Cloud ERP Checklist: 25 Questions to Ask Before You Sign
The gap between what a cloud ERP vendor shows you in a demo and what you experience after signing the contract is where most buying mistakes happen. Demos are controlled environments. The data is clean. The workflows are rehearsed. The edge cases that define your daily reality don’t appear. And the questions that would expose fundamental architectural limitations, pricing surprises, and accountability gaps don’t get asked — because most buyers don’t know they should.
This checklist is designed to close that gap. These 25 questions are the ones that reveal what a vendor’s marketing won’t tell you — the architectural truth, the real cost structure, the implementation model, and the long-term relationship you’re actually buying. Not every question will be relevant to every business, but any vendor who can’t answer most of them clearly and without hedging is telling you something important.
Print this. Bring it to every vendor meeting. The answers will separate the platforms that genuinely serve your business from the ones that look good until the contract is signed.
Architecture and Platform
1. Was this software built for the cloud from the ground up, or was it migrated from an on-premise product?
Why it matters: Cloud-native platforms are architecturally different from migrated ones. Native platforms were designed for multi-tenant delivery, continuous updates, and elastic scalability. Migrated platforms carry the architectural DNA of their on-premise origins — monolithic codebases, modular data silos, and version-locked upgrade paths — regardless of where the server sits. The answer to this question predicts your upgrade experience, your scalability, and your long-term total cost of ownership more than any feature comparison.
What to listen for: A direct answer — “built for cloud from day one” or “originally on-premise, migrated in [year].” If the vendor avoids the question or offers a vague answer about “cloud-optimized architecture,” they’re probably describing a migration they’d rather not discuss in detail.
2. Is the platform multi-tenant or single-tenant?
Why it matters: Multi-tenant architecture means all customers share a single, continuously updated platform with strict data isolation. This is what enables automatic updates, shared infrastructure economics, and the elimination of version fragmentation. Single-tenant means you run your own instance — which sounds premium but introduces dedicated infrastructure costs, customer-specific upgrade cycles, and the same version-management burden that makes on-premise ERP painful.
What to listen for: An unqualified “multi-tenant.” If the answer includes phrases like “we offer both options” or “it depends on the deployment,” dig into which model most customers run on and why some choose single-tenant. If single-tenant is the default, the platform likely wasn’t designed for multi-tenant delivery.
3. How are updates delivered to customers?
Why it matters: This is where architecture meets daily experience. True multi-tenant platforms deploy updates continuously to the shared platform — every customer is always current, with zero action required. Single-tenant and hosted platforms deliver updates as versioned releases that each customer must individually schedule, test, and deploy. The practical consequence is that customers on versioned platforms defer upgrades and fall behind, running software that’s months or years out of date.
What to listen for: “Every customer is always on the current version” is the answer you want. If the answer involves scheduling, maintenance windows you control, testing against your configuration, or professional services to manage the migration, you’re looking at a versioned model regardless of what the marketing calls it.
4. What version is your oldest active customer running?
Why it matters: This is the question that cuts through every architectural claim. In a true multi-tenant platform, there is only one version — the current one. Every customer runs it. If the vendor can answer this question with a specific version number that differs from the current release, customers are falling behind on updates. That tells you the platform doesn’t deliver continuous improvement regardless of what the website says.
What to listen for: Confusion or “that question doesn’t apply — everyone is on the same version” is the ideal response. A specific version number, or a careful explanation about how “most” customers are current, reveals the reality.
5. Is the data architecture unified or modular?
Why it matters: A unified data architecture means every function — finance, inventory, purchasing, sales, warehouse — reads from and writes to a single shared database. Transactions are immediately visible everywhere. No batch syncing. No reconciliation between modules. A modular architecture stores data in separate databases per function, requiring batch processes to keep them in sync — which introduces latency, creates reconciliation overhead, and makes “real-time” a relative term.
What to listen for: Ask the vendor to describe what happens at the data level when a warehouse receipt is scanned. In a unified architecture, the inventory count, PO status, financial accrual, and available-to-promise all update in the same transactional moment. In a modular architecture, some of those updates wait for a sync process. The specificity of the answer tells you which model you’re evaluating.
