Building a Sales Team vs. Owner-Led Sales

The owner who closes every deal caps the company’s growth at their personal capacity. One person can run maybe 100-150 estimates annually at quality levels. That’s $2-4M in revenue depending on average job size. Anything beyond requires multiplication.

Building a sales team is one of the hardest transitions roofing company owners make. The skills that made you great at selling don’t automatically make you great at building sellers.

The Owner Sales Trap

Owner-led sales works brilliantly until it doesn’t. The progression looks like this:

Years 1-3: Owner sells everything. Close rates are high because customers trust the owner. Relationships form with the decision-maker. The owner knows every job intimately.

Years 4-6: Volume grows but the owner struggles to keep up. Estimates get delayed. Follow-up suffers. Some leads go cold waiting. Revenue plateaus despite marketing investments.

Year 7+: The owner realizes they’re the constraint but can’t imagine hiring salespeople who could match their performance. Fear of losing customers to inexperienced salespeople freezes decisions.

This trap catches most roofing company owners. They become prisoners of their own sales success.

When to Make the Transition

Several signals indicate readiness for sales team building:

Lead volume exceeds your capacity. If qualified leads wait more than 48 hours for estimates, you’re leaving money on the table.

Your time is worth more elsewhere. An owner-hour spent on strategy, systems, or key relationships often returns more than an owner-hour spent running estimates.

Revenue has plateaued. When marketing produces leads but revenue doesn’t grow proportionally, the bottleneck is likely sales capacity.

Growth goals require it. If you want to double revenue, you need to double sales capacity somehow.

You hate it. Some owners excel at sales but hate doing it. Freeing yourself from tasks you hate improves quality of life and often business performance.

The Three Sales Team Models

Roofing companies typically adopt one of three sales models.

Model 1: Inside Sales Support

You remain the closer. An inside salesperson handles everything else.

They handle:

• Lead qualification and scheduling
• Appointment confirmation
• Basic follow-up
• Proposal preparation
• Contract administration

You handle:

• Running estimates
• Closing deals
• Key customer relationships

Best for: Owner wants to stay in sales but needs capacity multiplication. Works up to 2-3x current volume.

Model 2: Hybrid Team

You close some deals while salespeople close others.

They handle:

• Smaller residential jobs
• Repeat customers
• Less complex installations

You handle:

• Larger commercial deals
• Complex custom work
• Key relationship accounts

Best for: Transition period while testing and developing salespeople. Works to 3-4x current volume.

Model 3: Full Sales Team

Dedicated sales team handles all selling. You manage and occasionally participate in strategic deals.

They handle:

• All estimates and proposals
• All closings
• Ongoing customer relationships

You handle:

• Sales management and coaching
• Strategic accounts and partnerships
• Team development and recruiting

Best for: Companies ready to scale beyond owner capacity limits. Required for $5M+ growth.

Hiring the Right Salespeople

The roofing salesperson profile differs from general sales roles. Technical knowledge, field presence, and project management skills matter alongside pure selling ability.

Experience preferences:

Roofing experience has obvious benefits but comes with baggage. Experienced roofers bring industry knowledge but also ingrained habits that may conflict with your approach.

Adjacent experience (HVAC, windows, siding) offers relevant skills with less retraining. They understand home services sales dynamics.

Raw sales talent from other industries can work if you’re willing to invest heavily in technical training. Their selling instincts may be sharper than roofing veterans.

Essential characteristics:

Coachability. Can they take feedback and adjust? The best salespeople continuously improve.

Work ethic. Sales requires persistence. Estimate running is physically demanding. Lazy doesn’t survive.

Integrity. They represent your company. Shortcuts and exaggerations destroy reputation.

Technical aptitude. They must understand roofing well enough to communicate credibly.

Organization. Managing multiple leads, appointments, and follow-ups requires discipline.

Interview questions that reveal truth:

“Walk me through your last month’s sales activity in detail.” (Reveals actual work habits)

“Describe a deal you lost and what you learned.” (Reveals self-awareness and growth orientation)

“How would you explain underlayment to a homeowner?” (Reveals communication skill and technical knowledge)

“What did you dislike about your last company’s sales process?” (Reveals fit with your approach)

Compensation Structures

Sales compensation must motivate desired behaviors while protecting company interests.

Pure commission: High upside but attracts gamblers. Creates income volatility that drives turnover.

Pure salary: Easy to budget but doesn’t motivate extra effort. Best performers leave for higher-upside opportunities.

Base plus commission: Balanced approach. Base provides stability. Commission rewards performance. Most common structure.

Draw against commission: Commission-only but provides cash flow smoothing. Works for experienced salespeople who can generate volume quickly.

