I’d hate to share wins back to back but a desperado just posted a 6 figure paystub
$196k NET for June
#1 tech sales community in the world
Keep leading from the front
Alright I’m pretty sick of answering ‘how get tech sales job’ and resume questions
So here is the playbook on how we’ve helped hundreds of people since 2023 land tech sales interviews and job offers
How to write and position your resume wether you have sales experience or not and the strategy to secure more interviews
Comment ‘Trust Fidel’ below for Guide
Make sure DMs open
We tell ourselves we are being responsible by waiting for the housing market to settle, the cost of living to drop, or the bank account to hit a certain threshold but if we are brutally honest, blaming the economy is often just a socially acceptable form of Peter Pan syndrome. It’s a way to prolong the comfort of adolescence under the disguise of financial prudence.
The heaviest regret is looking back and realizing you traded your prime energetic years of fatherhood for an illusion of perfect timing that never actually arrives.
The secret is that you do not build the kingdom in order to have the children having the children forces you to build the kingdom.
When there is a family depending on you, the stakes fundamentally shift. You can no longer tolerate your own complacency. The pressure does not break you it demands that you level up your earning power. Securing the home, accelerating the career, and expanding your capacity stop being distant, "someday" goals and they become non-negotiable, immediate necessities.
Before kids, it is easy to drown in the noise. We burn immense energy on directionless anxiety, constantly asking, "What is my purpose?" or "Am I doing enough?" But the moment that absolute responsibility lands on your shoulders, that ambient dread simply evaporates.
The mission becomes ruthlessly clear. You no longer have the bandwidth for low-value distractions or existential doubt, because your purpose is sleeping in the next room.
My biggest regret is planning to have kids at 29 and not being “done” with kids at this time. In my opinion you should ideally have your first kid the first or second year into your professional career if you went to university maybe that’s 22 or 23, if you want into the trades even younger 19-20.
Not to mention by the times kids are out of the house married or independent you still have golden years to live with your suppose versus being 65 at your sons college graduation or maybe dying before watching your daughter walk down the aisle
Addressing the industry bigwig attacks on my community, Fidel and the concept of SDR job stacking.
I fully understand the panic from founders, thought leaders, and sales leadership. Job stacking SDR roles is a bold, disruptive concept.
It’s also exactly why "Fidel" remains anonymous.
Let’s be honest about why this "grey market" exists in the first place: Industry inefficiency.
When the standard SDR comp is still $80k pre tax for a fresh grad while inflation and the cost of living skyrocket, the market forces a correction. Wages haven’t moved in years, yet corporate earnings are at all-time highs. (I hate to sound like the real Fidel, but the math is what it is).
Are there bad actors? Sure. But my community has clear guardrails. We don't screw over employers. Our goal is to overdeliver for every client legally and efficiently. It’s more sustainable, and frankly, it makes more money and I’ve clearly documented this since inception
And let's clear up the legality of stacking 1099 contracts, because leadership seems confused about tax law.
Working multiple 1099 roles isn't just legal it is the IRS definition of an independent contractor. When a rep operates as a 1099, executing this active remote arbitrage through their own LLC, they are engaging in a strict business-to-business transaction.
The IRS explicitly states that true independent contractors must have the freedom to offer their services to multiple clients simultaneously.
If a company demands 40 hours of exclusivity, they legally have to hire a W-2 employee and pay for their benefits, taxes, and overhead. You cannot pay 1099 contractor rates and illegally demand W-2 exclusivity. That is misclassification.
The reality is, if leadership actually wanted to fix their broken pipeline models, they only have three real choices:
1. Rid the system of the role entirely due to its inherent W-2 inefficiency.
2. Develop real AI agents that can actually produce at a human level.
3. Transition to fractional 1099 contracts. Let's be brutally honest: with the right workflows, tools and strategy an SDR job is a 20 to 30 hour week role.
Since leadership has no clear answer and refuses to adapt, this arbitrage exists.
We are here strictly because of market inefficiency.
We exist due to leadership incompetency, a lack of wage adjustments for inflation, and a stubborn refusal to stay up-to-date with tools like TaskletAI, ChatAE, and Trellus that actually make reps hyper efficient.
Don't get mad at the Stacking arbitrage.
Fix your inefficiencies.
B2B tech sales doesn't just need a slight pivot or another thought leader's coaching framework.
The industry needs a revolution.
