Tech Sales Bootcamp — Program
Tech Sales Bootcamp — Program
A paced, ~10-week program that turns the tech-sales path from a self-serve course into a bootcamp: it sequences the lessons (Topics 1–10), the capstone deliverables (real artifacts, AI-reviewed against rubrics), the interview drills, and career services into one journey with weekly milestones.
It's self-paced — the weeks are a recommended rhythm (roughly 5–8 focused hours each), not hard deadlines. From Week 1 you carry one deal through the entire program: the capstone "Work One Deal End to End: From Cold Prospect to Closed-Won." You adopt one SaaS product to sell (Lumadesk, an AI-powered support helpdesk), work a single territory of mid-market accounts (named target: GearGrid), and produce the real artifacts an SDR-to-AE makes every day. Every deliverable advances that one deal, so by Week 10 the six artifacts tell one coherent story.
Core program (Weeks 1–10)
| Week | Learn (topics) | Capstone deliverable | Interview practice | ~Hours |
|---|---|---|---|---|
| 1 | Topic 1 (What is Tech Sales?), Topic 2 (Sales roles and the sales org) — (+ general Core Tech Baseline alongside) | Adopt your capstone product & territory (Lumadesk → GearGrid) | Behavioral: start drafting STAR stories (drive, resilience, coachability) | 5 |
| 2 | Topic 3 (How SaaS sales works), Topic 4 (The sales process and pipeline) | (set up your pipeline tracker skeleton) | sales-metrics-and-process: pipeline, funnel, OTE warm-up | 6 |
| 3 | Topic 5 (Prospecting and outreach) | D1 — ICP & Prospect List (Account Plan) (after Topic 5) | behavioral: STAR drills (reframe a non-sales background) | 7 |
| 4 | (apply Topic 5 — outreach craft) | D2 — Personalized Multi-Touch Outreach Sequence (after Topic 5) | mock-cold-call: cold-open and earn-time role-plays | 7 |
| 5 | Topic 6 (Discovery and qualification) | D3 — Discovery Call Plan & Qualification Notes (after Topic 6) | mock-discovery: open-ended questions + BANT qualifying | 7 |
| 6 | (revise D1–D3 from rubric feedback) | (no new deliverable — tighten the deal so far) | Mock-interview checkpoint #1 (mock-cold-call + mock-discovery) | 6 |
| 7 | Topic 7 (Demos, objections, and closing) | D4 — Tailored Demo Script & Objection-Handling Playbook (after Topic 7) | mock-discovery: objection handling to a confident close | 8 |
| 8 | Topic 8 (Quota and sales metrics) | D5 — Pipeline Tracker & Honest Forecast (after Topic 8) | sales-metrics-and-process: work backward from quota; diagnose a leaking funnel | 7 |
| 9 | Topic 9 (The sales tech stack) | (wire your pipeline tracker into a CRM-style stack view; refine the forecast) | motivation-and-company-fit: "why this product, who are its customers, how I'd sell it" | 6 |
| 10 | Topic 10 (Landing the tech sales job) + general Employability & Job Hunting | D6 — Sales Portfolio & 'Why Me' Pitch (after Topic 10) — assembles all 6 artifacts | Mock-interview checkpoint #2 (full mock across all 5 banks) + career services (below) | 8 |
By the end of Week 10 you have: the full curriculum learned (Topics 1–10), a 6-artifact portfolio that works one deal from cold prospect to forecasted close, repeated interview practice across all five drill banks, and your resume/LinkedIn ready.
Capstone deliverables at a glance
| # | Title | Unlocks after | ~Min |
|---|---|---|---|
| 1 | ICP & Prospect List (Account Plan) | Topic 5 | 75 |
| 2 | Personalized Multi-Touch Outreach Sequence | Topic 5 | 75 |
| 3 | Discovery Call Plan & Qualification Notes | Topic 6 | 60 |
| 4 | Tailored Demo Script & Objection-Handling Playbook | Topic 7 | 90 |
| 5 | Pipeline Tracker & Honest Forecast | Topic 8 | 60 |
| 6 | Sales Portfolio & 'Why Me' Pitch | Topic 10 | 50 |
Deliverables D1 and D2 both unlock after Topic 5 (prospecting); the program spreads them across Weeks 3 and 4 so each gets focused effort. Each artifact is self/AI-reviewed against its rubric and revised until passing, then accumulates into your portfolio.
Interview drill banks
Five banks, practiced on the rhythm above and revisited in both mock-interview checkpoints:
mock-cold-call— live cold-call and outreach role-plays: open with a relevant reason, earn time, hook on a problem, handle the brush-off, book the meeting. The SDR work-sample that decides most entry-level loops.mock-discovery— mock discovery and "sell me this pen" role-plays: ask open-ended questions before pitching, qualify with BANT, quantify pain, connect need to outcome, handle objections to a confident close.behavioral— STAR drills on the traits SDRs are hired for: drive and hitting targets, resilience to rejection, coachability, persuasion without authority, competitiveness — reframing a non-sales background.sales-metrics-and-process— process and numbers fluency: explain the pipeline and funnel, work backward from quota to activity, read win rate / conversion / pipeline coverage, define OTE, diagnose a leaking funnel.motivation-and-company-fit— "why tech sales, why this company" and territory-thinking: show genuine drive, research the product, identify its customers and how you'd sell to them, and close by asking for the role.
