30-Day Roofing Sales Onboarding Plan: From Zero to First Sale

Your new rep starts Monday. You've got him scheduled for 10 weeks of ride-alongs, product training videos, and shadowing. By Week 12, he'll be ready to knock his first door solo.

Except he won't make it to Week 12. According to industry research, 43% of new sales reps leave within the first 90 days. Your 12-week onboarding plan puts his first real appointment around Day 84—right when most quit.

Here's the disconnect: traditional onboarding treats roofing sales like enterprise software sales. It doesn't move fast enough. By the time your rep finally gets in front of homeowners, he's either gone or so rusty from sitting in training that he bombs his first 20 doors.

The Onboarding Crisis Nobody Talks About

The data on sales onboarding is brutal. According to Sales Management Association research, 62% of organizations admit their onboarding programs are ineffective. The average new sales hire takes 11.2 months to become fully productive. For roofing, where seasonality and weather windows compress your earning timeline, that's a death sentence.

Here's what that looks like in dollars: Research from DePaul University shows it costs $97,960 to replace the average sales rep. Add the lost revenue from burning through your best storm-damaged territories with undertrained reps, and you're looking at $150K-$200K per failed hire.

The root cause? Traditional onboarding is too slow and too passive. Reps spend weeks watching videos, sitting in on calls, and "learning the product" before they ever face real objections. Then when they finally go solo, they have zero muscle memory for handling homeowners who say "I need three more quotes" or "Your price is too high."

According to Zippia's sales training research, 84% of all sales training is forgotten within 90 days. That means your 10-week onboarding program? Most of it evaporates by the time the rep actually needs it.

Why Traditional Onboarding Takes Too Long (And Burns Leads)

Let's walk through what most roofing companies do:

Weeks 1-2: Product training. GAF vs CertainTeed vs Atlas. Architectural shingles vs 3-tab. Ice and water shield. Valley flashing. Drip edge. The rep sits through hours of manufacturer videos and tries to memorize specs.

Weeks 3-4: Ride-alongs. The rep shadows a senior rep on 15-20 appointments. He watches, takes notes, and asks questions afterward. He sees maybe 3-4 actual objections handled live.

Weeks 5-8: More shadowing. More product training. Maybe some CRM training. The rep is bored. He hasn't knocked a single door solo.

Weeks 9-10: First solo appointments. The manager assigns him "easy" leads—pre-qualified insurance jobs or referrals. The rep gets his first real objections and freezes. He's seen objections handled before, but he's never practiced responding himself.

Week 11-12: The rep is still struggling. He's closing maybe 10-12% when team average is 28-32%. He's frustrated. The manager is frustrated. The rep starts looking at other opportunities.

The problem: You gave him knowledge but no reps. He can explain the difference between GAF Timberline HDZ and CertainTeed Landmark Pro, but he can't handle "I need to think about it" without his hands shaking.

The 30-Day Onboarding Framework

This framework compresses the timeline without cutting corners. The difference? Reps get 100+ practice conversations in their first 3 weeks instead of watching 10 real ones. They build muscle memory before they need it.

Week 1: Foundation (Days 1-7)

Focus: Company culture, product basics, sales process overview

This week is about orientation and setting expectations. Don't try to teach them everything—teach them enough to understand the context for what comes next.

Day 1-2: Company Culture & Tech Setup

• Company vision, values, team structure
• Paperwork, benefits, compliance
• CRM access, email setup, phone provisioning
• Territory assignment and lead sources overview

Day 3-4: Product Knowledge Basics

• The 20% of product knowledge that covers 80% of conversations
• Architectural vs 3-tab shingles (and why we only sell architectural)
• GAF Timberline HDZ features and warranty (your primary offering)
• Ice and water shield requirements (building code vs best practice)
• Typical install timeline (weather-dependent)

What NOT to do: Don't dump 40 hours of manufacturer training videos on them

What TO do: 2-hour interactive session covering what homeowners actually ask about

Day 5-7: Sales Process Overview

• Your 5-step sales process from door knock to contract signed
• CRM workflow and pipeline stages
• Documentation requirements (photos, measurements, notes)
• Commission structure and quota expectations
• Assign first homework: Watch recordings of 3 successful appointments from your top rep

Week 1 Success Metric: Rep can explain your sales process start to finish and knows the basics of GAF Timberline HDZ.

Week 2: Skills (Days 8-14)

Focus: Door approach, pitch structure, objection fundamentals

This is where practice volume becomes critical. The rep needs to hear and respond to objections dozens of times before facing real homeowners.

