Software Sales Tips by Matt Wolach

Scale Your SaaS

The Best Outbound Prospecting Tactics with Jason Bay


Jason Bay, the Chief Prospecting Officer at Blissful Prospecting, delves deep into what it takes to be successful in outbound sales while discussing the best outbound prospecting tactics with Matt Wolach, the host of SaaS-Story in the Making Podcast.

Jason elaborates on the REPLY framework for effective messaging that converts. Jason also touches on the role of technology in creating enablement and the exact things salespeople should optimize for. Jason caps it all off with the best metrics to track.


Podcast: SaaS-Story in the Making

Episode: The Best Outbound Prospecting Tactics

Host: Matt Wolach, a B2B SaaS sales coach, Entrepreneur, and Investor.

Guest: Jason Bay, Chief Prospecting Officer at Blissful Prospecting.


Leverage Technology

These days, the average sales Joe is overwhelmed with tools to work with. From simple apps to complex, profession-specific software, salespeople constantly face changes to newly established status quos. The steady influx of new technology into sales makes sure that there is no status quo at all.

But there is something that never changes.  Jason says it is sales fundamentals. Sales fundamentals and technology are inseparable. This explains why Jason thinks aligning the duo smoothly can give salespeople an edge.

One piece of technology does not solve all sales problems. To Jason, sales efforts should be backed by different fitting technologies. Combining tech pieces creatively makes messaging more powerful and creates enablement.

Walk the Prospect’s Path

Some approach sales with formulas and manuals. Others think that there is no one right way to approach sales. There are no silver bullets, they say. But one thing is sure. Sales is for the prospect. As a salesperson, the prospect is at the center of your world.

Jason advocates investing heavily in understanding the prospect. Salespeople need to understand the prospects’ current state, their problems and priorities, the top things on their minds, and their desired and undesired future.

To Jason, nothing helps a salesperson craft or set up an effective message other than knowledge of the prospect and a well-nailed ideal customer profile.

Optimize for Conversation

Salespeople suffer the itch to hastily convert. Conversion is their end goal. As such they end up throwing the product or the marketed solution at the prospect. Desperation oozes out of their sales messages.  As you would expect, the prospects would put up a wall.

Focusing or optimizing for conversion is like trying to get to the top of a ladder with one step. Jason says salespeople should optimize for conversation first.  Optimizing for conversation helps salespeople discover the prospect’s core problems, and educate the prospect.

To Jason, salespeople should focus on reply rates. Doing this helps to build a proper funnel instead of an inverted pyramid funnel.  Salespeople should not be too focused on what they need from the prospect. They should be focused on how they could help.


Get Your Prospects to REPLY

“The reply framework is for the cold email. It is used to decide what goes into the email. The R stands for relevant results. Somewhere in your email, you need to talk about the result that your prospects care about.”

“The E stands for empathy. You need to acknowledge some sort of problem, some sort of aspiration. You need to show that you understand what it is like in your prospect’s world.”

“The P is for personalization. This stage is heavily opinionated.  Take your time and be purposeful. Try to get it right with the quality first approach. Try to connect with what the prospect’s brag about, where they are investing money, and where they are educating their customers.”

“The L stands for Laser-focus.”

“The Y is You-oriented. You want to make your prospect the hero. Talk about how you could help them win.”

Volume before Specifics

“There are some volume metrics that you need to track. There is a way to figure this out. Look at your average deal size. Look at your monthly expected revenue. Divide your monthly expected revenue by your average deal size to get the deals you need to close monthly. Then backtrack into the number of opportunities you need to create to close your calculated monthly deals.”

“Calculate the number of calls you need to make. Calculate the percentage of these calls that converted into a meeting. This helps you spot the differences in your pipeline.”

“Then go for the specifics. How many people opened the emails you sent them? How many people replied? What percentage of emails converted into a meeting? How many people are you engaging? These metrics help you forecast correctly.”

Move your Big Doors with Small Hinges

“For me, it is about taking something that is working fine to another level. How do we triple the response percent of a sales team that is getting one or two percent responses to their cold email? How do we improve what we are doing?”

“There is a saying in business that small hinges move big doors. That applies to this. It is usually a few tweaks here and there. A few tweaks to your emails, the follow-ups, the number of emails you send, what you say in calls, how you leave your voice mail. It is usually the simple tweaks, but many of our clients have landed meetings with Fortune 1000 companies using these tweaks.”



 [11:10] “When you don’t focus on understanding your prospect as a sales leader, you are robbing your salespeople of their resourcefulness.”

[13:08] “Somewhere in your email, you need to talk about the result that your prospect cares about.”

[19:09] “The mistake a lot of people make with their marketing is that they optimize for conversion instead of conversation.”


To learn more about Jason Bay and Blissful Prospecting, visit 

You can also find Jason Bay 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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