moving upmarket and missing my pitch

had a tough week in outbound this week. we are moving upmarket and my pipeline has had to adjust for that. it has been challenging but ive been able to experiment in the midmarket space. im thankful that weve been pushed in this direction to go after bigger opportunities. im excited to see where we end the month as a team.

Kondo: Superhuman for Linkedin DMs has paid to be mentioned at the end of this post. Thanks, Mitchell, for being the inaugural sponsor.

i wanted to highlight a dm interaction this week that felt really natural to personalize. not because aj was an “easy” target, but because his profile gives you a lot to work with. it’s colorful, it has personality, and the “taco sommelier” headline practically invites a more human opener. the message ties directly into how he presents himself, so it feels personal without forcing anything.

the key moment is calling out why i reached out. most people already know when a pitch is coming, so naming it lowers the tension and keeps the conversation comfortable. it turns a sales message into a real exchange instead of something transactional.

even though my pitch wasn’t strong, the rapport we built up front was enough for aj to ask follow up questions. that’s what moved this to a set, not the quality of the pitch itself.

looking back, i should have kept the pitch tighter and followed it with a simple discovery question. i also needed to tie everything to a clear outcome instead of feature dumping.

if the opener creates momentum, the rest of the conversation has room to breathe.

im using kondo here, by the way. you can use this link try it for a month for free. this is a great way to support me directly. :)

this week’s pick is dylan burritt. when i met him, he was graduating college and getting ready to move to california for his role at vanta. he liked the job. it wasn’t easy, but it was doable. and most people would have stayed on that path because it was the safe thing.

dylan didn’t. he left the safe thing to do the risky thing. he wanted to build. so he took a founding sdr role at span. the dude wanted to build and now he’s building.

span just raised their series a and dylan is clearly loving the role and thriving under the pressure. he’s doing an amazing job and he knows how to tap into his network to cover his blindspots. i admire him a great deal and i’m thankful to call him my friend.

go check out his journey. i’m sure he’d love to chat.

be yourself on linkedin

when you post, dm, or comment, be the same version of you that shows up everywhere else. if you aren’t being yourself, this is going to get really hard to keep up. wearing a mask every day is exhausting.

when you’re yourself, there’s almost no friction between you and the platform. the conversations feel easier. the ideas flow faster. people can actually connect with you instead of some polished version you think they want.

don’t play it safe. don’t sand the edges down. just be you. be militantly authentic.

most ant species will adjust their walking speed by up to 12 percent to match the pace of the ant directly in front of them.

kondo is supporting this issue, so i’ll just share one of the features that keeps me using it. it gives me a clean list of all of my connections. i can filter by those i haven’t messaged yet. linkedin doesn’t make either of those tasks easy. i hope you check it out. heres the link again for that free month.

you can see below that these are all of my connections where i havent had a conversation with yet.

by the way, i pretty much wrote this entire letter with chatgpt. if you want to see the process for the sake of transparency, here’s the thread where i built this issue. feel free to check it out. see you in 2 weeks!