Ramp Milestone Tracker (30/60/90 Days)

One copy of this tracker per new hire. Fill in the specific milestone for your org/segment where a range is given, then check off as they're hit. Review at each milestone date with the rep directly, not just internally.

Header (fill in once)

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30-Day Milestones

Product & Process Knowledge

• Can explain the product/value proposition in their own words, unscripted
• Has completed all required onboarding/certification modules
• Knows the CRM well enough to log a call without help

Activity

• Has shadowed at least 10 calls (see Call Shadowing Checklist)
• Has taken at least ___ live discovery calls solo (fill in your target, e.g. 15)
• Meeting weekly with mentor per the Buddy Program cadence

Skill Demonstration

• Manager has listened to/reviewed at least 2 live or recorded calls
• Can run the Universal Discovery Structure without a script in front of them
• Has correctly logged CRM notes per the CRM Hygiene Cheat Sheet on every call this week

Pipeline

• Has generated first ___ qualified opportunities (fill in target)
• Pipeline stages in CRM accurately reflect deal reality (manager-verified)

30-Day Status: ☐ On Track ☐ At Risk ☐ Behind — Notes: _______________

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60-Day Milestones

Product & Process Knowledge

• Can handle at least 8 of the 12 objections from the Objection Handling Cheat Sheet without hesitating
• Can name 2–3 relevant case studies/proof points for their most common deal type unprompted

Activity

• Running discovery calls fully solo, no shadow needed
• Weekly 1:1 cadence shifted to skill + pipeline mix (per Manager's 1:1 guide)
• Mentor sessions moved to weeks 3–6 cadence (2x/week)

Skill Demonstration

• Has run at least 1 full-cycle deal conversation from discovery through a next-stage advance without mentor/manager intervention
• Sales Readiness Self-Assessment retaken — total score improved vs. Day 1 baseline
• No section of the Self-Assessment scoring below 3.0 average

Pipeline

• Pipeline value at or above cohort median for day 60 (see Time-to-First-Deal Tracker for benchmarks)
• At least 1 deal in late-stage (proposal/negotiation) or closed

60-Day Status: ☐ On Track ☐ At Risk ☐ Behind — Notes: _______________

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90-Day Milestones

Product & Process Knowledge

• Fully independent on product positioning and competitive differentiation
• Can mentor/help a newer hire on at least one skill area confidently

Activity

• Full independent activity cadence matching tenured rep expectations for the segment
• Buddy/Mentor pairing formally closed out (see Sales Buddy/Mentor Program Playbook end criteria)

Skill Demonstration

• First deal closed-won (flag if not — this is the single biggest ramp risk signal; cross-check against Time-to-First-Deal benchmark)
• CRM hygiene fully self-sufficient, zero manager reminders needed in the last 2 weeks
• Sales Readiness Self-Assessment retaken again — total score ≥ 80/100 OR clear upward trend with a named remaining focus area

Pipeline

• Pipeline coverage at or above segment target (e.g., 3x quota in pipeline)
• Forecast accuracy for their own deals within acceptable variance (manager-defined)

90-Day Status: ☐ Ramped — Full Autonomy ☐ Ramped with Support ☐ Extend Ramp Plan ☐ Performance Concern — Escalate

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What to Do at Each Review

• If "On Track" at all three checkpoints: move to standard rep cadence, no special tracking needed after 90 days
• If "At Risk" at 30 or 60 days: name the specific blocker together with the rep (skill, volume, territory, personal) and adjust — don't just note it and hope 60 fixes itself
• If "Behind" at 60 days: escalate to a formal ramp-extension conversation before day 90, with a clear, written plan and a new checkpoint date
• If "Performance Concern" at 90 days: this feeds directly into a documented performance conversation — pull the Cost of a Bad Sales Hire Calculator to inform how much runway makes sense to extend vs. not