The Wise-Up: 6 Procure-to-Pay Implementation Lessons From the Trenches

Welcome to Part 2 of the digital procure-to-pay transformation trilogy: “The Wise-Up” (implementation) — where preparation meets execution. In Part 1 (“The Setup”), we sharpened the axe. Now it’s time to swing, cutting through challenges with focus and precision to deliver results.

For executives and CPOs, this is where leadership truly shows: keeping momentum alive after kickoff, engaging and inspiring teams through inevitable bumps, making difficult decisions when trade-offs arise, and ensuring go-live stays on track.

Having supported more than 50 implementations, I’ve seen how this phase transforms a sea of disconnected slide decks into a real, functioning solution. Below, I share six best practices for procure-to-pay implementation, drawn from hard-won lessons and the wisdom of our community — to help you lead with confidence and clarity through this critical phase.

Best practice #1: Remember your why and execute on your value case

Action item: Crystalize the correlation between buying software and delivering tangible business value that everyone can point to. Buying software alone won't save you. But executing against your value case (created during pre-implementation) will. Example: How will spending $500,000 per annum on software result in $500 million in savings? Be clear on whether you're targeting speed, cost, quality, and compliance — and go after it throughout the lifecycle of the project.

Why: Transitioning from the value case to success metrics early on helps drive and refine decision-making in design workshops and weave in best practices while staying focused on your core mission. Success metrics are a range of key performance indicators (KPIs) used to measure the effectiveness of the solution’s implementation and ongoing usage in spend management, procurement, and financial processes. They serve two purposes:

• Act like guardrails during design workshops and build phases, keeping teams aligned to outcomes
• Avoid "software shelfware" — where great tech sits unused because the business forgot why it bought it in the first place

Insights:

• Capture your success metrics using Coupa’s Business Insight pages within your Coupa instance for all to see.
• Limit Year 1 success metrics to no more than five to stay focused.
• Choose success metrics that directly tie to financial impact, savings, efficiency, visibility, compliance, or transparency.
• Make the value case a living document — use it as the foundation for defining success metrics and guiding the transition. Revisit it regularly during steering committee sessions and key decision points to keep everyone aligned and anchored to the original goals.

Best practice #2: Know your business — don’t boil the ocean

Action item: Remember your Vision Custodian — the person keeping the original goals alive? Involve him or her in this phase to help everyone shift to a risk-adjusted mindset. Your vision custodian can proactively map out organizational risks based on internal knowledge and past project experience. Examples:

• De-risk the project with a staggered rollout. Consider starting with a country pilot rather than a big-bang approach — especially if it's not the right fit for your business. A pilot allows you to learn, adapt, and improve before scaling. It also helps you demonstrate early wins and deliver value quickly.
• Plan for timeline slippage. What if incumbent systems need to stay live longer than expected? Build a Plan B.
• Anticipate month-end constraints. Critical subject-matter experts may be unavailable for workshops. Factor that into scheduling.

Think big, start small, scale fast.

Why: A risk-adjusted approach keeps teams vigilant and avoids complacency or overconfidence. Thinking about what could go wrong helps prevent it. For example, a staggered rollout starting with the Coupa Strategic Sourcing module is a quick win. It can deliver rapid time-to-value by speeding up RFx creation, supplier evaluations, and award cycles. These early successes create a virtuous cycle that drives adoption, builds confidence, and proves the value case early. It also supports cleaner data migration (see "Know Your Data" further down).

Insights:

Reflect on past implementation pitfalls. Were timelines missed? If so:

• Negotiate flexible exit and extension clauses with incumbent providers upfront.
• Include pre-agreed extension rates in your contracts to avoid last-minute vendor lock-ins.
• Don't announce termination dates too early — it preserves leverage and ensures continuity.
• Starting with modules like Coupa Strategic Sourcing can generate excitement and results early while giving time to prepare for broader rollout phases.
• Avoid migrating legacy transactions.

Best practice #3: Know your team — activate the core team and engage key stakeholders

Action item: Remember the team members you identified and briefed during pre-implementation? Activate them now:

• Ensure they’re engaged in project activities and design workshops.
• Stay in touch with them about completing (or staying on track with) their Coupa e-learning.

Yes, you'll have a System Integrator (SI), but it helps to remember that software is a little like buying flat-pack furniture. The SI assembles it, but you still need to understand how it all fits together. A trained internal core team can ask better questions and drive meaningful decisions.

Why: A trained team accelerates project velocity. Team members contribute effectively in design sessions, understand configuration discussions, and participate in test planning and execution. Most importantly, they champion the vision internally, helping shift the mindset from “how we do things now” to “how we will do things.” Their influence is key when challenges arise.

Use demos and visual storytelling (such as playbacks and prototypes) to help them see the change coming. Enroll participants in Coupa training early — before design workshops begin.

