---
name: rep-onboarding
description: Generate a personalized 30/60/90-day onboarding plan for a newly hired sales rep. Tailors week-by-week milestones, named call recordings, certifications, and manager check-in cadence to the rep's prior background, the segment they'll work, and your team's actual ramp data. Output is Notion-ready markdown the hiring manager edits in 15 minutes before day one.
---
# Rep onboarding plan
## When to invoke
Use this skill when a new sales rep has signed an offer and you need a personalized 30/60/90-day plan ready before their first day. The skill produces a single Notion-ready markdown brief covering weeks 1-12, with named call recordings, named certifications, named role-play exercises, and a manager check-in cadence calibrated to your team's historical ramp time.
Typical triggers:
- New AE or BDR has accepted an offer and starts in 1-3 weeks
- A tenured rep is being moved to a new segment (e.g. SMB up to mid-market) and needs a re-ramp plan
- A manager is hiring a backfill and wants to compare the auto-generated plan to their manual draft
Do NOT invoke this skill for:
- **Performance management of a ramped rep.** A ramping rep missing milestones is a coaching problem; this skill writes the plan, not the PIP.
- **Replacing the manager-rep conversation.** Day-one alignment, expectations on culture, and personal context belong to the manager. The plan is a scaffold the manager edits, not a script the rep follows in isolation.
- **Comp, quota, or territory decisions.** Quota carry, draws, and territory carve-outs are policy choices that belong to RevOps and Finance. The skill assumes those are already set and reads them as inputs.
- **Generic enablement program design.** The skill produces one plan for one rep, not a curriculum.
## Inputs
Required:
- `rep_name` — full name, used in the output header only
- `rep_background` — one of `first-sales-job`, `competitor`, `adjacent-saas`, `up-market-from-smb`, `down-market-from-enterprise`, or a free-text description if none of the canned categories apply
- `segment` — the segment the rep will sell into: `smb`, `mid-market`, `enterprise`, or a custom segment name your team uses
- `start_date` — ISO date; used to compute calendar week labels in the plan
Optional:
- `linkedin_url` — pulled to enrich `rep_background` if the canned category is too coarse
- `manager_preferences` — free-text from the hiring manager (e.g. "this rep is anxious about cold calling, front-load discovery shadows")
- `prior_ramp_data_path` — path to a CSV of prior reps' time-to-first-deal and time-to-quota in the same segment; the skill calibrates milestone weeks against this data instead of using defaults
- `comp_plan_summary` — one-paragraph summary of the rep's quota and ramp draw, included verbatim in the plan so the rep sees it day one
## Reference files
Always read the following from `references/` before generating the plan. Without them, the output is a generic 30/60/90 template that ignores your motion, your library, and your team's actual ramp curve.
- `references/1-segment-milestones-template.md` — what "ramped" looks like for each segment you sell into; the skill calibrates weekly milestones against this. Replace the template content with your team's real definitions.
- `references/2-resource-library-template.md` — your tagged Gong calls, Notion docs, certifications, and role-play scenarios, organized by stage of the motion. The skill picks from this list rather than inventing resource names.
- `references/3-manager-check-in-template.md` — the question scaffolding the hiring manager runs each week. The skill embeds week-specific questions from this file into the plan output.
## Method
Run these five sub-tasks in order. Steps 3-5 depend on context produced in steps 1-2; do not parallelize.
### 1. Classify the rep against your motion
Read `rep_background` plus optional `linkedin_url`. Map the rep to one of: needs-fundamentals (first sales job), needs-positioning (competitor hire — knows how to sell, doesn't know your story), needs-product (adjacent SaaS — knows the buyer, doesn't know the product), needs- multi-threading (up-market from SMB — single-threaded muscle memory), or needs-velocity (down-market from enterprise — used to long cycles). The rest of the plan keys off this classification.
Engineering choice: a fixed 5-bucket classifier rather than free-form categorization. Free-form classifiers drift across runs; the bucket the plan keys off must be stable so milestones stay comparable across reps.
