Tech Sales Break-In Bootcamp

Dayvisson DaSilva

Sales Executive - The Tech Sales Hacker

Two days to choose your tech sales lane and make your experience credible

Six months ago you decided on tech sales. Since then: a pile of applications, two screens that went nowhere, one recruiter who suggested you start as an SDR, and a quiet suspicion that you are doing this wrong.

You are. But not in the way you think.

And if you have not started applying yet — if you are an engineer or implementer who suspects there is a commercial path and does not know what it is called — this is the right room too.

The problem is not your effort. It is that you are applying to job titles instead of revenue motions. Tech sales is five of them: pipeline creation, closing, expansion, technical value and ecosystem selling, each with a different buyer, cycle and quota. Your experience maps onto one or two and badly onto the rest. Choose wrong and a strong career reads as irrelevant. Choose right and it reads as an obvious hire.

Almost every tech sales program is built for people with no career to translate. Yours is the entire asset.

I spent mine at IBM and Microsoft, and coached this transition one-on-one at $6-12K an engagement. This is that process, rebuilt for a cohort.

Two days. Then weekly group sessions for six months while you run the search.

What you’ll learn

To read the industry like an insider, choose the revenue motion your experience fits, and make that fit obvious to a hiring manager.

  • Score five revenue motions on the Role-Fit Map: proof, buyer familiarity, work fit, technical depth, bridgeability.

  • Watch two real career-switcher backgrounds scored live, with the full reasoning shown.

  • Leave with a seven-day validation test: three conversations, two job descriptions, one honest answer.

  • Use the Tech Sales Story Builder: Target, Customer, Problem, Commercial action, Evidence.

  • Apply the Untrapped Trust Loop — Clarity, Visibility, Communication — to earn Know, Like and Trust.

  • Deliver your story twice in breakouts, with structured peer feedback between rounds.

  • Build the list with the Target Company Scorecard: growth stage, ramp support, attainment culture, manager quality.

  • Use the Tech Sales Career Map to find roles beyond software vendors — services, partners, marketplaces, post-sale.

  • Complete a Relationship Map, then draft warm, introduction and cold value-first messages.

  • Learn the three-move response: acknowledge briefly, redirect to evidence, close on why it maps.

  • Build a five-story bank: a win, a loss, a hard stakeholder, influence without authority, fast technical learning.

  • Rehearse in scored pair role-play, then watch live hot seats on the hiring-manager question set.

  • Work the 30-Day Search Sprint tracker: weekly targets for research, conversations, applications and reps.

  • Separate leading from lagging indicators, and run a weekly review on what actually created response.

  • Commit publicly to your first three actions and the day each one happens.

  • Use the First-90-Days Success Plan: align on how success is measured before trying to impress.

  • Move through learn, contribute, own — and map the people who actually make deals move.

  • Draw on themes from dozens of Tech Sales Funnel Podcast interviews on surviving year one.

Learn directly from Dayvisson

Dayvisson DaSilva

Dayvisson DaSilva

7+ years as Tech Sales Executive at IBM & Microsoft. Career Coach - MBA

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Who this course is for

  • The Plateaued High Performer — consultants, operators and PMs, 8-15 years in. Pay has flattened; you won't restart at the bottom.

  • The Adjacent Pro — customer success, recruiting or partnerships. You get interviews, but your story sounds like a duty list.

  • The Technical Professional — engineers and implementers who want commercial work but never knew pre-sales existed.

Prerequisites

  • Experience

    2-15 years in any professional field. No sales background and no technical background required.

  • Skills

    Nothing specific. You need to be able to describe your own work in plain language and better sell yourself.

  • Tools

    A LinkedIn account, Zoom, and something to write in. Nothing to buy or install. ChatGPT or Claude preferred but not a must.

What's included

Dayvisson DaSilva

Live sessions

Learn directly from Dayvisson DaSilva in a real-time, interactive format.

Lifetime access

Go back to course content and recordings whenever you need to. Every template and recording stays yours, including after your Landing Lab access ends.

Community of peers

Stay accountable and share insights with like-minded professionals.

Certificate of completion

Share your new skills with your employer or on LinkedIn.

The Full Template Vault

Every framework as an editable tool with instructions and a worked example — Role-Fit Map, Story Builder, Target Company Scorecard, Relationship Map, Interview Story Bank, 30-Day Search Sprint, First-90-Days Plan.

