The 2 personalized touches that generate 80% of Chili Piper’s opportunities

Aug 27, 2020
Author: Sarah Hicks


Like many SDRs teams across the world, scrambling to respond to a global pandemic poised to obliterate their pipelines, Michael Tuso’s team re-evaluated their messaging. He explained, on a recent episode of the Predictable Revenue podcast, that he and his team experimented with a bunch of different messaging, but actually found that the messaging they had used historically worked best in this new context. So rather than trying to craft “empathetic” messaging – they doubled down on targeting.

They reached out to unaffected industries, and industries that were actually doing better as a result of the swing to remote work, and amplified their proven messaging. Instead of referencing the current circumstances and attempting to display understanding, their messaging focused on creating a business case for the target company. And as a result? They had the best month the company has ever had. 


Amid the eternal debate about the number of touches in a cadence required to book a meeting, rather than taking inspiration from other organizations, Michael decided to look at Chili Piper’s data. He found that 80% of their opportunities were being generated in the first couple of touches in a 5 touch email cadence. It was the result of another eternal debate in outbound – whether to personalize each message or pop contacts in a cadence and let the tools do the work – that led Michael to find the middle ground of personalizing the first 2 touches. 

As for the phone – Michael has his team treating it, for the first time, like a warm engagement mechanism, rather than its own channel for cold outreach. His SDRs might make a dial if a prospect is repeatedly opening their emails, or showed interest of some kind and then ghosted. 


First, for context, you have to know what Chili Piper does. Chili Piper Concierge is an inbound scheduling tool that helps qualified leads automatically book a meeting on your appointment calendar or start a phone call right after they fill out a form on your site. Usually, a lead fills out your demo form and gets a thank you page saying they’ll be contacted “shortly.” If they don’t hear from you in five minutes, their likelihood of converting drops by 10x. That’s why 70% of inbound requests never get booked.

So Michael’s first email is personalized in the direction of the business case. It is contextual and relevant to the specific company, and mentions how Chili Piper’s tool could improve inbound conversion from their web form 60-80%. His SDRs screenshot something about the target company’s inbound process and incorporate it into their messaging to prove that the outreach is personalized. While this visual component is a big help, the email won’t generate a response if the messaging isn’t right.


Finding the right messaging as a company takes a lot of experimentation, and a lot of reflection. According to Michael, you have to be attuned to your own internal “spam filter” to weed out anything that might feel too salesy. At Chili Piper, they have a meeting every week focused on just cadences and touch strategy. This is not an accountability meeting, it’s not activity-based, and is totally non-judgmental. They take this time to study what’s working and what’s not with any active cadences, and brainstorm with all parties involved, from the CEO down to sales/marketing interns. This means that SDRs aren’t just told “go book meetings”, they’re actively involved in a forum that teaches them how to book meetings.

When the team goes off to experiment, the process is very scientific. They change a single variable at a time, and iterate over an extended time period until they have something really solid. Michael swears that it’s not the messaging itself, but the process of how you find it that is most critical – because this is a process you are going to have to visit again and again as your product and the market evolves. 


There are a lot of sales leaders out on the airwaves that say “don’t just pitch your product”. But according to Michael, SDRs hear this message so much that it’s losing its potency. They can’t actually relate the idea to the message they’re sending out. As a result, when a prospect mentions a pain they have, SDRs still have a knee jerk reaction to pitch their product as a whole as the solution. To help his SDRs unlearn this habit, Michael forwards every prospecting email he receives to his team, so they are inundated with emails just as much as he is.

Next, he rehearses mock scenarios with his team before they launch any cadence and asks his team how they would feel if they were experiencing the messaging as a prospect. When an SDR is put in the position of the buyer, they can think critically about what they should do differently and they understand the emotional implication behind messaging. This helps reps write strong first emails, and pay attention to what the prospect is really saying and really cares about so they can write a strong follow up email.


We know how to write a killer first email, thanks to Michael, so we get a response. But what if that response is negative? Michael has learned that most objections that come through email are just smokescreens. With this 3 step framework, you can decipher whether that’s the case, or whether it’s a real objection. A lot of Michael’s email negotiation tactics are modelled on strategies from Christopher Voss’ Never Split the Difference, like mirroring, tactical empathy, calibrated questions, and shooting for the ‘no’.

1. Get to the heart of the concern

Pinpoint exactly what the prospect is saying or alluding to, and call it out. If they have an issue with x, don’t say you can do y. 

2. Reframe the conversation

Reposition the objection to get them to see it from a different perspective. 

3. Give a compelling reason for prospect to take action

A soft ask – it’s better to go for engagement and continue the conversation before asking for a meeting, than to ask for a meeting and put the prospect off. See our Outbound Labs experiment on soft asks here. 

Example: I hear your position. Let me ask one question: aside from your issue with contract length, to what extent did you like the idea of working with Chili Piper?

{{I hear your position. Let me ask one question. Aside from your issue with contract length}} Gets to the heart of concern and goes for reframe.

{{to what extent did you like the idea of working with Chili Piper?}} Soft CTA.


Michael and his rev ops team pull the data from all the touches in their cadences. At Chili Piper, they are analytical about every single micro-stage in the funnel. They know how many people to reach out to in a single account, over what period of time to generate an opportunity, and the ratios that exist between these metrics. They know not just how many replies they get to any particular email, but how many positive replies. They know how much revenue comes from inbound vs outbound, and not just how many meetings but how much revenue each SDR is producing. Michael maintains that SDR teams need to know each specific thing that is contributing to their success.

After years as a coach, guide, mentor, Top 25 Sales Leader, and Sales Development Leader of the Year, Michael Tuso has landed on some foolproof strategies for everything outbound. He nailed the pandemic-friendly messaging and his team had their best month to date. He knows the importance of the human touch in cold outreach, and has developed a framework for objection handling over email that Christopher Voss himself would approve. And most importantly, he studied his team’s historical metrics so they could back up their decisions with data, and amplify the touch strategy that brings in 80% of their opportunities. If being a sales leader is a balancing act between increasing top of funnel and making it repeatable – Michael has found his footing.  


Looking for what type of content to use when personalizing your first email? How to build a personalization at scale playbook

We agree with Michael – it’s a fine balance between completely personalized outreach and letting the tools do the work for you. Read about The Art of the Semi-Personalized Email Campaign

More on the importance of being personal: How Workfront’s prospectors heavily tailor their initial email outreach 

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