How to Run a 5-Day Roofing Sales Bootcamp

Every new hire goes through bootcamp

Untrained reps knock doors, say stupid things, and walk away. The homeowner goes on Facebook and calls you a scam. The brand damage is measurable. Every new canvasser, closer, or PM goes through the 5-day bootcamp. No exceptions.

Here is the curriculum.

Day 1: Company, product, safety

Morning (3 hours)

• Company history, mission, values
• Org chart and roles
• Products we sell: shingle brands, accessories, warranties
• Company differentiators vs competitors

Afternoon (5 hours)

• OSHA 10 hour basics (or full OSHA 10 certification over 2 days if time permits)
• Ladder safety: setup, climbing, tie-off
• Personal protective equipment: hard hats, harnesses, boots
• Fall protection for steep roofs

End day 1 with a safety quiz. Any rep under 80 percent on safety retakes the quiz until passing. No field work without passing safety.

Day 2: Roof systems and damage ID

Morning (4 hours)

Classroom session:

• Anatomy of a shingle roof: deck, underlayment, shingles, flashing, ventilation
• Shingle types: 3-tab, architectural, designer, impact-resistant
• Common failure points: flashing, valleys, pipe jacks, chimneys
• Wind damage vs hail damage vs wear and tear

Afternoon (4 hours)

Hands-on roof walk. Take reps to 2 actual roofs:

• Roof 1: sample storm damage. Walk the roof, identify damage, practice photo documentation
• Roof 2: clean roof with age-related wear. Practice distinguishing wear from damage

End day 2 with a photo test: rep submits 20 photos of marked damage on a practice roof. Must correctly identify 18 of 20.

Day 3: Door approach and pitch

Morning (4 hours)

Classroom session on approach:

• Door approach physics: stand sideways, clipboard at waist, smile
• Opener script (company standard)
• Conversation flow to inspection offer
• Objection handling: top 10 objections with scripted responses

Afternoon (4 hours)

Pitch practice. Rotate through pairs, each rep pitches 15 times to different partners playing different homeowner personalities:

• The skeptic
• The busy parent
• The elderly homeowner
• The friendly talker
• The door slammer

Video record the best and worst pitches. Play back as a group and critique.

Evening homework

Memorize the full opener script. Come to day 4 ready to recite.

Day 4: Adjuster meeting and contract

Morning (4 hours)

Insurance process deep dive:

• Claim filing: what the homeowner does
• Adjuster visit: what happens
• Our role: presenting evidence, walking the roof with adjuster
• Xactimate basics: how claims are priced
• Supplement process: what supplements we request and why

Afternoon (4 hours)

Adjuster meeting roleplay. Trainer plays the adjuster. Rep plays our role:

• Meet the adjuster at the curb
• Walk the roof together
• Point out damage the adjuster missed
• Provide Xactimate comparison
• Handle adjuster pushback

Each rep completes 3 roleplays.

End of day: contract review. Walk through the standard contract line by line. Explain what each section means and how to explain it to a homeowner.

Day 5: Field day and exam

Morning (5 hours)

Field day. Pair each new rep with a senior rep. Knock a live neighborhood. New rep observes first 10 doors, then practices the next 10 with senior backup. Senior rep gives feedback between each door.

Afternoon (3 hours)

Return to office for the exam:

• 25 question written exam covering all 5 days
• Topics: safety, product, damage ID, pitch, insurance, contract
• Passing score: 80 percent
• Practical component: recite the opener script without notes

Passing reps get a certification card and their official first field day the next Monday. Failing reps retake specific sections.

Materials and budget

ItemCost per repTraining binder and printed materials50 to 100Safety equipment (hard hat, harness if new)150 to 300OSHA 10 certification (online or in-person)50 to 150Trainer time (40 hours at blended rate)1,500 to 2,500Food for the week150 to 250Total per rep1,900 to 3,300

For a spring class of 15 new hires, budget 28,500 to 49,500. Significant investment. Pays back in higher close rates and lower brand damage.

Track graduates in your CRM

Log every rep's bootcamp completion date, exam score, and certifications in RoofKnockers. When you review a rep's performance later, you need to see their baseline training. For the retention framework after bootcamp, read our guide on off-season rep retention and training.

FAQ

Can I run a shorter bootcamp?

No. A 2-day bootcamp graduates unprepared reps. The brand damage outweighs the training savings. Do the full 5 days.

Who should be the trainer?

For a small company, the owner or sales manager. For a 5 million plus company, a dedicated trainer role. Pay the dedicated trainer 75,000 to 110,000. They should be an A player who loves teaching.

What about experienced reps who come from other companies?

They still go through bootcamp. Different companies have different pitches, different products, different processes. Cross-train them. Veteran reps who try to shortcut bootcamp often bring bad habits.