BONUS 1 - 24/7 Job Search Coach Agent

An AI coach trained on the frameworks you learn. Between Landing Lab sessions, use it to pressure-test your story, draft outreach to a specific person, research a target company, or prep for tomorrow's interview. It handles the 11pm questions, so the weekly hour stays on the hard ones.

BONUS 2 - Podcast SECRETS

Dozens of podcast interviews with tech sales practitioners and leaders, distilled into what they actually did — not episode recaps. Organized by theme: how they broke in, chose a role, built credibility, networked, interviewed, and survived year one.

Maven Guarantee

Your purchase is backed by the Maven Guarantee.

Course syllabus

2 live sessions • 18 lessons • 6 projects

Week 1

Aug 28—Aug 29

    Aug

    28

    Day 1 — Read the Industry, Choose Your Lane

    Fri 8/2810:00 PM—1:00 AM (UTC)

    Module 1: How the Industry Actually Makes Money

    4 items

    Module 2: Choose Your Revenue Motion — The Role-Fit Map

    4 items

    Module 3: Commit to a Target and Validate It

    4 items

    Aug

    29

    Day 2 — Prove It, Target It, Land It

    Sat 8/292:00 PM—5:00 PM (UTC)

    Module 4: Build Your Tech Sales Story

    4 items

    Module 5: Target 20 Companies and Reach Inside Them

    4 items

    Module 6: Interview, Then Launch Your 30-Day Search

    4 items

Schedule

Live sessions

6 hrs / week

Six live hours: three Friday, three Saturday. Never Sunday, and nothing required in between. Two days straight is deliberate. Your role decision feeds your story, your story feeds your target list, that list feeds your outreach. Built together, while each piece is still warm. Decide Friday, execute Monday. It is intense. That is the point.

    • Fri, Aug 28

      10:00 PM—1:00 AM (UTC)

    • Sat, Aug 29

      2:00 PM—5:00 PM (UTC)

Projects

2-5 hrs / week

Before: 45 minutes. Five accomplishments, one real job posting, a short orientation video. During: 6 live hours, plus roughly an hour of work between Friday and Saturday. After: 2-3 hours in week one to finish your Blueprint and run three validation conversations. Then 5-7 hours weekly while you search, including the one-hour Landing Lab.

Async content

1-2 hrs / week

Light before, useful after. Required before the weekend: a short orientation video and your evidence inventory — 45 minutes total. Everything after is reference, not homework: the Tech Sales Language Guide, the First-90-Days Success Plan, the template vault, session recordings, the Insider Field Guide, and a module on reading comp plans.

Testimonials

  • " Dayvisson is the best career coach that I've ever had ... He is clear and direct. There is no fluff around it."

    Testimonial author image

    Marcelo Menezes

    Digital Strategy Manager @ Google
  • "Dayvisson is an excellent professional and mentor ... He helped me landing a job at one of the top 500 Forbes Companies."

    Testimonial author image

    Laura Aviles

    Head of NA for Trad SD & Growth @ Google
  • " Dayvisson has been a fantastic career and life coach. He has helped me to set goals and make plans from choosing a major, future career plans and landing a dream job."

    Testimonial author image

    Felipe Ferreira

    Software Engineer Pre-Sales @ Oracle
  • "Thanks to Dayvisson and Art I successfully transitioned to my dream Tech Sales job at IBM."

    Testimonial author image

    Steffany Medina

    Account Executive @ IBM
  • " I joined of my dream companies thanks to Dayvisson's guidance and coaching!"

    Testimonial author image

    Carla Scott

    Inside Sales Specialist @ Fortinet
  • " I had no idea that I could break into tech. Dayvisson blew my mind with all the possibility. He was able to see all my transferable skills and guide me step by step to the offer."

    Testimonial author image

    Joseph Ojelade

    Security Compliance Engineer @ 1Password

Bonus 1 - The Tech Sales Hacker Agent

Your AI coach after the course ends - built on the 36-resource vault and 45 leader interviews.

Bonus 2 - The Tech Sales Hacker Field Guide

75 break-in lessons drawn from 45 recorded conversations with tech sales operators.

Frequently asked questions

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Reimbursement

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Everything L&D needs: email template, receipts, and certificate of completion.

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Team discount

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Save 20%+ when 2 or more teammates enroll in the same cohort.

Save 20%+ with a team

Private cohort

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A dedicated cohort with a custom schedule and curriculum, tailored to your team.

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$1,197

USD

Aug 28Aug 29
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