### 2. Calibrate milestone weeks against actual ramp data
If `prior_ramp_data_path` is set, compute the median week-to-first-deal and week-to-first-quota-month from the CSV for reps in the same segment. Set the plan's milestone weeks to those medians. If no data is available, fall back to defaults from `references/1-segment- milestones-template.md` and add a note: "milestone weeks are defaults; recalibrate after 5+ reps have ramped in this segment."
Engineering choice: median over mean. One outlier rep who ramped in week 3 or week 24 should not pull the plan's milestones. Median is the honest signal of what most reps actually do.
### 3. Pick named resources from the library
For each week of the plan, select 2-4 resources from `references/2- resource-library-template.md` matching the week's focus and the rep's classification. A needs-positioning rep gets more competitive-frame calls in weeks 1-2; a needs-fundamentals rep gets more discovery calls across weeks 1-4. Resources are referenced by name (e.g. "Acme discovery — Gong call ID gc_4821"), never by generic descriptor (e.g. "a good discovery call").
Engineering choice: named resources with stable IDs. Generic descriptors mean the manager has to re-pick everything; named resources mean the rep can self-serve from day one.
### 4. Set named-deal targets, not activity targets
By week 8, each rep should have a written list of 5-10 named target accounts from their territory (pulled from CRM via the optional `crm_query_path`). The plan asks the rep to produce account briefs for each, and the manager to score them in the week-8 check-in.
Engineering choice: named-deal targets over activity targets (e.g. "50 calls per week"). Activity targets reward motion without progress and hide rep struggle behind the dialer. Named-deal targets force both rep and manager to look at the actual work.
### 5. Embed manager check-in questions inline
Each week ends with a section labeled "Manager check-in" containing 3-5 specific questions pulled from `references/3-manager-check-in- template.md`, week-numbered. Generic check-ins ("how's it going?") get skipped; named questions ("what did you learn from the Acme discovery call you shadowed Tuesday?") force the conversation to specifics.
## Output format
The skill writes a single markdown file named `<rep_name>-onboarding- plan.md`. Literal example:
```markdown
# Onboarding plan — Jane Doe
**Start date:** 2026-05-12
**Segment:** mid-market
**Classification:** needs-positioning (competitor hire)
**Manager:** [hiring manager name]
**Quota / ramp:** [comp_plan_summary verbatim, or "TBD — confirm with manager day one"]
## Week 1 (May 12-16) — Product fundamentals + competitive frame
**Focus:** Learn the product enough to demo the wedge use case. Internalize the competitive frame against your prior employer.
**Activities:**
- Mon: Onboarding logistics, laptop, tools, intros
- Tue: Product walkthrough with PM (90 min); self-paced demo recording
- Wed: Read `positioning-one-pager.md`; watch competitive-frame calls listed below
- Thu: Shadow Acme discovery call with [senior AE]; debrief 30 min after
- Fri: Manager check-in (see questions below)
**Named resources:**
- Gong: "Acme discovery vs Competitor X" — gc_4821
- Gong: "Beta Corp objection-handling — pricing" — gc_5102
- Notion: `positioning-one-pager.md`
- Cert: Product fundamentals quiz (must pass week 2)
**Milestone:** Recorded 5-min walkthrough of the wedge use case, reviewed by manager.
**Manager check-in questions:**
1. Where does our positioning feel weak compared to your prior employer?
2. What's the one demo move you'd steal from the calls you watched?
3. Anything blocking you from starting week 2 on Monday?
## Week 2 (May 19-23) — Internal certifications + first role play
[...weeks 2-12 follow the same shape...]
## Milestones summary
| Week | Milestone | Calibrated from |
|---|---|---|
| 4 | First independent discovery call | median ramp data, n=12 prior reps |
| 8 | Named-target account list (5-10 accounts) with briefs | default |
| 10 | First closed-won deal | median ramp data, n=12 prior reps |
| 12 | Full quota carry | comp plan |
## Resource library used
[Flat list of every resource referenced above, with stable IDs.]
```
## Watch-outs
- **Over-prescriptive plans don't survive contact with reality.** A day-by-day plan for week 5 is a fantasy — by then the rep is in live deals on their own schedule. **Guard:** the skill writes day-by-day detail only for weeks 1-4; weeks 5-12 are weekly themes with milestone gates, not daily tasks.
