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What does the future of landscape software look like with AI?

  • July 30, 2026
  • 11 replies
  • 175 views

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I just attended The Herring Group’s webinar with Bobyard and posed a question that’s been on my mind for some time now.  It seems we didn’t really have time to dig into a complete answer.  Curious to hear what others in the Aspire community think or know about the topic.

 

I knew it was a good question when the initial response of the Founder/CEO of Bobyard was “sounds like one of my investors.”😊

 

“I'm very bullish on AI and we're incorporating it into nearly every part of our business. My concern isn't whether an individual AI tool is valuable—it's the long-term technology stack. Today it feels like we're bolting AI onto a collection of legacy systems, and the experience is fragmented.

How do you see this evolving over the next 3–5 years? Do companies like Bobyard become best-in-class AI tools that integrate deeply with platforms like Aspire, or do you think the next generation of enterprise landscape software will have AI built in from the ground up?

And beyond estimating, how do you see AI transforming scheduling, purchasing, project management, finance, and the rest of the operation?”

11 replies

mhellweg
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  • Inspiring
  • July 30, 2026

@JasonNavon-RossenLandscape I wonder the same thing but I’m not smart enough to have any inkling of an answer. It’s been interesting watching the evolution of it unfold in real time. Let us know if you figure it out!

 

Any big takeaways from the Bobyard Webinar? I wanted to go but ended up mising it…

 

 


swirtholg
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  • Inspiring
  • July 30, 2026

I believe the software companies will be looking to better integrate the AI over time. Its fragmented now because its moving so quickly and a lot of people are playing catch up. Software companies like Aspire won’t stand to be left in the dust, but they are still having to be super cautious because with each roll out it presents unforseen challenges. Aspire values reliability over quick tech adoption from what I’ve seen and experience. There are some other platforms out there that are AI heavy from the start, but are still unproven. Its up to the proven companies to adapt and preserve their value. 

Ultimately we still need the right data to make quick decisions, but AI helping process and crunch huge volumes of data that would otherwise take weeks or longer to process by hand is HUGE. 


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@JasonNavon-RossenLandscape I wonder the same thing but I’m not smart enough to have any inkling of an answer. It’s been interesting watching the evolution of it unfold in real time. Let us know if you figure it out!

 

Any big takeaways from the Bobyard Webinar? I wanted to go but ended up mising it…

 

 

  • Continued investment in the landscape industry by tech companies.
  • Construction/landscaping industry is an important/growing/necessary segment of our economy, but we’re seeing fewer college grads interested in the work.
  • Meeting landscape service demand with technology due to the decreasing/scarce talent pool.

 


David_Spiritus
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  • Participating Frequently
  • July 30, 2026

For what it is worth...I agree with Alex and Felicite here, It will ultimately likely require new paltform infrastrucutre built with AI….not bolt ons….

https://www.linkedin.com/posts/felicitemoormancofounderandceobosstech_this-could-have-been-the-story-of-bosstech-share-7488241016592809985-bzsT/?utm_source=share&utm_medium=member_desktop&rcm=ACoAAAEOEZYBoYiKIOdq5IouqWxPJ-cm7Fsfc90


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For what it is worth...I agree with Alex and Felicite here, It will ultimately likely require new paltform infrastrucutre built with AI….not bolt ons….

https://www.linkedin.com/posts/felicitemoormancofounderandceobosstech_this-could-have-been-the-story-of-bosstech-share-7488241016592809985-bzsT/?utm_source=share&utm_medium=member_desktop&rcm=ACoAAAEOEZYBoYiKIOdq5IouqWxPJ-cm7Fsfc90

I totally agree!  It doesn’t always make sense to renovate a house.  Sometimes you need to reset with a new foundation and build from ground up.


Kbaird
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  • Genius
  • July 31, 2026

I have a unique perspective on this. I have 2 failed SaaS startups under my belt before launching my tree care company.

I think that the softwares that survive the AI war are the softwares with open APIs that facilitate data aggregation.

Every single one of us knows a quirk in Aspire, or QuickBooks, or our payroll software that could "be fixed so easily." We all know how frustrating it is when we want data presented a very specific way and the native reports/tools just aren't built for it.

When I was in school not too long ago, my senior capstone class focused on Clayton Christensens disruption theory (read ‘The Innovators Solution’ its so good). The AI battle comes down to who wins data collection. Again in my opinion, whats going on now maps really well to the PC wars of the 80s and 90s. 

IBM built the PC and owned the customer, they outsourced the two layers that turned out to be the real chokepoints. Specifically, the processor to Intel and the operating system to Microsoft. Within a decade, the profits had migrated to those layers. IBM was left assembling commodity boxes while Wintel captured the economics. The company that owned the customer lost to the companies that owned the standard.

So which one is Aspire?

Case 1: Aspire is Microsoft. The system of record is the operating system of a landscape company. AI tools like Bobyard are applications running on top of it. Applications come and go. The OS persists. Data gravity plus workflow lock-in means ripping out your system of record mid-season is existential risk, so nobody does it. The point solutions that prove real ROI get acquired or copied, and the platform ships those capabilities native. I think this is the case. Software adoption is really hard to get blue collar employees to do. Getting field employees to be used to a new software is a non-starter.