Day 8-9: Door Approach Scripts + Practice

• Your proven door script (the exact words that get appointments)
• Handling immediate brush-offs: "Not interested," "We're not ready," "How did you get our address?"
• Practice exercise: Rep practices door script 20 times with variations using GhostRep's Objection Mastery platform

The AI throws realistic homeowner responses: sometimes they're friendly, sometimes hostile, sometimes in a rush. The rep practices pivoting based on homeowner energy without burning real leads or wasting manager time on role-plays.

Day 10-11: Pitch Deck Walkthrough

• Your proven presentation structure (problem → solution → proof → price)
• When to show photos of past work
• How to handle spouse objections mid-presentation
• Practice exercise: Rep delivers full pitch 10 times to AI, gets scored on structure, pacing, and confidence

Day 12-14: Objection Handling Fundamentals

The top 10 objections that kill 80% of deals:

1. "Your price is too high"
2. "I need to get 3 more quotes"
3. "My insurance deductible is too high"
4. "I'm not sure about GAF vs CertainTeed"
5. "Can you do it for $X less?"
6. "I need to think about it"
7. "My spouse isn't home"
8. "We're planning to move in 2 years"
9. "I'll call you back when I'm ready"
10. "Your competitor said they'd do it for $Y"

For each objection, the rep needs 15-20 practice reps before he internalizes the response. That's 150-200 practice conversations. You can't provide that volume through manager role-plays or ride-alongs.

This is where GhostRep's Objection Mastery becomes essential. The rep logs in for 45 minutes each day (Days 12-14) and practices handling "price is too high" objections 20 times in a row. The AI doesn't let him off easy—it throws variations:

• "My neighbor paid $15,000 for their roof"
• "I got a quote for $18,500 from another company"
• "That seems really high for what you're doing"
• "Why would I pay your price when others are cheaper?"

By Day 14, the rep has heard every version of the price objection and his responses become automatic. His hands don't shake. His voice doesn't crack. He knows exactly what to say.

Week 2 Success Metric: Rep completes 150+ practice scenarios and can handle the top 10 objections without hesitation.

Week 3: Simulation (Days 15-21)

Focus: AI roleplay progression, observation ride-alongs, first solo appointments

Week 3 transitions from pure practice to applying skills in real contexts.

Day 15-17: Advanced AI Roleplay Sessions

• 30+ full appointment simulations using GhostRep's AI Roleplay platform
• Progressive difficulty: starts with friendly homeowners, progresses to skeptical, then hostile
• Scenarios include:
  • Homeowner has 2 other quotes in hand
  • Spouse shows up mid-presentation and derails everything
  • Homeowner tries to negotiate down 20%
  • Insurance adjuster lowballed the claim
  • Homeowner is price shopping and won't commit

The AI tracks which scenarios the rep struggles with most and increases practice in those areas. If he's failing "spouse shows up mid-pitch" 60% of the time, the platform gives him 10 more of those scenarios until he figures it out.

Day 18-19: Ride-Along Observation

• Rep shadows senior rep on 6-8 real appointments
• Key difference from traditional ride-alongs: He's already practiced the objections he's about to see live
• After each appointment, 10-minute debrief: What objection came up? How did the senior rep handle it? How would you have handled it?

Day 20-21: First Solo Appointments (Easy Leads)

• Assign 4-6 "softball" appointments: pre-qualified insurance jobs or warm referrals
• Manager doesn't ride along physically BUT rep wears GhostRep's Bluetooth earpiece for real-time coaching
• When homeowner says "Your price is too high," AI whispers exact response through earpiece: "I understand price is important. Before we compare numbers, can I ask—what matters most: lowest price today, or the warranty that protects your investment for 25 years?"

The rep gets coached on EVERY appointment without manager needing to be physically present. After the appointment, manager reviews conversation transcript in 15-minute debrief.

Week 3 Success Metric: Rep completes 4-6 solo appointments with AI coaching and closes at least 1 deal.

Week 4: Launch (Days 22-30)

Focus: Solo appointments with manager debrief, real-world refinement, first close

Week 4 is about building confidence and momentum. The rep is mostly autonomous now but needs daily feedback.

Day 22-25: Solo Appointments with Structured Feedback

• 10-12 appointments without real-time AI coaching (rep flies solo)
• Daily 15-minute check-ins:
  • How many appointments today?
  • Which objections came up?
  • How did you handle them?
  • Review AI Roleplay practice data from previous night: what scenarios did he struggle with?

If practice data shows he's still failing "insurance deductible too high" objections 50% of the time, manager assigns 15 more of those scenarios before next day's appointments.

