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Sales Onboarding Program (30-60-90 Days) ​

Version: 1.0 | Last Updated: Nov 2025

Program Overview ​

Goal: New sales reps fully productive and hitting 50-75% of quota by Day 90

Learning Philosophy: Learn by doing - 70% hands-on, 20% mentorship, 10% formal training

Success Metrics:

  • Day 30: Product certified, first discovery calls booked
  • Day 60: Demo certified, first demos delivered
  • Day 90: First deals closed, 50-75% of monthly quota

Pre-Boarding (Before Day 1) ​

Week Before Start Date ​

Sent to New Hire:

  • Welcome email from Sales Manager
  • Equipment shipped (laptop, monitor, accessories)
  • Access credentials (email, Slack, Salesforce)
  • Pre-reading: Company overview, product overview
  • Day 1 agenda and expectations

Manager Prep:

  • Assign onboarding buddy (tenured rep)
  • Set up demo environment access
  • Schedule Week 1 meetings
  • Prepare first account list

Month 1: Foundation (Days 1-30) ​

Week 1: Company, Product & Market ​

Monday - Day 1

  • 9:00am: Welcome & orientation with HR
  • 10:00am: Meet the team (Sales, CS, Product, Marketing)
  • 11:00am: Systems setup (Salesforce, Outreach, Slack, calendar)
  • 1:00pm: Company history, mission, values (CEO/Founder)
  • 3:00pm: Sales process overview with Manager
  • 4:00pm: Set 30-60-90 day goals

Tuesday - Day 2

  • 9:00am: Product training Part 1 - Platform overview
  • 11:00am: Demo environment setup
  • 1:00pm: Customer persona workshop
  • 3:00pm: Ideal Customer Profile (ICP) deep dive
  • 4:00pm: Homework: Review customer case studies

Wednesday - Day 3

  • 9:00am: Product training Part 2 - Features deep dive
    • XP & Leveling, Achievements, Quests
    • Leaderboards, Team Collaboration, Chat
    • Micro-Learning, AI Admin, Rules Engine
  • 1:00pm: Use case workshop (OCM, Recruiting, IT, Sales, Agile)
  • 3:00pm: Competitive landscape overview
  • 4:00pm: Study competitive battlecards

Thursday - Day 4

  • 9:00am: Industry vertical deep dive (choose 2 focus industries)
  • 11:00am: Pain point → Solution mapping
  • 1:00pm: Value proposition workshop
  • 3:00pm: ROI calculator training
  • 4:00pm: Homework: Build sample ROI for fictional customer

Friday - Day 5

  • 9:00am: Week 1 review and Q&A
  • 10:00am: Product Knowledge Quiz (pass = 80%+)
  • 11:00am: Watch 5 recorded demos (best practices)
  • 2:00pm: First demo practice with buddy
  • 4:00pm: Week 1 debrief with Manager

Week 2-3: Sales Process & Methodology ​

Learning Goals:

  • Master discovery question framework
  • Understand qualification (BANT/MEDDIC)
  • Learn objection handling
  • Practice email outreach
  • Practice cold calling

Daily Schedule:

  • 9-11am: Training sessions
  • 11am-12pm: Role-play and practice
  • 1-3pm: Shadow sales calls (10+ calls)
  • 3-5pm: Self-study and homework

Key Activities:

  • Day 6-7: Discovery framework training + practice
  • Day 8-9: Email outreach templates + write first sequences
  • Day 10-11: Cold calling training + practice calls (internal)
  • Day 12-13: Demo script training + practice demos
  • Day 14-15: Objection handling training + role-plays

End of Week 3:

  • Discovery Call Certification (mock discovery with Manager)
  • Assigned first real accounts (20-30 prospects)
  • Begin prospecting activities

Week 4: Assisted Selling Begins ​

Learning Goals:

  • Start real prospecting (emails, calls)
  • Book first discovery calls
  • Begin shadowing live demos
  • Practice proposal writing

Daily Activities:

  • 9-10am: Account research and planning
  • 10am-12pm: Prospecting (emails, LinkedIn, calls)
  • 1-2pm: Shadow live customer calls
  • 2-4pm: Call reviews and coaching
  • 4-5pm: Update Salesforce, plan next day

