It only took back to back shitty weather rainouts to be able to say this buttttt

We have never been more back!!!!

It is my honor the finally be able to once again say….

It’s pickle pickle pickle time, pickle pickle pickle time, where ya at? Where ya at? There ya go!

**Like peanut butter jelly time, but infinitely better in pickle form

So let’s get the business out of the way.

Tomorrow morning, McCarren Park, 7:30-9:30 am Free Bagels and Coffee, Good Vibes, Familar Face, Infinite Smiles… and the best way to start your Friday morning:

Outdoor NYC TECH PICKLEBALL IS BACK BABYYYYYY

**We supply paddles and nets, but if you have an extra net you can bring I’ll love you forever (more than I already do)

Okayyy moving on to the fun stuff!

Pickle fun fact of the week: (not really a fun fact but fascinating regardless)

Have you ever heard of the great Lower East Pickle War? Yeahhhh, neither had I, but I went down a crazy rabbit hole this morning and wow, is it fascinating. Basically the only preview, I’ll give you is that it was a war in the early 2000’s that was waged over who was the legitimate pickle heir to Guss’s pickle empire that once ruled over Essex Street.

Just read it for yourself, I promise you won’t be disappointed:

The Great Lower East Side Pickle War

Okayyyy moving on from that… It’s Job Board 🔦 time!

Job Board 🔦

We’re starting a section in The Pickle where we give job board updates and updates on cool stuff happening in our communities ecosystem!

Sound cool right? I’ll let you be the judge for yourself:

Here’s what we have this week:

Sales Leadership - Hebbia

Founding Sales - Basis

Head of Sales - Focus AI

VP of Sales - January

Director of Commercial Sales - Finout

VP of Sales - Flex

Manager Sales Development - Vanta

VP of Sales - Gorgias

Free Money 💰

$500 cash referral - I think John is NUTS for running this - but grab it while you can :)

https://www.linkedin.com/posts/john-diloreto_know-a-sales-leader-who-needs-more-warm-leads-activity-7302744424088784896-m2RL?utm_source=share&utm_medium=member_desktop&rcm=ACoAAAg4ZnUBdSpFNTeb3bGl9GJ0o41qix-mGjs

Stuck in a Pickle: Lessons & Stories from Early Stage GTM Leaders

The best way to unstall stuck deals - Creativity

Once upon a time, I had a stalled deal with no clear next steps. (ever heard that one before?)

So I used the most ridiculous email I could think of to unstall and then close it.

Here it is, enjoy…. (heck, even steal it if you really want)

The context here is I was given a bunch of leads once I started this role that had discovery calls with us but had no clear next steps and stalled out. (1+ year ago)

So after getting intro’d to them via email, I tried my best to produce value driven emails and touch points, but after 3+ months of crickets from this account I sat back in my chair and thought…

What’s the most ridiculous thing that I can send them to get a guaranteed response and clarity on where this deal stands?

And this is the masterpiece that I came up with:

Now why did this work?

Well… first off, it’s kinda funny (at least I think) and somewhat creative.

And it's not just another boring "just following up" email but more importantly it gives them 3 clear options of how to respond and the first one is an easy out!

Now here’s the best part, this person responded to this email, “Thanks, #2 for us, we’re not interested at this time.” I said no worries…. at least I have clarity!!!

Well guess what? Exactly 2 weeks later I get an email from the same person,

“Hey Skyler, massive change of plans, we just adopted Notion org wide and need help ASAP, can you get on a call tomorrow?”

And boom, one month later, deal closed and their Notion workspace was on it’s way to the promised land 🤠

Lesson here (I think) is be more creative and shoot more shots.

***the subject line was "Don't Hate Me But"

Other note, with stalled deals, this email gets a ~30% response rate, try it for yourself!

NYC Tech Pickleball update

Theme of the week:

We are so freaking back baby!

Overheard quote of the week:

“I was depressed all winter without Tech Pickleball but now I’m back to being filled with happiness. I LOVE TECH PICKLEBALL”

Excited to see everyone tomorrow!!

Excited to add a picture in here soon!!

I will be rocking the pickle hat as always. If you want to chat, it will be borderline impossible not to be able to find me 😊

Andddd that’s a wrap!

We reallllly value your feedback and want to make this the best newsletter ever to support the community. Plz plz give us your most honest and blunt feedback on how we can improve it. We do this for you ❤️

Ps, know anyone who might be interesting in partnering with Tech Pickleball?? Hit up me, John or Tech Pickleball to discuss! We want to find more creative ways to expand and grow this community through awesome partners 🙂