It’s a BAAADDD day to be a pickle.

First things first - to join us next week, you’ll need to sign up for the Partiful: https://partiful.com/e/L7DM3gA500xzhGxQKoNH

Ok, now strap in, Ladies & Gentlemen, Skyler’s fingers hurt this week, so I’m filling in.

I bought these pickles last night in the supermarket in Greenpoint. And let me tell you, they absolutely slap.

You know what else does? Having unlimited contact data at your fingertips for prospecting. Outbound can be a total pain. Don’t make it any harder on yourself. That’s why we’re pumped to team up with Apollo.io next week for NY Tech Week.

We’re back at it again 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:

Who will we be seeing there tomorrow?

Moving on to the fun stuff!

Shout out to Tech Pickleball member CJ for sending this my way.. Did you know there is a brand called good girl snacks that sells “Hot Girl Pickles”?

https://goodgirlsnacks.com/collections/all

I guess they thought pickles needed a glow up. Wild they are SOLD out.

Anyhow, they sell pretty fire merch. Skyler where is our Merch!?

BUT WAIT THERE’S MORE

🌮 Taco fun fact of the week:

The hard taco shell was actually invented in the 1940s by a Mexican restaurant owner in New York who was trying to make tacos easier for Americans to eat without making a mess. Traditional Mexican tacos are served on soft corn tortillas, so those crunchy U-shaped shells that many people think of as "classic" tacos are actually a pretty recent American innovation! Even crazier - Taco Bell didn't serve soft tacos until 1988, almost 30 years after they opened. They finally caved to customer demand, but by then they'd already convinced millions of Americans that tacos were supposed to be crunchy.

Wait a second…

Why was there a Taco fun fact of the week in the pickle newsletter you ask?

Great question!

That’s would be because HeyTaco is this months Tech Pickleball sponsor!

What the heck is HeyTaco you ask?

HeyTaco is the easiest way to show your teammates some love. Drop a 🌮, make someone’s day, and build a better vibe at work—just like that.

Check them out at HeyTaco.com!

**I promise they’re the most fun work app on the planet and yes I will debate you on this

What’s something cool you can do with them? I’ll give you two of my favorites!

Taco Tuesday!

Taco Leaderboard? I’ll just go ahead and drop this tortilla here for you: Heytaco.com

I have more stickers than you can imagine and might have some special swag for you this Friday.

Come up and ask me about it! 👀

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

Last week, Company Ventures asked me (John) to talk to their new Spring Cohort about Enterprise Sales. Here are the two nuggets of wisdom I shared:

🧭 Network within the Org

(Example: CloudKitchens)

• Get multiple people at the company involved early

• A buyer champion is rarely enough for a larger org to buy something

• Every new contact is currency — use that trust to branch out

• Spin up a shared Slack/Teams channel (early!) and start embedding yourself

• Be a helpful, responsive partner — make it easy to keep you around

Real example:

At CloudKitchens, we didn’t just sell to one person.

We built relationships with stakeholders across operations, technology, and finance.

Eventually, the deal became a no-brainer — because everyone felt invested.

🎯 Co-Sell

(Example: Juice Press)

• Design the ideal solution — and bring partners with you

• Vet integrations, sketch workflows, and deliver the combined pitch

• Become the easy, no-brainer option for your champion to rally around

Real example:

At Juice Press, we didn’t just pitch our software.

We designed a full solution — combining GoParrot + Square + MarketMan.

We mapped the rollout, tested integrations, and made sure it all worked together.

Our value wasn’t just what we did.

It was how we made the whole stack work — so they didn’t have to.

JD

NYC Tech Pickleball update

Theme of the week:

RAIN RAIN GO AWAY!

Overheard quote of the week:

“Tech Pickleball is like sunshine on a rainy day”

Excited to see everyone tomorrow!!

We’re going to do some fun content if anyone is interested come find us!

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