Case 2: Aspire is IBM. If AI agents become the interface we run our businesses through, the system of record gets demoted to a database. A commodity box. The agent layer owns the workflow, the customer relationship, and the intelligence, and it can swap out the database underneath whenever something better comes along. Aspire keeps the data but loses the economics, exactly like IBM kept building PCs while Intel and Microsoft made the money. Im betting against this. Buy ServiceTitan Stock lol. 

IBM's box was easy to clone once Compaq reverse-engineered the BIOS. If an AI agent can one day cleanly migrate ten years of job costing history to a competitor over a weekend, the switching cost moat evaporates and Aspire is IBM. If that operational data stays deeply entangled with how crews, jobs, and billing actually work, Aspire is the OS.

One more lesson from that era. Intel itself almost died. They were a memory chip company until Japanese competition commoditized memory, and Andy Grove made the brutal call to abandon their core product and bet everything on microprocessors. The incumbent that survives is the one willing to cannibalize its own product before someone else does.

I like to tell people that Aspire is to landscapers what photoshop/lightroom is to photographers. It has been widely adopted, it’s become the industry standard. Hard to bet against that.  


mhellweg
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  • Inspiring
  • July 31, 2026

Such an interesting conversation! Thank you all : )


DStack
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  • Participating Frequently
  • August 10, 2026

Great thread, I'll throw in my perspective from the trenches.

I think the next 3-5 years split into two different stories. For the bigger landscape companies, it's basically a race to build (or buy) stuff people can actually trust to run a whole workflow from start to finish (or at least until human-gated approval), not just some AI chatbot slapped on the side. Kbaird's right that switching platforms is a pain (ask me how I know 😅), but I'd add one thing: trust is the real reason people stay put, not features. Landscape/service-based companies won’t switch software because something shinier came out but when there is a demonstrated and proven better way of doing things. The landscape industry is full of folks that are as busy as they are pragmatic - they just want something that saves time and works.

For smaller shops that are just getting started and aren't locked into a software ecosystem already, I don't think it's crazy anymore for an owner or operator who's decent with AI, or Claude Code, to just build their own little homemade setup. Stitch together whatever they're already using, whether that's a folder of spreadsheets, Google Drive, SharePoint, their accounting software, whatever. The bar for building something actually useful has dropped a ton this past year and I see that trend only continuing to accelerate in the months/years ahead. You don't need to be a programmer, you just need to be stubborn enough to figure it out.

For those of us already in Aspire though, having open access to the API is the real game changer. I've spent the last several months moving away from pulling custom reports by hand and into building out real automation that runs directly off Aspire's data. Honestly it's been half exciting, half eye opening how much you can actually do once you've got clean access to the data. That's where I think Aspire's future is, as the platform other stuff gets built on top of. Doesn't matter if it comes from Aspire themselves, a third-party developer, or some guy/hack burning through Claude Code tokens on nights and weekends (me). I'd think if I'm Aspire, I'm less concerned about who's delivering the tools, as long as I'm the platform and own the data.

I think we've moved beyond the question of if the industry wants these tools. The real question is who actually delivers something that works, keeps working and delivers a quantifiable ROI.


swirtholg
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  • Inspiring
  • August 13, 2026

@DStack these topic thread is definately peaking my interest in what I’m missing by not utilizing the API fully at this point. Thanks for providing insights. 


LegacyOutdoor
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  • Participating Frequently
  • August 17, 2026

Using both AI and the open API from Aspire, I’ve managed to built a fully functional app for our company. It enabled me to build a customer portal where the jobs auto update status based on what is says in Aspire and allows the customer to chat back and forth with our internal field staff as opposed to phone calls, emails, and texts message. Rather, the customer can just send a reply and the correct internal staff member can respond.

Also allowed me to build “tv boards” which show daily routes and also build a separate sheet where our project manager can assign crew members, trailers, trucks, and equipment to the specific jobs. The board shows job names and ticket names with the on site, actual, and estimated hours so guys can see daily where they’re at on job.

We can create opportunities straight from the app rather than using Aspire to create them.

They can also lookup the job specifically in the app to see service descriptions and everything.

I still have a lot of work to do with the app and it’s not officially released to our customers yet for use. But 2-3 months of on and off work in the app has shown me the possibilities. We currently use Monday.com for work flow. We’re no longer going to need it, that costs us $1000+ a month. We paid for MindCloud to integrate Monday and Aspire for $10,000. I was able to replicate what MindCloud did for us in probably less than a months time and do even more than we were wanting/expecting. So we are no longer using the MindCloud integration.

This will allow us also to intergrate Twilio and SMS notifications down the line. I already introduced it, it’s just kind of an early early beta for now.

If you have a team member that is capable and isn’t afraid of trial and error, you can do A LOT with the API and AI combo. 


DStack
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  • Participating Frequently
  • August 17, 2026

 

We can create opportunities straight from the app rather than using Aspire to create them.

 

That all sounds incredible, but I’d very interested to hear more about this in particular!