncomfortable from a business sense. I actually really liked OpenCart, but I didn’t love that. And you would just see him go kind of on these rants and people and, you know, I think that was a little tough to swallow when you’re running your business on it. So. But outside of that, you know, like the big commerce and the Shopify of the world, I think they do have a ton of resources and it’s hard, I think, for Woo to compete against that. But like I said, I think Automatic’s kind of waking up to that and starting to put in additional resources, especially on like the marketing and just the core experience of Woo, which, you know, I think from a mile away you can kind of see that they’re waking up to that. And that’s been really encouraging to see because when we dealt with Shopify, there was a lot of resources and Shopify did provide a lot of resources, especially to agencies. So, yeah, it’s at least encouraging that. I think Automattic’s starting to do that.

Robert Jacobi:
Well, very different business models between like a Shopify and a WooCommerce. Where do you think we’ll do both ends? But I’ll start with the positive. Where do you think Woo excels at besides being open source in sort of the technical experience for agencies versus like a Shopify or BigCommerce?

Matt Schwartz:
Yeah, I mean, I think definitely the major advantages, as I mentioned earlier, are just that you can really create the dream experience for your customer. You can solve their specific pain points, and that could be everything from the front end to checkout. Because we know Shopify doesn’t give you a lot of control over that checkout. Right.

Robert Jacobi:
We do now.

Matt Schwartz:
But to just, you know, the customizations that they might need with their products, like, you know, how their products are configured, what the sales cycle looks like, touch bases, you know, touch points on the site, stuff like that, I think you can just hone in really strong. The sky’s kind of the limit with Woo on that. And of course, it’s built on pretty familiar WordPress code. So if you’re already a WordPress agency, once you are comfortable with Woo, you know, it’s an easy, I think, transition. And I think obviously outside of that, just the community and the amount of apps, et cetera, is just huge. And I guess lastly, from the agency standpoint, by building in Woo, I think, you know, some people could argue this is good or bad, but I think it’s good, which is we do have more control than we do over something. With Shopify, clients have control over their data. We have access to that data. And that’s definitely another selling point. And you know, from a privacy standpoint, clients aren’t sharing all their sales and customers with a third party unless they want to. So all of those, I think, really make WooCommerce a really good fit for a lot of our clients. Again, not necessarily every client is a good fit for us, but, you know, when we work with clients, you know, we basically educate them on Woo because I do think that’s part of the process. You have to educate them on L.

Robert Jacobi:
And where do you feel Will could do a little better?

Matt Schwartz:
Well, speaking of education, they aren’t really a household name. And when you’re dealing with larger companies, they Definitely don’t trust it necessarily out of the box because they just don’t know it. Where they’ve heard of Shopify, you know, their kid made a Shopify site and drop ships, whatever. Right.

Robert Jacobi:
Well they don’t want to make their enterprise, you know, with their, their kid building the site out.

Matt Schwartz:
Yeah, it’s always kind of strange to me when yeah, they build that trust. But yeah, so many Shopify sites are these drop ship things which, you know, this may date the podcast. But you know, at this point I don’t know how much longer that drop ships model’s gonna work. But yeah, I, that is, we’ve had a lot of clients that have come to us larger that, you know, they trust the Shopify name. The other part of it is I think Shopify has invested, because they’re SaaS, they’ve invested a little bit more on like compliance because they’re not open source. Right. Like they’re selling a different product, a different business model as you mentioned. So they have made more inroads I think on that side of things. And that just goes into the education, the trust. So we definitely have to do a little bit more selling with Woo and then outside of that with Woo, you know, it’s the age old, you know, you have basically all the power but you’ve got all the responsibility. Just like with WordPress. Right. So you can build whatever you want, but you need to make sure it’s built the right way. You have to have the right team behind it and you really have to think about just scaling later on because you’re responsible for A to Z, from performance to security. And that’s not all a bad thing, but it is something you have to factor into the process. With Shopify and some of those other platforms, depending what you’re doing, you’re going to hit limits a lot faster. But that closed garden environment obviously prevents certain issues. Like I mentioned checkout, Shopify checkout rarely breaks because they just don’t let you do anything with it. Right. That’s a. But that’s one way to solve it. Right? That’s one way you can have any.

Robert Jacobi:
Color, any, any color car as long as it’s black.

Matt Schwartz:
Right? Yeah. And you know, there’s an argument to that and I get, you know, why that appeals to some clients until they start to hit those limits. But so those sort of things though are things with Woo that you know, we still have to focus on like so the performance, having the right hosting, all that stuff plays into it. So it’s a little bit More work on that side, depending on, you know, what the complexity of the site is.

Robert Jacobi:
This is like almost mentally awesomely excellent because we’re diving right into a bunch of SaaS questions I have that I was thinking about earlier. So how often does, you know, INSPRE wind up actually migrating customers off those or are most of your builds fresh?