- **Missing context-specific deal patterns.** A generic mid-market plan ignores that your mid-market motion has a specific procurement quirk (e.g. always a security review, always a 30-day legal cycle). **Guard:** the segment milestones template includes a "non-obvious motion quirks" section the skill embeds verbatim into the week-6 and week-9 plan sections, so the rep is not surprised by the first one they hit.
- **Milestone-as-performance-metric drift.** Once a milestone week ("first deal by week 10") becomes a number the rep is graded on, managers stop using it as a coaching signal and start using it as a stick. Reps then game the milestone (closing a tiny deal in week 10 to clear the bar) instead of building the muscle. **Guard:** the plan's milestones section explicitly labels each milestone as "calibration signal, not performance metric" and the manager check-in template's week-10 question is "if the rep didn't hit the milestone, what's the coaching action?" — never "is the rep on track?"
- **Stale resource library.** A Gong library tagged 18 months ago references calls with reps who have left, deals that lost, and a competitive landscape that no longer applies. **Guard:** the resource library template includes a `last_reviewed` field per resource; the skill skips any resource older than 12 months and surfaces a TODO for the enablement owner to refresh.
- **Resume-driven assumptions.** The 5-bucket classifier from step 1 is a starting hypothesis, not ground truth — resumes overstate, LinkedIn understates. **Guard:** the manager check-in for week 1 includes the question "did the classification we used (needs-positioning) match what you're seeing day-to-day?" and the plan can be regenerated with a corrected `rep_background` after week 2.
# Segment milestones — TEMPLATE
> Replace this template's contents with your team's actual segment
> definitions. The rep-onboarding skill reads this file on every run
> to calibrate milestone weeks. Without your real definitions, the
> generated plan defaults to industry-average ramp curves that almost
> certainly do not match your motion.
For each segment your team sells into, fill out one block. Add or remove segments as needed.
---
## Segment: SMB
**Definition:** {headcount range, ACV range, deal cycle median in days}
**What "ramped" looks like:**
- Owns a {N}-account book
- Closes {N} deals per quarter at {median ACV}
- Maintains {N}x pipeline coverage
- Runs {N} discoveries and {N} demos per week
**Calibration weeks (overwrite from `prior_ramp_data_path` if available):**
| Milestone | Default week | Notes |
|---|---|---|
| First independent discovery | 3 | |
| First demo run solo | 5 | |
| First proposal sent | 7 | |
| First closed-won | 10 | |
| Full quota carry | 12 | |
**Non-obvious motion quirks (embedded verbatim into the plan):**
- {Quirk 1 — e.g. "every SMB deal touches Stripe billing review; allow 5 business days"}
- {Quirk 2 — e.g. "decision-maker is almost always founder; do not waste time multi-threading"}
- {Quirk 3}
**Disqualifying signals during ramp (the rep should escalate, not push through):**
- {Signal 1 — e.g. "prospect asks for a SOC 2 report — that's an enterprise signal, requalify"}
- {Signal 2}
---
## Segment: Mid-market
**Definition:** {headcount range, ACV range, deal cycle median}
**What "ramped" looks like:**
- ...
**Calibration weeks:**
| Milestone | Default week | Notes |
|---|---|---|
| First independent discovery | 4 | |
| First demo run solo | 6 | |
| First proposal sent | 9 | |
| First closed-won | 14 | longer cycle than SMB |
| Full quota carry | 16 | |
**Non-obvious motion quirks:**
- {Quirk 1 — e.g. "procurement adds 3-4 weeks at end of cycle; bake into forecast"}
- {Quirk 2 — e.g. "security review is mandatory above $50k ACV; loop in CISO contact early"}
**Disqualifying signals during ramp:**
- ...
---
## Segment: Enterprise
**Definition:** {headcount range, ACV range, deal cycle median}
**What "ramped" looks like:**
- Co-owns {N} named accounts with the AE/SE pod
- Drives {N} executive briefings per quarter
- ...