There's a reason the alias is Fidel Cache Flow. The revolution is already here, Fidel is here whether leadership likes it or not
Closing my first $100k+ ARR deal in Tech Sales was a reality shattering moment and forced me to realize these hard lessons about money, its value and spending:
1. The Scarcity Illusion
Growing up, ur taught that money is incredibly hard to get and must be fiercely protected. Then you watch a VP or CFO sign off on a $120,000 software purchase without even reading the fine print at 11pm with less emotional friction than a normie experiences buying a used car. You quickly realize that scarcity is a localized and lower and middle class coded. At the enterprise level, capital isn't scarce at all its just sitting in massive, stagnant pools just waiting to be deployed by anyone who can prove it will generate long term leverage
2. Subjectivity of Value
To an individual, $120k is life-changing amount of money like a massive down payment on a house or literal annual salary. To an enterprise, $120k is a rounding error to plug a minor operational leak. You realize that the "value" of money has nothing to do with the amount of zeros and everything to do with the balance sheet of the specific entity spending it. You stop being intimidated by large numbers because you aren't asking for their personal money you are just reallocating corporate friction-reduction budgets that are waiting for you
3. The Singular "Decision Maker" lie
In SMB, you pitch founder or VP who can swipe a corporate card based on intuition or a good relationship. Crossing the six-figure threshold shatters that dynamic. You realize you are no longer selling to an individual ur selling to a risk-averse consensus. The strategy shifts from "how do we get this person to like the product?" to "how do we build a bulletproof business case that protects my champion from internal blowback?" You realize the real gatekeepers are the silent stakeholders like Legal, InfoSec, and Procurement who don't care about your features and only care about risk mitigation and the business case
4. HPP becomes mandatory
When you understand the sheer amount of organizational friction required to push a six figure contract across the finish line, you permanently abandon "spray and pray" outreach. Dragging a lukewarm, low-probability account through a 4 month enterprise cycle is a mathematical death sentence for your quota. Your entire top-of-funnel strategy narrows. You learn to execute High Probability Prospecting, exclusively targeting accounts where the macro environmental triggers, structural changes, or operational bleeding are so severe that the cost of doing nothing heavily outweighs your $100k price tag
5. The "Risk vs. Cost" Reversal
You learn that in the upper echelons of corporate spending, buying the cheap option is actually viewed as a massive career risk for the buyer. If a VP buys an unproven $20k tool to save money and the deployment fails, they look incompetent and risk their job. If they buy the $120k undisputed premium solution and it fails, they can safely blame the vendor. The realization is that premium pricing is a defensive feature, not a bug. Your high price tag signals structural safety, infrastructure, and certainty to the board
6. The Velocity of Urgency
A $10,000 deal stalls indefinitely because it isn't important enough to demand executive attention. A $100,000+ deal, once aligned with a critical, board-level mandate, can move with terrifying speed. You realize that corporate urgency is entirely dictated by the size of the fire.
Once the illusion of scarcity breaks, your sales execution fundamentally shifts. You stop negotiating against yourself before the proposal is even sent.
The psychological barrier of asking for a 6 figure signature vanishes bc you understand the mechanics of corporate capital.
This realization instantly hardens your pipeline criteria.
The desperation drops. You stop bending over backward for $15k pilots that drag on for 6 months that kill your quota and start practicing ruthless deal disqualification
The "sales guru" industry is financially incentivized to treat every symptom as a skill issue gap. If they admit that a reps core issue is just a terrible list or bad targeting, their 12-week objection-handling masterclass loses all its value.
It’s way easier to sell a magic script or a closing framework than it is to teach the grueling, unsexy work of high probability prospecting.
You can have a top rep with world-class psychology, flawless tonality, and perfect objection handling but if they are pitching an enterprise solution to a cash-strapped start up company with zero internal infra, they will lose 10 out of 10 times.
Conversely a completely average green rep who accidentally gets in front of a buyer who actively has the problem, the budget, and the immediate trigger event can stumble their way into a closed-won deal just by showing up with an order form
The industry loves to over-index on what happens during the call because it looks good on a whiteboard and TikTok video
the reality is that the game is won or lost before the first dial is even made. If you aren't ruthlessly filtering for accounts that actually have a high mathematical probability of buying, you're just forcing reps to brute-force a broken pipeline
How I Went from Army Officer to Tech Sales Account Executive 🧵
There aren’t many jobs where you’re immediately thrust into leadership with the autonomy to shoot guns and blow stuff up.
But military life isn't a 20-year plan for everyone. When it was time for my next chapter, I decided to try my hand at tech sales. Here is the exact playbook I used to transition:
@Hamnrye275024@ElBuho03 And I quote
Don’t have these?
Don’t worry. If you have their full name, date of birth, and the town they were born in, our team can take it from there.
Wrong guy
Made a million off corporate
Exited the game unscathed
Gave back lessons to the game
Made another million off info
I’m on my victory lap retard
Every person got their first sales job without experience. Utilize your background and resume and tailor it for the sales position you’re applying for by showcasing how you have the behaviors and traits of sales person even without the direct selling experience. Thinking about soft and people skills. Leadership, project management, communication skills ect
TODAY IS THE 3 YEAR ANNIVERSARY OF THE DESPERADO SALES GROUP
What started as vision to share notes for tech sellers firmly remains the #1 tech sales community in the world representing 2,600+ lifetime members, with 612 active spanning 27 countries & 6 continents
Looking back at where we started and seeing where we are now fills me with so much hope for what we can build next.