Career services (lite)
Delivered mainly in Week 10, drawing on the general Employability & Job Hunting track (general Topics 6–10: planning your pivot, LinkedIn, networking, resumes, interviewing). These are self/AI-reviewed against rubrics (no human mentor required).
Resume review rubric
- Outcome-focused bullets — 1: duties only · 2: some results · 3: quantified outcomes ("hit 120% of quota", "booked 15 meetings/month", "grew pipeline by $X").
- Sales vocabulary & relevance — 1: generic · 2: some sales terms · 3: clearly reframed for sales (prospecting, pipeline, quota/OTE, discovery, qualification, closing).
- Portfolio linked — 1: none · 2: mentioned · 3: linked and tailored — your one-deal portfolio (D6) shown as proof you can run the full motion.
- Clarity & format — 1: cluttered/typos · 2: clean · 3: crisp, one page, scannable in seconds (recruiters skim fast).
Worked example — one bullet, before → after. This is what a Level 1 bullet looks like rewritten to Level 3 on every criterion. The candidate's real job was restaurant server; the move is to reframe it in sales language with a number, not to invent sales experience.
- Before (Level 1 — duty, no result, no sales relevance):
Served customers at a busy restaurant and recommended menu items.
- After (Level 3 — quantified outcome, reframed for sales):
Upsold premium items and add-ons to 80+ guests per shift; finished #2 of 14 servers on upsell revenue for three straight quarters by reading each table fast and tailoring the pitch — the same discovery-then-recommend motion a sales rep runs.
What changed, mapped to the rubric: a number and a rank replaced the vague duty (outcome-focused); "upsold," "tailored the pitch," and "discovery-then-recommend motion" reframe it for sales without lying (sales vocabulary); it reads in one scannable line (clarity). Do this to your three strongest bullets. A second pattern — turning resilience into a number: "After a 40% no-show month, rebuilt my regulars from scratch through disciplined follow-up — recovered to baseline in six weeks" (handling rejection and persisting is the SDR's whole job). Then add a final line linking your portfolio: "Sales work-sample: worked one deal cold-to-close (GearGrid, $31.7k ARR forecasted) — [link]" (portfolio linked, Level 3).
LinkedIn review rubric
- Headline signals target role — 1: old title only · 2: mentions sales · 3: clear target + value ("Aspiring SDR | ex-[field] | driven to hit quota").
- About tells the pivot story — 1: empty/generic · 2: present · 3: confident pivot story (where heading, what drive/communication/resilience you bring, why, proof).
- Skills & proof — 1: none · 2: some · 3: sales skills listed (prospecting, discovery, CRM) + portfolio/projects shown.
- Activity — 1: inactive · 2: occasional · 3: connecting with reps/managers, engaging with target companies (territory-thinking in public).
Worked example — headline + About (same career-changing server).
-
Headline (Level 1):
Restaurant Server at Bistro 21 -
Headline (Level 3 — target role + background + value):
Aspiring SDR → Account Executive | ex-Hospitality, top-2 upseller | turning customer pain into pipeline | I run the job hunt like a pipeline
-
About (Level 3 — confident pivot story, ~120 words):
I'm pivoting into tech sales, and everything I'm good at already lives there: I'm at my best with a target, a scoreboard, and a customer to win over.
For three years in hospitality I lived on a number — I finished #2 of 14 servers on upsell revenue for three straight quarters by reading each guest fast and recommending what actually fit them. That's discovery and value-selling, just without the SaaS. When a 40% no-show month wiped my section, I rebuilt it through follow-up instead of taking the "no" personally — the exact resilience an SDR seat demands.
I've now run a full B2B SaaS deal end to end — cold prospect to a $31.7k-ARR forecasted close (work-sample in Featured below). Skills: prospecting, discovery & BANT qualification, objection handling, CRM/pipeline hygiene.
Open to SDR/BDR roles. If you're hiring, let's talk.
Notice how the About hits every rubric criterion: it states where you're heading, carries drive/communication/resilience with a number each, links proof (the portfolio), lists sales skills by name, and ends with an ask. Put the D6 portfolio one-pager in your Featured section so the headline's claim is one click from evidence — then earn the Activity point by following the SDR managers at your 10 target accounts and commenting on their posts (territory-thinking in public).
Mock-interview checkpoints
Use the AI mock interview (interview/mock-interview.md): Checkpoint #1 (Week 6) — mock-cold-call + mock-discovery, the two work-sample role-plays that gate most SDR loops; Checkpoint #2 (Week 10) — a full mock across all five banks (mock-cold-call, mock-discovery, behavioral, sales-metrics-and-process, motivation-and-company-fit). Track which rubric criteria you repeatedly miss and focus there.
