You hear “implementation,” you think: Months of disrupted operations, frustrated employees, and systems that never quite work as promised. 

And we won’t lie, the right software (as in: the last one you’ll ever have to implement) sparks a sea change in your operations. And change is hard. 

But it’s not only possible, but easier to avoid the really miserable parts of implementation. Most failures occur when companies try to do it alone, underestimate the commitment required, or try to skip the foundational work that makes everything else possible.

When implementation follows a predictable, proven pattern–i.e., with investment in proper team structure, realistic planning, and ongoing support, companies can turn their first-year struggles into second-year competitive advantages. 

The difference between implementation success and failure isn't luck or company size. It's understanding what you're signing up for and building the right support system from Day One.

Implementation Isn’t the Worst, but Doing It Alone Is

Let’s not pretend there aren’t some implementation horror stories out there. There are. 

But most horror stories come from companies underestimating the demands of a comprehensive software platform, under-resourcing the project, and making common mistakes that can quickly spiral into broken processes and endless frustrations.

Your first year with new software can easily become the launchpad for next year’s gains, with: 

✓ A realistic plan

✓ The right people

✓ Aspire's success ecosystem

Stick with us to learn: 

• How to set proper expectations for time commitments and team involvement

• Build the ideal implementation team, even with limited resources

• Follow a proven playbook to overcome common roadblocks

• Leverage AspireCare for ongoing support, and 

• Understand the realistic timeline for ROI—from the initial 90 or 120-day grind through year-one refinements to year-two's compounding returns.

Successful implementation with minimal stress requires clear-eyed goal-setting, thorough pre-work on clean data and processes, and a commitment to avoiding workarounds that can calcify into future problems.

Who’s Going to Be There? Setting Proper Expectations Upfront

Getting set up with business management software that makes an impact on revenue potential and profit margin isn’t as easy as just downloading an app and creating a user account. 

That means the landscaping contractors who understand the challenges of implementation and go through with it gain a decisive edge over the competition: Aspire users grow twice as fast as their non-Aspire counterparts.

Implementation succeeds when leaders:

• Set SMART (Specific, Measurable, Achievable, Relevant, Time-Bound) goals

• Define milestones

• Commit cross-functional time. 

This isn't a "one-person project"—that's one of the most common roadblocks companies face during onboarding.

"It wouldn't be something that [an] owner who already feels overwhelmed with their business should take on without at least planning for, you know, dedicating time and energy into that and having to find a way to do that," explains Chad Kirk, General Manager at Ambler Industries LLC.

Achieve more: Make implementation a team sport

The time commitment for implementation is real and varies by a company’s size and the complexity of its operations. This isn't just about attending meetings—it includes: 

✓ Watching class recordings

✓ Reading help documents, and 

✓ Hands-on system building. 

Whether it's one person carrying the full load or a team of three sharing responsibilities, the work requires dedicated focus and sustained effort.

The first two to three weeks are particularly intensive, requiring heavy decision-making about how your business will operate within the system. As Hannah Bauer, Manager of Growth Implementation at Aspire, explains: 

"These are the heavy-lifting weeks where we have to make decisions. You really have to understand the downstream effects, and you're going to get that education through meetings to get it all together."

With Aspire, you already have a built-in team member in your Implementation Manager, who is a super-charged resource with experience and insight for doing the hard work early to leverage the software for maximum benefit later.

"The implementation team was phenomenal. It was obviously multiple weeks of having to work and understand each stage of the Aspire system," notes Nate Negrin, President of SouthernEEZ Landscaping.

Common roadblocks to anticipate include:

Dirty or missing data → Schedule a data cleanup sprint before onboarding begins. Clean up your QuickBooks, finalize your chart of accounts, and establish naming standards.

"We'll fix it later" workarounds → Document current workflows and design standard operation procedures (SOPs) now. Workarounds that seem temporary have a way of calcifying into permanent problems.

Passive buy-in from leadership → Assign clear decision authority and accountability. Without owner engagement, teams often struggle with negative feedback and milestone delays.

And depending on the size of your organization, there can be additional challenges: "Smaller companies are just not using parts of the system because it's overwhelming and they have limited resources," observes Kory Beidler, C3 Consulting. 

The key is to start with core processes and expand gradually.

Companies that prepare properly and set realistic expectations often find the process more manageable than feared. "Our implementation experience was probably one of the easiest things we've ever done. It was hard, but it was so clearly defined. The communication was so great. Our implementation manager was there at all points in time," says Shandra Brannon, COO of Heritage Landscape Services.

Even Batman Needs Robin and Alfred: Creating the Ideal Implementation Team

The most successful implementations start with a core team of champions, each bringing essential expertise to the table. While the specific roles may vary by company size, these functions must be covered for implementation to succeed.

"We knew that everybody on our implementation team needed to be our key people who needed [to] buy into the system and were going to be the ones to touch it the most. 

“Having the right team on our side and having the right implementation team on the Aspire side made all the difference," says Shandra Brannon, COO of Heritage Landscape Services.

A project champion who serves as the central coordinator with authority and accountability to keep momentum moving. 

