Episode 321: Mastering the Art of Cold Calling with Jason Bay

GUEST: Jason Bay, Founder and CEO of Outbound Squad

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Sales is hard right now. 

Sales cycles have lengthened by 40% since 2020.

Fewer reps are achieving their quota in tech. 

So the question is: 

What are some strategies to help you stand out from the crowd?

To give us some insight into this question, we have Jason Bay, Founder and CEO of Outbound Squad, who aims to improve the skills of world-class sales teams with training courses and coaching. Jason has worked with clients such as Gong, Medallia, Zoom, Rippling to increase qualified meetings, qualified demos, and meetings landed by cold outreach. 

What is the “Outbound Equation”?

Jason says there are two components to outbound: quantity and quality. He calls this the “outbound equation”. Although it’s possible to debate whether sales are a question of quality or quantity, Jason believes both are needed to get the best results. Quantity refers to the amount of activity, whereas quality refers to “a combination of fit, message, and delivery”. Jason recommends cherry-picking the clients in order to really prioritize the very best contacts to reach out to and spend time with.

“There's so many ways that you can take 100 accounts and narrow them down to like 10 that are the most likely to respond right now. So that's the very first thing that you need to do as an account executive or SDR team, or as a company”.

Jason Bay, Founder and CEO of Outbound Squad

Implementing AI 

Jason emphasizes that AI is an “extra set of hands”, it’s not a brain. For instance, he says that AI tends to be poor at crafting emails, but it might be able to create 80% of the email content, which someone could later edit and finish—what AI is best at is completing “busy work”. Jason also notes that AI is excellent at detecting patterns in data, so it could be used by a salesforce to identify potential targets quickly. 

“It's going to be able to recommend next steps or troubleshooting in a deal based on objective criteria that it's pulled. Or maybe stuff that's pulled from transcripts and live recordings in conversational intelligence.”

Jason Bay, Founder and CEO of Outbound Squad

Improving Cold Calls

Salespeople often get rejections due to “invisible scripts”, which are essentially just preconceptions. Most people hear cold callers and immediately lump them all together—from B2C sellers to B2B sellers to people at the mall. The way for a salesperson to avoid a potential customer doing this is by showing them that they are different from spammers and telemarketers, which can include changing language and tone, and making sure to include personalization. 

“How can I just be real with this person and get them to be real with me? Typically, that's gonna be a more effective way. To do that is to acknowledge what I heard and to not argue with them and try to change their mind right away.”

Jason Bay, Founder and CEO of Outbound Squad

Improving Long-Term ROI

Jason says that one way to improve long-term ROI is by training the sales team well. He breaks this down into four steps: teach, practice, observe and coach. The teaching part is the tactics. The practice part is neglected, since reps tend to practice new techniques for the first time in live situations when the stakes are high—Jason recommends eliminating this and roleplaying various situations. Jason says that observation is also neglected, saying that sales managers should spend less time on dashboards and more time observing reps in action than giving feedback. Finally, effective coaching includes graded scores and self-assessment. 

“My biggest learning as a sales manager was not giving reps the answers all the time and helping them come up with their own answers and actually empowering them to do that”

Jason Bay, Founder and CEO of Outbound Squad

Now that you know how sales teams can be optimized, discover the full list of episodes at The B2B Revenue Executive Experience. If you enjoy the show, instructions to rate and review it are found here.

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