Why 60% of SaaS pipeline dies between discovery and proposal

If you are a CMO, CRO or PE operating partner and your SaaS pipeline looks full but closed deals aren’t following, read this. Ken Jisser breaks down why 60% of opportunities die between discovery and proposal. More importantly, he explains how to fix it. https://lnkd.in/e2x9bRjN

The discovery-to-proposal gap is where way too many deals go to die. This article nails why — and how to stop it from happening.

In SaaS, it’s easy to get lost in the sea of data, MRR, churn, CAC, NPS… the list goes on. But if you want to truly understand the connection you have with your customers, you need one metric to focus on, your North Star Metric. Your North Star Metric (NSM) isn’t just a KPI it’s the heartbeat of your product’s value. It measures the moment your customers get tangible impact from your solution and it aligns your entire company around delivering that outcome faster and more effectively. Think of it this way: Product teams innovate to move the NSM. Sales teams sell the promise of reaching the NSM. Customer Success ensures every client lives it daily. When your NSM is clearly defined, every department moves in sync with your customers’ success and that’s when growth becomes sustainable, not accidental. The key question every SaaS founder or operator should ask "What is the single metric that reflects the moment our customers truly win?" If you can answer that, you’re not just tracking performance, you’re measuring connection.

A few months ago, one of my biggest SaaS accounts was up for renewal. Everything looked fine on paper — usage was steady, satisfaction scores were good. But during one casual call, the client mentioned something that made me pause: “We’re reviewing all our tools this quarter. Nothing’s guaranteed.” That’s when it hit me. Renewals aren’t about contracts — they’re about connection. So instead of jumping straight into discounts or timelines, I went back to basics: ✅ Revisited their goals from the start of our partnership ✅ Showed exactly how our solution supported those outcomes ✅ Brought in our product and support teams to align on new priorities By the time renewal came around, it wasn’t a sales pitch. It was a conversation about what’s next. That deal renewed — not because of pricing — but because of trust. Being an Account Manager in SaaS today means wearing many hats: strategist, listener, problem-solver. But at the core, it’s about one thing: making sure customers still believe in the value we deliver. #SaaS #AccountManagement #Renewals #CustomerSuccess #B2B #SalesGrowth #Trust

This really highlights how renewals are built on trust, not discounts. Revisiting customer goals and proving ongoing value is what transforms a renewal from a transaction into a partnership. #SaaS #AccountManagement #Renewals #CustomerSuccess #B2B #SalesGrowth #Trust

The key metric I rely on to make our value stand out is the active adoption rate — the percentage of licensed users who are actively collaborating across Dropbox tools like Replay, DocSend, or Sign. I pair that with a SPICED framework approach to understand each customer’s situation, challenges, and desired outcomes. From there, I use an adoption dashboard that highlights trends in license usage, shared file activity, and cross-team collaboration. When customers can clearly see their teams’ engagement increasing — for example, a 25–30% lift in shared project activity or faster content turnaround — it connects Dropbox directly to measurable productivity and ROI. In short, I make our value visible by tying usage data to business outcomes, showing that Dropbox isn’t just a storage solution, but a driver of efficiency, collaboration, and growth.”

"Services prevent churn." Jon Mead said this to me this morning as we were geeking out over SaaS GTM, partnerships, and all the usual suspects. As a services guy running a SaaS-supporting services agency, I can bring receipts on this one. Sometimes a services partner prevents churn simply by solving a problem the SaaS customer can't (or won't) fix themselves. Sometimes it's by making the product stickier through customization, integration, or just helping the tool fit more neatly into the customer's world. And sometimes, it's purely relational. The customer stays because they trust the service provider. They like working with them. They feel supported. In a world obsessed with product-led growth, maybe it's worth remembering that service-led retention is just as powerful. What’s your take? Are services undervalued in SaaS retention?

Love seeing this conversation take shape Kyle! Kyle and I were chatting about how SaaS companies actually sell when I mentioned, "Services prevent churn." We talk a lot about product-led growth, but what keeps customers isn’t just the product, it's all the things that surround it. It’s the enablement, integrations, and real-world fit that services partners drive. The best SaaS companies know that retention isn’t only about usage; it’s about outcomes. And services are what turn great products into measurable outcomes. #ProductLedGrowth #ServiceLedGrowth #CustomerSuccess #RetentionStrategy #SaaSLeadership #Partnerships #SaaSCommunity #CXStrategy

Everyone talks about "retention" being the real growth driver in SaaS. But most teams still measure it wrong. Here’s how I look at it 👇 The best retention analysis answers one simple question: how much of the revenue being generated by our CURRENT customer base will we have 365 days from now? If they’re producing $10M in ARR today, will that number be worth $11M a year from now, or $9M – completely irrespective of who you add new? Most teams don't actually isolate that. Intentionally or not, they mix in revenue from new customers or expansion from accounts that signed up in the past year. Either way, they inflate their numbers and end up polluting the signal. It might look like stronger retention on paper, but it’s really just masking what your customer base is actually doing… Instead, think of it this way: If you completely froze new customer acquisition today and just looked at your existing customer base, what would happen to revenue over the next 12 months? When you isolate that, you start to understand the true mechanics of your business. Once you know what your current customers will do, you can calculate exactly how many new customers you need to add to hit your goals. But first, you have to isolate the existing customer base. It’s the foundation everything else builds on.

I’ve noticed something interesting in competitive SaaS markets The bigger the company, the harder it is to find the price. <Book a demo> <Talk to sales> <Custom quote> Before you even know what it costs They make leads go through multiple hoops before they qualify. While they can afford to slow buyers down, the same approach kills momentum for smaller SaaS. Smaller ones don’t have the luxury of a 6-step sales process. You need speed. And transparency creates it. So, how can you get early adopters to give you a shot? When there are 117 other SaaS that do the same thing your product does? If your market is too mature for your product to stand out, make your process stand out. Make your pricing visible. Here’s the logic: - Not everyone wants a sales call - Not all prospects are keen on spending an hour with a stranger - Not all can afford to wait days or weeks to solve an urgent problem - Not all are ready to invest time when they’re not even sure if they can afford When you’re transparent with your pricing, you catch the attention of certain kinds of prospects: - Those who value clarity fast - The impatient one who wants fast time-to-value - The frustrated switcher who’s done with gated pricing - The anxious evaluator who just wants to know, “Is this in my range?” Here’s one VOC to drive home: “... I need to get a solution up and running ASAP. And the longer it takes me to do so, the more likely I'll just buy from one of your competitors.” For smaller SaaS, transparency is a competitive moat. Sometimes the most persuasive move isn’t what you hide. It’s what you show. So if your pricing is hidden … is that a strategic choice? Or are you simply doing it because that’s what everyone else does? Because hidden pricing is a bet that prospects will do the work to find out. And when you're competing with 117 alternatives, that's a bet you can't afford to make.