Matt Schwartz:
Yeah, so we actually don’t do a ton of migrations off of them. We do some. It’s typically going to be a client that’s on Shopify and like I said, they’ve hit a limit because you can do a lot with their API. But it’s often like, what? Well, this is now getting very expensive and we don’t even have our own data and those sort of concerns come up and that’s where like a transition off makes sense. Outside of that though, we’re often either doing new builds or we inherit a lot of Woo sites, which is a fun time. You know, we have a whole audit process for that because, you know, and I get, I definitely get why some agencies just are like, now we’re re, we’re rebuilding your site. I don’t blame them for that. But you know, especially for our smaller clients, we’re like, okay, we’ve gotta do a deep dive, but let’s figure everything out going on with the site, get it up to best practices, figure out why you have 120 plugins and then take it from there. Yeah, and the last thing I’ll mention, which is random, you know, is within Shopify. Another reason we transitioned away from it was just a very different developer experience than WordPress. So having like a team that could do both was difficult because it just works a little bit different on how themes and you know, how you really handle your version control, all of that. It wasn’t rocket science, but it definitely required a different process than Woo, which Woo, for the most part just followed our standard WordPress process.

Robert Jacobi:
Just more complex, makes total sense. And you guys have your own SaaS product?

Matt Schwartz:
Yeah, so we have a SaaS product called Checkview and it’s an automated testing platform for those that don’t know. All that really means is it’s it end to end checks process on your website on typically your fully built out WordPress site. So that could be anything from checking if a form is working. So we’ll actually go send a little real bot over to your site and fill it out with Chrome basically or Chromium to something like, you know, woo, checkout. You can also create custom tasks like maybe you want to check you know, is a LearnDash course working? It can go through and click through the course, or it can log into a site. And what makes it a little different is that we. We built this for WordPress specifically because we were already basically using WordPress and we wanted to build something that we could use on all our sites. And there’s some tools out there that are very good, but they just require more setup time. Right. Because they weren’t built for WordPress. They’re agnostic. So this all kind of came though because we had over the years, a couple clients where it wasn’t all the time, but it was enough, where the clients like, oh, our email wasn’t working. How many leads did we lose? How much money did we lose because of this? And then there’s that awkward silence where you’re just like, well, am I about to get sued? So, you know, it all kind of worked out, but for me as an agency owner, it was scary and I just didn’t like having that feeling. And I just felt like we owed responsibility to our clients to, you know, do further testing, especially because they are often comparing us to things like. Or comparing WordPress to things like Shopify or Wix. You know, where they own that whole platform, they’re doing all the automated testing. You aren’t where with WordPress, you install a bunch of plugins. Yeah, the plugin developers are doing the best they can, but they can’t test everything. So you’re ultimately responsible as the agency for, you know, functionally, is the site doing what it’s supposed to be doing.

Robert Jacobi:
And then you’re using that throughout, I guess, your entire development life cycle. So from, you know, development to staging to prod, I assume.

Matt Schwartz:
Yeah, exactly. So we use it in all those environments. And it really depends on the site. We built it very flexibly, like I said, how you can use it. And it is a SaaS product. Cause you might be like, well, why’d you build it as a SaaS product? I thought you loved WordPress, but we did look at doing it in WordPress, but it was just going to be really difficult because, you know, it’s running Playwright, it has Docker instances, all that sort of stuff. So it’s basically a hybrid model now, which is, you know, definitely more common, I would say, in WordPress plugins today, where we basically have a plugin that does the communication, but all the heavy lifting is done in our SaaS. So that way it doesn’t slow down your site. And, you know, it’s lightweight when it’s running the test. Cause all the bots are really just running their tests from our servers. And then when it’s actually communicating the website to, let’s say, confirm did Gravity form send out the email? It goes to us, we confirm it, we check, did it go in the database? We delete that test from the back end. So that’s really all the helper plugin is doing.

Robert Jacobi:
And I like SaaS for all the reasons you mentioned in this regard. Because, yeah, you don’t need that extra stuff. Or another security vector with a heavy plugin.

Matt Schwartz:
Exactly.

Robert Jacobi:
Near a WooCommerce site, one of the more interesting players I’ve seen on the SaaS WooCommerce side recently that’s really going full steam ahead is OmniSend.

Matt Schwartz:
Yeah.

Robert Jacobi:
And I’m curious how OmniSend and players similar to that, do they benefit the WooCommerce experience for? You know, I’ll leave customers out of it because customers are pretty, actually pretty good at using E commerce. But really from the agency side of the universe.

