Software Sales Tips by Matt Wolach

Scale Your SaaS

Ways to Improve Sales through Humour and Community with Ross Pomerantz


Ross Pomerantz, the brain behind Corporate Bro and the “General” of The War Room, discusses his passion for sales, his crusade against the marginalization of salespeople, and his incorporation of comedy into sales with Matt Wolach, the host of SaaS-Story in the Making Podcast.

Ross also discusses the importance of belonging to a community of peers in the sales world. While sharing tested tips for success in sales, Ross also shares customer engagement rules in a sales process and the perfect way to go about content creation.  Ross caps it all off with a piece of advice to software founders.


Podcast: SaaS-Story in the Making.

Episode: Ways to Improve Sales through Humour and Community.

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

Guest: Ross Pomerantz, General of The War Room, and Head of Community at Bravado


Enjoy All that Comradeship Offers

Man was made to commune. Ross thinks Salespeople were too.  To him, the best help a salesperson could have comes from networking and communicating with folks with better sales experience. Ross believes that standing out on the shoulders of giants equals standing out.

In sales, there are no magic theories; there are no hard and fast rules. While trial and error is horrible, a salesperson has to open up to tonnes of solutions. A salesperson could bank on the diversity of opinions that belonging to a community of salespeople affords. Working on an aggregate of peer-reviewed solutions is a salesperson’s surest bet at success, so says Ross.

Try to Disarm Your Prospects

Sales is deeply maligned. Salespeople are not spared too. They are marginalized and thought low of. As such, people are always on their guard at every unavoidable encounter with salespeople. Ross thinks that the first thing a salesperson should do in a sales conversation is to try to disarm the prospect and address the possible reservations that the prospect might have to try to weaken the anti-sales defenses in the prospect’s psyche.

Ross advocates self-awareness for scaling or managing a salesperson-prospect interaction. To Ross, self-awareness entails putting oneself in the shoes of the prospect being addressed. By doing this, a salesperson becomes more of a human being than a script-rendering robot.

Stick to it, Stick by it, and Stick with it

In the sales game, consistency and persistence are your best friends. If you have done the hard work of putting perimeters on yourself, if you have set deadlines,  if you have painstaking mapped out a creative brief of dos and don’ts, if you have done some preliminary work on a perfect style of pitching, then you had better stick with it.

Ross says the right time would never come. You need to pick up the phone and do it. If you just keep going and you keep learning, it would only get better. You need to grind and put in the reps.  You need to take all the bits from the successful reps and make them your own.

Guide Yourself with a Process

Ross advocates having a reliable routine, a well-thought-out plan, and a process for dealing with sales situations. Ross thinks that having a process would take you through all stages in sales pushes you closer to success.

Prepare, Ross says. Not only would you feel good that you did, but you would also be ahead. You would not be engaging a prospect to learn, you would be talking like a salesperson with knowledge.


Better a Community Man than a Lone Ranger

“It is important that you network and communicate with folks going through similar challenges and folks with a better experience.  The good and the bad thing about sales is that there are no silver bullets; there is no good or bad way to do things.”

The good thing about belonging to a community of peers is that though you “get duplicate questions, you get thirty or forty people answering these questions.  So, you get different perspectives. You get a diversity of opinions. You get honest insights into hard questions.”

Be Self Aware

“The other part is self-awareness. You are calling people who do not want to hear from you. People are always on the defensive to every sales call. Try to disarm them. Take all the bits from successful reps and make them your own.”

“Work in self-awareness and try to put yourself in the shoes of whom you are talking to. It makes you more of a human being than a salesperson. People buy from people. Don’t be a robot going through a script. Try to connect with the person you are talking with. Change your style to suit who you are talking with.”

Just Do It

“One of the things I recommend is to put perimeters on yourself. The most difficult thing to do is to create content about everything. Set deadlines and stick to them.  Just keep going, keep learning, and it is going to keep getting better.”

“Do a creative brief of what you think your content should touch on and your dos and don’ts and your audience would know what’s coming. While experimenting, be consistent.”



[08:05] “The good and bad thing about sales is that there are no silver bullets.”

[15:53] “The most difficult thing to do is to create content about everything”

[19:29] “Take all the bits from successful sales reps and make them your own”

[22:08] “Get past the fact that nobody cares”


To learn more about Ross Pomerantz and Corporate Bro, visit:

You can also find Ross Pomerantz on LinkedIn at   

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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