Switching Accounting Software: Key Considerations for Subcontractors

Changing accounting software can feel like navigating a high-stakes construction project. It’s a complex process that requires careful planning, strategic execution, and a deep understanding of your financial workflows. This article will walk you through the critical considerations for a successful ERP implementation, helping you navigate this transition with confidence and minimal disruption.

Understanding the Risks of an ERP Switch

According to a 2018 industry report by Codex—a global tech recruitment firm—30% of ERP integrations fail to deliver on at least half of their intended benefits. Perhaps this is something you’ve experienced first-hand, or maybe this is a looming fear holding you back from making the jump. Whatever the reason, it’s important to acknowledge and understand the risks involved to avoid becoming part of this statistic.

1. Organizational Resistance: Employees can feel overwhelmed, balancing daily operational pressures with learning a new system. This resistance is often stronger at large, long-established organizations that have operated on legacy systems for decades.
2. Change Fatigue: Moving too quickly or too often increases the likelihood of mistakes, limits adaptability, and risks burning out your team.
3. Insufficient Training: Research shows that 33% of licensed software goes largely unused due to poor training, perpetuating the pain points the technology was meant to solve.
4. Lack of Buy-In: Change mandated from just those at the top level rarely works—it requires shared ownership across teams.
5. Restricted Screening: Along this same vein, failing to give end users a voice in the decision-making process could lead to investing in a solution that introduces new frustrations or inefficiencies to the organization.
6. Operational Complexity: Integrating new software means carefully untangling existing workflows. One missed connection during an accounting software transition can have a ripple effect that disrupts core financial functions.

Recognizing these pitfalls at the onset is crucial to not only preventing them from happening but also creating proactive strategies for a smooth transition.

8 Keys to a Successful Accounting Software Transition

1. Answer the important questions.

Successful software implementation isn’t just about chasing the latest technology; it’s about answering the three fundamental questions:

1. Why are we doing this? Assess current accounting software limitations by identifying specific operational pain points. Understanding where current systems fall short is important to creating a clear case for change.
2. What should we do? Systematically evaluate potential solutions—features, costs, compatibility, etc.—comparing software options against your key business requirements.
3. How will we implement this transformation? Create a structured implementation plan—leveraging the following strategies—for a smooth transition that delivers tangible results.

2. Secure alignment.

When executives, middle management, and project leaders are united in their understanding of the why, what, and how of the transition, it ensures technology decisions are driven by specific business needs—rather than what’s trendy or what certain individuals prefer. It also helps bridge the gap between executive vision and the daily realities of your subcontractor back office team—the folks who will ultimately be using the new accounting software. 

To achieve strong alignment:

• Communicate the vision: Clearly articulate the reasons for the software change and how it connects to overarching business goals.
• Encourage open dialogue: Create opportunities for leaders at all levels to share concerns, ask questions, and contribute to the implementation plan.
• Address concerns proactively: Anticipate potential areas of resistance, and have a plan for how to address them clearly and honestly. 
• Build consensus: Work toward a shared understanding and agreement on the implementation plan, timeline, and key performance indicators (KPIs).

3. Define and track KPIs.

While evaluating potential accounting software, you should have already identified the must-haves driving your final decision. Use these anticipated benefits to establish KPIs that will measure the success of your implementation. 

For accounting software implementation specifically, these KPIs may include things like time savings, cost savings, reduced errors, real-time information exchange—whatever will make the biggest difference to your business.

For example, trade contractors who use Siteline tend to track:

• How much faster they get paid (or how much Siteline has reduced invoice aging)
• How much time their billing teams save during the billing process
• How many fewer revisions are required on pay applications

Once established, circulate your KPIs to ensure everyone involved understands the targets they’re working for and how achieving these objectives will improve business outcomes. 

4. Establish a change management team.

A recent Gartner study revealed that the most transformative organizations empower their entire workforce—not just executives—to drive change. For example, our customers’ implementation teams typically include folks from accounting, project managers, and executives. By having at least one engaged advocate from each team, you can reduce friction, cultivate shared understanding, and secure buy-in across the organization. 

You also want to ensure your change management team clearly defines each of these roles: 

• The Project Manager: This person oversees the entire implementation process, delegates tasks, provides status updates to key stakeholders, and reports progress to the executive team.
• The Change Champion: An early adopter who generates excitement for the new software, understands its capabilities, and can effectively communicate its value to others.
• The Executive Sponsor: A high-level leader who provides strategic guidance and whose influence can help overcome significant implementation roadblocks.
• End Users: The frontline team members—in this case, your back-office team—who will use the software daily. They bring in critical insights that ensure the software meets operational needs.