Typical structures for roofing:

Entry level: $40-50K base + 3-5% commission on sold jobs Experienced: $50-70K base + 4-6% commission High performer: $60-80K base + 5-8% commission + bonuses

Commission triggers matter. Paying on signed contracts incentivizes quick closes. Paying on completed jobs incentivizes quality and appropriate customer selection.

The Sales Process Transfer

You must systematize your sales approach before others can replicate it. What you do intuitively must become explicit.

Document your process:

1. Lead qualification: What questions do you ask? What disqualifies a lead?
2. Appointment approach: How do you prepare? What do you bring?
3. Inspection method: What do you look for? How do you document?
4. Presentation structure: How do you present findings? What do you emphasize?
5. Pricing approach: How do you build estimates? What factors adjust pricing?
6. Objection handling: What objections arise? How do you address them?
7. Closing techniques: How do you ask for the business? What trial closes do you use?
8. Follow-up cadence: How do you follow up on pending proposals?

Create supporting materials:

• Estimate checklists
• Product knowledge guides
• Presentation scripts or frameworks
• Objection response guides
• Pricing matrices
• Proposal templates

New salespeople need these materials to perform anywhere near your level. Without them, they reinvent poorly what you do naturally.

Training and Development

Hiring salespeople is the beginning. Developing them is the ongoing work.

Initial training (weeks 1-4):

• Product knowledge
• Company process and values
• CRM and tools
• Ride-alongs observing experienced salespeople
• Shadowing and practice estimates

Supervised selling (weeks 5-12):

• Running estimates with supervision
• Manager review of all proposals
• Deal review and coaching
• Graduated independence

Independent selling (month 4+):

• Full responsibility for assigned leads
• Regular coaching and deal reviews
• Performance metric tracking
• Continued skill development

Ongoing development:

• Weekly sales meetings
• Monthly training sessions
• Quarterly performance reviews
• Annual conferences or outside training

The best sales teams never stop training. Skills atrophy without continuous sharpening.

Managing Sales Performance

Salespeople need clear expectations and accountability.

Key metrics to track:

• Leads received
• Estimates completed
• Proposals issued
• Contracts signed
• Close rate (contracts/estimates)
• Average job size
• Revenue by salesperson
• Gross margin by salesperson

Weekly rhythm:

Monday: Review prior week metrics. Set week priorities. Daily: Check progress. Address obstacles. Friday: Week summary. Pipeline review.

Monthly review:

Performance versus targets. Deal-level analysis. Coaching areas. Action plans.

Poor performers need help or exit. Most sales underperformance comes from skill gaps, effort gaps, or fit gaps.

Skill gaps respond to training. Effort gaps respond to accountability. Fit gaps require separation. Diagnose correctly before prescribing.

Common Mistakes in Sales Team Building

Mistake 1: Hiring one salesperson

One salesperson gives you no comparison. You can’t tell if results reflect the person or the market. Hire two when possible. Competition and comparison accelerate learning.

Mistake 2: Expecting immediate results

New salespeople take 3-6 months to reach productivity. Expect losses during ramp-up. Plan financially for the investment period.

Mistake 3: Inadequate lead flow

Salespeople need leads. If marketing doesn’t generate enough, salespeople prospect poorly or sit idle. Match lead generation to sales capacity.

Mistake 4: Over-managing or under-managing

New salespeople need high touch. Experienced salespeople need autonomy. Adjusting management style to individual needs optimizes results.

Mistake 5: No sales process

Sending salespeople out without documented process yields inconsistent results. Systematize before scaling.

The Owner’s New Role

As your sales team develops, your role shifts.

From: Running estimates and closing deals To: Recruiting, training, and coaching salespeople

From: Knowing every customer To: Knowing key accounts and relationships

From: Setting prices on each job To: Setting pricing strategy and reviewing margins

From: Individual contributor To: Manager of contributors

This shift feels uncomfortable initially. Your identity wrapped around being a great salesperson. Now success comes through others’ selling.

The transition takes most owners 12-18 months to complete emotionally, even after the team is functionally operational.

Start Here

Sales team building starts with documentation.

Start Here:

1. Document your sales process in detail. How do you qualify, estimate, present, close, and follow up?
2. Create a salesperson job description based on your real needs and culture.
3. Calculate what compensation structure makes sense for your average job size and margin.

Building a sales team multiplies your capacity. One good salesperson doubles revenue potential. Three good salespeople can 4x it.

The transition requires investment in systems, hiring, training, and management. Most importantly, it requires you to let go of being the best salesperson and embrace being the best sales leader.

Start the transition before you’re maxed out. The runway needed to build a sales team spans 12-18 months. Begin now.