‘Why Buy Now’: The Most Urgent Question Your Startup Needs to Answer

At Unusual Academy, we kick off our first session with a critically important startup truth:

“Only desperate customers buy from startups.”

Desperation, a cornerstone principle we build on throughout the Academy, means that a customer has an urgent, exceptionally painful problem that absolutely cannot be solved any other way. Think about it: if the problem wasn’t urgent or could have been solved another way, why wouldn’t the buyer just choose the path of least resistance and go with the less risky, safer alternative? If you’ve ever had a first meeting with a prospect but didn’t get to meeting two, lack of customer desperation is the likely culprit.

In this post, we explore one of the biggest issues founders have when selling early on — too much focus on solving big, important problems, rather than getting to the heart of why a customer should buy now: the most urgent problem your startup needs to solve.

Note: be sure to check out the Why Buy Now Worksheet, for step-by-step guidance on how to discover your Why Buy Now.

Storytelling That Sells: The Power of Three Whys

When I led product marketing at Okta, I was fascinated by how some sales reps crushed their number while other reps struggled, particularly when it came to competing against Microsoft, Okta’s 800lb gorilla adversary. Some reps had over 90% win rates, while others were shown the door after repeated losses. In these highly competitive deals, compelling storytelling was essential because the entire narrative had to be airtight to win the deal — especially when going up against a Goliath like Microsoft, the safer choice with huge incumbent advantages.

For context, Okta’s identity product competes directly against Microsoft’s Azure identity product. Both companies have the mission to “be the foundation for secure connections between people and technology.” — i.e. the control point for IT in a cloud-first world. As you can imagine, Microsoft was highly motivated to maintain their grip on this winner-take-all control point. Competition was so intense, they booted us from their annual customer event, set up ‘Kill Okta War Rooms’ in Redmond, regularly went over our reps’ heads by leveraging long-standing C-suite relationships, and gave away their software for free when they were in a competitive deal against us. These were — and still are — bare knuckles, take no prisoner contests.

To combat this existential threat, we conducted a win / loss analysis for our executive team by interviewing dozens of reps. We looked at product gaps, sales motion gaps, pricing/packaging gaps, business practice gaps, etc. What we found was that successful reps who crushed their number and beat Microsoft regularly did three things when selling that unsuccessful reps did not do:

1. Successful reps aligned with their customer on shared beliefs around how their world is changing. In Okta’s case, reps would align with customers on one or more of the following beliefs with IT leaders: companies are moving from on-premises to SaaS software, which challenges IT to serve its users; consumerization of IT favors ‘best in breed’ choice vs. vertical software stacks; IT leaders are becoming business enablers vs. implementers, etc. Alignment with shared beliefs is the core principle behind Simon Sinek’s ‘Start with Why’ and an excellent way to open a conversation.
2. Successful reps were wired into their customer’s urgent business priorities and had a broad view of their growth initiatives, as well as their challenges across the enterprise. In Okta’s case, successful reps spent a lot of time understanding the urgency behind moving to the cloud, such as the need to rapidly deploy multiple, mission-critical SaaS apps like Office365, Workday, or Box to meet a business unit’s needs. If IT could not deploy these applications fast enough, the business / users would go around IT.
3. Successful reps utilized Okta’s Business Value Team of consultants twice as often as their less successful peers to conduct a detailed business justification analysis that demonstrated with quantified, irrefutable proof the unique value of Okta’s solution vs. the competition’s solution. This included value drivers like time-to-market, cost, and productivity improvements.

Put another way, successful reps won competitive deals by telling stories that answer three key questions, collectively known as the “Three Whys”:

- Why buy anything: A shared belief around how the world is changing and the impact this change has on an organization.

- Why buy now: A deep understanding of urgent business priorities and the impact from the organization’s current (in)ability to meet these priorities

- Why buy you: Key capabilities needed to solve the urgent problem AND the unique value your company provides vs. the competition to deliver these capabilities.

Why are the “Three Whys” so powerful? Because answering these three questions concisely and completely leads a prospective customer through the three stages of the buyer’s journey to arrive at a decision that your company has the one and only answer to a very urgent problem. Here is how the “Three Whys” map to the buyer’s journey and how large, complex buying decisions are processed between the executive and staff functions of an organization:

To help understand this chart in simple terms, think of your most recent major purchase — a car, an education, a home, etc. Now consider how you made your decision. A change in your life caused you to investigate a big new problem or opportunity — a new baby, a need for specialized training, maybe a job relocation — so you had to buy something. You put a plan together (perhaps with your executive, your spouse!) with your priorities and a deadline that created urgency to buy now. And you conducted an evaluation based on a set of criteria to ultimately buy one product over another. Congratulations! You just traversed the buyer’s journey.