This person doesn't need to handle every task personally, but they must have the power to make decisions, clear blockers, and enforce standards across the organization.

An accounting champion who understands financial workflows, the chart of accounts, and month-end processes. 

They map cost drivers and protect existing accounting procedures while adapting to new system capabilities.

An operations champion who owns day-to-day workflows, estimating processes, and administrative functions. 

This person understands how work flows through the company and can design systems that match real-world operations rather than theoretical ideals.

"You need somebody on the operations side, and you need somebody devoted on the finance side. Make sure you are delineating the information as quickly as possible down to the team, as you're onboarding it," explains Brian Gray, Maintenance Division Director at Precision Landscape Management.

The small but mighty approach to success

For smaller companies, these roles often collapse into one or two people wearing multiple hats. The key is establishing clear time blocks and weekly checkpoints to ensure progress continues even when the same person is juggling operations, finance, and project coordination. 

→ Engagement remains critical regardless of company size.

"Smaller companies have to be engaged, at least to that point of making sure the numbers are all correct so that they can get what they want at the end, which is their data, and understand where they're doing well or not doing well," notes Kory Beidler, C3 Consulting.

When internal bandwidth is limited, Aspire's Education team and Pro Services can backfill critical gaps, providing specialized expertise and hands-on support to supplement smaller teams.

Nothing Worth Having is Easy: Overcoming Implementation Challenges

Strategic preparation and tactical execution are critical pillars in the foundation of a successful implementation. 

The companies that use their time during implementation to launch into the next stage of growth do more than learn the software. They systematically improve their business processes while building new operational habits.

Before kickoff, lay the groundwork: Inventory and clean your data while finalizing your chart of accounts and naming standards. 

Cleaning data before implementing new software gives business owners confidence that the generated reports are reliable. Map your current "as-is" workflows against your desired "to-be" state, and eliminate known workarounds that create inefficiencies. These temporary fixes have a way of becoming permanent problems.

During the build phase, maintain momentum. Weekly decision meetings, led by a Project Champion, provide your team with the opportunity to track decisions and milestones, ensuring visibility so that nothing falls through the cracks. 

Prioritize foundational processes in logical order: 

1. Estimating flows into scheduling, which 

2. Enables job costing, which 

3. Supports accurate invoicing. 

Build your system systematically rather than tackling whatever happens to catch your team’s attention for the week.

Drive adoption through engagement: “Implementation was hard because it made you think about updating and systematizing processes in real time without a lot of downtime," explains Nate Negrin. 

You can combat challenges in team engagement by incentivizing system usage through simple crew competitions or micro-rewards–pair training sessions with real tasks so people learn by doing rather than just listening.

Want that dream to work? You already know: It’s about the teamwork

The Champion of your implementation team can keep scope tight, clear blockers quickly, and enforce standards across branches and crews. "Companies that get ROI from Aspire get somebody that really steps up and really takes on that power user role and owns it," observes Kory Beidler.

If a company lacks a full commitment from its leadership and implementation team, it can be a recipe for struggle. "If an owner is not all in, they bought the product and they're not fully supporting it, it doesn't go well," Beidler notes. It’s not the responsibility of the Project Champion to handle every detail, but they must drive accountability and maintain focus when teams feel overwhelmed by change.

Do It Right the First Time: Using Aspire’s Ongoing Support & Education

Your “go live” date isn’t a finish line. It’s just another milestone on a never-ending journey of process optimization and iteration. The companies that avoid backsliding and maximize their ROI understand how to leverage Aspire's comprehensive support ecosystem for continuous improvement.

Your Customer Success Manager becomes your business coach beyond basic software support. They can help drive company-wide adoption through goal setting and cross-team usage strategies. 

CSMs help design incentive programs, identify optimization opportunities, and ensure you're extracting maximum value from your investment. Schedule quarterly reviews to align your progress with strategic business goals.

Education and Pro Services provide white-glove customization when you need intensive, tailored assistance. Whether it's one-to-one training sessions, end-of-month support during critical periods, or data migration projects, these teams work on your timeline rather than standard support schedules. 

As TJ Rau, Manager of Customer Success at Aspire, explains: "If a client gets to a point where they need some more intensive education, even sometimes re-implementation, the Aspire Pro services team is positioned and has the resources to help them with that more on their timeline at a faster pace."

AspireCare ensures seamless ongoing support through a ticket portal for standard requests, and Zoom sessions for complex troubleshooting covering four specialized divisions: 

• Care Services

• Technical Services

• Education

• Accounting

The preserved context from implementation to AspireCare ensures that you aren’t starting with a blank slate if issues arise. 

"I never found myself in a place where I am looking for the answer. The support team always helped me," says Can Akbay, Strategy and Operations Lead at City Leaf. 

Best practices to avoid "re-implementing" later

1. Standardize processes early and document any changes you make. Aspire's flexibility can become a liability if different team members create their own workarounds. 

2. Schedule those quarterly CSM reviews to catch optimization opportunities before they become problems. 

3. Track data accuracy relentlessly—especially labor time, materials, and work tickets—because trustworthy job costing depends on clean inputs.

   

Grind for a Few Months, Get Gains for Years

Everyone’s implementation story holds the same kernel of truth at its center: the persistent will be rewarded. 