Targets:

  • 50 outbound emails sent
  • 25 cold calls made
  • 5 discovery calls booked (for Week 5)
  • Shadow 10 customer interactions

End of Month 1 Checkpoint:

  • Product Knowledge: ✅ Certified
  • Discovery Skills: ✅ Certified
  • Pipeline: 5+ discovery calls booked
  • CRM: All activities logged properly

Month 2: Ramp-Up (Days 31-60) ​

Week 5-6: First Customer Interactions ​

Learning Goals:

  • Deliver first discovery calls (with Manager attending)
  • Conduct first demos (with Manager co-presenting)
  • Handle objections in real situations
  • Begin building pipeline

Daily Activities:

  • 9-10am: Account research and call prep
  • 10am-3pm: Customer calls (discovery, demos)
  • 3-4pm: Call debriefs with Manager
  • 4-5pm: Follow-ups, Salesforce updates

Week 5 Targets:

  • 5-7 discovery calls conducted
  • 2-3 demos booked
  • 15-20 new prospects added to pipeline
  • 100 outbound touches (emails + calls)

Week 6 Targets:

  • 2-3 demos delivered (Manager co-presenting)
  • 1-2 proposals sent
  • 10 active opportunities in pipeline
  • First technical/POC discussions

Coaching Focus:

  • Post-call reviews: "What went well? What would you change?"
  • Discovery question effectiveness
  • Demo pacing and engagement
  • Objection handling in real scenarios

Week 7-8: Independent Selling with Support ​

Learning Goals:

  • Deliver demos independently
  • Write proposals without templates
  • Navigate technical discussions
  • Advance opportunities through pipeline

Week 7 Targets:

  • 3-4 demos delivered (solo with Manager available)
  • 2 proposals sent
  • 1 POC/pilot proposal
  • 20 active opportunities

Week 8 Targets:

  • 4-5 demos delivered independently
  • 3 proposals sent
  • First deal in negotiation/closing stage
  • 25-30 active opportunities

End of Month 2 Checkpoint:

  • Demo Certification: ✅ Certified
  • Proposal Writing: ✅ Proficient
  • Pipeline: 25-30 active opportunities
  • Deal Stage: 1-2 deals in closing stages
  • Quota Attainment: 25-50% of monthly target

Month 3: Full Productivity (Days 61-90) ​

Week 9-12: Independent Seller ​

Learning Goals:

  • Manage full sales cycle independently
  • Close first deals
  • Hit 50-75% of quota
  • Master time management and prioritization

Daily Rhythm:

  • 9-10am: Pipeline review and prioritization
  • 10am-3pm: Customer-facing activities
  • 3-4pm: Follow-ups and proposals
  • 4-5pm: CRM hygiene and next-day planning

Weekly Targets (Weeks 9-12):

  • 5-7 discovery calls
  • 4-5 demos
  • 3-4 proposals sent
  • 1-2 POCs/pilots initiated
  • 30-40 active opportunities in pipeline

Key Milestones:

  • Week 9: First deal closed 🎉
  • Week 10: Demo delivery at expert level
  • Week 11: Managing full sales cycle solo
  • Week 12: Second deal closed, hitting 50-75% quota

End of Month 3 Checkpoint:

  • Closing Certification: ✅ Certified
  • First 2 deals closed: ✅
  • Quota Attainment: 50-75% of monthly target
  • Pipeline Health: 2-3x quota coverage
  • Full independence: ✅

Certification Program ​

Product Knowledge Certification (Day 10) ​

Format: 50-question quiz + verbal Q&A

Topics:

  • Platform features and capabilities
  • Use cases by industry
  • Competitive differentiation
  • Pricing and packaging
  • Integration capabilities

Pass Criteria: 80% on quiz + Manager approval

Discovery Call Certification (Day 21) ​

Format: 30-minute mock discovery call

Evaluation Criteria:

  • Pre-call research and preparation
  • Question quality and flow (SPIN)
  • Active listening and note-taking
  • Pain point identification
  • BANT qualification
  • Next steps and follow-up plan