Aligning your story to the buyer’s journey means you aren’t really “selling” so much as partnering with a customer as a trusted advisor on how they can best achieve their priorities. This approach also gives your story a driving purpose that will put you in the driver’s seat throughout a competitive sales cycle.

Now onto the critical part. One of these Why questions is WAY more urgent to answer than the other two — Why Buy Now.

Why Buy Now

If there’s one thing we’ve learned via the Get Ahead Platform at Unusual, it’s that many startups consider Why Buy Anything (BIG problems) and Why Buy Now (URGENT problems) as one in the same thing. There are a few reasons for this:

• We are conditioned to tell stories using a ‘problem / solution’ method. So, we munge together big and urgent problems into one statement, typically at the expense of getting really specific around urgency.
• 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.
• 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 (see our how-to-guide).

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 heading — their specific priorities, hair on fire issues, and alternatives. The former is great for an investor pitch. “There’s a big market for compliance automation in the cloud.” The latter is essential for aligning to customer priorities, “I need to demonstrate SOC 2 compliance of my AWS environment to this prospect or I won’t win their business.”

With that in mind, let’s come back to our buyer’s journey and focus on a few Why Buy Now examples:

Why Buy Now is all about how a customer internalizes the changes in the market and the resulting, management-sponsored projects that capitalize on an opportunity, solve an urgent problem, or both. Here are a few examples:

Okta
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: >5) SaaS applications.

Shujinko (an Unusual Ventures-backed Company)
Big Problem: Getting cloud compliant is manual and requires expensive investments in staff or professional services.
Urgent Problem: I need to certify to my customer that I’m compliant or I’ll lose their business.

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 and my NPS is taking a nosedive.

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

The other part of ‘Why Buy Now’ is what alternative(s) the customer has today. If there’s an urgent problem that can be solved by what exists in their environment today, there’s no need to consider something new. This is often referred to as the ‘good enough’ problem and is where promising deals go to die. Big platform vendors like Amazon, Microsoft, and Google are great at squashing startup competition by releasing an inferior, but ‘good enough’ initial product as part of a bigger product that customers already own (and then driving Fear, Uncertainty, and Doubt — or FUD — by marketing the ‘good enough’ product as just as good as yours!)

One 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. Put another way, 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.)

How to Discover ‘Why Buy Now’

Attached is a worksheet that provides step-by-step guidance to help you find your Why Buy Now. The objective is to understand a customer’s perception of two opposing forces:

Urgent business need AND current solutions don’t work

The more urgent the business need is and the less capable the customer is at solving the problem with existing resources/solutions, the stronger your Why Buy Now statement. The converse is also true. If I have a pressing business need but can solve the problem with what I already own, there’s no urgency to do anything different (i.e. I’m having my first child, so need a big car, but already own an SUV). The wider you can spread the gap between these two motivators, the more urgency a customer will feel.

Instructions for finding your Why Buy Now are on the first page followed by a worksheet with six questions you can use to develop your Why Buy Now statement. At the bottom of the worksheet, you can create a discovery question or two that can then be asked in a meeting to determine whether a customer has an urgent Why Buy Now problem. These questions are also great for outbound demand gen / sales development efforts.

Fast Track Your Founder Selling

In summary, big problems (Why Anything) are the result of broad, tectonic shifts in the technology landscape. Urgent problems (Why Buy Now) are the result of narrow, business-driven need. Both are important to discuss with a customer, but when in doubt, focus on urgency over importance.

Bottom-line, finding your company’s “Why Buy Now” will lead to more sales conversions, accelerate deal cycles, and boost your competitiveness. It will require insight derived from many customer conversations to arrive at the right answer, but it is well worth the effort as early as possible to discover your Why Buy Now.

TL;DR

• Only desperate customers buy from startups. Desperation means that a customer has an urgent, exceptionally painful problem that absolutely cannot be solved any other way.
• A lot of founders confuse big, important problems (aka: ‘Why Buy Anything’) with narrow, urgent problems (ie. Why Buy Now), which often leads to prospects deprioritizing the need for your solution.
• Finding your “Why Buy Now” requires insight derived from direct customer interaction, as the answer to this question starts with the customer, not with a bigger market trend or your founder insight.
• We created this Why Buy Now Worksheet to help founders narrowly define the urgent problem their company solves.
• Finding your Why Buy Now will lead to more sales conversions, accelerate deal cycles, and boost your competitiveness.

Editor’s note: At Unusual Ventures, we’ve made it our mission to offer unprecedented levels of help and guidance to founders at the seed stage. Part of that mission means demystifying what it takes to build a company and democratizing that knowledge so that anyone with the rage to master entrepreneurship can start a business and have a greater chance at success. In the spirit of that mission, we will be publishing some posts over the next several months that are intended to describe our approach to early-stage company-building and equip seed-stage founders with the advice and tools they need to move forward on their entrepreneurial journey.