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Simple Hack to Improve Your Sales Messaging

Sales Hacks to Improve Sales Messaging
Prospecting & Sales DevelopmentSelling & Closing

Editor’s Note: Guest post by Krista Caldwell, leader of Sales Development at Tulip Retail, a Toronto-based SaaS company helping large retailers mobilize their sales associates. Krista is also our co-host for Sales Hacker Series Vancouver.

Communicating over email with strangers is core to the SDR role, so the most effective SDRs are masters of gauging prospects’ communication style and responding in-kind.

Even when you’ve nailed down your ICP, it’s super challenging to get the tone right in emails to every prospect at scale. When a prospect stops responding to my emails in a discussion I often question if I got the tone wrong in my last email:

  • Was my “Cheers” too forward?
  • Does she understand “LOL”?
  • Was my brevity offensive

Last week a friend recommended a web app called Crystal that makes it much easier communicate appropriately by analyzing public data on a given prospect to tell me how he or she wants to be spoken to.

Before I send an email from Gmail, the app scans my message and makes short, actionable suggestions about the words, phrases, style, and tone I should use to reach the recipient in the way that they like to communicate, rather than my own.

Based on my prospect’s blog posts, LinkedIn profile, and other public online data, the app makes suggestions like “Change “I’d love to” to “I want to”” or “Remove “Sorry for the delay””.

Ideal Customer Profile


In combination with email template Gmail extensions like Yesware, Tout, or Signals, Crystal lets sales reps semi-automatically personalize template messages to match their prospect’s communication style.

The basic tool is free. You can check it out for yourself here.

What do you think? Do you have any other strategies for customizing the tone of your emails for customers, or do you think it’s important?

What do you think?

Do you have any other strategies for customizing the tone of your emails for customers, or do you think it’s important?

Krista Caldwell is co-host for SalesHacker Series Vancouver and Account Strategist at, a Pipeline Automation System built for Predictable Revenue