- Predictable Revenue: Founders Edition
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- why deals die
why deals die
Collin Stewart
March 28, 2025
Hello Predictable Revenue community,
Quick book update: I’m on my final round of copy-edits for the book and should be shipping those off early next month. Once I’m finished there, I’ll be ramping up the pre-sales campaign.
Most founder-led sales calls start great—prospects love the demo, they're excited about the product, and the conversations leave you feeling confident. But then...nothing. The deals stall, fade away, and no one pulls out their credit card. The reason? You haven't clearly connected your product to real, measurable value that your prospects genuinely care about.
What Founders Get Wrong About Value
Too many founders mistake enthusiasm for intent. Prospects might rave about your cool features or innovative tech, yet still never buy. The excitement alone doesn't close deals—only clear, measurable business outcomes do. If your pitch doesn’t explicitly show how your product moves a needle the customer values, your sale will stall. "Interest" without a connection to business value is a dead end.
Another common pitfall is assuming customers can intuitively connect your product features to their business outcomes. They won't do that heavy lifting—it's your job to clearly demonstrate the link. You need to bridge the gap between excitement and actionable value clearly and explicitly, helping your prospects see the direct path from your solution to their bottom-line outcomes.
So, how do you pinpoint exactly what value means for your customer?
The Three Pillars of Real Business Value
When you're selling, there are only three core pillars your solution should clearly tie to:
Make More Money: Accelerating revenue growth, increasing sales velocity, enabling upsells or expansions. This could mean reducing sales cycles, improving conversion rates, or unlocking new revenue streams.
Save Money: Boosting efficiency, improving productivity, reducing operational costs. This involves clearly quantifying how your product reduces labor, overhead, or other measurable expenses.
Decrease Risk: Preventing losses, ensuring compliance, reducing uncertainty and protecting reputations. Risk is often overlooked but can be an extremely compelling reason for a prospect to buy—particularly in regulated industries or where reputation and stability are critical.
Your solution must clearly map onto one or more of these pillars to resonate with real decision-makers. Identifying these pillars in your own product isn't guesswork—it starts with effective customer development. If you’re still building out your product, incorporate the following questions into your future interviews to make sure you’re setting your future salesperson-self up for success. If you have an established product but you’re struggling to close deals, I recommend sitting down with your existing customers and asking them these questions.
Use Customer Development to Uncover Real Value (Three Magic Questions)
Your customer development conversations aren't just about validating your product—they lay the groundwork for your future sales process. Your goal is to find people with unmet needs that are worth solving. The first two questions help you quantify the size of the unmet need and the last one helps you understand how solving it would tie to one of the core value pillars:
Importance: “On a scale of 1-10, how important is solving this problem to you?” Dive deeper here—why is it important, and how does it impact their broader business goals?
Satisfaction: “On a scale of 1-10, how satisfied are you with how you're currently solving this?” Probe further by asking about specific pain points or gaps that their current solution leaves unaddressed.
Impact: “If you solved this, what would the impact be on your business?” Encourage them to quantify this impact explicitly. Push them to tie this specifically to making more money, saving money, or decreasing risk.
The answers to these questions will clarify exactly which pains your customers care most about solving—and how urgently they need solutions. It will also guide your product roadmap, making sure you're building features that your market truly values.
Once you clearly understand these value insights, the next critical step is integrating them directly into your sales process.
Turn Customer Development Insights into Your Discovery Process
Insights from customer development should directly shape your sales discovery conversations. Think about it this way, you invested time interviewing 50, 100, 200 potential customers and understanding where the gaps are. They showed you their problems and why they’re a priority. Now, we need to use what we learned about our typical buyer to determine whether the prospects in our funnel are a good fit for us right now. Your goal in a discovery process isn't simply to check off the qualification boxes—it's to build a concrete business case that your prospect can confidently present to their internal stakeholders. Without real, numerical evidence of your solution’s value, it’s nearly impossible for prospects to justify buying from you internally.
Remember, no one buys software for the sake of "good vibes." They buy solutions that have a meaningful impact on their business. To help prospects make the right decision, you need to be able to clearly articulate the value your software provides and ask questions that uncover whether it aligns with their goals.
But! Not all people that are in pain care about solving it.
I once hit a speed bump in my old Jetta that knocked a hole in my exhaust. Any mechanic would say that I should fix it - and I knew that too - but I simply didn’t have the time. I was aware of the problem but I didn’t care about solving it right now. The people you meet in a sales process will be the same, so when you’re conducting your discovery, it’s important to try and understand where they are in their buying journey. Are they aware of the problem? If so, do they care about solving it? Here’s how to categorize potential buyers.
Problem Unaware: Prospects who don’t realize they have an issue. Your task: educate first, gently guiding them from unawareness to awareness by clearly illustrating the hidden costs or missed opportunities they face.
Problem Aware but Don’t Care: They acknowledge the problem but aren't motivated to fix it immediately. Your approach: understand what would need to change for it to become a priority and then keep in touch.
Problem Aware & Motivated: They recognize the problem and want to get it solved. These are your ideal buyers—prioritize these conversations and provide clear, compelling evidence of how your solution directly resolves their urgent pain points.
Being aware about your prospect's buying mode helps you understand how to serve them best. While I’d love to say that I’ve had great success changing people’s buying mode, the reality is that people rarely change their perception of reality based on a sales conversation. The best you can do is ask good questions and find a way to support them as their thinking evolves. Their muffler might be hanging on by a thread but they don’t care because the engine is on fire. The more you uncover in the sales process, the better equipped you’ll be to understand whether a deal is going to move and how / when you can make an impact.
Conclusion & Takeaways:
Before your next call, run this quick value checklist:
Do I clearly understand which pillar of value (make money, save money, decrease risk) my product addresses?
Have I quantified the business impact to clearly build my prospect’s internal case?
Do I know which buying mode my prospect is in, so I can adjust my sales strategy accordingly?
Remember: If you can't clearly tie your product to real business value, you don't have a deal. Make every sales interaction count by ensuring your prospects see, feel, and can confidently communicate the concrete business value your solution offers.
Happy closing,
Collin