Outside Sales Representative

Chicagoland Territory | New Construction & Replacement 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. 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