Outside Sales Representative

Chicagoland Territory | New Construction & Renovation Projects

We’re expanding our window and door business and are looking for an experienced outside sales professional who enjoys building something from the ground up. This role is ideal for someone who thrives on opening new relationships, establishing a territory, and growing a meaningful book of business over time.

If you’ve spent your career selling to contractors, builders, or GCs-and you enjoy the hunt as much as the win-this could be a strong next step.

This is a territory-build role, focused on developing new contractor, builder, and GC relationships throughout Chicagoland, with the ability to support customers nationally through drop-ship capabilities. While the primary focus is the Chicagoland market, we are able to support customers and projects nationwide through drop-ship capabilities across the continental United States.

You’ll represent a broad portfolio of vinyl, wood, and composite windows and doors, supporting both new construction and replacement projects across multiple vendor lines. The territory offers room to grow and flexibility in how you approach the market, with success built through consistent activity, follow-up, and strong execution.

What Success Looks Like:

• Rather than inheriting a large book of business, you’ll have the opportunity to create one.
• Year 1 goal: Build toward approximately $2M in annual sales
• Longer-term opportunity: Grow to a $7M+ annual run rate as the territory matures
• Develop a healthy pipeline that supports sustainable growth while maintaining margin
• This role is well-suited for someone who enjoys shaping their own territory and taking ownership of results.

What You’ll Be Doing

• Building new relationships with contractors, builders, and general contractors
• Calling on owners, estimators, project managers, and purchasing teams
• Prospecting through a mix of phone outreach, jobsite visits, referrals, and follow-up
• Supporting the quoting and estimating process (with internal resources)
• Managing projects from quote through order accuracy and coordination
• Using CRM tools to manage pipeline activity and forecast opportunities
• Staying visible in the market through consistent jobsite and customer presence

Who This Role Tends to Fit Well

• Prefer new business development over account maintenance
• Are comfortable opening doors and building relationships over time
• Take a value-based selling approach rather than competing only on price
• Like having autonomy while being accountable for results
• Enjoy working in a construction-driven, relationship-oriented environment

Experience Required:

• 7+ years of B2B outside sales experience calling on contractors, builders, or GCs
• Demonstrated success developing new accounts and growing revenue
• Comfort with prospecting, jobsite visits, and relationship development
• Experience managing quotes, specs, takeoffs, or coordinating those efforts
• Familiarity with the Chicagoland market and construction landscape
• Strong organization skills and CRM discipline
• Valid driver’s license and ability to travel locally

Experience Preferred

• Experience selling windows, doors, or related building materials
• Background in both new construction and remodel/replacement work
• Experience winning business away from established competitors
• Comfort navigating more complex quotes and project timelines

Why This Role Is Different

• Opportunity to build a territory rather than inherit one
• Access to multiple vendor lines to meet a wide range of customer needs
• Support structure that allows you to focus on selling and relationships
• Long-term growth potential as the business expands

Benefits

• Competitive base salary + industry-leading commission program (uncapped potential!)
• 21 paid days off in your first year - including our Family Focused break between Christmas and New Years!
• Holiday bonuses + additional earning opportunities (discretionary)
• Employer-paid medical, dental, and vision plans + 401K with top-tier company match
• Career growth in a team-oriented, family-focused company