Matt Schwartz:
Yeah. I mean, I think a lot of the hybrid kind of SaaS approaches work really well for the agency because it does take a lot of the heavy lifting off the agency. I mean, there are benefits to SaaS, you know, we can’t ignore that. Right. And I think it actually helps level the playing field for WordPress because, you know, as WordPress has matured, obviously at the same time sasses have grown and there’s more and more sasses out there because there are benefits. So I think by companies taking this approach, they’re really allowing people to have the flexibility of WordPress, still own a lot of their data in a lot of ways, but get the power of SaaS. Right. Which there’s a lot of benefits there. So I think it’s actually really great, which is, you know, why we built a hybrid SaaS. But in general, we use it at the agency side, you know, as well, you know, based on what we’re doing, you know, even our maintenance, you know, we use things like WP remote. Right. That’s a SaaS. Right. But it’s obviously a hybrid SaaS, how it’s kind of working. And that works really well for us. We could use something like main WP, which is a great product. It’s just more work on us though, and we just have limited capacity. So you have to really decide what’s best for you. And you can also pick and choose as an agency owner, like maybe certain things, you know, you want to fully own that process or you want your client to. And Then other things, you know, you are going to take the SaaS approach based on what makes sense, you know, for that client as well as yourself. And just your own philosophy.

Robert Jacobi:
I think just curious on I’m not knee deep in WordPress commerce every day like you know, you guys are. I keep want to say I can’t help saying Inspry now. Inspry.

Matt Schwartz:
I mean that that is grammatically the correct way to say it. So I don’t blame you. It and it goes with the whole Agile approach. That was the original plan before everyone called it Inspry and I just ended up saying well we’re going to go buy Inspry now. So it was. But one other thing I was going to mention is, you know, we also kind of make that decision as an agency with the client. So we’ll be like, hey, we can create a, we can use a CRM in WordPress, right, as a plugin or we can use a SaaS to do it right and usually we’ll have that conversation go over the benefits of each wave with them so they’re fully educated. A lot of times on our smaller clients like they can get away with like a CRM, for example, built into WordPress. I think it’s again harder to make that argument as the company grows just because of again the scaling with the database and all of that information in WordPress. It’s not that it can’t be done, but is that the best use of time and budget for that client? So you know, if it’s pretty obvious, you know, they’re going to fit into a smaller bucket. I think using a more lightweight built in CRM works really well for our clients. But you know, if they’re already a pretty massive company that is used to dealing with some SaaS products and they’re comfortable with SaaS products, you know, it’s really hard to ignore that they’re probably.

Robert Jacobi:
Already on Salesforce or HubSpot or.

Matt Schwartz:
Exactly. Yeah, we’re not going to pull them off, you know, for that. Often we don’t. That is true, we often don’t but. And I think that’s the mix. Like, you know, it’s never going to be a perfect world but you know, having them on WordPress and them seeing those benefits for like the custom experience that they’re getting and them seeing that value is great, but they can still use, you know, their sasses of choices for things like CRMs, et cetera or whatever their company governance requires.

Robert Jacobi:
But I’m going to sort of end with one slightly modified version of a big question that Matt Mullenweg recently asked on the Socials. I did not have a good answer for this.

Matt Schwartz:
Oh, I’m nervous now.

Robert Jacobi:
So Matt asked what would be the best agency to elevate the WordPress brand. So I’ll put it into what would be the best agency to elevate the WooCommerce brand. I’m curious how you’re going to answer that, because I have my own take on that question.

Matt Schwartz:
Do you mean like actual individual agency or do you just mean in general, like the type of agency?

Robert Jacobi:
Let’s go with both. I mean, you on the spot.

Matt Schwartz:
Okay. Well, I’m going to answer first with probably, I think the type of agency because that’s a little easier to answer. So I think definitely to elevate the WooCommerce brand, an agency that, you know, has enough resources to build, you know, a very custom, tailored solution for a client is really going to show the power of Woo. If you the end of the day. And that could be enterprise, but it could also be under enterprise doesn’t have to be enterprise, but they definitely need like a substantial budget, I think, to really show what Woo is capable of. Because like I argued before, if you’re just selling widgets in Shopify, and this is just my opinion, and you know, every widget’s red and you sell a million of them, do your thing, I’m not going to stop you. Like, it’s fine for that, but as soon as you really want to get into that custom experience with, you know, customers, I think that’s where Woo shines. And that’s where I think an agency, you know, focuses on. And that’s really what we try to do. Right? Like, we don’t take on clients that just need to sell very basic products a lot of times because, you know, they have different expectations and their expectations around the experience are usually just not very involved.

Robert Jacobi:
It.

