ooligo
claude-skill

Personalized rep onboarding plan generator

Difficulty
intermediate
Setup time
60min
For
revops · sales-enablement
RevOps

Stack

A Claude Skill that generates a 30/60/90 onboarding plan tailored to a new rep’s prior background and your specific sales motion. Pulls a curated set of best-rep Gong calls, your messaging docs, and a competency matrix, and outputs a Notion-ready plan with weekly checkpoints, recommended call recordings, and graded exercises.

What you’ll need

  • Claude Code or Claude.ai with the Skill installed
  • Gong access and a tagged library of best-rep calls (discovery, demo, negotiation)
  • Notion API token and a template page
  • A competency matrix doc (what a ramped rep can do)
  • The new rep’s resume or LinkedIn URL

Setup

  1. Tag a Gong library. In Gong, build a folder of “gold standard” calls per stage of your motion. Aim for 10-15 calls covering different segments, deal sizes, and buyer types.
  2. Install the Skill. Drop rep-onboarding.skill into ~/.claude/skills/. Set GONG_API_KEY and NOTION_TOKEN. Point references/competency-matrix.md and references/sales-motion.md at your docs.
  3. Generate. build_onboarding_plan(rep_name="...", linkedin_url="...", segment="mid-market"). The Skill produces a Notion page with weeks 1-12 broken into daily tasks: shadowing, certifications, role plays, and self-paced reading.
  4. Manager review. The hiring manager spends 15 minutes editing — adjusting based on what they know about the rep — and shares the page on day one.

How it works

The Skill reads the rep’s prior background and asks: where do they need most reinforcement? A rep coming from a competitor needs less product training and more positioning differentiation. A rep moving up-market from SMB needs more multi-threading and procurement training. A rep who’s never sold needs more fundamentals.

It then maps weeks to a structured progression: week 1 product fundamentals plus shadowing, week 2 internal certifications, week 3 supervised live calls, weeks 4-8 ramp to first independent deals, weeks 9-12 full quota. Each week ends with a manager checkpoint and a measurable artifact: a recorded role play, a passed certification, a first-call writeup.

The Gong calls are not generic — they’re chosen to match the segment the rep will work and the gaps the Skill identified.

Watch-outs

  • Resume-driven assumptions. Resumes lie. The plan is a starting point, not a contract. Manager edits are mandatory.
  • Stale Gong library. Update the tagged library quarterly or it ages out of usefulness fast.
  • Plan vs. execution. The plan is worthless if the manager doesn’t run the checkpoints. Pair this with a manager-side weekly review automation.

Stack

  • Gong — source of best-rep call examples
  • Notion — destination plan and checkpoint tracker
  • Claude — plan synthesis tailored to the rep’s background