The Skyp Newsletter
Insights, tips, and strategies for modern AI-powered outreach and sales automation
Insights, tips, and strategies for modern AI-powered outreach and sales automation
Customers asking support for a workaround are often telling you exactly what they'd pay more for. A customer opens a support ticket asking how to work...
A customer opens a support ticket asking how to work around a limitation in your product. Support resolves the ticket, marks it closed, and moves on. Nobody connects that ticket to the fact that the customer just told you, in their own words, exactly what they'd pay more for.
Support tickets are one of the most underused data sources in B2B expansion strategy, because support and growth functions rarely talk to each other, and the signal sitting in your support queue rarely makes it anywhere near the people who own expansion revenue.
Customers asking support for a workaround are often describing a use case your product doesn't currently support well at their tier — which is functionally a feature request and a willingness-to-pay signal, even though it never gets labeled as one. "Is there a way to do X" is frequently a more honest expression of need than anything a customer would volunteer in a sales conversation, because they're asking in the moment they're actually trying to solve a real problem, not performing for a salesperson.
This is different from a feature request submitted through a formal feedback channel, which tends to be filtered through what the customer thinks is reasonable to ask for. A support ticket asking for a workaround is often a raw, unfiltered expression of an actual need, submitted at the exact moment the need is most acute.

Individual support tickets are noisy and not particularly actionable on their own. The signal becomes useful at the pattern level — when you see the same workaround request, or a cluster of related requests, recurring across multiple accounts, especially accounts that are otherwise healthy and engaged.
This pattern usually indicates one of two things: a genuine product gap worth building toward, or an existing capability that already exists at a higher tier and simply isn't being surfaced to customers who clearly need it. The second case is the more immediately actionable one — it's a direct expansion opportunity that requires no product work at all, just connecting a customer's expressed need to a capability they could be paying for today.
This requires a deliberate process, because support and growth teams don't naturally share data or workflows. The practical version: a tagging system in your support tool that flags tickets indicating an unmet need that maps to a paid tier or add-on, reviewed on a regular cadence by someone connected to the expansion motion — not necessarily a dedicated headcount, but a clear, recurring process rather than an ad hoc one.
The accounts that surface through this process should route into your expansion outreach the same way a usage-based trigger would — personalized based on the specific need they expressed, timed close to when they expressed it, while the problem is still top of mind. A customer who asked for a workaround last week and gets an expansion conversation a month later has often already found another solution or given up on the use case entirely. The window for this kind of expansion conversation closes faster than people expect.

The deeper issue this points to is how much valuable growth signal exists in functions that don't report to growth and aren't measured on growth outcomes. Support is measured on ticket resolution time and customer satisfaction, not on expansion pipeline generated. There's no natural incentive for the support team to flag expansion-relevant signals, even when they're sitting on exactly the data that would make expansion outreach dramatically more effective.
Building the bridge between support and growth requires either incentivizing support to flag these signals — which can create its own distortions if not designed carefully — or building light-touch tooling that surfaces the signal without requiring support reps to do extra work as part of their core job. The companies doing this well tend to favor the tooling approach, because it doesn't ask a team that's already measured on different metrics to take on additional responsibility they're not compensated for.
Skyp is built around the same principle this post is making — that the best growth signals are often sitting outside the obvious sales and marketing data stack, in places like product usage and account activity that point to a real, specific need. When outreach is triggered by something concrete a prospect or customer is actually doing, rather than a generic segment or threshold, it lands as relevant instead of like a sales push, because the timing and the reason behind it are genuine.
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