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Sales Tech For Better Cold Emails Conversion in 2021-2022

Cold outreach can be scary sometimes.

No matter how good you or your company are, at the end of the day, it’s about initiating a conversation between two strangers.

Earlier in my career, I believed skills as negotiating, handling objections, and closing are the only factors that determine my success. Oftentimes, I clearly underestimated the starting point of every sales journey — my first email, LinkedIn message, or call.

Talking to more than 20 proactive sales professionals (both executives and individual contributors), I was seeking the answer to a pretty simple question.

“What’s the hardest part of writing a good cold email?”

I got a bunch of good answers, but here are a few ones that stood out to me:

  • do thorough research —> understand your prospect’s world to make sure you’re adding enough value
  • keep it clear and concise —> make your message personalized and relevant without being too long and salesy
  • write the way you talk —> turn the complexity of your solution into a simple language to sound more conversational

Considering all the above-mentioned points and the rapid growth of the sales tech industry, here we come to the most interesting part…

How can we better equip ourselves with the right tech to sharpen our outreach?

Luckily, there are some really smart tools on the market that help sales professionals go above and beyond the regular approach to prospecting.

I’ve put together a brief list of what I’m using at the moment. Hope you find them handy too:

1. Crystal Knows

Doing research is fun. Diving deeper into your prospects’ profiles, their industry, solutions. Gaining some understanding of their personal and professional interests, motivators, and challenges.

But what’s even more fun is to get a picture of your prospect’s personality in a few clicks. That’s what I love to do using Crystal Knows.

It doesn’t replace the need to do my research, but it greatly helps adjust my message based on a particular type of personality. As an example, here is my personality assessment:

To make sure that Crystal Knows positively influences my prospecting process, I like to:

  • focus on things that really matter for my prospect and avoid stressors
  • pay extra attention to energizers — things that motivate my prospect
  • tweak my writing style and wording, so my tone will match their personality


According to Crystal Knows prediction, it comes naturally for Jonathan, one of my prospects, to getting bored easily.

This got me thinking about the idea to replace my common message structure Trigger +Value Offering + CTA with this one:

Trigger +Engaging question + Value offering + CTA


I had another prospect Julie, who seemed to be most motivated by fun, excitement, and storytelling. Keeping that in mind, I used a more easy-going email flow than usual:

2. Grammarly

Grammar is a huge pain. Being a non-native speaker, I found it challenging to write perfect emails for a long period of time.

The first messages I sent were really clunky, which I believe made me look a bit unprofessional. Ops, I’m sorry my dear prospects. I was too young and inexperienced at that point.

Since 2015, Grammarly has become an essential part of my toolset. I use it every single day to:

  • cross-check my emails or any other piece of text for grammar, spelling and punctuation mistakes
  • score my emails based on word count indicators, readability level and vocabulary usage which illustrates the overall quality of my writing
  • control the correctness, clarity, engagement, and delivery assessment of my emails

3. Hemingway

At my first job, I was working with CTOs and Directors of Engineering from tech giants.

I was a rookie with a basic understanding of how prospecting works and what an ideal email looks like. Absorbing the writing style of my colleagues and making the first attempts to personalize messages on my own. That was the best I could do.

But I was sure that if I was selling a super sophisticated solution, I had to sound tech-savvy.

“End-to-end IoT solution, bidirectional communication, hardware- and transport-agnostic”…

And a whole bunch of similar phrases as part of my boring pitch combined with a formal writing style (just to make me look cool).

“The longer and more formal my message, the more likely I’ll get a response.” —  my biggest false assumption.

Fortunately, times have changed. These days I rely on the Hemingway app to:

  • avoid sentences that are hard to read
  • use better alternatives to some of my phrases
  • ensure that my email is easy to understand

When I end up writing at the 10th or 11th-grade level, I follow all the recommendations throughout the text to simplify my email. My goal is to get to the 9th-grade or even lower as this interval is considered good and easy to understand based on Hemingway’s classification.

4. IBM Tone Analyzer

In the past, I have always dealt with the fear of sending messages that might be misinterpreted. Even our best intentions can be read in a completely different way because of some personal, professional, or cultural characteristics.

Let’s say in Eastern Europe people are more direct and formal. In the US, there many more people who appreciate emails written in conversational language.

A few months ago, I heard about IBM Tone Analyzer which quickly became an invaluable addition to my current toolkit.

Behind a pretty raw and fancy-free design, it has extremely powerful functionality. What I find most helpful is their scoring of my text at both document and sentence levels.

If I need to quickly double-check that my message is written in a positive manner, I can use the scoring at a document level. It will show me all the tones that are recognized throughout the email and if I see “Joy” among them – Woohoo, success!

When I need to analyze text on a sentence level, the tool highlights sentences that indicate a particular tone present. This gives me a better understanding of how I can formulate my thoughts in the future if I need to emphasize a specific tone.

IBM Tone Analyzer prevents me from appearing as angry, sad, or scared because I unconsciously used the wrong wording. As a result, I have a good idea of how my message will sound to my prospect.

To sum up:

Writing skills don’t always come naturally. Even though “write the way you talk” sounds like a reasonable encouragement, it usually follows by a range of uncertainties. Is my email engaging enough? Do I need to add more context? What if my message will be considered too direct? The list goes on and on…

A powerful set of tools will never eliminate the need to apply your unique skills and bring authenticity. It will rather point you in the right direction, motivating you to connect with your prospect on a deeper level.

Another gold nugget is that by continuously using any of these tools, you practice your skills over and over again, get feedback, and improve.

A few things I encourage you to habituate:

  • make a personality assessment the integral stage of your research and prospecting
  • make sure both clarity and engagement levels are good before pressing a “send” button
  • always learn to write simpler (my #1 challenge)
  • pay extra attention to the tone of your email to provoke only positive emotions and feelings

Next time you start writing your cold email, make sure you warm it up a bit using all the available data and tools!