Day 26-28: Refinement Based on Real Feedback

• Analyze patterns from Week 4 appointments:
  • What objections is he still struggling with?
  • Is he rushing the pitch or taking too long?
  • Is he asking for the sale or waiting for homeowner to bring it up?
• Targeted practice on specific weak points
• 2-3 ride-alongs where senior rep observes his appointments and provides immediate feedback

Day 29-30: First Close Target

• Goal: Close 1-2 deals this week to build confidence
• If he hasn't closed yet, manager rides along on next 2 appointments to diagnose and fix specific issues
• Celebrate the first close publicly—text him immediately, tell the team, take him to lunch

Week 4 Success Metric: Rep closes 1-2 deals and demonstrates 22-26% close rate (team average 28-32%, so he's within range).

Metrics to Track During Onboarding

Don't just track "did they show up and complete tasks." Track leading indicators that predict success.

Why these metrics matter:

Practice volume (Week 2): If a rep completes fewer than 100 practice scenarios, he won't have enough repetitions for responses to become automatic. This predicts failure on first solos.

First deal closed (Week 3): According to sales onboarding research, reps who close a deal in their first 30 days have 58% higher retention after one year. The early win builds confidence and momentum.

Close rate (Week 4): Team average is 28-32%. New reps should be within 10% of team average by Day 30. If they're closing <18%, they're not improving fast enough and need intensive intervention or aren't a fit for the role.

Red Flags That Predict Failure (Catch Them Early)

Research from Leadership IQ found that 89% of new hire failures are due to soft skills deficiencies, not lack of product knowledge. Watch for these early warning signs:

Week 1 Red Flags:

• Doesn't ask questions during training → Shows lack of engagement or fear of looking stupid
• Arrives late to Day 1 or Day 2 → Reliability issues before they even start
• Complains about commission structure or quota → Won't hit goals, already has excuse prepared

What to do: Have direct conversation by Day 5. If attitude doesn't shift, cut losses now rather than invest 3 more weeks.

Week 2 Red Flags:

• Completes <100 practice scenarios → Isn't putting in the work, won't be ready for Week 3 solos
• Defensive when receiving feedback on practice sessions → Can't be coached, won't improve
• Makes excuses for not practicing → "Too busy," "I learn better in real situations," "I don't need that much practice"

What to do: This is your last chance to course-correct. Explain that practice volume is non-negotiable. If they still resist, move to termination before Week 3.

Week 3 Red Flags:

• Freezes on first solo appointment → Didn't actually internalize Week 2 practice
• Skips steps in sales process → Rushing because he's nervous, not following proven framework
• Blames leads for not closing → "These leads are bad," "They weren't really qualified"

What to do: Add 5-10 more AI Roleplay scenarios per day. If no improvement by Day 25, have honest conversation about fit.

Week 4 Red Flags:

• Close rate <15% → Massive gap from team average, unlikely to catch up
• Avoids asking for the sale → Fear of rejection killing close rate
• Still struggling with same objections from Week 2 → Not learning from practice or feedback

What to do: If close rate is <15% by Day 30, extend onboarding for 2 more weeks maximum. If still <20% by Day 44, move to termination. Don't drag it out.

The Bottom Line

Traditional onboarding wastes time teaching reps product knowledge they forget and makes them watch appointments instead of practicing. By the time they're ready to go solo, they've either quit or they're so undertrained they bomb their first real objections.

The 30-day framework works because it front-loads practice volume:

• 150+ objection scenarios in Week 2
• 30+ full appointment simulations in Week 3
• Real-time AI coaching on first solos in Week 3-4
• Daily feedback based on practice data and conversation transcripts

According to G2's sales enablement research, companies with structured onboarding programs help new reps become productive 3.4 months sooner than those with weak programs. In roofing, where storm seasons are compressed and weather windows matter, 3.4 months is the difference between a rep contributing $180K in revenue or being gone before they close their 10th deal.

The key insight: you can't learn roofing sales by watching. You learn by doing. The problem is you can't afford to have new reps "learn by doing" on your best storm-damaged leads. That's why AI-powered practice platforms changed the game—they let reps get 200+ reps in their first month without burning a single real lead or requiring 40 hours of manager time doing role-plays.

By Day 30, your rep should be closing 22-26% of appointments (within 10% of team average) and hungry for more. That's when you know the onboarding worked.

And when it does work? According to UrbanBound's research, organizations with standard onboarding have 50% greater new hire retention. You've saved $97,960 in replacement costs and built someone who'll produce for years instead of months.

Your next hire starts Monday. Give them 30 days to get ready, not 12 weeks to quit.

Related Resources

• AI Sales Training for Roofing Companies
• 5-Step Performance Improvement Plan for Roofing Sales Reps
• Custom Training in Minutes with Brand Logic