I spent part of my career in e commerce, in the years when online retail was still arguing with itself about whether people would ever hand over card details to a stranger.
The industry solved that. Not with reassurance, and not by getting better at saying trust us. It solved it by building trust into the mechanics of the product, in ways that cost real money and gave up real control.
I now work in B2B software, and I watch teams make the exact mistake retail outgrew two decades ago. They treat trust as a messaging problem. It is a product problem, and the difference shows up in what you are willing to sacrifice for it.
What retail actually did
Look at what changed in online shopping and almost none of it was copy.
Returns became free and easy. That is not a marketing decision, it is an expensive operational commitment that transfers risk from the buyer to the seller. It works because it is costly. A promise that costs the promiser nothing carries no information.
Reviews became public and unfiltered, including the bad ones. Retailers fought this initially, for obvious reasons. Then they discovered that a product with only five star reviews reads as fake, and that visible criticism makes the praise credible. Giving up control of the narrative bought more trust than controlling it ever did.
Order tracking became granular to the point of absurdity. Knowing your parcel has reached a depot does not help you. It changes nothing you can act on. But uncertainty is the actual discomfort in waiting, and visibility removes it even when it removes no delay.
Prices became total, including delivery, before the final step. Because the industry learned that a surprise at checkout does not just lose that sale. It costs you the customer.
Every one of those is a product decision with a cost attached. None of them is a claim.
The same four moves in B2B
Now hold enterprise software up against that list, and the gaps are uncomfortable.
Exit. Retail made returns free. Most B2B software makes leaving as hard as it can, and treats that friction as retention. It is not retention, it is captivity, and buyers have become extremely good at detecting it during evaluation. Being able to say clearly how a customer gets their data out, in what format, on what notice, is a trust feature. It costs you something, which is exactly why it works. I would rather lose a customer who wanted to leave than sign one who noticed the trap.
Public failure. Retail published bad reviews. The equivalent here is the status page and the incident write up. Teams that publish honest post mortems, including what they got wrong and how long it took to notice, are consistently more trusted than teams with suspiciously clean histories. Nobody believes the clean history. They assume you are hiding it, and they are usually right.
Progress visibility. Retail obsessed over tracking. Software still routinely leaves customers in silence between the sale and the value. Onboarding that shows where you are, what remains, and what is currently blocked reduces anxiety even when it does not reduce time. This is nearly free to build and it is skipped constantly.
Total price. Retail killed the checkout surprise. B2B reinvented it as implementation fees, mandatory onboarding packages, usage overages, and the tier where the feature you actually came for turns out to live. Every one of those is a checkout surprise wearing a suit.
Where the analogy breaks
There is one real difference, and it cuts against B2B.
In retail, the buyer is the user. The person who takes the risk feels the outcome themselves, and their exposure is a single purchase.
In B2B those are different people and the exposure is career sized. A buyer choosing a system is putting their judgement in front of colleagues who will remember. If it fails, the failure has their name on it for years.
Which means the fear is not really about the product. It is about being visibly wrong. Everything that reduces the personal cost of being wrong is a trust feature: a genuine pilot rather than a demo, a clean exit, references who will speak honestly, a small first commitment that proves something before anyone stakes a reputation on it.
That is why the pilot is not a sales tactic. It is the single most effective trust mechanism available in B2B, and teams undermine it constantly by making pilots too smooth to be informative. A pilot where nothing goes wrong teaches the buyer nothing except that you can control a demo.
The test I use
When I am unsure whether something we are considering builds trust or just claims it, I ask one question.
Does this cost us something if we are lying?
A security page that lists certifications costs nothing to write and is trivially inflated, so it carries almost no weight beyond the compliance checkbox. A published uptime history costs you every time you have a bad month, so it carries real weight.
Free returns cost money. Honest post mortems cost pride. Easy export costs leverage. Public roadmaps cost flexibility.
Trust is built almost entirely out of things that are expensive to fake. Everything else is decoration, and buyers stopped reading the decoration a long time ago.
Where to start
Pick the one your customers would most want and you would least like to give.
For most software companies it is the exit. Write down exactly how a customer leaves. What they get, in what format, how quickly, at what cost. Publish it.
If writing that down makes you uncomfortable, you have learned something important about your product, and so has every prospect who ever quietly wondered the same thing and did not ask.
I am Issam Fathi, a technology strategist and the product manager of AssetEye by Dronetjek, based in Tetouan, Morocco. I help companies build, adapt, and grow through technology.
