You can send brutally simple emails
I think a lot of salespeople get tripped up overthinking their emails.
The simplest way to become a better “emailer” is to write like you talk.
For example, a real follow-up email I sent this weekend:
That’s literally it.
Context on this deal:
This customer was “Closed Lost” earlier in the year
Checked in with him over email a few weeks back
Spoke to him last Thursday
Friday morning, emailed him following up
Sent the above message Sunday after I hadn’t heard back
Got a great, engaged response, went back and forth
Signed last night
Now, sure. I own the company with my partners. The customer is a founder. It’s sort of “exec-to-exec” so maybe you’d modify your approach slightly based on your and your customers’ roles, but the general idea should be clear: people like a relaxed, confident selling style.
Like if I were an AE emailing a similarly senior buyer, I might send something like the following as a follow-up to a bigger email:
Curious your thoughts coming out of our convo Thursday?
One of the most powerful sales skills is being able to follow up relentlessly to move things along without the other person getting annoyed. This vibe of email is a good one to add to your bag of tricks.
Let me know what you guys think about these email examples as a common topic in the newsletter. Been getting a lot of positive feedback on them. Good way to stretch everyone’s thinking and get new ideas.
LIVE sales training next week (signup link)
Feels like every sale is competing against “my CXO wants us to try and do this with Claude first…” or “we’re gonna try to build this on our own…”
But the tide is turning. The best teams are consistently overcoming this.
Luke and I are going deep on the details:
Real talk tracks
Visuals you can show your customers
The main overall strategy to get your customer to PREFER to buy
Join us next Tuesday, October 20 at noon Eastern on Zoom: SIGN UP HERE.
(Missed last week’s training on using repetition to persuade? Recording on YouTube here.)
Stop looking sloppy in interviews →🤵
Look, this is a bit of a third rail issue, but one of our main motivations at the firm (and in this newsletter) is to truly help salespeople land great jobs.
These mistakes might not tank a candidacy on their own, BUT they definitely hurt perception and should be avoided.
An outfit that’s not calibrated at all for the role (e.g., workout clothes for a buttoned-up enterprise role)
A totally plain white wall with cold white lighting that looks like an interrogation room
One of those fake digital Zoom backgrounds (even blur isn’t ideal)
Bad lighting (backlit, or sitting in the dark)
Bad internet or bad audio (not always controllable, but you should test for key interviews)
Camera bouncing around a ton
Fans going or anything moving in the background
Other people in your Zoom background
Background noise from a coffee shop / public place (unless pre-informed with good reason)
Not turning video on right away, almost like it's reluctant
Zoom name that's anything other than your full name (no initials, first name only, etc)
Bringing your own AI notetaker
Looking like you're reading answers off the screen
These are all within your control, which is what rubs a lot of hiring managers the wrong way.
Let me know if there are any others you think I should add to this list in future!
Housekeeping
We’d love to connect with you (or someone in your network!) if you’re:
Breaking into tech sales or making a career change - we’re always happy to connect with aspiring sellers, in NYC or remotely.
An AE in NYC - all experience levels.
Looking for your next remote AE role - lots of founding, MM, Ent AE roles in the mix.
We’d also love to hear from you! Anything we can do to make the weekly email better?