Software Sales Tips by Matt Wolach

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Sales Tips

Avoid These 4 Mistakes When Transitioning Sales from Founder to Team

Avoid These 4 Mistakes When Transitioning Sales from Founder to Team Are you a founder who’s struggled to hand off sales responsibilities to your team successfully? You’re not alone. Many software founders hit a brick wall when transitioning from being the primary salesperson to empowering their team to sell effectively. Let’s discuss four critical mistakes […]

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Sales Tips

How to Choose the Right Sales Trainer: A Comprehensive Guide

How to Choose the Right Sales Trainer: A Comprehensive Guide Staying ahead requires continuous learning and development. Whether you’re a seasoned software sales professional or leading a sales team, investing in the proper sales training can make all the difference in achieving your goals. However, with so many options available, how do you determine if […]

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Sales Tips

Do we need sales training?

Do we need sales training? If you’ve ever asked yourself “Do we need sales training?” you’re not alone. In software sales, the question of whether sales training is necessary often surfaces. Through my experience and the inquiries I receive, there needs to be more clarity about when and if software sales training is appropriate. Today, […]

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Sales Tips

Shift Away From This Huge Sales Mistake

In the software sales world, every word spoken holds the potential to shape the outcome of a deal. During a client review session, I heard a phrase that could spell disaster for SaaS sales leaders: “I’m sorry that our team hassled you.” Beneath its polite veneer lies a fundamental flaw in the mindset that jeopardizes […]

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Sales Tips

Why Commission Caps Are a Bad Idea

In the software sales world, one question often arises as to whether to cap commissions for sales representatives. Recently, a client approached me with this very inquiry, sparking a discussion on the effectiveness of such a strategy. Today, I want to share why better approaches exist than capping commissions and what alternative solutions can drive […]

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Sales Tips

Unlocking Sales Success: Lessons from the Car Dealership

In the world of sales, every interaction is an opportunity. Whether you’re selling cars or software, the principles of effective salesmanship remain constant. Recently, I had an eye-opening experience while purchasing a vehicle for my wife. What I encountered at the dealership shocked me, but it also provided valuable insights into the software sales world.  […]

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Sales Tips

Defying Impostor Syndrome in SaaS Sales

In the fast-paced world of software sales, it’s not uncommon for sales reps to grapple with Impostor Syndrome. The fear of being inadequate, especially when educating buyers about their business, can be a daunting challenge.  Let’s explore how embracing the education aspect of the sales process can not only dispel Impostor Syndrome but also build […]

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Sales Tips

What if the Buyer Asks You for the Cost Before the Demo?

What if the Buyer Asks You for the Cost Before the Demo? In the software sales world, one common challenge arises when clients insist on knowing the cost upfront, even before exploring the full spectrum of value your product or service can offer. Let’s discuss how to handle this delicate situation and turn it into […]

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Sales Tips

How To Convert More Leads To Demos

Turning leads into successful demo calls is a crucial aspect of the sales process. Many companies, however, struggle to get potential leads to show up for their initial calls. Let’s discuss steps to enhance your lead-to-demo conversion rate and ensure that more leads make it to that all-important first call. The 45% Dilemma There is […]

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Sales Tips

Two Powerful Ways to Close More Demos

Two Powerful Ways to Close More Demos In the competitive SaaS industry, your demo’s success can decide between a closed deal and a missed opportunity. Your presentation’s delivery is paramount, Let’s discussand in this article, we’ll delve into two crucial elements that can transform you into an outstanding software presenter. Drawing inspiration from the world […]

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Sales Tips

7 Reasons Why You Have High Churn

7 Reasons Why You Have High Churn Churn can be detrimental in the fast-paced software industry, eroding the hard work and dedication to creating a product or service. Today, I share seven often overlooked reasons for high churn rates and strategies to eliminate churn. Contrary to common belief, it’s not always about the product itself. […]

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Sales Tips

Is Sales Specialization the Answer to More Deals?

In the fast-paced world of software sales, businesses often grapple with a crucial decision: Should they invest in full-cycle reps who can handle every aspect of the sales process, or should they opt for specialization, dividing tasks among individuals with specific roles? This burning question is at the forefront of discussions for many software sales […]

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Sales Tips

How to Be an Amazing Closer

In this fast-paced world of software sales, the ability to close deals efficiently and effectively is a crucial skill. As a B2B software sales coach with a close rate of 81%, I share the top tips for becoming an exceptional closer. Let’s explore the importance of the entire sales process, focusing on the often-overlooked starting […]

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Sales Tips

5 Reasons Your Demos Aren’t Leading to Sales

As a software sales coach, a recurring question I encounter is why demos often fail to result in successful sales. It’s a common challenge that many software sales leaders face—wondering why their software product demos don’t lead to conversions.  Let’s dive into five critical reasons behind this issue, shedding light on potential roadblocks that might […]

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Sales Tips

Mastering Unscripted Sales Calls: The Perfect DEAL Process

I want to share my personal journey and insights into mastering the art of unscripted sales calls. You might be wondering whether we need a script or not and what to do when faced with an unscripted situation. Sales calls and demos are the heart of any software sales process and the buyer’s journey. Ensuring […]

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Sales Tips

Embracing Sales: It’s Not a Dirty Word

Have you ever felt like the word “sales” makes you want to cringe? Trust me, you’re not alone. Recently, I watched a movie that got me thinking about this, and I wanted to share my thoughts with you. The film that sparked my reflection was “Wonka,” a delightful take on Willy Wonka’s journey. In the […]

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Sales Tips

How Small Sales Teams Can Beat Big Competitors: A Winning Strategy

It’s common to feel intimidated by big companies with seemingly endless resources. They have substantial funding, established brand names, and an extensive customer base.  But here’s a secret: many big software companies actually struggle with sales. Let me explain why this happens and how small SaaS sales teams can take advantage of these weaknesses to […]

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Sales Tips

The Science of Sales: Using NLP Techniques to Boost Your Close Rates

Last week, I discussed why sales can be considered an art, but today, I want to dive into the scientific aspect of closing deals. So, let’s get nerdy with science and explore how we can use Neuro Linguistic Programming (NLP) to improve our close rates. Before we dive into the world of NLP, it’s essential […]

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Sales Tips

Mastering the Art of the Software Demo: A Theatrical Approach

As a software sales coach and seasoned sales professional, I’ve learned that mastering the art of the software demo can be a game-changer when it comes to closing deals. Some may wonder whether it’s an art or a science, but it’s both. Today, I want to share some insights on how to truly excel in […]

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Sales Tips

How to Win More Deals by Changing Your Pricing Presentation Strategy

    I want to share a game-changing tip to prevent prospects from running away from you. It’s something I’ve been teaching my clients in software sales, and it can prevent those frustrating scenarios where potential clients suddenly go dark on you. Let’s dive right into it. One of my clients, Mihai, based in Romania, […]

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Sales Tips

How to Shorten Your Sales Cycle

Today, we’re diving into the dynamic world of shortening SaaS sales cycles. Imagine turning an 18-month sales journey into seven days — sounds extreme, right? Yet, it’s not a fantasy. It’s a tangible outcome within reach if you follow a strategic approach. This week, let’s unpack the critical aspects influencing the length of software sales […]

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