FIDEL CACHE FLOW ARCHIVE

Enterprise Software Sales, Run a few 6 figure WiFi biz

[FIDEL CACHE FLOW @FidelCacheFlow]

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

[FIDEL CACHE FLOW @FidelCacheFlow]

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

[FIDEL CACHE FLOW @FidelCacheFlow]

The traditional path to upward mobility in the UK and Canada is dead. Hyper-inflated cost of living, brutal tax brackets, and stagnant wages make standard corporate tracks a mathematical trap. Job stack entry-level SDR/BDR roles to push your effective earnings to $100–$200/hr. Do not fall for the "high-ticket closer" trap 100% commission gigs lack stability, corporate infrastructure, and consistent lead flow. You need the predictable base salaries and established systems of tech to fund the operation. 1099 Tech SDR roles carry base salaries (typically $50k–$70k USD base, plus OTE) without requiring sales experience and location freedom. Stacking two of these immediately guarantees a six-figure USD baseline before a single meeting is even booked.

Once the SDR contracts are stacked and your calendar is operationalized, use the remaining time to spin up actual WiFi money businesses. Keep the active remote arbitrage paying the bills while you build pure productized income streams (like info products, affiliate or e-commerce) in the background.

Relocate to LCOL areas like LATAM. You maintain perfect time-zone alignment with North American markets while dropping your living expenses to the floor. Earning strong fiat while spending in a low-cost-of-living environment allows you to aggressively hoard cash. Take the massive delta between your stacked income and your LCOL expenses and buy your freedom. Within a few years, you will have the liquid capital to either build a new life via overseas visas and citizenship programs, or return to your home country with enough cash to completely bypass the local debt trap and afford assets and the cost of homeownership outright.

The traditional model of buying a house on a single corporate income is structurally failing in these markets. Historically, a normal house-price-to-income ratio is 3x to 4x. In 2026, the average UK ratio sits at 8.2. In London, it requires 10.6x the average earnings. The average home in Canada hovers near $676,000 CAD. In major economic hubs like Ontario and British Columbia, over 25% of households are spending more than 30% of their gross income purely on shelter costs, completely suffocating their ability to save or invest. 

It’s time for radical action

[FIDEL CACHE FLOW @FidelCacheFlow]

17 dials a day

223% quota attainment

Power of High Probability Prospecting

Fantastic work, keep going

[FIDEL CACHE FLOW @FidelCacheFlow]

This type of stuff keeps me motivated

Made possibly by SDR contract stacking

Proud of you bro

[FIDEL CACHE FLOW @FidelCacheFlow]

If you’re born working class, youre taught to keep your head down, grind for scraps, and not question the narrative. That mindset gets drilled into you from day one family, school, friends, all reinforcing it. To break out gotta unlearn that conditioning that voice telling you to stay small, stay safe, stay loyal to the struggle. It’s not just about making money it’s about rewiring how you think, talk and carry yourself to even get a seat at the table with the top echelon. Be honest the rich don’t just let you in cause you’ve got a Ferrari and prestigious job. They’re gatekeepers, sniffing out whether you’re ‘one of us’ You’re working class roots stick to you like grit..your accent, your manners, the way you don’t know which fork to use at their fancy dinners. They’ll smile, but they’re watching, waiting for you to slip up and prove you dont belong. You’ve got to mimic their codes, their confidence, their unspoken rules, and that takes time. Years, sometimes. It’s not enough to hustle you’ve got to perform their version of life while still proving useful to them. Even when you start breaking through, there’s another layer of trust. The rich dont trust easily. They’ve got their networks, clubs, their prep school buddies to them, you’re a risk, a potential fraud who might not know the game. You’ve got to network relentlessly, kiss up without looking desperate, and show you can play their politics without stepping on their egos. It’s like running a marathon while balancing a stack of plates. One wrong move say the wrong thing, vibe the wrong way and they’ll freeze you out, no explanation needed. Then there’s the guilt, the part nobody talk about. If you’re climbing, you’re leaving people behind along the way your family, your friends, the ones still stuck in the grind. They see you changing, talking different, moving different, and they start whispering. Sellout. Traitor. You feel it in your bones, that tug to stay loyal to the people who raised you, who had your back when you had nothing. So you try to bring them with you hook them up with jobs, teach them the game…but it’s not easy. The system’s built to keep most of them out, and some don’t even want to come. They’re too deep in the conditioning you’re trying to escape.

In the end, moving up isn’t just about money or hustle it’s a mental and social gauntlet. You’re fighting your own upbringing, the suspicions of the rich, and the weight of loyalty to your roots. Every step feels like a betrayal of where you came from or who you’re trying to become. That’s why it’s so damn slow. You’re not just climbing you’re rewriting your entire existence while carrying the ghosts of your past and the judgment of your future

[FIDEL CACHE FLOW @FidelCacheFlow]

This

[FIDEL CACHE FLOW @FidelCacheFlow]

Limited this to 100 spots.

We filled that before 48h promo ended

Still have folks looking to join so I’ll open up another 50 spots til Saturday

Link in reply

[FIDEL CACHE FLOW @FidelCacheFlow]

Want to earn in USD or EUR but still live like royalty overseas?

@graemelamperson has personally vetted 60+ LATAM cities and is dropping the exact playbook for extreme geo-arbitrage.

