Software Sales Tips by Matt Wolach

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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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Sales Tips

Is a Product-Led Growth Strategy Best?

In the world of software startups, the debate rages on: Product-Led Growth (PLG) versus Sales-Led Growth. Every software founder envisions their product as the next big thing, spreading like wildfire through word-of-mouth referrals, creating a loyal customer base that multiplies organically. But is this reality or wishful thinking? Let’s dissect this conversation that’s on everyone’s […]

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Sales Tips

3 Things Top Closers Do

3 Things Top Closers Do In the competitive world of software sales, closing deals is the ultimate measure of success. While many salespeople strive to achieve this goal, only a select few consistently excel at it.   If you aspire to reach the pinnacle of success in SaaS sales, it’s crucial to model your approach […]

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Sales Tips

Secrets of B2B Sales Success

Secrets of B2B Sales Success Do you want to elevate your B2B sales game and close more deals for greater profits? If the answer is yes, then you’re in the right place.  Let’s unveil the secrets to B2B sales success that top-notch salespeople use but rarely share. It’s time to break free from the conventional, […]

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Sales Tips

Do You Need More Features to Sell More?

Today, I want to address a common question I get from clients and fellow software founders: Do we need to create new product features to increase sales?   It’s a valid question and one that I’ve pondered myself. Let’s explore this question and discover that the answer may not be what you expect. The Total Addressable […]

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Sales Tips

The Interview Question You MUST Ask Sales Rep Candidates

Are you a software founder who is currently looking to hire a new sales rep? If you are, you need to know the right questions to ask. This week, I discuss an essential question you need to ask to determine whether the candidate is the right fit for your sales team.  The question I’m talking […]

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Sales Tips

Ways To Improve Your Sales Skills

Ways to Improve Your Sales Skills Are you looking to enhance your software sales skills and close more deals? Sales is not an innate talent but a learned skill that you can develop and master over time.  Let’s discuss five effective strategies to help you improve your sales skills and become a more successful salesperson. […]

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Sales Tips

How To Run a Discovery Call

In the world of software sales, a crucial step often gets overlooked but can make all the difference between closing a deal and losing a potential customer: the discovery call. But how do you run an effective discovery call that actually gets results? Today, we’re diving into the secrets of running a fantastic discovery call […]

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Sales Tips

Why My Startup Failed – 6 Big Mistakes I Made

In the world of software startups, success stories often overshadow the painful failures that pave the way. I understand this all too well. My first startup was a complete failure, but I gained a ton of valuable lessons from that experience. Let’s dive into the story of my first startup, a disaster. Sharing these experiences […]

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Sales Tips

Winning in Business: Lessons from a College Football Game

Winning in Business: Lessons from a College Football Game In the fast-paced business world, we often face challenges and setbacks that make us question our strategies and goals. We strive to generate leads, close deals, and ultimately achieve growth, but sometimes, things must go the right way.  At a recent college football game I attended […]

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Sales Tips

Avoid These 3 Common Prospecting Mistakes for Successful Outreach

Avoid These 3 Common Prospecting Mistakes for Successful Outreach In today’s digital age, effective prospecting is crucial for any software business aiming to expand its reach and generate new leads. However, there’s nothing more frustrating than receiving a poorly crafted cold email that’s riddled with mistakes. Let’s delve into these mistakes and learn how to […]

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Scale Your SaaS

Differentiate From Your Competition in Unique Ways – with Arian Radmand

EPISODE SUMMARY In the fast-paced world of Software as a Service (SaaS), closing deals and retaining customers can be challenging. Many businesses fall into the trap of relying solely on email communication, bombarding prospects and clients with messages that eventually get ignored or deleted. This approach leads to missed opportunities and unsuccessful deal closures. But […]

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Sales Tips

Close More Software Demos by Following the Airline Model

Selling Software: What Airlines Can Teach Us In software sales, we can learn a valuable lesson from airlines. It may seem odd but it’s a lesson that transcends industries and can help software companies like yours grow, close more deals, and ultimately reach your goals. So, what’s this secret that airline companies have mastered, and […]

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Scale Your SaaS

From Kuwait Refugee to Multi-Millionaire – How Lloyed Lobo Used Community-Led Growth to Succeed

EPISODE SUMMARY How did one man go from a war refugee to a successful multi-millionaire? Check this out: Lloyed Lobo had a tough childhood, living in Kuwait right when Saddam Hussain invaded. His story about how his family got out, and then how he learned how to thrive is amazing. He earned much of his […]

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Sales Tips

How Long Should My Demo Be?

  In the world of software sales, the art of delivering an effective demo is crucial. Potential clients want to see your software’s value to their business, and a well-executed demo can make all the difference. A common question arises: “How long should a software demo be?” In this new sales tip, we’ll dive into […]

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Scale Your SaaS

Niche Down, But When to Niche Up? – with Ryan Janssen and Drew Goulart

EPISODE SUMMARY Starting a business is like embarking on an exhilarating journey full of challenges, triumphs, and learning experiences. This is especially true for software startups, where the landscape is constantly evolving, and innovation is the name of the game.  In this week’s episode of Scale Your SaaS, we’ll dive into the insights shared by […]

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Sales Tips

I Got Sold Hard – and It Felt Great

Sales is an art form that transcends industries, and the ability to master it can make a significant difference in achieving business success. While many might associate sales primarily with software or technology, the truth is that valuable lessons can be drawn from diverse domains. In this video, I delve into a fascinating anecdote highlighting […]

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Scale Your SaaS

Your New Growth Mantra: Follow the Customer – with Jon Darbyshire

EPISODE SUMMARY In the software world, we often find ourselves grappling with a multitude of decisions. Should we take this path or that one? But what if there was a way to consistently make the right decisions? Enter Jon Darbyshire, Co-Founder, and CEO of SmartSuite. SmartSuite is a platform that streamlines business processes and workflow […]

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Sales Tips

The Five Biggest Mistakes When Giving Pricing

  We’ve all been there – a promising sales call with a great product demo, only for everything to turn chilly when it’s time to discuss pricing. It’s a situation that leaves both salespeople and potential clients frustrated, and more often than not, deals fall through. But fear not, because we’re diving into the top […]

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Scale Your SaaS

Understanding the Power of AI – with Jon Ricketts

EPISODE SUMMARY In the rapidly evolving landscape of technology, the power of AI is undeniable. One company that has harnessed the potential of generative AI is Writerly. I sat down with the Co-Founder and CEO, Jon Ricketts, to delve into the inspiration behind the platform, its journey, and its invaluable role in content creation.  Join […]

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Sales Tips

Mastering the Art of Discovery: 3 Powerful Questions to Boost Your Sales Close Rates

Are you tired of struggling to close deals quickly? Do you wonder if there’s a secret sauce that could transform your software sales process into a deal-closing machine? Well, you’re in luck because, in this post, we’re diving deep into the world of effective discovery questions that can double your demo close rates. Unveiling the […]

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