Landing an SDR Dream Job, A Startup Bet, Tech Openings, & Cold Call Come-Ups

Before we dive in this week, we want to take a moment to send prayers to Charlie Kirk and his family. Times are tense right now, and moments like this remind us how fragile everything really is.

Check in on your people. Hug your loved ones. Reach out to the ones you haven’t talked to in a while. Cooler heads have to prevail, and it starts with our actions everyday.

Welcome to the very first edition of The Pipeline Press, brought to you by Pipeline Papi, Lindy Boy, Quota Cowboy, and Rookie Rep. Every Friday, you’re getting stories, tips, job openings, and a little lifestyle drip to keep the edge sharp and the mission clear. PROMOTION, QUOTA, EARNINGS. Follow us on X if you aren’t already, we are all very active in the tech sales space if you want to continue the convo or have any questions.

Let me kick off our very first Pipeline Papi Press with a wild story about how I turned tweeting into a ticket to my dream job.

It all started with a tweet from one of the biggest names in the tech sales community on X. He posted that his company was hiring and that top SDRs were making $50k a quarter. If you had the numbers to back it up, he wanted you to DM him.

So I did. I sent him everything, my Salesforce leaderboard showing I was the top appointment setter, a couple of shout-outs from my manager, a testimonial video from my old company’s president of sales, and my latest quarterly review. Basically, I threw the kitchen sink of proof at him.

He liked what he saw and got me an interview. I prepped like crazy, read everything about the company, scoured RepVue, watched interview tip videos, you name it. They were super AI-forward, which gave me a chance to show off the Pipeline Papi SDR Bot I’d built. That definitely scored me some points.

But the journey had a twist. I did a mock call and honestly, I blew it. I pushed for the wrong product and thought I’d lost my shot. Luckily, because I’d built a relationship on X, the guy who referred me went to bat for me. They put me on the bench basically, which is their shortlist for future hires.

I figured that was it. I was bummed but kept tweeting daily as usual. Then out of the blue, someone else DMed me. Turns out he ran a team at the exact same company. We chatted, thought I was a fit, and just like that, I landed the job. None of this would’ve happened without building Pipeline Papi and putting myself out there. That’s why I always say: Don’t just lurk. Create, connect, and you never know what’ll happen.

Moving forward I’m going to be walking through how I built up an account, created content, utilized AI, perfected the right tone and voice, and how I networked on X to create real opportunity.

Hey lads, it’s your boy Lindy. First off, thanks for supporting the newsletter week numero uno. We have so much good #alpha to drop your way.

I am starting week 1 with my favorite piece of advice to SDRs. BE LIKABLE. Sounds really simple, right? You’d be surprised how many people fail this simple test.

You know who gets promoted when it’s 50/50 between two people? The guy who the boss likes better. Who gets the best leads or warm leads that were previously worked? The guy who the boss likes better. SDR’s who generally succeed, also have great relationships with their AE(s).

Reply quickly to Teams/Slack ALWAYS. You work remote, the longer you don’t reply makes it seem like you aren’t working.

Sales team meeting advice: When they ask for your update, find a way to credit your manager. “We got X meetings based on Y strategy that our manager implemented.” The more you hype them, the more they know YOU are on THEIR team. And it will pay off.

Simple actionable advice friends. Trust Lindy!

Howdy ladies and gentlemen. It’s Quota Cowboy. We’re kicking off this portion of the newsletter discussing what we are all looking for these days. A ton of risk!

Jokes aside, I am starting my new role at a Series A startup this week. It’s by far the riskiest move of my professional career thus far, but the upside is definitely there.

For newer folks to Tech Sales, you have your large orgs like Oracle, your mid-sized shops that compete for the same clientele, and then the land of startups. To me, when looking at startups as a potential landing spot, it really matters about 1. Product & 2. Are they pre-revenue or making money?

In my case, the startup I’m joining is actually making money, with about 100 customers. This was a key point for me, as the entire part of my job can really be about helping scale and building up to the enterprise level.

I’ll be giving periodic updates as my journey in StartupLandia continues, but for the duration of this newsletter, I will be reaching out to elite AE’s & SDR’s across the Tech Landscape. How they got started, how they moved up and got promoted, and their perspective on what is moving the needle, and most importantly, how to keep leveling up your game and break into new, badass roles so you can retire your lineage.

As the great Roman Roy would say: “Everything’s high risk if you’re a pussy.”

Being an SDR is one of the most simple, yet toughest jobs. Our whole job is to book meetings. When you boil it down - that is it. Book meetings.

However, that can hurt SDRs more than it helps them.. sometimes.

One of the earliest lessons I learned as an SDR: Not every response needs to turn into “What time works for you to meet?”

Here is the typical inexperienced SDR mistake:

Let’s say you finally get a reply. Great. Then they immediately push for a meeting. Then the prospect goes cold. And the SDR continues to hammer them with follow-ups & pushes them further away.

With that being said, there are times when it is a good thing to ask for a meeting right away. I do it. I will continue to do it. But oftentimes you need to have the information present for it to make sense to ask for the meeting.

Here’s what works better: playing the long game

This re-engages them, builds credibility, and most importantly, BUILDS VALUE.

Remember, we are more than just “meeting setters.” We’re value creators first. The best reps don’t treat every response like a finish line, they treat it like the start of a greater conversation. Play it smart and the meeting will come.

Currently hiring for:

Reach out to him here on X if you fit that description.

P.S. The Pipeline Papi SDR Bot is live. Your SDR copilot for custom cold call scripts, objection handlers, discovery questions and more, for EVERY Prospect. Built to make booking meets 10x easier.