Emailing Executives: Be the Cool Rep

Emailing Executives: Be the Cool Rep

SaaS and tech sales can be a cold, dark realm, and with tech companies sprouting daily, it’s easier to stand in with your selling peers than not. There are numerous reps at numerous companies reaching out to the same target accounts and the EXACT same contacts at the EXACT same time as you. Sure your product has differentiators, and sure your elevator pitch is butter on every cold call, but are you cool?

The most impactful piece of advice I ever got from my first VP, Sales – a very compact and snarly executive – was during a mandatory after-hours training session with under performing reps. At random, he chose reps to role play cold calls, acting as our target contact, a VP of Sales. After a small handful of boring and mirrored attempts, he stopped the exercise with transparent annoyance in his voice.

“Stop it. Be the cool rep,” he said. He continued by sharing his phone screen displaying a packed calendar with more overlapping appointments than a collage poster. He challenged us, “How are you going to make your way into this schedule, huh? – By being the cool rep.”

To me, being cool is a magnetic characteristic that more often than not can’t be pinpointed to a single trait, but is an aura of charisma all the same. Maybe it’s what someone does, or how they do it; but either way it works, it’s liked, and it makes others want to do it too, or at the least be associated with those perceived as cool. In short, being cool is to be successful at being standing out while drawing people to you and your cause.

Being cool is a magnetic characteristic that more often than not can’t be pinpointed to a single trait, but is an aura of charisma all the same

If you sound like every other sales rep with a basic one-liner jammed with Tech’s catch phrases of the quarter, with a voice that sounds nervous or worn from 30 prior cold calls that day then “you’re f*cked,” as our said VP would recite in forecasting calls. You have to make the person on the other end want to talk to you, and you do so by being cool.

It starts by being you. Trying to be something or someone you’re not will be detected by senior execs instantly, and they’ll brush you off like dirt on Jay-Z’s shoulder. You were hired at your current role not just because your LinkedIn looks great, but because there’s something about your personality that the hiring manager liked, most likely something similar to why you have friends to hang out with on the weekend. You bring something unique to the table. Maybe you’re brilliant, funny, relate with others quickly, whatever. But whatever it is use it.

I have a healthy self-awareness as being witty – it’s just a part of who I am and always have been. But when I started my sales career, it was like I left my personality on my side of my iMac and sent the most boring and grammatically correct emails – emails so bad that even my sales director asked if I wanted to be in legal services because “Not even our corporate lawyer writes emails this dry.” Not until my VP told me it’s okay, and even encouraged, to be the true me did it click that my response rate was low because my approach mirrored those in the middle of the pack – those who were too afraid to be cool.

It took some time and quite a bit of trial and error, but after a few shrugs and a muttered “F it” to myself before clicking Send did I build the confidence to send emails I would want to read – emails that break through the noise of a rushed and overcrowded day in the life that is senior management. Setting meetings and connecting via cold emails is still challenging, but I can say my response rate has increased dramatically from those beginning days, and now I make sure that my emails, whether short or long, have myvoice in it. What I write might not always land (or even be read), but my messaging is my unique flavor instead of the bland tasteless emails sent in bunches daily that are ignored and deleted.

To see examples of cool emails via social selling, check out “Social Selling: 3 Emails that Work." 

-Devin Reed

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