5. Develop a realistic timeline.

ERP implementations often span a year or more. As such, creating a realistic timeline—with some built-in buffer time to account for any adjustments needed along the way—is crucial for keeping your implementation on track.

If you’re not sure where to start, consider:

• Consulting your vendor: They should be able to provide you with some general guidelines and milestones you can build your plan around.
• Collaborating with your change management team: Work together to develop a schedule that accommodates existing workloads, training needs, and potential conflicts.
• Working backward from your goals: Establish checkpoints and deadlines by working backward from your end goals. For example:some text
  • By [date], all end users should have their login credentials set up.
  • By [date], X number of projects should be migrated to the new system.
  • By [date], the team should have completed X number of training modules.
• Sharing your plan: At the risk of stating the obvious, share your plan internally and with your vendor, ensuring that everyone has a central reference point for key dates and milestones. 

6. Tap into vendor support to maximize training.

As mentioned earlier, one of the most prevalent software implementation pitfalls is not having the training and support required for your team to embrace the new system. This is where understanding vendor support and leveraging their materials comes in handy. Remember, vendors are often measured on how successfully their clients utilize their software—their success is your success.

To maximize the impact of your training program: 

• Inquire about support offerings: Understand the vendor’s implementation and onboarding process. Do they offer training sessions, or is learning self-directed? What resources are available? Are there any associated costs with training and onboarding?
• Clarify data migration: Whenever you’re switching from one system to another, determine who is responsible for data migration—your team or the vendor—and whether both systems will operate concurrently during the transition.
• Develop a training plan: Collaborate with your vendor to create a program tailored to your company’s needs, implementation goals, and current workloads. Consider breaking training into multiple sessions and offering refresher courses as needed.
• Incentivize participation: Encourage attendance through incentives like catered lunches, gift cards, and other small rewards.

7. Understand integration capabilities.

Not all integrations are created equal. Some are file-based, others are pre-built, and some may require custom configurations. Getting as much information from your vendor on the software’s integration capabilities is clutch to ensuring it connects with your existing systems. 

Key questions to ask include:

• What other platforms does the software integrate with?
• What specific data and information will flow between the systems?
• Is the data transfer batch-based or real-time?
• How frequently will the data be synchronized across the integrated systems?
• How does the data move from one system to another?

If you have an in-house IT team, involve them in evaluating whether the proposed integrations meet your requirements.

8. Protect your cash flow lifeline.

During ERP implementation, your accounts receivable (A/R) workflow is most vulnerable—one wrong step and your cash flow could take a hit. Siteline offers a critical safety net for commercial subcontractors when they’re switching accounting systems, ensuring nothing slips through the cracks. Translation: Your billing is quick and accurate. Everything gets billed—including retention—and everything gets paid.

Here’s how Siteline protects your A/R during an accounting system transition:

• Automated billing: Transforms custom pay apps into a streamlined workflow, handling calculations, taxes, and lien waivers seamlessly.
• Real-time A/R tracking: Provides complete visibility into pay app status across all projects and clients, automates reminders to clients for past-due invoices, and keeps your team in sync for faster payments.
• Connected field and back office: Bridges the gap between field and office teams with centralized SOV and change order management for faster, more accurate billing.
• Stress-free onboarding: Provides a dedicated onboarding specialist who creates a training program tailored to your company’s needs—free of charge. Most of our customers are confidently billing in Siteline within 2 weeks.
• Seamless integrations: Siteline integrates with all major accounting software in the construction space, ensuring smooth data transfers and a streamlined subcontractor billing experience. We can also set up integrations at any time. 

One of our metal and glazing customers reduced their A/R aging by 20 days and saved three days each month on billing by leveraging Siteline—time that can be spent on other strategic initiatives (like switching accounting software instances). 

What has stood out most to them is how intuitive our product is. “My favorite thing about Siteline is its ease of use, which has translated into huge time savings for me. And we all know time is money."

Switching accounting software is a significant undertaking, but with careful planning and the right tools, it doesn't have to derail your team or your workflows. By focusing on these strategies, you can help ensure a smooth transition for your team. 

And if you're looking for an easy way to streamline and optimize your A/R throughout the process (and beyond!), Siteline is here to help. Book a demo today to learn more.