Implementation
6. Who handles implementation — your team or a third-party partner?
Why it matters: Vendor-direct implementation means the people configuring your system built the software and understand it at an architectural level. Third-party implementation means a consulting firm with certification-level knowledge is interpreting the product for your business. The difference shows up in timeline, cost, depth of configuration, and — most importantly — accountability. When something goes wrong in a three-party arrangement, blame circulates. When the vendor implements directly, there’s nowhere to hide.
What to listen for: “Our team handles implementation directly” is the strongest answer. “We have a network of certified implementation partners” means the vendor has outsourced the most critical phase of your relationship to a firm whose revenue model rewards duration and complexity.
7. What’s the typical implementation timeline for a company our size?
Why it matters: The answer calibrates your expectations and reveals whether the platform was designed for the mid-market or scaled down from an enterprise product. Mid-market implementations on purpose-built cloud platforms typically measure in weeks to a few months. Enterprise ERP implementations through consulting firms routinely take 12–24 months. If the timeline sounds like an enterprise engagement, the product probably is one — regardless of how it’s marketed.
What to listen for: A specific range based on companies similar to yours, not a vague “it depends.” Every vendor should be able to give you a realistic window based on your user count, warehouse count, integration requirements, and data migration complexity.
8. What does your implementation process look like step by step?
Why it matters: A vendor with a mature, repeatable implementation methodology can describe it clearly — discovery, configuration, data migration, integration, testing, training, go-live, and post-launch support. A vendor who improvises implementations or defers the details to a consulting partner may not have a consistent process, which increases risk and unpredictability.
What to listen for: Specificity. Clear phases with defined milestones, deliverables, and responsibilities. Ask who from your team needs to be involved at each phase and how much of their time it requires. The quality of this answer correlates strongly with implementation outcomes.
9. How do you handle data migration from our current system?
Why it matters: Data migration is the highest-risk workstream in most ERP implementations, and how a vendor approaches it reveals how seriously they take the transition. A vendor that treats data migration as a commodity task — “just export your data and we’ll import it” — is underestimating the effort and setting you up for data quality problems post-launch.
What to listen for: A structured approach: data mapping templates, cleaning guidance, validation checkpoints, trial migrations before go-live, and reconciliation protocols. Ask whether the vendor has migrated data from your specific legacy system before and what challenges they encountered.
10. What does post-go-live support look like for the first 90 days?
Why it matters: The first 90 days after go-live are when the real learning happens — when your team encounters scenarios that didn’t come up in training, when edge cases surface, and when the system meets the full complexity of daily operations. A vendor that’s deeply engaged during this window catches issues early and builds your team’s confidence. A vendor that hands you off to a ticketing queue the day after launch is telling you implementation was a project to them, not a partnership.
What to listen for: Dedicated support contacts who know your configuration, proactive check-ins, defined response times for critical issues, and a plan for addressing the optimization opportunities that inevitably emerge in the first months of live operation.
Cost and Pricing
11. What is the total cost of ownership over five years — including everything?
Why it matters: The subscription fee is the least useful number in the evaluation. What matters is every dollar you’ll spend over five years: subscription, implementation, data migration, integration, training, support, upgrades, add-on modules, and internal labor. This is the number that determines whether the investment makes financial sense and how it compares to alternatives.
What to listen for: A vendor willing to build a comprehensive five-year projection that includes all cost categories — not just their subscription — is a vendor with transparent economics. A vendor who deflects, qualifies extensively, or insists that “it’s hard to estimate” those costs is a vendor with surprises in the pipeline.
12. What is and isn’t included in the subscription fee?
Why it matters: Subscriptions that look affordable can become expensive when essential capabilities are priced as add-ons. Some vendors include everything — infrastructure, updates, core support, and full platform functionality — in the per-user fee. Others charge separately for modules, premium support, upgrade services, and infrastructure.
What to listen for: A clear, complete list. Then map that list against your actual requirements. If core distribution capabilities like multi-location inventory, EDI, or standard reporting require paid add-ons, the quoted subscription price doesn’t reflect what you’ll actually pay.
13. Are there any costs for upgrades or version migrations?
Why it matters: On true multi-tenant SaaS platforms, this question doesn’t apply — updates are continuous and included. On single-tenant or hosted platforms, version migrations can carry significant professional services fees that recur every one to three years. Over a five-year period, these upgrade costs can rival the original implementation investment.
