Roofing Sales Representative - 1099

Apple Roofing; Chicago (IL); On-site; USD 70,000 - 100,000; Full time

Job summary

Apple Roofing is seeking experienced roofing sales professionals in Chicago, IL. As a sales rep, you’ll leverage your existing network to drive sales while managing the full sales cycle. The role requires a strong background in the roofing industry, a reliable book of business, and excellent communication skills. Enjoy independence as a 1099 professional with the support of a national brand dedicated to helping you succeed. Join us and take your business to the next level.

Qualifications

• Strong experience in the roofing industry.
• Active book of business or existing referral network.
• Reliable transportation, smartphone, and internet access.
• Access to basic inspection tools.
• Highly organized.
• Outgoing, competitive, and a ‘hungry’ spirit.

Responsibilities

• Leverage your existing network and relationships to drive immediate opportunities.
• Own the full sales cycle from inspections to signed contracts.
• Conduct accurate roofing inspections and educate clients on their options.
• Provide high-touch, professional service that builds trust.
• Manage your pipeline using our CRM system.
• Be a visible and trusted face of Apple Roofing in your community.

Skills

Strong experience in the roofing industry

Confident closer

Excellent communicator

Highly organized

Outgoing and competitive spirit

Job description

Own Your Business – with the Support of a National Brand

Apple Roofing is looking for experienced roofing sales professionals who are ready to go all-in. If you have a book of business, a solid reputation, and the grit to grind like your name’s on the building – this is your platform to scale.

This isn’t a side hustle. We want committed pros who are serious about growing with us – not just adding another logo to their portfolio. You’ll operate with the freedom of a 1099, but with the full backing of a national brand built to help you win.

Why Partner with Apple Roofing?

• Be Independent – Not Invisible: You run your business, but you’re fully connected. We’re here to support professionals who show up, put in the work, and stay hungry.
• Scale Your Sales, Not Your Headaches: Leverage our support team, national resources, and tech stack to close faster, get paid quicker, and grow without bottlenecks.
• Work Smarter, Earn Faster: We streamline production and back-end operations so you can stay focused on clients and contracts.
• A Brand That Works as Hard as You Do: Apple Roofing is raising the bar in roofing – and we’re building a team of sales reps who match that ambition.

What You'll Do:

• Bring Your Book: Leverage your existing network and relationships to drive immediate opportunities.
• Own the Full Sales Cycle: From inspections to signed contracts – you're in control from first contact to close.
• Inspect & Advise: Conduct accurate roofing inspections and educate clients on their options.
• Deliver Excellence: Provide high-touch, professional service that builds trust and earns referrals.
• Stay Organized: Manage your pipeline using our CRM system and ensure no lead falls through the cracks.
• Represent the Brand: Be a visible and trusted face of Apple Roofing in your community.

Requirements

• Strong experience in the roofing industry
• Active book of business or existing referral network
• Reliable transportation, smartphone, and internet access
• Access to basic inspection toolsA confident closer and excellent communicator
• Highly organized
• An outgoing, competitive and a ‘hungry’ spirit that propels you to success

If you’re an experienced sales pro ready to go all-in with a roofing company that actually supports you – Apple Roofing is ready to back your grind with the tools and reputation to grow faster.