Matt Schwartz:
You could still build it in Woo, and there’s nothing wrong with that. But I do think for the clients that are selling more complex products, for example, you know, like, we’ve done a lot of work around like window, door, configurator, stuff like that. You know, those are really complex products. There’s a lot of logic going on. You could build that in Shopify. It would be a nightmare. But you could, I think in Woo, we can do a much better job and we really can build everything out at once. Similarly, if, if you’re trying to build like a, I would say like a platform, let’s say you’re a An education company. We’ve done a lot of this where, you know, we’ll combine Woo with like a LMS with memberships. And the benefit of that is they again have a very tailored experience for their students that goes through and gives them everything in one platform. And you know something, there are other platforms that are SaaS based, but again, you’re going to hit those limits. And with something like that, I find with E commerce or really anything functionally, you start to hit SaaS limits very early on. If you’re just building brochure sites, it’s less of a concern. So I do think an agency that is building a more visible, complex E commerce experience, that’s really where it would make sense to focus on. Again, it doesn’t mean we need to leave the small businesses behind it all because I do think they have a place there, but I do think that would be a way to elevate it because I think trust is something that Woo is still earning basically with some companies and some organizations and just that household brand, like that’s the way to get there, I think. So it’s partly about the agency. I think it’s also the type of customers that we can get at Woo. And to start earning their trust and building those stories with them basically is going to build it. Because I think that’s basically what happened to WordPress in general. Right. Like eventually WordPress obviously had the small, had the lower end of a lot of the market and then they started to build up and then they start to build trust with larger organizations. And I think that does help with the Overall branding of WordPress. And I think WOO has to do a similar thing. And I think automatic, to be honest, is trying to. I think it’s still definitely a process, but they’re working on it. So I don’t know. That’s all I got.

Robert Jacobi:
Is there a need for a Woo SMB and a Woo ent or just let Shopify’s of the world take over the SMB side?

Matt Schwartz:
That’s a no. Yeah, that’s a great question. I think it’s more of Woo continuing to improve the backend experience and the performance. Those two things to me are major. And that’s really WordPress in general. Right. Like it’s. You could make the same argument. Well, do we just let WIX take over all the brochure sites, et cetera? I don’t think you necessarily have to, but we need to continue to improve performance. And that onboarding experience of when you even like spin up a site, you know Is it going to be, especially on the SMB side, how can we make that process more frictionless? I think if Woo is going to become or stay relevant for SMBs, but I don’t think that necessarily means we have to have a whole new version. But I could definitely see like hosting companies, for example, continuing to kind of build their own flavor of Woo that has a better onboarding experience. You don’t have to know everything about a website, which is the same thing I think that they’re trying to do with WordPress in general. Right.

Robert Jacobi:
Like a distro, you know, in the Linux.

Matt Schwartz:
Right, yeah. And that could even go a step further. Like, you know, maybe hosting company A has, you know, spins up an automatic version, you enter your domain and you know, they have made some modifications on how certain things work, but not necessarily, you know, taking down core in that process, but more just a facelift and an education for small businesses. That’s one way I think they could compete. And there has been some work there. I know for a while Woo even had a product, it was like Woo Express that tried to do that. So I think hopefully at some point that and other hosting companies will work towards those sort of things and I think it will help Woo stay relevant with the SMBs. I do think it’s a little more Woo will always, I think, have a little more insulation and justification on the small business side because it’s so custom and because even small businesses need a lot of customizations done. It’s just, you know, can they afford it? I think more on the brochure side, just WordPress in general, that’s the part that’s, you know, a little harder I think to justify for some small businesses today, depending on what they’re growing into.

Robert Jacobi:
I Look at the WordPress side of it and I think Automattic and you know, other products and services and hosting companies have sort of answered wixpack quite well. I mean.comwordpress.com is a great solution. Tons of hosts have their own site builders now connected to WordPress. Companies like Extendify are driving that, you know, across a lot of the sort of, you know, I guess, you know, brochure, SMB side, you know, WordPress sites. Wow. Gosh, we could probably go on for another hour, huh?

Matt Schwartz:
Yeah, I was like, I think we could just keep going but I know we can’t go on forever, but this has been really good.

Robert Jacobi:
Hey Bob, we’ll have to do a part two. Matt, this is fantastic. How can we get a hold of you? How can we find out more about you. And not Inspire. Not Inspry, but Inspry.

Matt Schwartz:
Yeah, definitely. Definitely. You know, check us out just on our website, inspir.comthe. I’m also pretty involved in like the admin bar. So shout out to the admin bar. I’m in that Facebook group. I’m in the slack as well. That’s usually where you honestly find me. I’m also in the slack for Woo. Usually those are the main places I’m at. I’m usually not an Excel to be honest. But yeah, hit me up at any of those spots and you know, I’d love to chat either about Woo or you know, any sort of pain points people are having or check for you given demo. All that good stuff.

Robert Jacobi:
Awesome. Thank you so much Matt. We appreciate your time and the conversation.

Matt Schwartz:
Of course. No thank you. Great questions. Yeah and hopefully we can do this some other time but this is great. Thank you.

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  1. […] more insights like this? Check out the full episode of Woo AgencyChat for a deeper dive into agency life, open source, SaaS integrations, and everything […]

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