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
Dashboards won't tell you why deals are stuck or how to unstuck them
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Onto the newsletter!
It’s all too common to go through a quarter with a solid pipeline, just to finish totally flat. You were intentional, you were managing the team, the team was delivering–meetings booked, discovery calls, all of it.
Everything looked like success right up until when you missed your forecast.
If you’re like me, you want to just do something immediately. Like add more to the top of the funnel–more outbound, more ads, more MQLs, more demos.
If you’re slightly more thoughtful, your next reflex is to dig into dashboards. Figure out where things went wrong.
But the core issue is probably something deeper, maybe even happening before your reps even get on that first discovery call.
If you don’t diagnose and address the root problem, more volume just means more deals stalling in more stages. And worse–reps missing quotas, becoming demoralized, and more. The opposite of more growth.
Most growth teams optimize for pipeline creation. They are held to some view of opportunities opened: qualified meetings booked or something like that. But not all discovery meetings are created equal.
Pull your last two quarters and look at average days per stage, not overall cycle length. You will almost always find one stage where deals cluster. Just sitting, not moving. Maybe you talked about the same deal on 3 pipeline meetings.
That is where your revenue is disappearing.

Most teams look at total cycle time and miss the specific stage. Dig in. It is usually one of two: demo to proposal, or proposal to legal. Both are fixable.
Once you find the problem stage, dig in. Ask what is different about the deals that move quickly through that stage. Do the fast ones tend to have a champion actively pushing internally? Are stalled ones proposals submitted into a void, followed up for weeks with no reply? Being your ICP doesn't mean they're buying right now. Get curious and try to figure out what is going on.
But looking at that stage may still miss the root cause. A key driver of deals that close is lead quality–which starts at the top of your funnel. Usually close rates fall off because it became structurally worse. AI-generated outbound made it cheap to book a meeting with almost anyone, the team running it pushed for a broad ICP so they could more easily hit their numbers, and now you’re meeting with people that look like your ICP–maybe even are your ICP–but aren’t ready to buy.
Having your SDRs hit activity targets is important. Booking meetings is important. I don’t mean to take anything away from that. But a meeting is not always a qualified opportunity. You have to ask questions and be genuinely curious on the discovery call to understand if the prospect actually has a pain, authority, budget and urgency.
Signal data can be extremely useful–or it can be misleading. This data consists of things like posting a job opening for a CISO, or hiring a new Chief of Staff. The specific signals will vary for every company (even within the same product category) and are key to helping you narrow down your outreach funnel.
Signal data can be exceptionally useful but it can also be misleading, because the same signal may mean two different things. If you use intent data or AI scoring, audit which signals actually predict your win rates versus which ones just feel relevant. Visiting your pricing page twice is not the same as evaluating your category. Liking a LinkedIn post by your competitor does not mean someone’s job is on the line if they don’t solve this problem. Three G2 reads from someone in IT is not three G2 reads from a VP at fiscal year-end.
Most intent scoring tools treat all engagement as equal. It isn't.

The signals that matter can also change over time. What was a key buying signal in Q1 might not be as valid or useful in Q3. Revalidate qualification criteria periodically–quarterly for high-velocity teams so–you're optimizing for the right future customers. One easy way to do this is to review call recordings with AI.
Look for patterns across your discovery and demo calls–not pains, necessarily, but what happened recently at the company. A funding round can be both–a pain, because a founder now has a hiring plan they have to hit. Or it could be a catalyst–now they have budget and are going to conferences, so when before they were happy to book themselves, now they need a business travel solution so their whole team can get organized (as one possible example).
Of course, your reps have to be curious and ask questions for this to show up in your calls. When it does it is gold.
Want more control over your pipeline with signals built in? Skyp just partnered with BirdDog to integrate the leading signals platform into the leading outbound platform for teams selling high value products.
Diagnosing the problem requires real work, but can be done relatively quickly and effectively. How then do you fix it?
For smaller companies the fix is straightforward. If your reps are doing their own outbound, have them adjust their qualification criteria. Good reps will figure this out, but they may feel they need permission to do something significantly different. Especially if you had done good research previously.
For all reps who own their own pipeline generation, qualifying leads properly or making sure to address blockers earlier in the process–as early as the discovery call–will benefit them directly.
For larger companies the fix can be more painful. If your SDR team is in house, their incentives usually focus on meetings booked and possibly activity. If you change your criteria that may result in a larger pool of prospects to go after–but usually it doesn’t. Usually you “niche down” and realize that you were casting too broad a net, and need to focus on a narrower part of the market where pain is more acute or timing is more urgent.
Because SDRs are usually measured on some combination of meetings booked and activity, this can be a tough adjustment. That doesn’t make it less necessary. It may help to communicate the reason for the change clearly, and to provide tools or other workflows to enable them to make the change. The only thing worse than telling an SDR that their patch is now smaller for the same quota is telling them to figure it out for themselves. This will result in thrash and missed targets for everyone.

We’ve seen this in our own market. Our original ICP, founders, were at first eager customers. Then as Claude Code became more capable and widespread, and the ability to write a passable (if not great) sales email with AI became possible out of the box, things changed. Founders felt less urgency (they can send a handful of emails with Claude) and less willingness to pay (paying thousands looks like a poor choice compared to just using their all-you-can-eat Claude Max subscription).
I’m sure this played out for other AI companies as well–even some big ones. I pick on Bolt a lot (they can take it) but for me, when Claude Code came out I churned–no need for a second subscription to do something close to the same thing. When I had figured out using Railway and Vercel, I no longer needed the bundle that Bolt provided.
Bolt, I’m sure, has moved upmarket–as has Skyp. We’re now focusing on growth leaders and larger teams because many of them still have pains. My theory is that all of this GTM Engineering hiring is going to either lead to great job security for those GTM engineers, or regret by the companies who hired them when they depart. Because not only does the business climate change, but so does the environment and tooling.
And with it, the signals and triggers that result in deals moving through your pipeline and actually closing. Did someone say it gets easier?
Want more control over your pipeline with signals built in? Check out Skyp–we just partnered with BirdDog to integrate the leading signals platform into the leading outbound platform for teams selling high value products.
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