Your new sales rep starts Monday. You send them a Notion page with product docs, a Salesforce login, and a calendar invite to shadow some calls.
Six months later, they're still ramping and not hitting quota.
This is onboarding failure: overwhelming new reps with information instead of equipping them with the specific skills to run deals.
Great onboarding isn't about information transfer. It's about skill development and deal readiness in the shortest time possible.
Here's how to build onboarding that gets reps productive in 30 days, not 6 months.
The 30-60-90 Framework (Compressed to 30 Days)
Most companies take 90+ days to onboard reps. You can compress this by focusing on what matters for early deal success.
Week 1: Product and market knowledge
Goal: Rep can explain what you do, who you serve, and why it matters
Activities:
- Product overview (what it does, core features, key differentiators)
- ICP and persona training (who buys, why they buy, what they care about)
- Competitive landscape (who you compete with, how to position)
- Shadowing 5-8 discovery calls and demos
Deliverable: Rep presents product pitch to onboarding buddy and answers basic questions
Week 2: Sales process and deal mechanics
Goal: Rep understands your sales motion and can execute basic steps
Activities:
- Sales process overview (stages, exit criteria, typical timeline)
- CRM training (how to log activities, update opportunities, find information)
- Discovery framework training (what questions to ask, how to uncover needs)
- Demo script training (how to structure demos, key talking points)
Deliverable: Rep runs mock discovery call and demo with manager
Week 3: Objection handling and competitive positioning
Goal: Rep can handle common objections and competitive situations
Activities:
- Objection handling playbook review
- Battle card training (how to position vs. competitors)
- Pricing and negotiation guidelines
- Role-playing objection scenarios
Deliverable: Rep handles 5 objection scenarios in role-play
Week 4: Live deal practice with support
Goal: Rep runs real deals with oversight
Activities:
- Rep takes 3-5 discovery calls (shadowed by manager initially)
- Rep delivers 2-3 demos (manager in attendance)
- Rep writes first proposals (reviewed by manager before sending)
- Daily feedback sessions with manager
Deliverable: Rep independently runs discovery call and demo with minimal coaching
By day 30: Rep should be able to run full sales cycle with oversight, not solo yet but functional.
The Onboarding Content: What to Teach vs. What to Skip
Most onboarding programs try to teach everything. This overwhelms new reps with information they don't need yet.
Prioritize by urgency:
Tier 1: Need to know in first 7 days
- Core product value proposition
- ICP and buyer personas
- Basic discovery questions
- Demo script for common use cases
- CRM basics (logging calls, updating deals)
Tier 2: Need to know in days 8-30
- Competitive positioning and battle cards
- Objection handling scripts
- Pricing and discounting guidelines
- Proposal and contract process
- Detailed product features
Tier 3: Learn after 30 days
- Advanced product capabilities
- Niche use cases and verticals
- Complex deal structures
- Partner ecosystem and co-selling
- Product roadmap deep-dives
Don't front-load everything. Teach what's needed when it's needed.
Shadowing That Actually Teaches
"Go shadow some calls" is lazy onboarding. Structured shadowing teaches intentionally.
Shadowing framework:
Pre-call brief:
- What stage is this deal in?
- What's the prospect's main pain point?
- What's the goal for this call?
- What should new rep listen for?
During call:
- New rep takes notes on specific framework (discovery questions asked, objections raised, how handled)
- New rep muted, no participation yet
Post-call debrief:
- What did the rep do well?
- What questions did they ask that uncovered key insights?
- How did they handle objections?
- What would you have done differently?
Volume: New rep shadows 10-15 calls in first two weeks, with structured debriefs after each.
This turns passive listening into active learning.
Role-Play That Doesn't Feel Awkward
Most reps hate role-play because it's forced and generic. Make it realistic and contextual.
Effective role-play structure:
Scenario-based:
Don't say "practice your pitch." Say "You're talking to a VP of Sales at a 200-person company who's frustrated with forecast accuracy. They're also evaluating [Competitor X]. Run discovery."
Specific scenarios feel real and force reps to apply frameworks, not recite scripts.
Progressive difficulty:
- Week 1: Easy scenarios with friendly prospects
- Week 2: Moderate scenarios with objections
- Week 3: Hard scenarios with skeptical prospects and competitive situations
Build confidence progressively.
Record and review:
Record role-plays. Have rep watch their own performance and self-critique before manager feedback.
"What did you do well? What would you change?"
Self-awareness accelerates improvement.
Partner with peers:
Don't make all role-play rep-to-manager. Pair new reps with peers to practice together.
Less intimidating, more reps, more practice.
The Onboarding Buddy System
New reps shouldn't navigate onboarding alone. Assign an onboarding buddy.
What buddies do:
- Answer day-to-day questions ("Where do I find battle cards?")
