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A sales onboarding plan that ramps in eight weeks, not six months

Six months is not a ramp, it is a bet. Here is what to document before anyone starts, and what evidence to require at each of the eight weeks after.

JOSH DEMPSEY5 MIN READ1,126 WORDS

Ask a revenue leader how long a new rep takes to contribute and the honest answer is usually six months. Ask what actually happens during those six months and the answer gets vague.

That vagueness is the whole problem. A ramp nobody designed is a ramp nobody can shorten, and it turns every hire into a bet resolved by whether the new person happened to sit near someone good.

What six months actually costs

Run the arithmetic once and it stops being an abstraction. At a $120k base against a $120k variable, six months of unproductive ramp is roughly $120,000 in salary and benefits against near-zero output. Add a territory sitting idle for two quarters. Add the manager hours spent answering the same questions for each new hire because nobody wrote the answers down.

Then add the part that does not appear on any spreadsheet: at six months you still do not know whether the hire was right. You find out in month seven or eight, which means a mishire costs a year.

A ramp nobody designed is a ramp nobody can shorten.

Why it takes six months

Four causes, and none of them are the new person.

Nothing is written down. The motion lives in the heads of the two people who are good at it, and both of them are busy closing. A new rep learns by osmosis from whoever is nearest, which means your ramp quality is a seating chart.

Onboarding is product training. A week of feature walkthroughs teaches recall. Recall collapses the first time a buyer asks something unexpected, which happens on roughly the first call.

There is no definition of week four. Without milestones nobody knows whether a rep is on track until the quarter ends, and by then intervening is expensive and late.

Coaching starts when there is a problem. By that point the habits are set and you are unlearning rather than teaching.

Before anyone starts: write down what your best rep does

This is the step that gets skipped and it determines everything after it. Shadow your strongest rep for a week and document the actual sequence, not the idealised one they would describe if you asked.

Six moments are worth capturing.

Pre-call. What they research, where they look, how long it takes, and what they deliberately do not bother with. That last part is most of the value.

The open. The exact first ninety seconds, including how they earn the right to ask anything at all. New reps default to pitching because nobody gave them an alternative.

Discovery. The five questions they always ask, and the two they only ask when something feels off.

The hard question. The five things serious buyers ask that most of your reps cannot answer cold. Write the answers down. This is the single highest-return page in the document.

When it goes quiet. What they actually do in week three of silence, in order. Most pipeline dies here and most onboarding ignores it completely.

The close. How they establish process, timeline and signatory without asking those words directly.

That document is your ramp plan and your hiring profile at the same time. It tells you what to teach, and it tells you what to interview for.

The eight weeks

Every milestone is stated as something the rep can do. Attendance is not evidence. "Completed product training" tells you nothing; "answers three of the five hard questions cold" tells you everything.

Week 1. The company, the market, and who you actually win with. Evidence: can name your best-fit customer and say why, unprompted.

Week 2. Product fluency, mechanism rather than features. Evidence: answers three of your five hard questions cold, with no notes.

Week 3. The motion, stage by stage, with exit criteria. Evidence: can explain what has to be true for a deal to advance.

Week 4. Live drills and recorded practice calls. Evidence: runs a full discovery without reading from anything.

Week 5. Shadowing, then co-selling on real accounts. Evidence: leads a section of a live call with a senior rep present.

Week 6. Owning first-call meetings on real pipeline. Evidence: books and runs their own first meeting.

Week 7. Multi-threading and stakeholder mapping. Evidence: names the buying group on one of their own live deals.

Week 8. Full ownership, with coaching rather than supervision. Evidence: has a qualified opportunity with a dated next step the buyer owns.

Notice that weeks one through four contain no selling. That feels slow and it is the reason the whole thing is faster. A rep who cannot answer a hard question in week two will spend weeks five through twenty burning territory learning it live on real buyers.

The intervention rule

If a rep misses two consecutive checkpoints, that is a conversation in week four. Not a performance plan in month five.

Almost all ramp failures are recoverable early and almost none are recoverable late. The point of checkpoints is not to grade people. It is to buy back the four months you would otherwise spend hoping, and to make the conversation about a specific missed milestone rather than a vague feeling that things are not working.

It also protects the rep. Being told in week four that your product fluency is behind is a fixable problem. Being told in month six that it is not working out is a career event.

If you are mid-ramp with someone struggling right now

You do not need to wait for the next hire to use any of this.

Take your five hard questions, ask them today, and see which land. If the gap is fluency, that is fixable in three weeks of drilling. If the rep can answer everything cold and still is not converting, the problem is upstream in targeting or positioning, and no amount of coaching the rep will fix a list that was wrong.

Separating those two cases takes an afternoon and it is the difference between a save and a mishire.

After week eight

Coaching is the first thing dropped when a quarter gets tight and it is the thing that compounds. Protect it by making it small enough that dropping it is never justified.

Thirty minutes a week, one deal, chosen by the rep. Not a pipeline review. Who else has to say yes and have you met them. What happens to their business if they do nothing. What is the next step, what is the date, and who owns it.

Once a month, listen to a full recorded call together. One thing they did well, named specifically. One thing to work on, and only one. Reps cannot fix five things at once, and pretending otherwise is how coaching becomes noise.

Where to start

Do not build all eight weeks this month. Write your five hard questions and drill them fifteen minutes a week.

That one habit does more for ramp time than any onboarding deck, and you will find out immediately how many of your current reps would pass their own week two.

The full version, including the shadowing template and a worksheet for your five hard questions, is in The Ramp Plan.

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