Most sales onboarding is a week of product training followed by "go shadow some calls." That's not onboarding—it's abandonment with extra steps.
Good onboarding is a system. It has owners, timelines, milestones, and gates. The manager knows exactly what the rep should know by day 30. The rep knows exactly what's expected to pass day 60. Enablement has checkpoints to course-correct before it's too late.
This checklist breaks down who owns what from pre-start through day 90. Use it as-is or adapt it to your team—but don't wing it.
Pre-Day-1: Before They Start
The first day should feel organized, not chaotic. Prep before the rep arrives.
Manager Responsibilities
- Send welcome email with start logistics (time, location, who to meet)
- Share pre-reading: company overview, product docs, market context
- Confirm laptop, accounts, and tools will be ready
- Set up 1:1 cadence for the first 30 days (recommend 3x/week)
- Identify their onboarding buddy (tenured rep)
- Prepare 30-60-90 day expectations doc
Enablement Responsibilities
- Provision LMS access and pre-work assignments
- Schedule first-week sessions (product, ICP, process)
- Prepare call recordings for listening assignments
- Set up onboarding tracking in your system (Notion, Sheet, or tool)
HR/Ops Responsibilities
- Complete background check and paperwork
- Provision hardware and shipping
- Set up accounts: email, Slack, CRM, dialer, video
- Add to appropriate distribution lists and channels
Gate check: Do not start day 1 without laptop, CRM access, and 30-60-90 doc ready.
Week 1: Orientation and Foundation
The goal of week 1 is context, not competence. The rep should understand who you sell to, what you sell, and why it matters—not master it yet.
Day 1
- Welcome meeting with manager (30 min): team overview, expectations, communication norms
- Meet onboarding buddy
- Complete HR and IT setup tasks
- Tour of key tools: CRM, dialer, email, calendar, Slack
- Read company overview and value proposition docs
- Listening assignment: 2 call recordings (discovery + close)
Day 2
- Product overview session (60-90 min)
- ICP and persona deep-dive
- Review competitor landscape
- Start shadow rotations: observe 2 live calls
- Begin CRM and activity standards training
Days 3-5
- Complete product training modules (or sessions)
- Shadow 3-5 additional calls
- Review sales process and stage definitions
- Intro to sales playbook and key scripts
- First 1:1 with manager: initial impressions, questions, blockers
- Self-assessment: "What's still unclear?"
End of Week 1 Milestone:
- Rep can articulate ICP, product value prop, and basic sales process
- Rep has observed 5+ live calls
- Rep can navigate CRM and log activities
Weeks 2-3: Skill Building and Practice
Now the rep starts doing, with close supervision and fast feedback loops.
Week 2
- Role-play: cold call opening (manager or buddy feedback)
- Role-play: discovery questions
- Live call practice: shadowed outbound with manager listening
- Objection-handling workshop or module
- Deep-dive on 2-3 common objections
- Email/LinkedIn sequence training
- Begin prospecting with manager review before send
Manager responsibility: Listen to 100% of calls this week. Give feedback same-day.
Week 3
- Role-play: full discovery call (end-to-end)
- First solo calls (manager monitors, debriefs after)
- Demo training (if applicable)
- Pricing and packaging overview
- Review call recordings together (self + manager notes)
- Midpoint check-in: what's clicking, what's not?
End of Week 3 Milestone:
- Rep can run a basic cold call independently
- Rep demonstrates correct CRM hygiene
- Rep can handle 2-3 common objections
- Manager has heard 10+ calls and given feedback
Weeks 4-6: Ramping Volume and Building Confidence
The rep starts carrying real activity expectations. Manager shifts from watching every call to sampling and coaching.
Week 4
- Transition to independent prospecting with spot-check
- Discovery certification: live call graded by manager or enablement
- Pipeline review: understand forecasting expectations
- Continue objection-handling practice
- Intro to multi-threading and stakeholder management (for AEs)
Discovery certification criteria:
- Asked open-ended questions
- Uncovered at least one pain point
- Connected pain to product value
- Proposed a clear next step
Week 5
- Full activity expectations begin
- Demo certification (for AEs): live demo graded
- Manager listens to 25% of calls (random sample)
- First pipeline review with manager
- Cross-functional intro: marketing, product, customer success
Week 6
- Quota or activity target at 50%
- Independent pipeline management
- Manager 1:1s shift to weekly (from 3x/week)
- Coaching focus based on call patterns
End of Week 6 Milestone (Day 45):
- Rep is running calls independently
- Discovery certification passed
- Demo certification passed (if AE)
- Manager has moved to spot-check and coaching cadence
- Rep shows pipeline or activity progress toward goal
Weeks 7-9: Performance Toward First Outcomes
The rep is now operating mostly independently. Coaching focuses on specific skill gaps and pipeline management.
Week 7
- Activity target at 75%
- Full pipeline ownership
- First negotiation or close coaching (if deals in play)
- Continued call review: 2-3 per week
- Objection-handling refresh based on real call challenges
Week 8
- Full activity target
- Advanced skill session: multi-threading, competitive deals, negotiation
- Manager 1:1 focus shifts to deal strategy
- Begin prep for day-90 readiness review
Week 9
- Full performance expectations active
- First close or qualified opportunity milestone (role-dependent)
- 360 feedback collection: manager, buddy, enablement
- Rep self-reflection: what do you need to work on?
Weeks 10-13: Day 90 Gate
By day 90, you should know whether the hire is working. The readiness review formalizes that judgment.
Day 90 Readiness Review Components
Quantitative:
- Activity metrics vs. ramp target (calls, emails, meetings)
- Pipeline metrics vs. ramp target (opportunities, value)
- Outcome metrics vs. ramp target (meetings set, deals closed, quota)
Qualitative:
- Call quality assessment: random sample graded by manager or enablement
- Deal quality assessment: are opportunities real and properly qualified?
- Coachability assessment: does the rep apply feedback?
- Cultural fit assessment: do they represent the team well?
Decision:
- Extend onboarding: Rep is progressing but needs more time (30-day extension)
- Transition to full performance: Rep is ramped and operating independently
- Exit decision: Fundamental skill or fit gap unlikely to close
Day 90 Gate Checklist
- All certifications passed (discovery, demo, objection handling)
- Activity at 80%+ of full expectations
- Pipeline or outcome metrics trending positive
- Manager has confidence in rep trajectory
- Rep has completed self-assessment
Ownership Summary
| Phase | Manager | Enablement | Rep |
|---|---|---|---|
| Pre-start | Welcome, buddy, 30-60-90 doc | LMS setup, pre-work | Complete pre-reading |
| Week 1 | Daily check-ins, set expectations | Training sessions | Learn context |
| Weeks 2-3 | Listen to all calls, daily feedback | Workshops, certifications | Practice, shadow, role-play |
| Weeks 4-6 | Sample calls, certifications | Certification grading | Ramp activity, pass gates |
| Weeks 7-9 | Weekly coaching, deal strategy | Skill reinforcement | Full performance |
| Day 90 | Readiness decision | Assessment support | Self-reflection |
Why This Structure Works
The checklist forces three things that ad-hoc onboarding misses:
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Milestones make progress visible. Everyone knows whether the rep is on track at week 3, week 6, and day 90.
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Gates force quality over speed. You can't rush past discovery certification just because you need bodies on the phones.
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Ownership prevents drift. When no one owns onboarding, enablement thinks the manager does it, the manager thinks enablement does it, and the rep is alone.
A new hire failure at month 6 often started as a month 2 problem that no one caught.
Ramp new reps faster with structured milestones, certification gates, and continuous coaching. Download the checklist or see how Miki Onboard tracks it automatically.