How to Evaluate Software Vendors (Without Getting Burned)

Software demos are designed to make you say yes. That’s not cynicism — it’s just business. The sales rep shows the best features, uses perfect sample data, and glosses over the parts that don’t work as smoothly. By the end of 45 minutes, you’re nodding along thinking “this will solve everything.”

Then you sign a 12-month contract, spend three months on implementation, and discover that the feature you cared about most requires the enterprise tier. Or that the integration with your accounting software is “coming soon” (and has been for two years). Or that exporting your data means a CSV dump with no relational structure.

I’ve seen this play out dozens of times. Here’s how to avoid it.

Before the Demo: Define What You Actually Need

Most businesses skip this step and it costs them. Before you talk to a single vendor, write down:

Your must-haves. Not features — outcomes. “We need to reduce quoting time from 20 minutes to 5” is a must-have. “We need a drag-and-drop form builder” is a feature that may or may not help you get there.

Your deal-breakers. What would make a tool unusable? Common ones: no API access, no Australian data hosting, no offline capability for field workers, mandatory per-user pricing above a certain threshold.

Your current pain points. Be specific. “Our CRM is slow” isn’t useful. “Looking up a customer’s job history takes 4 clicks and 8 seconds because we have to cross-reference two systems” gives any vendor (or developer) something concrete to solve.

Your integration requirements. List every system the new tool needs to connect to. For each one, note whether you need real-time sync, batch updates, or just occasional data transfer.

Questions to Ask During the Demo

About the Product

• “Can you show me this with our actual data?” A demo with perfect sample data proves nothing. Ask to load real (anonymised) data from your business and run through your actual workflow.
• “What happens when [specific exception] occurs?” Every business has edge cases. Partial deliveries, change orders, split invoicing, rush jobs with different pricing. Ask about yours specifically.
• “Which features require a higher pricing tier?” Many vendors show enterprise features during the demo while quoting you the standard price. Get clarity on exactly what’s included in the tier you’d actually pay for.
• “What’s on your roadmap for the next 12 months?” This tells you two things: whether the features you’re missing are coming, and whether the vendor is investing in the product or coasting.

About Integration

• “Do you have a full REST API?” Not “integrations” — an actual API. Integrations through Zapier or built-in connectors are fine for simple needs, but they break under load and limit what you can do. A proper API means you can build whatever you need.
• “Can I see the API documentation right now?” If the documentation is sparse, outdated, or requires a sales call to access, that tells you how seriously they take integration.
• “What’s the rate limit on your API?” Some vendors allow 100 API calls per minute. Others allow 10. If you’re syncing data in real-time between systems, this matters enormously.

About Data

• “How do I export all of my data?” The answer should be straightforward — full data export in a standard format (CSV at minimum, JSON or SQL dump ideally) with all relationships intact. If the answer involves “contact support” or “we can arrange that,” be cautious.
• “Who owns the data?” This should be unambiguous in the contract. Your data is yours. Some vendors claim rights to aggregated or anonymised versions of your data. Read the terms.
• “What happens to my data if I cancel?” You should have at least 30 days to export everything after cancellation. Some vendors delete data immediately. Others charge for post-cancellation access.

Red Flags That Should Make You Pause

No free trial or pilot period. If the vendor won’t let you test the product with your real workflows before committing, they know the demo experience doesn’t match the daily experience.

Annual contracts only. Monthly billing should be an option. If the only option is a 12-month commitment, the vendor is relying on lock-in rather than product quality to retain customers.

Vague pricing. “Contact us for pricing” often means “pricing depends on how much we think you’ll pay.” Transparent pricing is a sign of a confident product.

The roadmap feature. If the feature you need most is “on the roadmap” or “coming in Q3,” treat it as if it doesn’t exist. Roadmaps change. Priorities shift. You’re buying what the product does today, not what someone promises it will do tomorrow.

High implementation costs relative to the subscription. If the software costs $500/month but implementation costs $30,000, that’s a sign the product requires significant customisation to be useful — which means it doesn’t fit your needs out of the box.

No customer references in your industry. Every vendor has happy customers. If none of them are in your industry or at your company size, you might be an experiment rather than a fit.

Contract Terms Worth Fighting For

Month-to-month option. Even if you pay a premium for monthly billing, the flexibility to leave is worth it. You can always switch to annual later once you’ve confirmed the product works.

Data portability clause. Your contract should explicitly state that you can export all data in a standard format at any time, including after cancellation, with a reasonable window (30-90 days).

Price lock for at least 12 months. SaaS vendors raise prices. Get a written commitment that your per-user rate won’t change for at least a year, ideally two.

Clearly defined SLA. What’s the guaranteed uptime? What happens when it’s breached? “99.9% uptime” means less than 9 hours of downtime per year. Get it in writing, with credits or remedies if they miss it.

Exit clause. If the product fails to meet agreed-upon requirements within the first 90 days, you should be able to exit without penalty. Some vendors will agree to this if you ask — most won’t volunteer it.

The Evaluation Scorecard

Rate each vendor on these dimensions (1-5 scale):

Dimension	What to Assess
Functional fit	Does it handle 90%+ of your core workflows without workarounds?
Integration depth	Full API, good documentation, reasonable rate limits?
Data portability	Can you export everything, easily, at any time?
Pricing transparency	Clear pricing, no hidden tiers, predictable scaling costs?
Contract flexibility	Monthly option, fair exit terms, price lock?
Industry fit	References from businesses like yours, at your scale?
Support quality	Responsive, knowledgeable, available in your timezone?

A vendor who scores 4-5 on all dimensions is rare. What matters is which dimensions matter most to you — and that you’re not scoring a 2 or below on any deal-breaker.

When Evaluation Reveals a Gap

Sometimes you evaluate every vendor on the market and none of them score well enough. Your workflow is too specific, your integration needs are too complex, or your data model doesn’t fit any off-the-shelf product.

That’s not a failure of the evaluation process — it’s a finding. And it’s a valuable one, because now you know exactly what you need (the evaluation process defined it) and exactly what the market can’t provide (the scorecard showed you the gaps).

That’s when custom software becomes a serious conversation. Not as a default, but as the answer to a question you’ve thoroughly explored. And the evaluation work you’ve done — the must-haves, the deal-breakers, the integration map, the edge cases — becomes the requirements document for a custom build. None of that effort was wasted.

The best software decisions are the ones made with full information. Whether you end up buying, building, or doing a bit of both, the process of evaluating properly ensures you’re choosing with your eyes open rather than hoping the demo was an honest preview.