Software Sales Tips by Matt Wolach
KEY TAKEAWAYS Introducing price too early or too late in a SaaS demo both create problems. Timing matters as much as the number itself. Price anchored to a specific pain from Discover lands completely differently than price presented as a standalone number. The biggest pricing mistake is apologizing for the price before the prospect has […]
KEY TAKEAWAYS Discovery is the first phase of the Perfect D.E.A.L. Process, and the one most SaaS reps rush through or skip entirely. A full discovery call has a structure with four distinct stages, not just a list of questions asked in any order. The goal is not to qualify the prospect. It is to […]
KEY TAKEAWAYS Hiring your first SaaS sales rep before your process is documented is the single most common reason that first hire fails. Readiness is not about revenue size. It is about whether your own Perfect D.E.A.L. Process pattern exists outside your head. The fastest ramp comes from handing a new hire your actual Discover […]
KEY TAKEAWAYS “We need to think about it” is rarely a genuine no. It is usually a sign that something in Discover was missed or left unresolved. The instinct to accept it politely and follow up later almost always loses the deal. The instinct to push back hard almost always damages the relationship. There is […]
KEY TAKEAWAYS If every deal closes because you personally got on the call, you have a bottleneck, not a sales process. A real sales process is your own Perfect D.E.A.L. Process pattern, documented specifically enough that someone else could run it. The gap between founder-led sales and a scalable process is almost always documentation, not […]
KEY TAKEAWAYS Most failing SaaS demos have nothing wrong with the product. The problem is almost always structural. Four specific structural mistakes account for the majority of demos that felt strong in the room but never closed. These mistakes all live in the Associate and Lead phases of the Perfect D.E.A.L. Process, even when Discover […]
KEY TAKEAWAYS The Perfect D.E.A.L. Process breaks every SaaS sales conversation into four phases: Discover, Educate, Associate, Lead. Each phase depends entirely on the one before it. Skipping Discover means Educate has nothing real to work with. This is the exact framework behind five straight Inc 5000 awards for fastest growth, before it became something […]
In the competitive world of SaaS, closing deals is everything. It’s that critical moment when all the hard work you’ve poured into your product, marketing, and lead generation finally pays off. But what happens when your close rate is underwhelming? How do you make sure you’re keeping potential revenue on the table? I was a […]
Software sales can often feel daunting, especially when thrust into it without much preparation. Maybe you’ve built a fantastic product, or perhaps you’re helping out a friend. Whatever your entry point, one thing is clear: to succeed in sales, you must excel. Simply being good isn’t enough because, in SaaS sales, only the best win […]
If you’ve seen The Wolf of Wall Street, you likely remember the iconic scene at the end where Leonardo DiCaprio’s character, Jordan Belfort, tells an audience member to “sell me this pen.” This seemingly simple exercise is a powerful lesson in the art of sales, teaching us three essential principles that can transform your approach […]
In the world of software sales, the ability to deliver compelling demos can make or break your success. Yet, as I’ve pointed out, there’s one crucial element that many SaaS salespeople overlook. If you’re giving demos and not closing deals, this might be the missing piece you need to start implementing immediately. The Missing Ingredient […]
In the high-stakes world of software sales, fostering a competitive yet collaborative environment is essential for success. As a B2B Software Sales coach and seasoned leader in building software sales teams, I joined Scott Leese and Richard Harris on the Surf and Sales podcast and shared some tips on balancing competition and camaraderie within a […]
In the fast-paced software sales world, the demo is the most powerful tool in your arsenal. It’s the heartlinchpin of your sales process, capable of turning prospects into customers or driving them away. Yet, as I’ve been reviewing numerous software demos lately, I’ve noticed three critical elements that are almost universally missing. Addressing these omissions […]
In software sales, following up can make or break a deal. Yet many SaaS sales leaders need help with following up effectively, and some even question whether they should follow up. As a seasoned sales coach, I often hear these concerns from my clients. Today, I want to share insights on mastering the follow-up after […]
When it comes to selling software, one question I frequently encounter is whether an automated demo on a website can effectively drive sales. Many hope that prospects can just watch a demo and then decide to purchase. The short answer? It depends. Let’s discuss the nuances of using automated demos and understand when they are […]
In the world of software sales, time allocation is crucial. Yet, many software leaders are spending their time on the wrong activities. If you’re aiming to grow and scale your software business, you need to reassess where your efforts are going. Today, we’re focusing on the importance of allocating time towards growth activities, particularly closing […]
In the competitive world of software sales, I’ve noticed a common strategy: emphasizing low prices. But this approach is fundamentally flawed. Contrary to popular belief, customers do not necessarily want the cheapest product. Instead, they seek value. Let’s explore why selling on value rather than cost is crucial and how to implement this sales strategy […]
The Power of Stories in Software Sales: A Lesson from Capri I’m currently on the beautiful island of Capri in Italy, and I have a fascinating story that perfectly illustrates the importance of storytelling in software sales. You won’t believe how an Italian heritage tale connects to our industry, but trust me, it’s worth hearing. […]
The Three T’s of Cold Email Outbound Success: A Guide to Boost Your Campaigns Today we’re diving into the essentials for cold email outbound success in the software world. These key elements all start with the letter “T,” and mastering them can transform your email campaigns from mediocre to fantastic. If you miss out on […]
How to Handle a Group Software Demo Handling a group demo with several decision-makers can be daunting, but you can turn this challenge into a substantial opportunity with the right approach. Here’s how to excel when you find yourself presenting to a group, ensuring that every participant is engaged and convinced by your demo. 1. […]
3 Reasons Why Your Software Demo Didn’t Close I’m coming to you from sunny Arizona to discuss something crucial for all you software sales professionals: why your demos aren’t closing deals. I often hear folks saying, “I did a great demo. The prospects seemed to like it, but they never signed up. Why?” Let’s dive […]