Milestone map
Milestone map
3 milestones
Log a Real Sales Pipeline and Close a Deal
8–12 weeks (real sales cycles vary)
Build and work a real sales pipeline: at least 10 opportunities tracked in a CRM or spreadsheet, at least 5 discovery calls completed and documented, and at least 1 deal closed (won or lost) with a documented close reason. This must be for a real product or service — your employer's, your freelance work, or a side business — not a simulated exercise. The pipeline must have tracked stages (e.g. prospect / qualified / proposal / negotiation / closed) and a close date for every opportunity.
Proof required
Submit a screenshot of your CRM or pipeline spreadsheet showing 10+ opportunities with stages and close dates, notes from 5 discovery calls (prospect name/company, key pain points surfaced, next step agreed), and a one-paragraph description of the closed deal: what was sold, to whom, at what value, and the close reason (won/lost and why).
What gets checked
- 10+ real opportunities with real company names — a pipeline of 10 opportunities at the same company or 10 at '$1 contract value' suggests the pipeline was constructed to meet the requirement rather than to actually sell
- Discovery call notes name specific pain points in the prospect's own words — 'they have growth challenges' is not a specific pain point; 'they said manual reconciliation takes their team 2 days per month' is
- Close reason names the specific reason won or lost — 'price' is not a reason; 'prospect chose competitor because competitor offered 6-month payment terms we could not match' is
Resources
Foundationstart here
Depthgo deeper
What a verifier looks for
- Ask the submitter to describe the most common objection they encountered across the 5 discovery calls — genuine sales pipeline experience always surfaces recurring patterns
- Check the discovery call notes for specificity — ask the submitter to read one prospect's pain point from the notes; if it could describe any company, it is not specific enough
- Ask what the submitter would change about their discovery process based on the results — genuine sales learning from a first pipeline always produces specific process adjustments
- Ask for the close reason on the lost deal (if any) — lost deals reveal more about the sales process than won deals; a submitter who cannot explain why they lost has not reflected on the result
- A pipeline of small or trivial deals where the sales process has no real complexity — freelance projects under £100 have little in common with B2B or B2C sales processes
- Discovery call notes that describe what you said rather than what the prospect said — the value of a discovery call is in what you learned about the prospect's problem, not in what you pitched
- A closed deal where the prospect was a friend or family member who bought to be helpful — the close must involve a genuine purchase decision by someone without a pre-existing personal obligation to buy
Develop and Present a Formal Proposal
3–5 weeks (proposal development + meeting + debrief)
Develop a formal written proposal for a real opportunity — a prospect from M1, a new freelance client, or a complex deal at your employer — and present it to the prospect or decision-maker. The proposal must address: the prospect's specific problem (in their language from the discovery call), your solution and why it fits their specific situation, commercial terms (price, scope, timeline), and an ROI estimate or business case for the buyer. The proposal must be presented verbally — in person, by video, or by phone — with a follow-up conversation. Document the objections raised and how you handled them.
Proof required
Submit the written proposal, evidence that it was presented (a calendar invite, email scheduling the meeting, or screen recording), and a 200-word debrief: the specific objections raised by the prospect, how you responded, and what happens next (next step agreed, or lost and why).
What gets checked
- Proposal includes a ROI estimate or business case — 'our solution saves time' is not a business case; 'based on your estimate of 2 days/month on manual reconciliation at £[hourly cost], our solution would save approximately £X per year' is
- Debrief names specific objections — not 'they had concerns about price' but 'the CFO said the cost was 40% higher than the competing quote from [vendor]'
- Next step is specific and time-bound — 'follow up next week' is not a next step; 'reconvene with the CTO on [date] to review the technical integration questions' is
Resources
Foundationstart here
Depthgo deeper
What a verifier looks for
- Ask the submitter to explain the ROI calculation in the proposal — they must be able to reproduce it from the prospect's own numbers, not just quote a formula
- Ask what the most challenging objection was and whether the response satisfied the prospect — genuine proposal experience surfaces objections that were not anticipated
- Ask what they would change about the proposal based on the debrief — the most common learning is that the business case was not specific enough to the prospect's situation
- Confirm the proposal was presented verbally — ask the submitter to describe what they said when they first presented the proposal and what happened immediately after
- A written proposal that was emailed without a verbal presentation — the presentation is where objections are surfaced; written proposals without verbal follow-up rarely produce useful learning
- An ROI estimate that uses round numbers without explaining the methodology — if you cannot explain how you calculated the ROI, neither can the prospect justify it to their finance team
- Debrief that attributes the outcome to factors outside your control ('the timing was bad') without identifying anything adjustable about the proposal or the presentation
Present Your Sales Record to a Senior Sales Professional
1–2 weeks (60–90 min session)
Present your M1 pipeline and M2 proposal to a qualified reviewer: a senior account executive, sales director, or VP sales with 5+ years of closing complex deals. The reviewer challenges the discovery approach (what else should you have uncovered in those calls?), the proposal structure (what is the weakest section and why?), and the objection handling (what would you say to that objection now that you didn't say in the meeting?). The reviewer then role-plays a cold discovery call — playing the prospect — and asks the submitter to conduct a 10-minute live discovery session.
Proof required
Submit your M1 pipeline screenshot and M2 proposal plus the reviewer's written assessment: the discovery challenge and response, the proposal weakness identified, the objection handling challenge and response, the cold discovery call feedback (what worked, what did not, one specific improvement), and their sign-off confirming their role and a live session.
What gets checked
- Cold discovery role-play feedback includes at least one specific technique that worked and at least one specific moment that the reviewer would handle differently
- Proposal weakness identified by reviewer is a structural weakness (missing business case, weak ROI calculation, no clear next step) not a formatting issue
- Reviewer sign-off confirms 5+ years of closing complex deals (not SDR/BDR role only; not sales training or consulting without personal quota ownership)
Resources
Foundationstart here
What a verifier looks for
- In the cold discovery role-play, play a realistic prospect with a real problem — give the submitter something real to uncover rather than a cartoonishly easy buyer; the most revealing moment is when the prospect gives a vague answer and the submitter must choose how to probe
- Watch whether the submitter starts with discovery questions or with a pitch — starting with a pitch is the most common and most diagnostic failure mode
- Ask the submitter what they would do differently after the role-play — genuine sales learning from a cold role-play always produces specific technique adjustments
- Reviewer minimum qualification: 5+ years of quota-carrying sales (AE, senior AE, or sales director); sales development or sales enablement roles without personal quota ownership are not sufficient
- Cold discovery role-play where the submitter turns it into a pitch rather than a discovery — discovery sessions that start with a pitch before understanding the prospect's problem is the most common and most important sales mistake to diagnose
- A reviewer who is primarily a sales trainer rather than a quota-carrying closer — the challenge questions require someone who has personally closed deals under pressure
- Discovery challenge response that is theoretical ('I should have probed deeper') rather than specific ('I should have asked "what happens to your team in the 2 days while reconciliation runs?" to surface the real cost of the problem')