The following timeline can help set realistic expectations and maintain momentum when the work feels overwhelming.

Days 0–90 or 120: The grind 

There’s no denying the first few months (three months for Corporate and Growth customers, four for Enterprise) are a heavy lift. You’re:

✓ Building your system

✓ Cleaning data

✓ Making foundational decisions, and 

✓ Changing habits

Expect a temporary dip in operational speed as teams learn new workflows and adapt to different processes. This productivity decrease is normal and temporary—every successful implementation experiences this adjustment phase.

During these first months, you're essentially rebuilding how your business operates while continuing to serve customers and complete projects. 

The cognitive load is significant, but the foundation you're building will support everything that follows.

Remainder of Year 1: Refine and scale 

Companies that jump into implementation with clear goals and an incisive strategy experience the first real payoffs in the first year. You'll tighten estimating accuracy, gain real-time job costing visibility, clean up month-end processes, and unlock meaningful reporting capabilities. 

The system starts working for you rather than requiring constant attention.

"Now that we're streamlined and we know how to use everything, it frees me up to focus on other aspects of the job," explains Jared Woodend of Decra-Scape Inc. This is where the initial time investment begins paying dividends through improved efficiency and decision-making capability.

Year 2 and beyond: Compounding returns 

"Any growth-minded business needs to be on software like Aspire because you need to be able to grow into this. You're going to add new divisions. You're going to grow rapidly," notes Kory Beidler, C3 Consulting. 

The platform becomes infrastructure for scale rather than just a tool for current operations. Following the first year, the transformational results don’t stop. You gain:

✓ Higher margin control

✓ Faster billing cycles

✓  More predictable scheduling

✓  Better backlog visibility

All of these benefits add up to give landscaping companies the confidence to expand into new markets based on solid operational data.

"I'm making very good, intelligent decisions about my business. That's really impacting my business and making my life and my work easier," says Jeff Kettler, VP Sales at LMC. The system becomes an integral part of how you compete and grow.

Some companies see dramatic growth acceleration. 

“The first year (with Aspire) was hard,” admits Brian Gray, Maintenance Division Director at Precision Landscape Management. “But the second year that we've been using it, we've been able to make some significant financial decisions based off what's coming out of it.”

Aspire became a source of truth for Gray, helping him chart a course to hit Precision’s ambitious financial goals. 

“We're on track to do $8.5 or $9 million this year,” Gray said. “To break that down into daily chunks of, ‘How am I going to get that?’ It's a lot easier to get everybody on board that way.”

Are You Ready for Success? (Checklist)

Before you begin implementation, use this quick self-assessment to ensure your organization is positioned for success:

□ We have a documented Champion with decision rights. This person has the authority to make binding decisions, clear blockers, and enforce standards across the organization. They don't need to handle every task, but they must drive accountability.

□ Data standards and naming conventions are finalized and enforced. Clean QuickBooks, an established chart of accounts, and consistent naming standards create the foundation for reliable reporting and job costing accuracy.

□ Adoption plan includes incentives and role-based training. Teams respond better to change when there's positive reinforcement for using new systems. Plan simple competitions, micro-rewards, or recognition programs to encourage engagement.

□ We have a Year One Journey class plan plus quarterly CSM reviews. Continuous learning and optimization prevent backsliding. Regular check-ins with your Customer Success Manager ensure you're maximizing your investment and staying current with new features.

□ AspireCare ticketing and Zoom escalation path documented for the team. When issues arise, everyone should know how to get help quickly. Having clear support processes reduces frustration and keeps implementation moving forward.

If you can check all these boxes, you're ready to turn implementation from a daunting project into a strategic advantage. If not, spend time addressing the gaps before you begin—the upfront investment in preparation pays dividends throughout the entire process.

Enough Talk, Ready to See This in Action?

You won’t just stumble into perfect implementation of software, just as you won't magically grow profits. But once you decide to stop accepting "good enough" and commit fully to the process, there’s no limit to the success you’ll achieve. 

Implementation isn’t a leap of faith when you have the right framework, support system, and realistic expectations. 

Aspire super-charges new customers’ ability to crush implementation with a proven methodology that combines CSM coaching, Education, and Pro Services support, along with AspireCare's ongoing assistance, guiding landscaping contractors from Day One confusion to Year Two competitive advantage.

The window for easy growth in landscaping has closed. Rising costs, labor shortages, and sophisticated competition have made operational excellence mandatory for survival. 

The companies implementing robust business management systems now are building the infrastructure to thrive while their competitors struggle with spreadsheets and gut instincts.

"We see it as a never-ending supply of knowledge and information," says Jeff Liston, President of Billmar. That mindset—viewing implementation as the beginning of continuous improvement rather than a one-time project—separates the companies that maximize their ROI from those that merely survive the process.

Your choice is simple: keep doing what you're doing and hope the market gets easier, or invest four months of intensive work to build the foundation for years of competitive advantage.

Schedule a demo to map your first 90 or 120-day (depending on software tier) journey and design your path to year-two gains. Implementation isn’t easy, but staying where you are is no longer an option.