What to listen for: “No — every customer is always on the current version and updates are included” is the answer that eliminates an entire cost category from your TCO. Any answer involving scheduling, testing, or professional services means upgrade costs are a permanent line item in your ERP budget.
14. What are the user minimums, and how does pricing scale as we add users?
Why it matters: Understanding the pricing floor and the growth trajectory protects you from surprises as the business scales. Some vendors maintain consistent per-user rates. Others use tiered pricing that increases costs at certain thresholds or require package upgrades to add capacity.
What to listen for: Clear per-user pricing with a defined minimum, consistent rates for additional users, and no tier-driven price jumps that penalize growth. Ask specifically whether warehouse floor users, mobile device users, and occasional-access users are priced differently from full system users.
15. What does implementation cost, and what’s the billing structure?
Why it matters: Implementation is typically the largest upfront cost, and how it’s structured affects your cash flow and your risk exposure. Fixed-fee implementations give you cost certainty. Time-and-materials engagements can escalate unpredictably. Milestone-based billing ties payment to progress. Understanding the structure before you sign protects you from budget overruns.
What to listen for: A specific cost estimate with a defined billing structure — not a range so wide it’s meaningless. Ask what happens if the project takes longer than estimated. Ask whether scope changes trigger additional fees. Ask what’s included in the implementation fee versus what’s billed separately.
Functionality and Fit
16. What percentage of your customer base is in our industry and at our company size?
Why it matters: A vendor whose customers are primarily in your industry and at your scale has a product shaped by businesses like yours, a support team experienced with your challenges, and a roadmap driven by your needs. A vendor where you’d be an outlier — different industry, different size, different complexity — will struggle to serve you well regardless of how capable the software looks in a demo.
What to listen for: Specific percentages or at least honest characterization. “Distribution is our primary market” is very different from “we serve a wide range of industries including distribution.” The first means your needs shape the product. The second means your needs compete with everyone else’s.
17. Can you demo our most complex workflow end to end?
Why it matters: Vendor demos are rehearsed to showcase strengths and avoid weaknesses. Asking the vendor to demonstrate your most complex, most operationally critical workflow — your trickiest order scenario, your most convoluted pricing structure, your most demanding warehouse process — reveals whether the platform handles your reality or just approximates it.
What to listen for: Willingness to try, and the quality of the execution. A vendor confident in their platform’s depth will welcome the challenge. One that deflects or insists on showing their standard demo first is concerned about what your scenario will reveal.
18. How does the system handle our pricing complexity?
Why it matters: Distribution pricing is rarely simple. Customer-specific pricing, volume tiers, contract terms, matrix pricing, cost-plus calculations, promotional overlays — if the platform can’t handle your pricing model natively, every order becomes a manual exercise that slows processing and introduces errors.
What to listen for: Ask the vendor to demonstrate your specific pricing scenarios — not theoretical examples, but the actual structures your business uses. If the system handles them through standard configuration, you’re looking at a platform with genuine distribution depth. If the answer involves custom development or workarounds, the pricing engine isn’t built for your complexity.
19. How does inventory management work across multiple locations?
Why it matters: Multi-location inventory is foundational for distribution companies with more than one warehouse. The system needs to maintain real-time visibility across all locations, handle inter-location transfers, support location-specific allocation rules, and provide accurate available-to-promise calculations that consider inventory across the network — not just at a single site.
What to listen for: Real-time inventory updates across all locations from a single unified view. Ask what happens when two orders at different locations compete for the same available inventory. Ask how transfers between locations are handled — is it a seamless system transaction or a manual export-import process?
20. What integration capabilities does the platform offer?
Why it matters: Your ERP will connect to e-commerce platforms, EDI networks, shipping carriers, payment processors, and potentially dozens of other systems. The integration architecture determines the cost, reliability, and maintainability of those connections over time.
What to listen for: Well-documented APIs, webhook support for event-driven integration, and pre-built connectors for your specific systems. Ask who maintains the connectors — the vendor or you. Ask what happens to integrations when the ERP updates. Vendor-maintained integrations that are tested with each platform update eliminate an entire category of post-launch maintenance cost.
Vendor Relationship
21. What’s your ownership structure, and how is the company funded?
Why it matters: Your ERP vendor is a long-term partner. The ownership structure affects whether the company invests in product development or extracts margin, whether your segment remains a priority, and whether the vendor will exist in its current form five years from now. Founder-led companies tend to invest in product and customer relationships. Private-equity-owned companies often prioritize cost reduction and revenue optimization. VC-funded companies may be chasing growth metrics that don’t align with customer satisfaction.
