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This is a guest post @BowTiedCocoon. He gives practical advice on job searching, interview prep, and picking the right companies — to help people land high-paying tech sales jobs (often $200-300k+ per year).

I often get questions about how to break into tech sales. Many of them include common themes - where to apply, resumes getting ignored, failing recruiter screens, bombing hiring manager interviews, or lacking executive presence in final VP rounds.  This post (and the video at the end) covers the "five points of failure" in most job searches AND how to overcome them to get hired. Let’s dive in.

Hi everyone - BowTiedCocoon here.

I get asked a lot about breaking into tech sales - or leveling up into better companies.

The questions are usually the same:

Below, I've laid out the 5 points of failure I see in nearly every client that comes to me for help — and how to fix each one.

1) Don’t know where to apply? — This usually means two things. First you’re not clear which sales role best suit YOUR specific experience (SDR, Inside Sales, AE SMB or AE Mid Market etc). Second, you don’t know who are the organizations that will allow you to clear 6-figures out of the gate and max your career opportunities. Solution? We’ll cover the process you can apply to find the right position at the right firm and ensure you’re building your career in a booming industry or hyper growth org.

2) Can’t get a first interview? — Either your CV is weak and doesn’t pass screen test at the top sales orgs OR you’re not applying to enough roles. Solution? Revamp your CV (1 pager or NGMI) and farm referrals at your target companies to skip the line and get interview. Here I will provide you with some examples, and might offer a few CV review to some of you. Yes will be free.

3) Can’t pass first call w/ recruiter? — These guys are usually clowns and just ensure you’re not insane so you don’t waste the hiring manager’s time (ie we call those “gatekeepers”). If you get flushed out of the process here, it’s because the gap between the person depicted on your CV is too big. Solution? We’ll cover all the Q&A possible, and how to answer them in a way that you’ll systematically make it to the next stage.

4) Get dequeued after meeting hiring manager? You failed to demonstrate your understanding of the role, and what it takes to hit the ground running and crush your numbers consistently with little to no maintenance. Solution? I’ve developed the 4-Step Cocoon Process to blow away any hiring manager. The idea is to come at the interview as if you already had the job, and bring with you 1) territory plan 2) list of potential account with DM info to show your hunting skills 3) An email sequence to book meeting 4) a call script to demonstrate closing skills. The Hiring Manager will be on the floor and get all horny real fast. EZ PEEZEE

5) Failing the final round sales leader (VP/ Sr Dir etc)? You failed to demonstrate executive presence, and as consequence the VP is not comfortable putting you in front of a large account to represent his company. Solution? Read 10K filing and drive meaningful conversion such as how the role your applying for fit in a larger corporate strategy. The goal is to make the sales leader speak about themselves, and this can be done by asking the right questions (will reveal those to you).  

If this framework was useful, the video below expands on it with concrete examples — how to spot the right companies, how to position yourself in interviews, and where most people quietly get screened out.

No new concepts. Just the same ideas applied in a more practical way.

And if this way of thinking resonates, I write a short email once a week breaking down how I approach tech sales careers — company selection, hiring dynamics, interview positioning, and long-term leverage.

It’s not for everyone. But if you’re trying to be intentional about where you end up next, you’ll probably find it useful.

You can join here (free):
👉 www.insidethecocoon.com/blueprint

Until Thursday,

TSG

P.S. I reply to all emails.