Sales Onboarding 30-60-90 Day Plan Builder
Create a structured 30-60-90 day onboarding plan for new sales hires with clear milestones, training modules, shadowing schedules, and ramp-to-quota expectations.
Prompt Template
You are a sales enablement leader who has onboarded 100+ reps across startups and enterprises. Create a 30-60-90 day onboarding plan for: **Role:** [SDR, AE, Account Manager, Sales Manager, etc.] **Company type:** [startup, mid-market, enterprise, agency] **Product/service:** [brief description of what they'll be selling] **Sales cycle length:** [e.g., 2 weeks, 3 months, 6+ months] **Average deal size:** [e.g., $5K, $50K, $500K] **Sales methodology:** [e.g., MEDDIC, Sandler, Challenger, SPIN, none yet] **Team size:** [how many sales reps on the team] **Tools used:** [CRM, sequencing tools, call recording, etc.] **Ramp expectation:** [when should they carry full quota?] **New hire's experience level:** [first sales role, experienced but new to industry, senior hire] Provide: 1. **30-60-90 day plan** with: - **Days 1-30 (Learn):** Product knowledge, ICP deep dive, tool setup, shadow calls, certifications - **Days 31-60 (Practice):** First outbound campaigns, supervised calls, pipeline building, first meetings - **Days 61-90 (Perform):** Independent selling, quota ramp %, deal progression, coaching focus 2. **Weekly milestones** — specific, measurable checkpoints for each week 3. **Certification checklist** — what the rep must demonstrate before being cleared to sell independently 4. **Shadowing schedule** — who to shadow, what to observe, debrief questions 5. **Scorecard** — quantitative metrics to track ramp progress (calls, meetings, pipeline, closed) 6. **Manager check-in agenda** — weekly 1:1 template for the first 90 days 7. **Common ramp pitfalls** — top 5 reasons new reps fail in the first 90 days and how to prevent them
Example Output
30-60-90 Day Plan — Account Executive, B2B SaaS ($30K ACV)
🟢 Days 1-30: LEARN
**Theme:** Absorb everything. No pressure to sell.
Week 1 — Orientation & Setup
- Complete HR onboarding and tool access (Salesforce, Outreach, Gong, Slack)
- Read the sales playbook cover to cover
- Shadow 3 discovery calls and 2 demo calls
- Complete product certification level 1 (features, use cases, pricing)
- Debrief: Write down your top 10 questions after week 1
Week 2 — ICP & Market Deep Dive
- Study the ICP document: industries, titles, pain points, buying triggers
- Review 10 closed-won deals in Salesforce (read notes, listen to Gong calls)
- Review 5 closed-lost deals — why did they say no?
- Meet with Customer Success: what do happy customers say?
- Attend a live customer QBR (observe only)
Week 3 — Competitive Intelligence
- Complete competitive battle card review
- Role-play: pitch our product vs. top 2 competitors (with manager)
- Shadow 2 more demos, focus on objection handling
- Write your own 60-second elevator pitch (get feedback)
Week 4 — Practice Runs
- Deliver a mock discovery call to your manager (recorded)
- Deliver a mock demo to a peer (recorded)
- Complete product certification level 2 (technical depth, integrations)
- Build your first target account list (50 accounts)
**Milestone:** Can articulate the ICP, product value prop, and top 3 competitive differentiators without notes.
🟡 Days 31-60: PRACTICE
**Theme:** Start doing the job with training wheels on.
Week 5-6 — Outbound Launch
- Launch first outbound sequence (50 prospects)
- Make 30+ calls per day
- Book first 3-5 meetings independently
- Manager listens to all calls via Gong and provides async feedback
Week 7-8 — First Meetings & Pipeline
- Run discovery calls independently (manager joins first 3 silently)
- Deliver first solo product demo
- Build $100K in qualified pipeline
- Weekly pipeline review with manager
**Milestone:** Ran 5+ independent discovery calls, delivered 3+ demos, $100K+ pipeline.
🔴 Days 61-90: PERFORM
**Theme:** Operate independently. Carry ramped quota.
Week 9-12 — Quota Ramp
- Carry 50% of full quota in month 3
- Manage full pipeline independently
- Progress at least 2 deals to proposal/negotiation stage
- Attend weekly team pipeline review, present your top 3 deals
- Close first deal 🎉
**Milestone:** 50% quota attainment, 2+ deals in negotiation, operating independently.
Ramp Scorecard
| Metric | Month 1 | Month 2 | Month 3 | Full Ramp (Month 4+) |
|--------|---------|---------|---------|---------------------|
| Quota % | 0% | 25% | 50% | 100% |
| Calls/day | 0 (shadow) | 30 | 40 | 50 |
| Meetings booked | 0 | 8 | 15 | 20 |
| Pipeline created | $0 | $100K | $200K | $300K |
| Deals closed | 0 | 0-1 | 1-2 | 3+ |
Certification Checklist (Must Pass Before Day 30)
- [ ] Product demo (scored by manager, min 80%)
- [ ] Discovery call role-play (recorded, min 80%)
- [ ] Competitive positioning quiz (written, min 85%)
- [ ] CRM hygiene check (all fields filled correctly on 5 sample records)
- [ ] Elevator pitch delivery (60 sec, from memory)
Common Ramp Pitfalls
1. **Skipping product knowledge for activity** — Reps who rush to call without deep product understanding burn leads.
2. **Not listening to enough Gong calls** — You learn more from 10 recorded calls than 10 hours of training slides.
3. **Avoiding the phone** — Email-only reps ramp 2x slower. The phone is uncomfortable but essential.
4. **Sandbagging pipeline** — New reps under-report pipeline to manage expectations. This hides coaching opportunities.
5. **No debrief after calls** — Every call in months 1-2 should have a 5-minute self-debrief: what worked, what didn't, what to try next.
Tips for Best Results
- 💡Have new reps listen to 20+ Gong recordings in week 1 — pattern recognition from real calls beats any training deck.
- 💡Don't assign quota in month 1. The pressure to hit numbers before understanding the product leads to bad habits that are hard to unlearn.
- 💡Pair new reps with a 'buddy' (not their manager) — someone they can ask 'dumb' questions without feeling judged.
- 💡Use a certification gate before allowing independent selling. If they can't pass a mock discovery call, they're not ready for real prospects.
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