Before we dive into the content this week, I’ve got something special:
Killer opportunity here for talented SDRs.
The mid-market SDR team I’m on is hiring, and my manager asked me to help source some talent. We’re talking one of the most prestigious names in tech, full remote, and you will make six figures if you perform.
This is the type of role that puts your career on fast forward. You get the logo on your resume, take full advantage of the internal training and tools, hit quota hard, and start unlocking serious acceleration professionally and financially.
If you're reading this newsletter, you're probably exactly the kind of rep we’re looking for. So if you want in, DM me on X with a BRAG BOOK (Exactly what that entails below) and I’ll get you on the radar.
Ranked in Forbes World’s Best Employers
Welcome to The Pipeline Press, brought to you by Pipeline Papi, Lindy Boy, Quota Cowboy, Rookie Rep, & Ant Calabrese. 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’s get into it.
How to Build a Brag Book with Pipeline Papi
So you want to break into a top-tier role where the competition is crazy and the odds are wild? Here’s the secret: build a brag book.
The Reality Check
For the last role I applied to, there were 7,000 applicants and only 4 people got chosen. The odds are INSANE to say the least. Most people just toss in a resume and pray. That’s absolutely not the move in 2025 and will get you nowhere.
The best way to land your next role is by building a personal brand that attracts recruiters and hiring managers to you. Inbound leads are king. But if you're not there yet, a brag book is the next best thing, and it's not done by 99% of people applying.
What’s a Brag Book?
It’s your proof of performance. It’s your highlight reel. It’s the thing that makes a hiring manager stop scrolling and say, “We need to talk to this person NOW.”
It takes more than just throwing some statistics on your resume. Everyone’s doing that (and realistically, anyone can make up any number). You need proof of top performance. Real numbers from your dashboard, call recordings, testimonials from managers and co workers etc.
How I Built Mine
Show You’re a Top Performer: I pulled Salesforce dashboards, screenshots of KPIs, call metrics, and team leaderboards to prove I wasn’t just talking big but I was actually doing what my rest,e said.
Include Your Reviews: I added my latest quarterly review filled with positive feedback from managers. If yours is glowing, use it. It’s direct proof of your work ethic.
Capture Shout-outs: I screenshotted every “SDR of the Month” win, every kudos email, and any recognition from leadership. It shows you’re also respected and getting noticed (leadership and promotion potential).
Ask for a Testimonial Video: I reached out to a former VP of Sales and asked for a 90-second video vouching for my coachability and work ethic. Align it with what the new company is looking for.
Put it all together, send it through to a few AEs or hiring managers, and watch what happens. You won’t be praying for call backs anymore I’ll tell you that.
Final Take
Most people don’t go this far. This is EXACTLY why you should go this far. The bar is low. If you do this, you’ll stand out. My DMs are open if you want me to look over your brag book. Let’s make sure you’re the one they pick.
Chronicles of Lindy: Sales Origins Volume 1
What’s good, fam? The Lindy Gawd has been MIA for a few weeks. Real life hit hard: overtime at work, baby on the way, and I’ve got a prize-money pickleball tournament this weekend. No excuses though… I’m back.
Today I want to pull the curtain back on how I actually got into tech sales, why I’m still obsessed with it, and what keeps me grinding.
Rewind to 2021. Post-COVID, everything still felt weird. I’d just finished a master’s degree (useless, but free. honestly a story for another day) and landed what I thought was my first “real” adult job: Management Trainee at a hardware tech distributor in a new state. It sounded prestigious. Turned out “management trainee” = unpaid dues, zero actual training, and a fast-track to burnout.
First stop? Six months in the warehouse. My job was to document SOPs, fix broken processes, and somehow train the crew. If you’ve ever spent time around warehouse lifers, you know the vibe: zero filter, zero Fs given. No judgment; just not the world I grew up in. (Highlight of that era: yes, I did get forklift certified. Still proud of that one.)
After half a year I realized I’d been forgotten about. No path to actual management in sight. Time to take matters into my own hands.
That’s when I stumbled onto Money/Tech Twitter. Somehow I found Kellen (still have no idea which rabbit hole led me there, divine intervention perhaps?), and right around the same time he dropped his course on breaking into tech sales. Simultaneously, I discovered Aspireship. They offered free training and guaranteed job placement in sales if you finished in 30 days. I was so desperate to escape the warehouse that I crushed it in one week.
Next thing I know, I’m remote, repping a startup called Gravy. For the uninitiated: Gravy is a customer-churn recovery service, which is basically modern-day collections with extra steps. Cold-calling people who canceled their subscriptions and trying to win them back. The environment was an absolute meat grinder. Pure sweatshop energy.
It was brutal. Like, soul-crushing some days. But I was finally in tech sales, making friends with the top reps, studying what separated the killers from everyone else, and even booking a couple outbound meetings that turned into real closed-won deals. First taste of that sweet commission? Life-changing.
Things started clicking. I moved back home to be with my girlfriend (now wife), we were house-hunting, and for the first time in my life I was making decent money. We found our dream house, put in the offer, and on the exact day we closed… I got slapped with a 5-day PIP along with 20 other SDRs. The mandate: book one qualified meeting that actually shows, or you’re gone by Friday.
Impossible bar. Everyone got canned. No severance, no warning, nothing.
And that, ladies and gentlemen, is how the tech sales gauntlet treats you sometimes.
But I dusted myself off, kept learning, and here we are, still swinging.
More chronicles of Lindy coming soon. Appreciate y’all for riding with me.