Today @ 5p EDT

Live inside the Desperado Sales Group.

Learn how to decouple your income from high-cost environments, slash your tax exposure, and keep 80%+ of your margins.

Link in reply.

See you there

[FIDEL CACHE FLOW @FidelCacheFlow]

Yes.

Live for the next 48h

$10 entry

Link in reply

[FIDEL CACHE FLOW @FidelCacheFlow]

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.

[FIDEL CACHE FLOW @FidelCacheFlow]

If you boil down the sales role to a base level, your job is discernment, reading between the lines, and uncovering the real truth and the fastest way to sink a deal, build unqualified pipeline, and miss quota is accepting prospects polite lies

To truly command a deal, you need to pressure-test the prospect’s internal logic, flush out their biases, and expose exactly where your competitors are hiding.

If they can't or won't answer these, you don't have a deal…you have a conversation.

1. Quantifying the Business Impact (The Status Quo Cost)

If it doesn’t hurt, they won't buy.

What is this stalling costing the business every single day it stays in 'evaluation'?

>We miss next quarter’s deadline to fix this - which of your KPIs takes the direct hit?

>Forget the technical fix. What is the executive team actually expecting to see on the ROI line in year one?

>Have you actually math'd out the cost of doing nothing versus the investment we’re looking at today?

2. Dissecting Competitive Standing

Assume you aren't the only option.

>When you stack our approach against the market, where is the gap widest for better or worse?"

>What’s the one feature or 'must-have' you saw elsewhere that's still stuck in your head?

>Be blunt: where do we actually rank against the other options on your desk right now?"

> If committee walks away from us to sign with a competitor, what would be the main trigger for that decision?

3. Navigating the Financial Framework

Budgets aren't real until you understand how the CFO thinks.

>Does this project actually fit into an approved budget bracket for this fiscal year, or are we pulling from somewhere else?

>When this hits the CFO’s desk, what's their primary lens saving upfront cash or long-term TCO?

>Outside of our sticker price, what are the internal 'soft costs' (implementation, headcount) that usually kill decisions here?

>If the budget becomes a wall, do we have the flexibility to phase this rollout, or is it all-or-nothing?

4. Validating the Decision Path (The Last Mile)

The deal isn't closed until procurement says it is.

>Who is the one person internally we haven't talked to yet who can still kill this business case?

>What are the typical 'last-mile' landmines your team hits once a contract gets sent to procurement?

>Are we the actual benchmark you’re using to grade everyone else, or are we being measured against someone else's standard?

>Work backward from a successful Go-Live date. What is the hard deadline we have to hit to make that real?

5. Flushing Out Internal Bias (The Silent Killers)

Deals die in the dark. Force the internal politics into the open.

>Is the selection committee already leaning a certain direction? What’s driving that bias?

>What’s the one unvoiced concern sitting in the room that’s going to slow us down later?

>Play devil's advocate: if your team decides to just delay this for another six months, what's the narrative?

Ask hard questions. Uncover the truth about your deal, your time is valuable and you simply can’t afford to accept polite lies

[FIDEL CACHE FLOW @FidelCacheFlow]

Quick reminder

Your job as a salesperson is to maximize your time with prospects with intent.

Everything above that is the consideration of marketing, market trends and external factors which bring prospects down the funnel.

How do we identify intent?

Trigger events which invoke a realization in the mind of prospect that current state or status quo is not sustainable path forward

We are NOT in the game of story telling, lead generation, or nurturing.

Identifying existing demand, and tailoring solutions to remove the bottle necks of their business that are preventing future profitability, scale or risk

[FIDEL CACHE FLOW @FidelCacheFlow]

When you land a new role or inherit territory, the fastest way to book meetings & close business is leveraging existing data rather than starting with cold outreach

We created “New Territory Sales Playbook”

A data-driven execution framework for building immediate pipeline velocity and avoiding wasted sales cycles.

This playbook is responsible for $100m+ in sales qualified pipeline built since 2023

Comment ‘Desperado’ for access

[FIDEL CACHE FLOW @FidelCacheFlow]

https://t.co/JwNGFrEDdX

[FIDEL CACHE FLOW @FidelCacheFlow]

How @MGamble22 went from athlete to earning $180k/yr SDR Contract Stacking

Twitter space tomorrow @ 5p EDT

https://t.co/JwNGFrEDdX

See you there

[FIDEL CACHE FLOW @FidelCacheFlow]

Alright Gents -

Opening up the June SDR Cohort

5 spots available.

SDR Stacking to $130k-300k in 90 days

$3,999 entry

What’s included?

Step by step how to source contracts, set up the infra to manage multiple quotas, and scale to $130-300k/yr run rate

21-day class, 2x 60-90min sessions per week

Phase I: Sourcing Contracts
-1:1 Resume fix
-Contract Profile optimization
-How to Qualify contracts
-Conducting Interviews
-SDR Contract interview role play

Phase II: Infrastructure
-Tech Stack Implementation
-AI Agent Implementation
-Sourcing and scaling VA’s

Phase III: Sales Training
-Set up outbound systems
-Crafting outbound messaging
-ICP & Lead Targeting
-Lead Intent & Trigger Events
-Developing message-market-fit

100p Remote
No Degree required
No Sales experience required
Internationally available - yes the UK too

We kick off this Saturday.

Payment plans available

DMs open