Salary-negotiation drill
The single most underspecified piece of most job hunts — so here it gets the same learn → do → see a model treatment as a capstone deliverable: a framework to run, a fully worked sample offer with a model counter-script, and a rubric the AI scores you against while it role-plays the recruiter.
Framework — four moves on any SDR/AE offer
- Decode the offer before reacting. Separate base (guaranteed) from variable/commission (earned at 100% of quota). The two together are your OTE (On-Target Earnings). Ask for the split, the ramp (reduced/ramping quota for the first 1–3 months), and whether commission is capped. Never negotiate on base alone — OTE and ramp are where the real money and risk live.
- Buy time, warmly. Don't accept or counter on the call. "I'm genuinely excited — thank you. Can I take 24–48 hours to review the full package?" A calm pause is itself a signal you're not desperate, which is exactly the trait a sales org respects.
- Anchor to a researched market range, then make ONE counter. Look up the range for the role, level, and city (Levels.fyi, Glassdoor, Repvue for sales OTE, recent reports). Counter once, tied to your value and a fast ramp — not to your rent. Put a number on the table, don't just say "more."
- Weigh the whole offer, not just pay. Promotion path and timeline to AE, ramp quota (is it humane?), territory quality, manager and team, draw vs. true commission. A slightly lower base with a fast SDR→AE path and a real territory beats a higher base on a dead desk.
Model answer — a worked sample offer and a model counter
The sample offer (entry-level SDR, mid-market SaaS, mid-size US city):
| Component | Offer | Notes |
|---|---|---|
| Base salary | $50,000 | Guaranteed |
| Variable (commission at 100% quota) | $20,000 | Paid on meetings booked / pipeline sourced |
| OTE (base + variable) | $70,000 | The number recruiters quote first — confirm what's guaranteed vs. earned |
| Ramp | 3 months at reduced quota | Variable partly guaranteed during ramp? — ask |
| Path | SDR → AE in ~18–24 months | Get the criteria in writing |
Market check (do this yourself before countering): for entry-level SDRs in mid-market SaaS, base commonly lands ~$45k–$60k with OTE ~$65k–$85k depending on city and product price-point (verify on Levels.fyi / Repvue / Glassdoor for your market — don't quote these as gospel). This $50k/$70k offer is mid-range — reasonable, with room for a modest, well-justified ask.
The model counter (what you'd actually say/write):
"Thank you — I'm genuinely excited about the SDR role and the SDR-to-AE path here; this is exactly the team I want to ramp on. Based on what I'm seeing for mid-market SDR roles in [city] — base in the mid-to-high-fifties with OTE in the mid-seventies — I'd love to land at a $55k base, keeping OTE around $75k. I'm confident I'll ramp fast: I've already worked a full deal end to end — cold prospect to a $31.7k-ARR forecasted close — so I'll be contributing pipeline early. If the base has no flexibility, could we look at a higher ramp guarantee for the first three months or a 6-month comp review tied to hitting ramp quota? Either works for me — I'm ready to sign and get started."
Why this counter works (the moves, labeled): it opens warm and reaffirms the role (you're negotiating because you want it, not against them); it anchors to a researched range, not a personal need; it makes one specific number ($55k base / ~$75k OTE), not a vague "more"; it justifies with value and a fast ramp (the portfolio is the proof); and it gives a graceful fallback (ramp guarantee or comp review) so a "no" on base still moves the deal forward — exactly how a good rep handles an objection (Topic 7). Then you evaluate fit, not just pay — a fast, written SDR→AE path can be worth more than $5k of base.
Rubric
The AI role-plays the recruiter and scores your negotiation. Levels: Needs work (1) / Solid (2) / Excellent (3). Passing = every criterion at Solid or above.
- Reads the offer correctly — 1: confuses base with OTE or ignores commission · 2: separates base / variable / OTE · 3: also probes ramp, commission split, cap, and SDR→AE criteria before countering.
- Buys time without flinching — 1: accepts or panics on the spot · 2: asks for time · 3: asks for 24–48h warmly and confidently, signaling non-desperation.
- Anchored, single, justified counter — 1: no number, or "just more," or counters on rent · 2: one number tied to some research · 3: one specific number anchored to a real market range and justified by value + fast ramp, with a graceful fallback (ramp guarantee / comp review).
- Weighs the whole package — 1: fixates on base only · 2: mentions OTE · 3: explicitly weighs promotion path, ramp quota, territory, and team against pay — and can say when a lower base is the better offer.
How it fits together
Lessons teach the concept → the matching capstone deliverable makes you do it on a real deal (and the AI reviews it) → interview drills rehearse explaining and performing it (cold call, discovery, the numbers) → career services package it for the job hunt. That loop — learn, do, get feedback, present — is what makes this a bootcamp rather than a reading list. Because every deliverable advances the same Lumadesk → GearGrid deal, the portfolio you finish with is one story a hiring manager can follow end to end.