Selling platform work to leadership - the pitch nobody taught you

When thinking about how to prioritize and communicate initiatives in a retail environment, I find it useful to separate things into two buckets:

• Initiatives directly tied to customer-facing value
• Platform, backend, or data infrastructure evolution

Quantifying ROI is never easy, but it's at least somewhat more tractable in the first case. How much revenue will this new feature generate? Will it bring in new customers? Will it reduce friction in the user journey and move the needle on conversion, or surface where drop-off is quietly eroding value today?

When it comes to platform evolution, the goals are crystal clear to the tech team. We're typically working to reduce maintenance burden and incident frequency, speed up time to market, migrate away from legacy stacks that are increasingly hard to hire for, or lay the groundwork for capabilities the current architecture simply can't support. These are legitimate strategic investments, and most of them can be quantified, but they rarely land with the same force as a well-framed customer outcome or a revenue opportunity.

So how do you make the case for platform and backend work? The trick is learning to translate engineering value into the language of business outcomes, risk, and market positioning, the same vocabulary that drives every other strategic conversation.

Lead with unlocked value.

Start by painting a picture of what the current system prevents you from doing. What customer-facing capabilities are off the table until this work is done? Is it the ability to A/B test new products across a subset of locations before a full rollout? Better-targeted marketing campaigns? More sophisticated loyalty tier structures? This is essentially a positioning argument. You're showing leadership what's on the other side of the investment, and putting a number on the opportunity those unlocked features represent.

Then frame the risk.

What's the downside scenario if nothing changes? Security vulnerabilities leading to data breaches, loss of customer trust, and lasting reputational damage? A growing volume of incidents translating into hours of downtime and direct revenue loss? Risk has a dollar sign attached to it, and that's a language leadership speaks fluently.

And then, only then, make the engineering case.

Faster delivery, increased team productivity, fewer incident hours, lower turnover among engineers who don't want to maintain decades-old technology. This stuff matters, it matters a lot, but it's the third argument, not the first. Think of it as the sustained return: the operational leverage you unlock once the strategic case has already been made.

The underlying principle here mirrors good product strategy more broadly. Lead with outcomes, not outputs. The platform work is the output. The unlocked revenue, the mitigated risk, the faster time to market, those are the outcomes. Frame it that way, and the conversation changes.