What to listen for: Transparency about ownership and investment philosophy. Ask directly whether the company has taken PE or VC funding and how that affects product investment decisions. A vendor that’s candid about their business model is one you can plan around. One that deflects is one you should evaluate with extra scrutiny.
22. What does your product roadmap look like for the next 12–24 months?
Why it matters: The roadmap tells you where the platform is headed — whether the vendor is investing in capabilities relevant to your business, whether your industry’s needs are shaping development priorities, and whether the trajectory aligns with where your business is going.
What to listen for: Specific initiatives and timelines, not vague commitments to “innovation” and “AI.” Ask how customer feedback influences the roadmap. Ask whether distribution-specific enhancements are a priority or a secondary concern behind other industries. A roadmap shaped by your market means a platform that gets more valuable to you over time.
23. Can we speak with three reference customers similar to our business?
Why it matters: References should be operational peers — similar industry, similar size, similar complexity. Their experience is the most reliable predictor of yours. Vendors with happy customers in your segment will provide references eagerly. Vendors who struggle to produce relevant references may not have them.
What to listen for: When you talk to references, skip “are you satisfied?” and ask operational questions. How long did implementation actually take versus the original estimate? What did the total cost end up being versus the initial projection? Have they gone through an upgrade, and what did that cost? What would they do differently? Do they feel like a priority customer? These questions reveal the lived experience behind the satisfaction rating.
24. What happens to our data if we leave?
Why it matters: Vendor lock-in is a legitimate concern, and the best way to evaluate it is to understand the exit path before you enter. A confident vendor will have a clear data export process, defined timelines, and standard formats that allow you to migrate to another system without being held hostage.
What to listen for: A documented data export process with standard formats (CSV, XML, API access to your data). Ask whether there are fees for data extraction. Ask how long the vendor retains your data after termination. Ask whether you can export at any time during the contract or only at termination. A vendor that makes it easy to leave is a vendor confident you won’t want to.
25. Why should we choose you over the other vendors we’re evaluating?
Why it matters: This is the question that reveals what the vendor believes their actual differentiation is — not their marketing positioning, but what they genuinely think sets them apart when forced to articulate it directly. The answer tells you what the vendor values and whether that aligns with what you need.
What to listen for: Specificity and honesty. A vendor that answers with concrete architectural advantages, implementation model differences, industry depth, and customer outcomes is one that knows their strengths. A vendor that answers with vague claims about innovation, partnership, and world-class service is one that hasn’t differentiated in a way they can articulate. The best answer isn’t the most polished one — it’s the most specific one.
How to Use This Checklist
Don’t treat these 25 questions as a scorecard. Treat them as a filter.
The first five questions — architecture, tenancy, updates, version currency, and data model — are qualifiers. If a vendor’s answers reveal a cloud-migrated, single-tenant platform with versioned updates and modular data, you’ve learned something fundamental about the long-term experience and cost trajectory, regardless of how good the demo looked.
The implementation and cost questions expose the gap between the quoted price and the actual investment. A vendor who answers these transparently is one whose economics genuinely favor the customer. One who hedges is one whose profitability depends on costs you haven’t been shown yet.
The functionality questions verify whether the platform handles your operational reality — not a generic version of it. And the vendor relationship questions determine whether the organization behind the software is one you can trust as a long-term partner.
No vendor will score perfectly on every question. But the pattern of answers will make the right choice clearer than any feature matrix or analyst ranking ever could.
What Bizowie’s Answers Look Like
We built Bizowie to answer these questions well — not because we designed the company around a checklist, but because we designed it around the principles these questions test.
Cloud-native from day one. Multi-tenant. Continuously updated — every customer, always current. Unified data architecture with no batch processing and no module silos. Vendor-direct implementation by the team that built the software. Per-active-user pricing with core distribution functionality included and advanced distribution and manufacturing modules available for operations that need them. Purpose-built for distribution. And a company whose entire business is focused on making mid-market distribution companies successful.
Bring this checklist to our demo. Schedule a conversation with Bizowie and ask us every question on this list. We’ll answer them directly — because transparency isn’t a talking point for us, it’s how we built the business.