Regional Sales Manager

Premium Pergola; Village of Cedarhurst (NY); Remote; USD 100,000 - 500,000; Full time

Job summary

Premium Pergola is seeking a driven Regional Sales Manager for the Chicago area, focusing on client consultations and sales. This remote position includes local travel and offers uncapped commission potential, with top earners exceeding $500K. Ideal candidates will have 5+ years of sales experience and strong CRM skills.

Benefits

Uncapped commission

Travel expenses covered

Full training and onboarding

Opportunity for regional leadership role

Qualifications

• 5+ years of sales experience, preferably in construction or niche products.
• Self-starter with excellent communication and organizational skills.
• Experience with CRM systems like HubSpot.

Responsibilities

• Meet with clients to consult and close sales.
• Prepare proposals and manage follow-ups.
• Visit job sites for preliminary measurements.

Skills

Communication

Organizational skills

Sales experience

CRM experience

Site measurement

Excel skills

Tools

HubSpot

Job description

Regional Sales Manager – Chicago Area (Remote + Field Visits)

Location: Chicago area (Remote, with local travel)

Employment Type: 1099 Contractor

Compensation: Commission-based — $200K+ expected; Top earners reach $500K+

About Us

Premium Pergola is the highest-rated pergola company in the U.S., delivering stunning outdoor living spaces with exceptional service. As we expand into new markets, we’re looking for a driven Regional Sales Manager to lead our growth in the Chicago area.

What You’ll Do

• Meet with clients (Zoom & in-person) to consult and close sales
• Prepare proposals and manage follow-ups
• Visit job sites to take preliminary measurements
• Use HubSpot to manage leads and deals
• Hit and exceed sales targets
• Represent Premium Pergola with excellence and professionalism

What We’re Looking For

• 5+ years of sales experience (construction or niche product sales a strong plus)
• Self-starter with excellent communication and organizational skills
• Experience with HubSpot or similar CRM
• Ability to conduct basic site measurements
• Bonus: Excel skills or management experience

Role Requirements

• Must be based in or near Chicago
• Travel locally for site visits
• Willing to travel to New York for in-person training (2–4 weeks)
• Comfortable working independently and managing your schedule

What You Get

• Uncapped commission – earn $200K+ (top earners hit $500K+)
• Travel expenses covered
• Full training, onboarding, and sales materials provided
• Opportunity to grow into a regional leadership role

You’re a Great Fit If You’re...

• A natural closer with grit and drive
• Organized, motivated, and hungry to grow
• A team player who contributes to shared success

Ready to Build Something Bigger?

Join a rapidly growing, high-performance team at Premium Pergola. You'll have the tools, support, and compensation structure to earn big and grow fast.

Apply now and let’s talk.