Outside Sales Representative
Richards Building Supply$55,000–$65,000/yr63rd Street, Chicago, IL; 111th St, Chicago, IL; Rolling Meadows, IL; Joliet, IL; Montgomery, IL; Calumet City, IL; Aurora, IL; Carol Stream, IL; Elmwood Park, IL; Frankfort, IL; Itasca, IL; Homer Glen, IL; Kankakee, IL, United StatesFull-timeListed 8mo agoTools for this application (partners): NEWCV (opens in new tab) (resume) · LoopCV (opens in new tab) (tracking) · Huru (opens in new tab) (interview practice) · Snov.io (opens in new tab) (hiring manager's email) · HeadshotPro (opens in new tab) (headshot) · micro1 (opens in new tab) (side work) what each does
The posting
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
Our sales team is comprised of highly motivated individuals that are passionate about Richards Building Supply and generating new business opportunities around high quality products.
APPLY TODAY!!!
It’s more than a job, it is your Career! Submit your resume today to join our exciting and growing family
Req ID #ZR Chicago
Richards Building Supply is a wholesale building material distributor serving 16 states with 67 locations! As a family owned, operated and focused company, Richards Building Supply has spent nearly 50 years building a thriving and profitable organization, as well as invaluable business relationships. Richards stocks a comprehensive line of products such as residential and commercial roofing, siding, windows, decking, soffit, doors, molding, rainware, cabinets, and more!
Learn more about us here: https://www.richards-supply.com/about
Terms and Conditions / Privacy Policy: https://www.richards-supply.com/privacy-policy/
Richards Building Supply believes in hiring military veterans at any level for any position. We know your service trained you in many of the areas we value, such as; leadership, teamwork, performance, integrity, and safety. If your experience matches our requirements, we want you to apply today.
It’s more than a job, it is your Career! Submit your resume today to join our exciting and growing family.
Taken from Richards Building Supply's own posting, last seen live on 14 Nov 2026.
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The application
Your details, then 18 questions (2 written).
- 1.Which location are you applying for?Pick one · optional
- 2.If hired, can you supply proof of your age?Yes or no
- 3.If hired, can you supply the required documentation to verify your lawful right to work in the United States?Yes or no
- 4.Are you willing to undergo a background check, in accordance with local law/regulations?Yes or no
- 5.Please share additional details (optional)Written answer · optional
- 6.Are you interested in an outside sales role that requires cold calling and prospecting daily?Yes or no
- 7.Are you comfortable with frequent rejection as part of the sales process?Yes or no
- 8.Which best describes your interest in sales?Pick one: I’m actively in sales today · I’m not in sales but want to move into it · I’m exploring sales but unsure · Other
- 9.If OTHER, please explainWritten answer · optional
- 10.What types of work environments have you primarily worked in? (Check all that apply)Pick any (7 options)
- 11.Have you worked directly with contractors, tradespeople, or field crews?Pick one: Yes · No · Other
- 12.Are you comfortable building a customer list from scratch through cold outreach?Yes or no
- 13.Which best describes how you prefer to generate new business?Pick one: Proactive outreach/cold calling · A mix of cold outreach and warm leads · Primarily warm leads · I’m not comfortable with cold outreach · Other
- 14.Are you able to manage your schedule, follow‑ups, and customer commitments independently?Yes or no
- 15.What tools do you use to stay organized? (Check all that apply)Pick any: Outlook · Excel · CRM system · Phone calendar · Paper planner/notebook · Other
- 16.This territory requires independence and structure‑building. Are you comfortable working without an established customer base?Yes or no
- 17.How do you respond when a customer is direct, blunt, or frustrated? (Select all that apply)Pick any
- 18.Which best describes how you typically communicate with customers?Pick one: Easy to talk to · Respectful and patient · Good listener · Clear and direct · Sometimes too blunt · Sometimes I interrupt or talk over others
From Richards Building Supply's apply page, checked 12 Nov 2026.
About Richards Building Supply
Family-owned wholesale distributor of roofing, siding, windows, doors, decking and other exterior building products, selling to remodeling contractors, builders and general contractors from local branches.
Pay schedule: Outside reps are salaried with uncapped commission and inside reps hourly with overtime, some inside seats posted as temporary full-time, and all get discretionary holiday bonuses, employer-paid or subsidized medical, dental and vision, a 401(k) match and a paid company closure between Christmas and New Year's.
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