My rule at Skyp: if a GTM channel isn't working after 3 months, I kill it.

Take Google Ads.

40 days in it was on the chopping block. I was angry every time I logged in–perhaps not the best management tactic, but I learned from Dave Kashen that anger might be my subconscious telling me something might need to change.

Then in just 3 days we closed $7,750 in new MRR directly attributable to ads.

1.6x ROAS–of all time spend, not just that week or month.

So Google Ads lives on. But many other experiments don’t.

Thing is–this is a terrible approach for most people.

Skyp has a 48 hour sales cycle. Someone sees an outreach or an ad, they book a call, they buy or they don't. The feedback is immediate. Three months of nothing means the channel is broken.

Do some people take months to decide? Yes. We’ve had a couple of those.

But they are the minority. Either you need Skyp or you don’t. Either you have budget or you don’t. Very, very few actual buyers drag it out.

Why?

We sell to founders and sales leaders, at a low budget with low commitment.

Sure, we could insist on annual deals. But then we’d lose our fast sales cycle.

Sure, we could add features for marketers. But then we’d lose our fast sales cycle.

We built the product and the selling process around how our target customers buy.

Which is why our process wouldn’t work for other people.

An enterprise software customer of ours — selling into much larger media companies — runs a completely different game. Deal sizes start at $250k. Sales cycles run 12–18 months. Sometimes longer.

Same "not working after 90 days" logic would have ended their Google Ads program long ago.

They spent $120k over a full year with zero closed revenue.

That spring, a $1mm deal showed up on the doorstep–100% because of those ads. The buyer had clicked months prior, talked about it internally, done the whole journey thing, and boom. A million in revenue.

So they still do Google Ads, too.

But the money isn't even the hardest part of a long-cycle sale.

The hardest part is the politics.

At Skyp, I'm usually talking to the decision-maker. There's no internal committee. No approval chain. The person on the call can say yes.

At $250k+, that almost never happens.

You win a believer inside the account. You do great discovery. You build real rapport. And then you hand the deal to someone who has to re-sell it internally — without you in the room.

Most deals don't die because the buyer said no.

They die a thousand other ways.

Finance doesn’t want to budget for it.

It’s a top priority–but third behind two others that got the budget. Or the attention.

Your salesperson wasn’t on top of it enough, and in that week when she was out–a competitor swooped in, got to the CEO via the board, and now they’re going with a different solution.

Doesn’t even matter that the competitor’s solution is vastly inferior.

You’ve got to run the GTM process for the product and customers that you have.

That means if you have a 24-48 hour sales cycle, great. You can make snap decisions.

If you have a 12-18 month sales cycle you have to be patient.

If you try outbound, and then switch to Google 2 months later, you’ll learn worse than nothing: you’ll learn the wrong lessons.

Outbound might have worked had you given it time.

Google might not work, but because of that outbound effort maybe it does.

You can’t control your customer’s buying process.

What can you control?

What business you are in (if you are just starting out). All other things being equal, faster sales cycles are better. But they’re never equal–in my industry, retention is the bigger problem, not acquisition.

I see the appeal in a $1mm sale that takes 12 months, while that founder might see the appeal of a $24k sale that takes 2 days.

You can choose your bets wisely, and resource them properly.

Have an intern write your sales emails, or do it right?

Have Claude tell you how to run Google Ads, or hire vetted experts?

You can focus and be patient

Even with a fast sales cycle, we know it takes at least 3 months to run an experiment. Google yielded nothing for the first month. It took time to dial things in.

Know which game you're playing — and build your strategy, your patience, and your budget accordingly.