Pass Criteria: 4/5 on all criteria + Manager approval

Demo Certification (Day 45) ​

Format: 45-minute demo to internal stakeholders

Evaluation Criteria:

  • Demo preparation and customization
  • Opening and agenda setting
  • Feature demonstration (flow and clarity)
  • Tying features to customer pain points
  • Handling questions and objections
  • ROI discussion
  • Strong close with next steps

Pass Criteria: 4/5 on all criteria + 2 Manager-observed customer demos

Closing Certification (Day 75) ​

Format: Negotiation role-play + proposal review

Evaluation Criteria:

  • Proposal quality and customization
  • Negotiation skills
  • Objection handling
  • Value reinforcement
  • Contract navigation
  • Mutual close plan creation

Pass Criteria: Successfully advance 1 real deal to closing stage + Manager approval

Onboarding Buddy Program ​

Buddy Responsibilities ​

Week 1-2:

  • Lunch on Day 1
  • Daily check-ins (15 min)
  • Answer questions about tools, culture, process
  • Share "lessons learned"

Week 3-4:

  • 2-3 call shadows
  • Review first emails and call recordings
  • Share personal prospecting tips
  • Introduce to key contacts

Month 2-3:

  • Weekly coffee chats
  • Ad-hoc questions and support
  • Celebrate first wins together

Manager Coaching Schedule ​

Daily (Weeks 1-4) ​

  • 15-minute end-of-day check-in

Weekly (Month 2-3) ​

  • Monday: Week planning and pipeline review (30 min)
  • Wednesday: Mid-week check-in (15 min)
  • Friday: Week review and coaching (45 min)

Monthly ​

  • 30-60-90 Day Review
  • Goal setting and feedback
  • Career development discussion

Self-Study Resources ​

Required Reading ​

  • [ ] Company pitch deck and messaging guide
  • [ ] Sales playbook
  • [ ] Competitive battlecards (all)
  • [ ] Top 10 customer case studies
  • [ ] Product documentation
  • SPIN Selling by Neil Rackham
  • The Challenger Sale by Matthew Dixon
  • Never Split the Difference by Chris Voss
  • Atomic Habits by James Clear (our product philosophy)

Video Library ​

  • 20 recorded demos (watch and critique)
  • 10 discovery call recordings
  • 5 negotiation/closing recordings

Success Metrics Dashboard ​

Month 1 Scorecard ​

MetricTargetActualStatus
Product Quiz Score80%+___
Discovery Calls Observed10+___
Discovery Calls Booked5+___
Certifications Passed2/4___

Month 2 Scorecard ​

MetricTargetActualStatus
Discovery Calls Delivered15+___
Demos Delivered8+___
Proposals Sent3+___
Pipeline Value$50k+___
Certifications Passed3/4___

Month 3 Scorecard ​

MetricTargetActualStatus
Discovery Calls20+___
Demos Delivered15+___
Proposals Sent10+___
Deals Closed1-2___
Quota Attainment50-75%___
Pipeline Coverage2-3x___
Certifications Passed4/4___

Troubleshooting & Support ​

Common Challenges ​

"I don't understand the product deeply enough" → Schedule 1:1 with Product team, review docs, practice more demos

"I'm not booking enough meetings" → Email/call volume review, messaging audit, target ICP check

"Demos aren't converting to proposals" → Discovery quality review, demo skills coaching, follow-up improvement

"I'm overwhelmed" → Time management coaching, prioritization workshop, reduce account load

Escalation Path ​

  1. Onboarding Buddy (quick questions)
  2. Sales Manager (coaching, skills)
  3. Sales Ops (systems, process)
  4. VP Sales (major blockers)

Graduation: Day 90 ​

Graduation Criteria:

  • ✅ All 4 certifications passed
  • ✅ 1-2 deals closed
  • ✅ 50-75% quota attainment
  • ✅ Healthy pipeline (2-3x coverage)
  • ✅ Manager approval

Graduation Celebration:

  • Team announcement
  • 1:1 with VP Sales
  • Month 4+ quota assignment (100% of target)

Ongoing Development:

  • Monthly sales training
  • Quarterly quota reviews
  • Annual career planning

Program Owner: Sales Enablement & Sales Management Review Cadence: Quarterly based on new hire performance data

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