Office Hours: The Ramp Questions Enablement Leaders Keep Asking Me
Same six questions, every quarter, from every enablement leader building a ramp program. Straight answers to all of them.
I get the same six questions from enablement leaders every quarter, almost word for word, usually from someone who's just inherited a ramp program that isn't working and has been told to fix it by Q3. The questions are good. The answers they usually get are diplomatic. Here are the ones I'd actually give.
"How long should ramp take?"
As long as it takes to hit proficient on the four or five competencies the role actually requires — not a fixed number of days picked because it looks tidy on a slide. Most orgs default to 90 days because it's a round number that fits a fiscal quarter, then act surprised when reps who were "ramped" at day 91 still can't run a cold discovery call without a script in front of them. Measure ramp in competency-tier terms — did this person hit proficient on discovery, objection handling, and negotiation — and let the calendar be a consequence of that, not the driver of it. If you need a number for planning purposes, use a Sales Ramp-Time Calculator built on your own historical time-to-proficiency data, not an industry benchmark that has no idea what your product complexity looks like.
"Should ramp differ by segment?"
Yes, and most programs quietly know this and build one program anyway because two tracks is more admin. An SMB AE closing four-figure deals on a six-touch cycle needs volume-handling skill and fast qualification. An enterprise AE closing seven-figure deals over nine months needs multi-threading, stakeholder navigation, and negotiation under real scrutiny. Those are different competency weightings, not the same curriculum at different speeds. If your ramp program is one track split by tenure rather than by segment, you're training enterprise reps to be fast and SMB reps to be thorough — backwards for both.
"What do we do about a manager who won't grade honestly?"
This is the one nobody wants a straight answer to, so here it is: a manager who consistently rates every rep as "doing great" isn't being kind, they're avoiding a harder conversation later, and they're breaking your ramp data in the process. If your calibration meetings show one manager's ratings sitting a full tier above everyone else's for the same behaviour on tape, that's not a coaching-style difference — that's a manager who needs to be told directly that inflated grading costs the rep a real shot at fixing a gap while it's cheap to fix, and costs you clean data on whether your ramp program works at all. Don't quietly route around it with a second scoring layer. Say it in the calibration session, in front of peers, with the recording playing.
"Should ramp be time-boxed or competency-gated?"
Competency-gated, with a time-boxed backstop for cost control. Pure time-boxing graduates reps who aren't ready because the calendar said so. Pure competency-gating with no backstop lets a program run indefinitely for a rep who isn't going to make it, at cost to your budget and their morale. Gate on proficiency, cap at a maximum — say, 120 days — and if someone hasn't cleared the bar by the cap, that's a conversation about fit, not an extension of ramp.
"Do we need a certification exam at the end?"
You need a certification event, not necessarily a written exam. A graded live call — or a realistic simulated one — against your competency rubric, reviewed by someone other than the rep's direct manager, tells you far more than a multiple-choice test on product features. Product knowledge is a floor, not the bar. The New Rep Certification Scorecard should be measuring whether the rep can run a discovery call at proficient level under real conditions, not whether they memorised the pricing tiers.
"What's the single biggest thing that blows up a ramp program in year two?"
Drift. The program that launched with a clean competency rubric, calibrated managers, and clear gates slowly turns into whatever the most recent hire's manager felt like doing, because nobody owns re-certifying the managers who deliver it. You calibrate the curriculum once at launch and then never again, while the sales floor's actual skill bar keeps moving. Eighteen months in, half your managers are grading against the original rubric and half are grading against their own private standard, and your ramp-time metrics start meaning two different things depending which manager a rep happens to report to. Re-calibrate quarterly, or the program you built stops being the program that's actually running by the time anyone notices. Build the discipline into your rollout from day one with a proper First 90 Days Sales Onboarding Framework and put a recurring calibration date on the calendar before you launch, not after the metrics go strange.
None of these answers are complicated. They're just slightly more work than the version most enablement teams ship, and slightly more honest than the version most managers want to hear about their own grading.