Breaking the Ice – Cold emailing an “art” or “science”

About the Author – London Nagai started off in the Army as an Infantry Officer and saw his first job in the start up world with Foursquare. He then took on roles at 42Floors, Appboy (NYC+SF), but now back where he belongs in NYC with TheSquareFoot as the SDR Manager. Check out London on LinkedIn and Twitter.

London PictureCold emailing (prospecting) can either be seen as an art or a science. In my experience, many people see cold emailing as an “art”. With that mindset,it is necessary to understand that each individual artist has a style, if they were to draw the same picture over and over most likely that process would not lead to success. This is why I believe that email templates can be a double edged sword for sales people who are utilizing cold emails to reach out to prospective new business contacts..

Business Development Reps (AKA BDRs) are often tasked by their managers to achieve and fulfill specific metrics. Big picture, sales math has created a sense of X number of these will lead to Y number of this and a Z net profit. This might work in a more mature market, where the need is established and its just a matter of picking the right company. However, I find it varies much more with new products/technologies.

The templates I utilize within my organization are a result of the countless hours being lead and managed by Dave Greenberger at Foursquare. Dave is a huge proponent of keeping it “conversational” and blending personality into emails and cold calls, this has led me to be successful and I continue to utilize this method daily.


With this method it is important to NOT make the prospect feel like engaging in your initial outreach will lead to an hour long conversation or presentation. You should allow and position the email to be a dialogue. n today’s age, where many emails are opened via iphone, short bursts of information and quips can gain trust that will in return set you up to do a more elaborate demo in the near future.


This aspect is a hard one to master. By simply saying you and the prospect went to the same school or the fact you both worked somewhere will not entice someone to buy your product. If you use this pieie of knowledge as an entrance point rather than the number one reason for taking a meeting, you can and will get much better results. You also have to remember that your email, if done right, should lead to a phone call. Dont be the funny guy on email if you aren’t on the phone. Make sure your personality in your email reflects you on the phone/real life.

Example Script: “Noticed you were a Navy guy…. I was an Army Officer in another life..don’t hold it against me!” Then at the end of the email, show some additional personality without saying “take my call, we both were in the military!”


You get hit a million times from a million people who have the “magic bullet” (and I know I have reached out before)

I want to make this as painless for you as possible, instead of a textbook size barrage of emails, I want you to choose your own adventure. Respond with the number that best fits you:

  1. Send me periodic updates on retention and engagement tools you have built for companies like Dominos, Etsy, and Sound Cloud (1-2 per month)
  2. Sorry not sorry, I don’t want anything
  3. I have someone who handles our retention/engagement and will loop him/her in
  4. I handle this and would like to give 30 min for you to give me your best pitch.
  5. Send me more info and I will review when I am beyond bored without WiFi. (insert personal note here, whether it’s a connection on LinkedIn or a comment on their product)

Thanks for your time, London Nagai


Bad news, this is a cold email….good news is I am keeping it short:

  • Improve LTV of Customer
  • Retention and Engagement of user base
  • We can not help with people complaining about free lunches
  • Lyft, Sound Cloud, Trivia Crack, Dominos, Etsy and the list goes on and on of real results
  • I encourage you to try to call my bluff and ask for hard numbers on specific use cases
  • If you never want to hear another message from me respond with “London leave me alone” and I will take the hint. (once again, add personalized message here)

AddiIllustration depicting a phone with a cold caller concept.tional advice:

  • Keep templates for follow ups,many of the same questions will arise with future prospects.
  • Initial outreach, especially in a new market, I suggest understanding your own personal style and creating outreaches that vary.
  • Be unique, be sincere and be you!

Please share any game changing cold email templates that you have utilized in the “art” of cold emailing in the comments section below.