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Why Buy Now? is the second question in the Unusual Customer Story Framework and is specific to where a customer is heading — their specific priorities, hair-on-fire issues, and alternatives.

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As a startup, TIME is a luxury that founders don't have. The No. 1 killer of startups is slow moving customer prospects. The feedback cycle is essential to product-market fit and prospects who lack true urgency won’t provide the input a startup needs to succeed on the timeline they have to survive.

In addition, if there’s one thing we’ve learned via Unusual Ventures Founder Services, it’s that many startups consider Why Buy Anything? (BIG problems) and Why Buy Now? (URGENT problems) as one and the same thing. There are a few reasons for this.

Why founders make the mistake of thinking Why Buy Anything? and Why Buy Now? are the same

1. We're conditioned to tell stories using a "problem / solution" method.

We munge together big and urgent problems into one statement, typically at the expense of getting really specific around urgency.


2. Many founders use their investor pitch when selling to customers.

This is a REALLY BAD IDEA. The two audiences are distinctly different in motivation and pain points.


3. It takes A LOT of time to figure out the hair-on-fire urgency behind a problem.

Compared to Why Buy Anything? and Why Buy You?, Why Buy Now? takes more time because you can’t create the answer yourself. Why Buy Now? requires insight derived from asking the right questions in customer meetings to get it right.


One way to think about the distinction between the two questions is that Why Buy Anything? is about where the market is heading, while Why Buy Now? is specific to where a customer is going — their specific priorities, hair-on-fire issues, and alternatives. Why Buy Anything? is great for an investor pitch — for example, “There’s a big market for compliance automation in the cloud.”

Why Buy Now? is essential for aligning to customer priorities — for example, “I need to demonstrate SOC 2 compliance of my AWS environment to this prospect or I’ll lose the customer.”


To put Why Buy Now? into an equation:

Urgent business need
Incentive to act


To explain further, let’s come back to our buyer’s journey:

Why Buy Now? for enterprise is all about how a customer internalizes the changes happening to their business and then funds initiatives to capitalize on an opportunity, solve a problem, or both. Progressing our examples from the first Why Buy Anything? section, here are two examples:



Big problem: Moving from on-premises software to SaaS breaks traditional identity technologies and techniques.

Urgent problem: My business has started going around my IT team because I can’t deploy all of these (eg: more than five) SaaS applications.

Dashbase (an Unusual Ventures-backed company)

Big problem: Searching increasingly large logs is becoming a problem for my support team.

Urgent problem: My level 1 support calls have all become level 3 customer escalations.

Incentive to solve: So my NPS is taking a nosedive and my customers are churning.


See the difference? Going from Big to Urgent requires a lot of customer empathy and getting really, really specific to the acute, urgent pain that requires immediate action.


Final thought on Why Buy Now? and how answering this question effectively can transform your entire go-to-market

Notice in the chart above that the Why Buy Now? process gets elevated to the executive (or at least director) level. This is due to priority setting being a senior-level function and why sales leaders frequently ask their team to “get high in an account.” It’s not just to get to the ultimate decision-maker — which is certainly important — but also to get a jump on the competition by understanding the business priorities a prospect has before the evaluation cycle begins and lower-level staff start evaluating features and capabilities across multiple vendors. 

Identifying Why Buy Now? is how to go from a ‘product’-based go-to-market to a ‘solutions’-based go-to-market 

Solutions-based go-to-markets attach to high-level business initiatives sponsored by senior management vs. product-based go-to-markets that target lower-level staff and often lead to difficult-to-win feature bake-offs. You can see the common business initiatives that we attached to at Okta on the company’s solution page (i.e., increase M&A agility, protect against data breaches, collaborate with partners, etc.).

If the prospect hasn’t tried to hack together some other alternative solution, it means the problem really isn’t a priority! So ask this question and then LISTEN. If no hack is offered, that’s your clue to move on from this prospect for now. Bleeding people apply bandages. If no bandage has been applied, it’s not an urgent problem.

You’ll know you have this right when you’re able to naturally segue into a discovery question like “how is your company currently solving this problem” and the prospect spends a few minutes talking about their current approach and — hopefully — it’s deficiencies. Or, even better, says something like “this year, we have a project to do XYZ.” Either way, you exit the Why Buy Now? phase with a qualified opportunity. Pain is urgent… and ideally budget is or will be spent. Now we can present the new world.

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