Hitting 3 years and reaching this global scale is a massive milestone, but more than anything, it's fuel. It challenges me to level up my own leadership, stretch my own vision, and set an even higher standard of sales execution so I can continue to give you my absolute best.
If we are going to win, we are going to win together at the highest level possible.
To say thank you, and to help you map out your own ambitious path for the back half of the year, I’m opening up access to DSG for $10 for the next 24 hours.
This is my way of giving back to the broader tech sales community and token of appreciation for your support thus far
We have some massive goals for the back half of the year, and we are completely re-engineering how we deliver value to ensure this ecosystem stays at the very top. Here is the road map for where we are heading:
High-Value Guest Speakers & Group Calls: We will continue to deliver massive insight with top-tier heavy hitters dropping knowledge and dedicated DSG group calls covering critical career and sales topics.
The Transition to the DSG Course Format On 8/1, we are officially shifting to a structured course format.
I have consolidated every single Telegram chat, DM, Tweet Thread, and over 1,200 hours of private 1:1 Zoom consults to build what I believe to be the best tech sales course available on the market.
A Consolidated Slack Community: Alongside the course, the community will be streamlined into a single, high-signal Slack group chat supporting all reps across the ecosystem: BDRs, SMB AEs, and SDR Contract Stackers alike. (Note: We will not be grandfathering pricing or cohort alumni into this new course format).
The FidelAI LLM Bot (Fall 2026): The new course format serves as the exact functional building block for FidelAI, which we expect to go live later this Fall. This custom LLM bot will be integrated into the ecosystem to give you on-demand strategy, framework breakdowns, and roleplay support based directly on our proven methodology.
It’s been a wild, unforgettable ride these past three years, but we are truly only just getting started. I am genuinely excited to see how this community transforms and how many more lives and careers we can impact as we scale into the future.
Let’s continue to innovate the industry, stay on top of the leaderboards and prove the industry wrong about earning potentials, promotion timelines and pushing the envelope on what’s possible
Thank you all for being the heartbeat of the Desperado Sales Group. Let’s get to work.
Scroll Linkedin
“Cold calling is dead”
Scroll DSG
“Hey man. Set 5 meetings this week already. Appreciate the advice”
Completely different worlds.
You choose who to surround yourself with
1. Sort, Don't Sell
Stop trying to convince or persuade people who don't care.
Your job is to sort the market, not convert it. Detach from outcome: identify prospects experiencing the specific pain you solve right now, qualify them in, and immediately filter everyone else out
2. Reverse-Engineer the CRM
Do not wait for standard onboarding to incorrectly teach you who your buyer is.
Go into the CRM on day one and analyze every closed-won deal from the last 12 months. Identify the exact signals, trigger events, tech stack, and buyer personas that led to revenue, then clone that profile
3. Focus on High-Probability Triggers
Blasting generic, cold lists is a waste of your time, accounts and territory.
Prioritize accounts showing active buying signals like executive leadership changes, specific job postings, or company expansions. Craft your outreach around a hyper-focused Point-of-View (POV) hook tied directly to those specific triggers
4. Mine the "Closed-Lost" Graveyard
Pull CRM report of all deals marked "Closed-Lost" 6 to 12 mo ago due to timing, budget and competitor.
These accounts are already educated on your product, and a reset budget cycle or a failed competitor implementation makes them prime targets for quick wins.
5. Build Elite Pipeline, Not Just Meetings
Never throw low quality, and unqualified meetings over the fence just to hit an activity quota metric for your company.
Partner closely with your Leadership and AEs, understand what a highly qualified opportunity looks like, and protect their calendar. Delivering clean, high-probability pipeline builds the internal leverage required to fast-track your career.
6. Accelerate via Profiling Calls
The fastest way to lvl up your cold calling and prospecting skills is through rapid exposure via profiling calls.
Dial into accounts purely to map out their internal structure, validate ICP, verify tech stack, and identify decision makers. This high volume, and low stakes approach quickly desensitizes you to rejection and sharpens ur sword before pitching C suite in your high value Tier 1 account targets.
7. Clone Top Performers
Do not reinvent the wheel.
Connect with the top two reps on your team immediately for exposure to their workflows and digestion of their "alpha" their exact sequences, custom POV hooks, and daily workflow routines. Borrowing an already optimized, winning infrastructure is the fastest shortcut to quota attainment and propel your career advancement.
Hope this helps.
Go be great