Software Sales Tips by Matt Wolach

Scale Your SaaS

VIDEOCAST – How to Move Upmarket to Reach $100 Million – with David Hart


David Hart, COO and Co-Founder of Screencloud, discusses the lucrative market of SaaS as well as his success story in upscaling to $100 million, with Matt Wolach, host of the Saas-Story in the Making Podcast.

David also talks about the significance of stagnation in the industry and how to shake it off by effectively scaling companies to their full potential.


Podcast: SaaS-Story in the Making

Episode: How to Move Upmarket to Reach $100 Million 

Host: Matt Wolach, a B2B SaaS Sales Coach, Founder, and Investor

Guest: David Hart, COO and Co-Founder of Screencloud


Show the Market What It Wants

What made you start the software company that you have today? It’s because you wanted to solve other people’s problems, correct? Making life easier with a simple solution – which is your creation.

An easy life is what people want to see. If they see it in your company and in the vision of the people around it, they will opt for your product. The people who do are the ones who saw your right content at the right time, and at the right moment for them to take action.

Be Aware of the Competition

A rocking product and a solid sales process – all set. But that does not mean you should slack off and wait for the money to magically come knocking at your door. 

Hundreds, if not thousands of new SaaS startups spawn each day and the second you become complacent with your efforts for the company – it will soon become the reason for them to steal your market and leave nothing for your original idea.


Be Intentional in Your Growth

David said: “The reason for [plateauing] is we weren’t thinking about it the right way. We were thinking of doing the work and just sitting back and waiting for that cash to come in. We weren’t really investing any money or time or effort into it.”

Matt replied: “If you’re just kind of “la di da”, guess what? Somebody’s gonna come up behind you and take your market from you.”

This highlights the effects of a bad perspective of the company and the kind of thinking that in such an early stage, if you build it, they will come

This doesn’t happen in real life and as a startup founder, you must find a way to continue to evolve and grow for the betterment of your company.

Settling Scores

Matt shared some great tips on boosting sales: “Having a scoreboard, having this information definitely increases productivity.”

“In this story, there’s a steel mill. At the steel mill, the steel owner was really upset he didn’t think that the production was very strong, so he asked the day crew how many steel rolls they created that day and they said “Six.” He took a piece of chalk and wrote a six on the floor and walked away. The night shift came, and they saw a big six and asked, ‘What was that six?’ The manager replied: ‘Oh, that’s how much the day shift did.’ Seven were produced by the night shift that time.”

This story shows the importance of a number to aim for. When numbers are consistently hit without improvement, it introduces inaction and complacency in the software company.

Matt’s advice is to introduce friendly competition and a scoreboard inside the company. This way, this gives the crew a reason to push harder than they did yesterday.

Don’t Stop the Hustle

David says, “As you hire more people, as software founders, you don’t have to do the dirty work anymore. But I think when it comes to [founder outreach], it absolutely has to be founders, hustling, using their network.”

“There is no silver bullet. It’s just hustle, keep going.”

“It really does take a tremendous amount of effort and people pushing to the right direction to get a SaaS company off of the ground.“

Scaling is good, but once you attain a certain number of employees working for the company, it is easy to pull back a little on the throttle since most of the heavy lifting is already taken care of by another person.

But in the industry, and as stressed by David and Matt, that once you become complacent, you’re giving the competition a chance to overtake you and steal your market, leaving you with the spoils and the leftovers and ending up with you watching the competition become what your company could have been.



[08:44] If you can show content, and the right content, if you can surface it in the right way, to the right people, and at the right time, how does that connect your company and why does that matter?

[20:11] We need to understand the real pain point. Why do they need that? Is it about productivity? Is it about clients? Is it about an early warning system?

[21:10] There is no silver bullet. It’s just hustle, keep going.

[26:53] If you stand still, they’re gonna come and catch up to you.


[05:08] It really does take a tremendous amount of effort and people pushing to the right direction to get a SaaS company off of the ground. 

[12:14] Having a scoreboard, having this information definitely increases productivity.

[21:50] The quickest path to success is to find out what someone else has done well and model off of that.


Learn more about David Hart and his company Screencloud here:

You can also find David on LinkedIn here:

For more about how host Matt Wolach helps software companies achieve maximum growth, visit                                               

As part of the founding team in his first SaaS product, Matt owned the sales & marketing processes. But he struggled to sell and gain traction for the company. It took years of learning and tweaking before Matt created The Perfect DEAL Process, an innovative yet easy to implement method for closing more software deals. To find out more, visit

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