The Pickle: Volume 28

We survived the heat wave. Now let’s get back to the courts.

What’s better than it being it being 100 degrees and humid you ask?

It not being 100 degrees and humid!
**Do yourself a favor and check the weather for tomorrow, looks a lot better 😉

Last week, we had an epic event. Massive turnout, nonstop games until 10:30 AM, and some seriously good vibes. Huge shoutout to everyone who came out and made it one of the best days yet 🙏

If you missed last week, don’t worry, we’re doing again this Friday. 💥

And then next Friday. And then the Friday after that. And after that. And after that after that.

Pickle lifestyle. Pickle dream. Pickle community.

See you there for bagels + coffee + community. Nothing gets me more fired up. **Maybe even ice cream if you’re lucky 👀

🚨 This Week’s Game Plan:

We’ve got the perfect collaboration to announce 👀 You asked, we listened. What’s the one thing that’s been missing in the summer?

SWEAT TOWELS DUH

But not just any sweat towels. Oso branded sweat towels!!!

Wait what? Oso? What is that? And what is that cool polar bear?

Seriously, look at how cool this polar bear is:

Oso is an authorization platform helping developers build access control into their applications. It provides core abstractions for modeling and iterating on authorization, plus powerful policy tooling and a fully managed service.

Want to learn more?

Come find one of their team members on the courts tomorrow or meet an Oso engineer.

⏰ Show up early. Paddle raffles, sunshine, and coffee/bagels all go fast.

☀️ It’s going to be hot so highly recommend bringing water and sunscreen!

🍦 What would you do for a Klondike bar? What about an Oso bar?

Tomorrow you might just find out. See you there!

🥒 Pickle fun fact of the week

The State Vegetable of Connecticut is the Cucumber (Because of Pickles)

In 1998, a group of elementary school students in Connecticut petitioned the state government to declare the cucumber as the official state vegetable — and they won.

Why the cucumber?

Because Connecticut has deep historical roots in the pickle industry. The town of Fairfield was once a major pickle-producing area, and the state has long been associated with cucumber farming and pickling. The students argued that cucumbers deserved the honor due to their importance in the state's agricultural and economic history, especially for making pickles.

**Does that mean we should move to Connecticut???

🏓 Stuck in a Pickle

Guest Feature: Taylor Martino

Former national champion diver → sales coach to top startups

Don’t scale your sales team like a solo act.

If your reps can’t win without you on the call, you’re not a leader—you’re a bottleneck.

That’s one of the tough lessons Taylor Martino sees early-stage founders and sales leaders learn the hard way when scaling from $0 to $10M ARR. A former elite athlete turned revenue leader, Taylor now coaches Series A and B startups on building sales orgs that actually scale—starting with the right managers, the right comp plans, and the right messaging.

Here are her top 5 tactical truths:

1. Player-coach kills scale.

It sounds scrappy, but when your “manager” is still closing deals, no one gets coached—and growth stalls fast. Designate real managers early (even fractional ones) so your team has someone focused on them.

2. Promoting your top rep? Onboard them.

Don’t throw them into the deep end. Taylor’s 90-day new manager plan includes:

→ Identity shift coaching

→ Clear goals and feedback loops

→ Real 1:1s and pipeline reviews

→ Teaching them how to manage you

3. Comp plans can quietly kill motivation.

BDRs shouldn’t be paid on things they can’t control. Taylor rebuilt comp plans to reward meeting quality—not quantity. The result? Shorter cycles, happier reps, and less micromanagement.

4. Map your pitch to pain, not product.

Buyers don’t care about your features. They care about what hurts. Taylor’s framework?

Message → ICP → Channel → Feedback → Iterate weekly

Validate 3–5 pain-based pillars before you scale outbound.

5. Hire the builder, not the brand name.

Skip the big logos. The best early-stage reps are scrappy, curious, and creative. One of Taylor’s go-to interview tests:

“Pitch me a fake company. Bonus points if it’s weird.”

📌 Final serve:

Startup sales teams are built one strong manager and one smart comp plan at a time. As Taylor puts it:

👟 Learn more about Taylor’s coaching here.

NYC Tech Pickleball update

Theme of the week:

HEATWAVE CAN’T STOP OUR MOMENTUM

That’s all for this week. Smash you Friday.

Bring sunscreen, energy, and maybe… some ice cream 😏

And who could forget the pictures??

Look at all those amazing smiling faces.

Thanks as always to everyone who comes out and makes it special

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

Email us at [email protected] or [email protected]