- Share real examples ("Here's a discovery call I did last week, listen to how I handled the pricing objection")
- Provide informal feedback ("Your demo was good, but you talked too fast—slow down")
- Make onboarding less isolating
Who should be buddies:
- Reps who have been there 6-12 months (recent enough to remember onboarding pain)
- Reps who are performing well (you want new reps learning good habits)
- Reps who want to mentor (don't force it)
Structure buddy engagement:
- Week 1: Daily check-ins
- Week 2-3: Every other day
- Week 4: Weekly
Buddies aren't managers—they're peers who've been there recently.
The Onboarding Milestone Map
New reps need clear goals to work toward. Create milestone checkpoints.
Week 1 milestone: Product knowledge certification
- Rep presents product pitch to manager
- Rep answers 10 common prospect questions
- Pass/fail: Do they understand what we do and who we serve?
Week 2 milestone: Discovery call certification
- Rep conducts mock discovery call using framework
- Rep demonstrates ability to ask probing questions
- Pass/fail: Can they uncover prospect needs?
Week 3 milestone: Demo certification
- Rep delivers full demo to manager acting as prospect
- Rep handles 3 objections during demo
- Pass/fail: Can they run compelling demo?
Week 4 milestone: Live deal execution
- Rep runs 3 discovery calls with real prospects
- Rep delivers 2 demos
- Rep writes 1 proposal
- Pass/fail: Can they execute sales process with oversight?
Passing criteria is clear: If rep doesn't pass milestone, they don't proceed. More practice and retesting required.
This ensures quality standards without arbitrary timelines.
The Resource Hub: One Place for Everything
New reps shouldn't hunt for resources. Create single source of truth.
Onboarding hub should include:
Product knowledge:
- Product overview deck
- Feature demo videos (2-3 min each)
- Competitive battle cards
- Common use case guides
Sales process:
- Discovery question framework
- Demo script templates
- Objection handling playbook
- Proposal templates
- CRM how-to guides
Practice materials:
- Role-play scenarios
- Recorded example calls (good and bad)
- Self-assessment checklists
Support:
- Who to ask for help (and when)
- Buddy contact info
- Manager 1:1 schedule
Make it searchable: New rep should be able to find any resource in under 30 seconds.
First Deal Support: Setting Reps Up to Win
New reps' first deals are terrifying. Provide scaffolding.
First discovery call:
- Manager shadows, muted
- Manager takes notes on what went well and what to improve
- Immediate debrief after call
- Rep owns follow-up with manager reviewing before sending
First demo:
- Rep practices demo day before with manager
- Manager attends demo, muted
- Manager can jump in if rep gets stuck (safety net)
- Debrief after: what worked, what to improve
First proposal:
- Rep drafts proposal
- Manager reviews and provides feedback
- Multiple revision rounds if needed
- Manager approves before sending
First negotiation:
- Manager joins call to observe
- Rep leads, manager provides backup
- Debrief on negotiation tactics after
Gradual release of responsibility: coach → observe → support → fully independent.
Measuring Onboarding Success
Track metrics to know if onboarding is working.
Time to first deal closed:
How long from start date to first closed-won deal?
Target: 60 days (30 days onboarding + 30 days average sales cycle)
Certification pass rates:
What % of new reps pass each milestone on first attempt?
If <80% pass rate, milestones are too hard or training is insufficient.
Ramp time to quota:
How long until new rep hits 100% of quota consistently?
Target: 90 days (after 30-day onboarding, 60 days to full productivity)
Retention at 90 days:
What % of new reps are still with company at 90 days?
If <90%, onboarding or hiring process has problems.
Compare cohorts: Are recent onboarding cohorts improving vs. previous cohorts?
If not, your onboarding isn't getting better.
Common Onboarding Mistakes
Mistake 1: Information dumps
Sending new reps 100 pages of docs to read doesn't teach skills.
Fix: Bite-sized learning (15-20 min modules) with practice after each.
Mistake 2: No hands-on practice
Reading about discovery frameworks doesn't prepare reps to run discovery.
Fix: Role-play and live practice starting week 2.
Mistake 3: Sink-or-swim mentality
"Figure it out" isn't onboarding.
Fix: Structured support with clear milestones and feedback.
Mistake 4: One-size-fits-all
New reps with 10 years of sales experience need different onboarding than fresh college grads.
Fix: Adjust pacing and depth based on experience level.
Mistake 5: Onboarding ends at day 30
Day 30 is foundation, not finish line.
Fix: Ongoing coaching, skill development, and feedback through first 90 days.
The Real Goal
Sales onboarding isn't about teaching everything. It's about building confidence and competence to run deals successfully.
Focus on skills that matter for first deals. Practice intensively. Provide support and feedback.
By day 30, reps should be functional. By day 90, they should hit quota.
That's how onboarding drives revenue, not just orientation.