Generations started in 2020 in Wauwatosa with a straightforward premise: do the work correctly, use real crews rather than subcontractors, and stand behind it. Nearly half a decade later the company has grown into a full-service exterior and interior contractor serving the majority of southeastern Wisconsin — from roofing and siding through windows, gutters, kitchens, bathrooms, basements, and home additions.
Every project runs through the same core people. That's not a company size limitation — it's a deliberate choice. When the same team handles assessment, installation, and follow-through on every job, the standard stays consistent.
Zachary founded Generations in 2020 and built the company around principles that don't change: every estimate is free, every quote is in writing, and every job gets a walkthrough at the end. He runs the business with a focus on accountability over volume — the in-house crew model, the no-subcontractor standard, and the written-quote commitment all trace back to how he set the company up from day one.
Alexis is the person most clients hear from first, and she manages communication through every stage of the project — from first inquiry through estimate scheduling, project updates, and post-completion follow-up. She brings 2+ years in the roofing industry and 4 years in remodeling, giving her a full-scope view of every project. Haley Johnson described working with her directly: "Lexi and Niko were so easy to work with and incredibly genuine throughout the whole process. They communicated clearly and followed through on every commitment."
alexisquesada@generationsrr.comNicholas, Lucas, and Luke handle installation and production on every job. They're Generations employees — not day laborers or subcontracted crews — which is what makes the quality standard consistent across every service we offer.
Most contractors at our scale subcontract significant portions of their work. Roofing companies hand off siding. Remodeling companies hire out specialty trades. Generations doesn't operate that way.
One standard of quality — every job, every service type, whether it's a roof replacement in Brookfield, a kitchen renovation in West Allis, or a full exterior restoration in Wauwatosa.
One point of contact — the homeowner deals with Generations throughout. No third party to track down when something needs attention after the job is complete.
One claim on combined projects — when hail damages a roof and siding simultaneously, one contractor documents the complete exterior scope, manages a single insurance claim, and schedules one crew to complete all the work.
Direct accountability — when something needs to be corrected after a job, Generations is the contractor who fixes it. There's no subcontractor relationship to navigate.
One company handles all of it. Jerad Wagner, who has used Generations across investor properties and his own home, described the range accurately: "Whether you are an investor or working on your primary residence, they can suit all of your needs."
Residential replacement, repair, reroof overlays, storm damage restoration, and insurance claim documentation. Commercial roofing includes flat roof maintenance programs. CertainTeed and TAMKO certified — warranties from 10 to 30 years.
Residential roofing services →Siding installation and replacement in vinyl and fiber cement, window installation, seamless gutter systems and guards, and decks and patios. All exterior work completed by the same crew that handles roofing.
Exterior services — siding, windows & gutters →Blown-in attic insulation to DOE Climate Zone 6 R-49 to R-60 standards, attic air sealing, and ventilation assessment. Installed as part of our roofing service scope — because the connection between the two is direct.
Attic insulation Milwaukee →Kitchen renovations, bathroom remodels, basement finishing, and home additions. Full interior remodeling scope completed in-house by the same crew that handles every exterior project.
Interior remodeling →Generations carries full general liability insurance and workers' compensation covering every employee on every job. This isn't a checkbox — it's the difference between a contractor whose work is backed by real coverage and one who hands liability back to the homeowner when something goes wrong.
We also carry insurance for the specific work we do on storm damage claims. When we inspect a property after a hail event, prepare documentation, and attend the adjuster meeting, we do that as a licensed, insured contractor whose report carries weight — not as a claims facilitator whose involvement adds a layer without adding accountability.
Our office is at 2222 North Mayfair Road in Wauwatosa — directly on the line between Milwaukee County and Waukesha County. That location is deliberate. Half our clients are in Milwaukee County, half are in Waukesha County, and the Mayfair Road address keeps us close to both without a drive that inflates project costs. Beyond those two counties, we work across southeastern Wisconsin.
Luke Weiland, a five-year home inspector who sends his clients to Generations, described the territory accurately: "I recommend them for all exterior and general contracting needs. Easy to work with and they do the job right."
Free estimate. Written scope before any deposit. In-house crew. Walkthrough at completion. That sequence doesn't change based on the size of the project or the service type.
We assess the scope honestly and don't charge for the time. Whether it's a roof inspection or a full kitchen renovation, the assessment is free and comes with a written recommendation.
You know exactly what the work includes, what it costs, and what the warranty covers before you decide anything. No verbal estimates. No surprises after work starts.
The same team that assessed the scope completes the installation. No subcontractors, no day laborers, no handoff to a third party partway through the job.
We walk the completed project, confirm everything met expectations, and don't leave until the property is clean and the result is right.
"Not only was the quote reasonable, but the crew completed the entire job within a day and within a couple of weeks of us signing. Zachary and the team are kindly waiting to finish the job once the baby birds leave."
"Zachary is a great owner and truly cares about customer service, which is a refreshing thing these days."
"Whether you are an investor or working on your primary residence, they can suit all of your needs."
If you have a project — large, small, or not yet clearly defined — call or email. Alexis Quesada handles all inquiries personally.
Milwaukee & Waukesha County · Alexis responds personally
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Roofing · Siding · Windows · Remodeling · Southeast Wisconsin