Return of The Mack with Quota Cowboy
What’s good my people, QC has been a bit MIA as of late because of a mix of travel and having to get a surgery done, so ya boy’s been out for the count recently.
We’ll be talking about coming back from PTO/medical leave, because at some point we all have to take some time off for one reason or another.
If you are like me, I genuinely feel bad taking time off. I don’t know why, but when I submit PTO I just feel odd. Sure, they all say “take your time for self-care”, but let’s be real you are being judged based on your performance. So if you are a killer and top of the org, you are probably good and in their eyes “earned it”. If you aren’t, it can be stressful because you don’t know who to trust.
We’ve heard and seen of people being let go due to upcoming pregnancies, sickness, etc. It shouldn’t always be this way, but life ain’t fair.
So before you request or go on PTO, do everything in your power to go scorched earth and blow your number out. Put in longer hours, make more calls, any show of extra effort not only shows your management you are grinding, but it will also ease your own mind for when you take the time off.
I’m definitely the guy that is thinking about my pipeline and numbers when I’m on PTO, so that last point is important to me because then I can truly chill and not be worried for when I come back.
If you didn’t do those steps and are about to return from PTO, then I would show up day 1 absolutely ready to kill. Double your calls, send recordings for feedback, take the initiative so their “eyes” aren’t on you.
I had a prospect that I was going back and forth with right ahead of my time off, I finally booked him the day after my PTO started and when I told my boss he was so stoked. Couldn’t believe I put in the extra time when I didn’t have to.
This is the type of effort you need to show if you plan on taking off some time. Because sales is a “what have you done for me lately” type role, and don’t ever forget that. The loyalty is in the numbers you deliver, and it’s most definitely earned.
Have a great weekend everyone I hope this was helpful and glad to be back!
-QC
The Rookie Rundown: How & Why You Should “Manage Up”
Most new SDRs think the key to standing out is just hitting quota, and if you consistently do that for long enough then you will get promoted. While yes, hitting and exceeding quota is incredibly important I hate to break it to you, there are politics involved as well.
Here’s the truth:
Your performance isn’t only about YOU.
It directly impacts your manager’s performance too.
Every SDR and AE should learn one skill early: how to make your manager look good.
Because when you win, they win & when they win, you win.
Thought I would share some tips on how I like to “manage up”
Keep them informed before they have to ask.
Don’t make your manager chase you for updates, be proactive.
Send short, clear recaps of pipeline progress, key wins, and blockers.
Don’t just bring them problems, bring potential solutions too.
Proactive > Reactive.Give them credit publicly.
If your manager helped you close a deal or coached you through something, say it out loud.
Leadership notices the reps who elevate others, plus everyone loves credit when they help out!!Make their job easier.
Clean CRM. Clear handoffs. No surprises.
When you’re the rep theyneverhave to worry about, that trust compounds fast.
Managing up isn’t about kissing ass.
It’s about partnership and career leverage.
The best reps don’t just sell.
They make leadership’s lives easier & slowly build trust, just like you would in a sales cycle.
Until next week.
Rook ♜
X: @rooktorep
The Dragon’s Lair: Rejection, Confidence, & Why Most People Tap Out of Sales Too Early
One thing you learn quick in sales:
you’re going to hear no a lot. That’s just part of the job.
Most people don’t struggle because they can’t sell, they struggle because they take rejection personally. They start caring way too much about what a random prospect thinks about them, and it makes them timid, hesitant, or needy. All the things that kill your chances of closing anything.
The fix is confidence. Not hype-yourself-up-in-the-mirror confidence, just being solid in who you are and what you bring to the table.
When you actually believe in yourself and the solution you’re selling, you stop reacting emotionally to “no.” You stop chasing. Your tone evens out. Your calls get smoother. You ask better questions. You sound like someone worth listening to.
This is why I’ve always done well in sales. When I get on a call with a prospect, agency, contract, whatever, I’m genuinely interested in what they’re doing. I’m not pushing anything. I’m confident in my ability to help, and it shows. Most of the time, people end up wanting to work with me because the energy is relaxed and direct. No theatrics.
And if they don’t buy?
Fine. It doesn’t affect me at all.
I’ve closed 120+ deals and close to a million ARR at this point. I know I’m good at what I do. I know I’ve helped a lot of companies. One person telling me “not right now” isn’t making me question who I am.
That mindset is everything in sales. Detach from the outcome. Focus on doing the job right:
• Show up prepared
• Ask real questions
• Actually listen
• Try to help
• Be straight with people
After that, it’s on them. Timing, budget, priorities, half the stuff that stops a deal has nothing to do with you anyway.
The biggest shift is not letting a stranger’s decision decide how you feel about yourself. When you stay confident in your ability, not arrogant, know that rejection isn’t a big deal anymore.
And once rejection stops getting in your head, sales gets a lot simpler.
Job Openings W/ Chad Staffsalot
Currently Hiring For
SDRs:
NYC - new grad top 150 school 60 base 90 ote uncapped and commission
NYC - 1 YOE strong preference in fintech - 110 base 130 k ote uncapped
SF - new grad top 50 school 80 base 100 ote
SF - new grad top 25 school or athlete or somewhere in the middle 80 base 135 ote
Main Companies: Office Hours, Meow, Solidroad, Simple AI, Vapi
AEs:
Sf/nyc - comm-midmarket-enterprise aes min 2 yoe as a direct seller at snowflake / figma / vercel type companies (technical product sales)
100-200 base 200-400 ote depending on segment being worked and Yoe.
Main companies: dust.tt, factory.ai, decagon, sequence, unify
Reach out to him HERE on X if you fit any of these descriptions
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.