**Calibration weeks:**
| Milestone | Default week | Notes |
|---|---|---|
| First account-team integration | 6 | |
| First exec briefing run | 12 | |
| First closed-won (existing pipe) | 24 | |
| Full quota carry | 26 | typically end of year 1 |
**Non-obvious motion quirks:**
- {Quirk 1}
- {Quirk 2}
**Disqualifying signals during ramp:**
- ...
---
## Last edited
{YYYY-MM-DD} — update this on any change so the skill can warn when the file is stale.
# Manager check-in framework — TEMPLATE
> Replace this template's contents with your team's actual check-in
> questions. The rep-onboarding skill embeds week-specific questions
> from this file into each week's plan section. Generic check-ins
> ("how's it going?") get skipped — these named questions force the
> conversation to specifics.
The skill expects every week 1-12 to have a block of 3-5 questions. Add weeks 13+ if your ramp runs longer.
## Operating rules for the check-in itself
- 30 minutes, weekly, on the calendar before the rep starts
- Manager prepares: review the milestone for that week, look at the rep's CRM activity, watch one of the rep's recorded calls if any
- Rep prepares: come with the named resources reviewed, one specific question they could not answer, one thing that surprised them
- The check-in is a coaching signal, not a status update — if it's becoming a status update, change the questions
## Week 1 — Onboarding logistics + first impression
- Where does our positioning feel weak compared to what you saw at your prior employer?
- What's the one demo move from the calls you watched that you'd steal?
- Anything blocking you from starting week 2 on Monday?
- Did the classification we used ({classification}) match what you're seeing day-to-day? If not, what should it be?
## Week 2 — Internal certifications + first role play
- Walk me through the product fundamentals quiz question you almost got wrong.
- In the role play, where did you stall? Was it the buyer pushback or your framing?
- Which named resource from the library was most useful this week? Which was a waste?
## Week 3 — Supervised live calls
- On the {Acme | Beta | …} call you co-ran, what would you do differently?
- Where did the senior AE rescue you that you didn't notice in the moment?
- Are you ready to run a discovery solo next week? Honest answer.
## Week 4 — First independent discovery
- Walk me through the disco call. What did you learn that the prospect didn't say directly?
- Which next-step did you ask for? Did they commit?
- What would you change about your opening 90 seconds?
## Week 5 — Discovery loop, second deal
- Compare your week-4 disco to your week-5 disco. What got better? What got worse?
- Are you finding the buyer or are they finding you? (i.e. are you running outbound or inbound?)
- Which segment quirk from the playbook hit this week?
## Week 6 — First demo solo + multi-threading
- Where in the demo did the buyer's eyes glaze over?
- Who else is in the buying committee? How do you know?
- {Embed segment quirks for week 6 — e.g. mid-market: "have you scoped the security review yet?"}
## Week 7 — Pipeline build
- How many qualified opportunities do you have, and which two are most likely to slip?
- Walk me through the worst-fit opp in your pipe. Why is it still there?
- Are you skipping discovery because you're chasing the close? Honest answer.
## Week 8 — Named-target account list
- Walk me through your 10 named targets. Why these?
- Which two are out-of-ICP and you're keeping them anyway? Why?
- For your top 3, what's the next concrete step in the next 14 days?
## Week 9 — First proposal / pricing conversation
- How did you frame the pricing? What was the buyer's reaction?
- Did you use the pricing playbook or freelance? Why?
- {Embed segment quirks for week 9 — e.g. mid-market: "is procurement engaged yet?"}
## Week 10 — First close attempt
- If the deal closes, what was the unlock? If it slipped, what's the diagnosis?
- If the rep didn't hit the milestone (calibration signal, not performance metric), what's the coaching action?
- What's the next deal that looks closeable in the next 30 days?
## Week 11 — Pipeline health + forecast accuracy
- Walk me through your forecast. Which deal are you most wrong about?
- How is your pipeline coverage trending vs. quota?
- What's the one habit you've built that didn't exist in week 1?
## Week 12 — Ramp review
- Looking back, which week was the most useful? Which was a waste?
- What should we change for the next rep we onboard into this segment?
- Are you ready to carry full quota? What support do you still need?
## Last edited
{YYYY-MM-DD}