Insights: In the pre-implementation phase, the focus was on board-level business case approval. Implementation is where end-user buy-in becomes critical:

• These users will live in the system daily and they must believe it will improve both the company and their roles.
• Add celebration events to key milestones to recognize hard work and help end-users reflect on progress made.

Now — not testing or go-live — is the ideal time to ramp up education. Maximize the value of education by purchasing a Coupa Learning pass which allows one user to complete training and pass the seat to another. Build your assembly crew early and include a system administrator in your training plan to support long-term self-sufficiency.

Best practice #4: Know your policies and processes — design for process change

Action item: Be well-prepared for each workshop. Use Coupa’s standards as a benchmark for design discussions, but gaining internal buy-in may require evidence-backed conversations.

• Leverage documentation gathered during the pre-implementation phase (such as policies, SOPs, and audit findings) to validate assumptions and challenge outdated practices. This helps determine whether requirements are truly necessary or simply legacy habits.
• Identify if issues raised in workshops stem from process flaws, system limitations, personnel behavior, or outdated policies — and tackle those root causes.

Why: Workshops should focus on why change is needed, not re-selling the software:

• Use audit findings to justify change and highlight system benefits.
• Take on an “adopt, not adapt” approach. When you shift to a fit-to-standard mindset, you can drive process improvement and avoid ERP replication by asking questions like, “Why wouldn’t this work here?."
• Base design on data, introduce clear policies like “No PO, No Pay,” and define consequences backed by evidence.
• Don’t automate a poor process. Instead of disappearing, they only become scaled and much more difficult to fix later on.

Insights:

• Establish a central source of truth: Set up a central collaboration site (such as SharePoint and Confluence) to store all relevant documentation. If external consultants developed any policy streams, ensure internal ownership. Someone within your organization must be able to explain and defend the policies to reduce future dependency.
• Define golden principles for design: Create a set of design principles to anchor decisions and stay focused on what matters most. Identify whether non-standard requirements fall under Tax, Legal, or Statutory (TLS) categories. Any exceptions should be supported by audit evidence or compliance documentation to keep the design clean and purposeful. Remember to leverage your spend classification if this was done in the past.

Best practice #5: Know your data — manage data integration and cleansing

Action item: Review the Data Quality Issue List created during pre-implementation and then dig deeper.

• Build a data cleansing framework anchored to the future business model: which suppliers, categories, and contracts you want to manage going forward, not just what you inherited.
• The data lead nominated in the pre-implementation phase is critical for defining frameworks and sticking to them with surgical precision.

Why: Expect major pushback citing statutory, archival, or retention needs. Stakeholders will grow nostalgic about legacy data. Is it important? Sometimes. Relevant to your Coupa go-live? Rarely. The mission is to build a clean, working dataset that will allow Coupa to deliver value from Day 1. Without ruthless focus, you risk cluttering your launch with obsolete data. Keep the mission front and center.

Insights: Focus discussions on hard facts: suppliers you’ve actually paid in the last 24-36 months, the volumes, the contractual terms, the category strategy. This reality check trims the fat and sharpens a practical, usable supplier base . You can always add more later. Defer debates about “what might be needed someday” unless backed by hard data.

• Tip #1: Use the Coupa Vendor Match Report early to sharpen this view even more.
• Tip #2: Secure a valid email address for all your suppliers. The email address is key for multiple processes without Coupa (such as inviting them to sourcing events, transmitting POs via email, and getting supplier data updates).

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Best practice #6: Know your IT and architecture landscape — execute system integrations

Action item: Get a clear picture of how Coupa will integrate with: ERP, HRIS, Single Sign-On (SSO), supplier risk systems, and other systems. This involves understanding the utilization and data flows: who sends what, when, and in what format. Treat integrations as mini-projects within the big project — each needs clear owners, timelines, and success criteria.

• Refer to the IT and architecture landscape mapped in the pre-implementation phase.

Why: System integrations can quietly become the biggest risk to your timeline. Poorly scoped, unprioritized, or "assumed easy" integrations are among the top causes of project delays. Procurement doesn’t operate in a vacuum — cleansed data must flow seamlessly across systems to unlock Coupa’s full value.

Insights:

• Get IT involved early, especially if this is their first cloud implementation. Reset on-premise mindsets (and these will take time to change).
• Securing integration resources to design, build, test and maintain integrations between Coupa and other systems. You don’t want to lose momentum because other strategic initiatives weren’t accounted for.
• Test with real data: Refresh lower environments with production-like data and define exit criteria. This approach will reveal the quality of data to support the new process.
• Leverage Coupa’s standard toolkits to reduce complexity and avoid rework.
• Avoid unnecessary complexity. It’s easier to scale up than cut back later.