LANDSCAPE APPRENTICE — SKYLINE EXTERIORS
Chicago, Illinois · Full-Time · No Experience Required
We started by knocking on doors and cutting grass.
That is the honest version of this story. A few years ago, Skyline Exteriors was a young company with big ambitions and not much else. We built it from the ground up — project by project, client by client, neighborhood by neighborhood — on the North Shore of Chicago.
Today, Skyline is one of the fastest-growing premium outdoor living companies in Chicagoland. We design and build extraordinary outdoor spaces for homeowners in Winnetka, Glencoe, Lake Forest, Highland Park, Wilmette, Hinsdale, Barrington, and beyond. Full backyard transformations. Custom patios and pergolas. Outdoor kitchens and dining spaces. Lighting systems. Planting designs. Hardscape and softscape installations built to a standard that the best neighborhoods in Chicago expect and that we refuse to compromise on.
Our clients invest $30,000 to $150,000 in the spaces we build for them. They choose us not because we are the cheapest option — we are not — but because they have seen what we do for their neighbors and they want exactly that. The work is serious. The craft is real. And the company doing it is growing faster than almost anyone in this market.
We are looking for our next Landscape Apprentice. Someone who wants to be part of what we are building — not just someone to fill a spot on a crew.
What Skyline actually does — and why it matters
Most people do not realize how transformative this work is until they see it happen.
We take a flat, neglected, underused backyard and turn it into the space a family actually lives in. A homeowner in Lake Forest who has been staring at the same cracked concrete patio for six years walks out the morning after we finish and sees a custom natural stone patio with a built-in outdoor kitchen, a cedar pergola overhead, landscape lighting that makes it usable after dark, and plantings that make it feel like the space was always supposed to look this way.
That transformation is real. It is physical. You can see it, touch it, and stand in it. And it was built by a crew of people who showed up every morning and did the work.
Here is what that work looks like:
Hardscape Installation — Patios, walkways, retaining walls, driveways, pool surrounds, and outdoor kitchen structures built from natural stone, Unilock pavers, concrete, and premium materials that are meant to last decades.
Pergolas and Outdoor Structures — Custom-built cedar, aluminum, and composite pergola structures that anchor an outdoor living space and give it the architectural presence the rest of the home deserves.
Outdoor Kitchens and Living Spaces — Full outdoor kitchen builds including grills, countertops, refrigeration, fire features, and dining areas that turn a backyard into a room.
Landscape Design and Planting — Softscape installations including trees, shrubs, perennials, ornamental grasses, and seasonal color that make the built space feel alive and intentional.
Outdoor Lighting Systems — Low-voltage LED landscape and architectural lighting that extends the usability of every space into the evening and makes the property look extraordinary from the street.
Seasonal Maintenance and Snow Removal — Year-round service relationships with the clients we build for, including premium residential and commercial snow removal across the North Shore.
This is not mowing lawns. This is building spaces that change how families use their homes. There is a difference — and the people who work here feel it.
Who we are — the real version
Skyline was founded by a guy who played college football at Iowa, came home, and started knocking on doors. No roadmap. No investors. No safety net. Just a belief that a company willing to do the work at a higher standard than anyone else in the market would eventually become something worth building.
We are still that company. We are just bigger now — and we are growing faster than we ever have.
We are not a corporate landscaping company. We are not a franchise. We are not a company where you are employee number 847 and nobody knows your name. We are a young, founder-led business with a clear vision of where we are going, a team that is invested in getting there, and a culture that treats the people doing the work as the most important part of what we are building.
We have helped team members purchase homes. We have promoted people from apprentice to crew lead to manager. We have given people a career they did not know was available to them. We intend to keep doing that — at a larger scale every year.
The ecosystem — what you are actually joining
Skyline is not a job. It is an ecosystem for people who love this industry and want to build a real career inside it.
We have the Design + Build side of the business — the premium outdoor living installations described above. We have the snow removal operation, which becomes its own world in the winter. We have BloomedBox, our seasonal planting subscription that services the same homeowners year-round. And we are growing all of it simultaneously.
What that means for you: there is always more to learn. There is always a next level. There is always a project you have not done yet. There is always a skill that will make you more valuable, better compensated, and more trusted.
We are building internal career paths because we believe that the people who helped build Skyline should be the ones leading it.
The growth path — written specifically for the person reading this
Here is exactly where this role goes if you want it to:
Landscape Apprentice — You come in, you learn, and you absorb everything you can from the senior crew members around you. You develop the fundamentals — how to read a plan, how to install materials correctly, how to work safely and efficiently, how to represent Skyline on a client's property. You earn trust by showing up and doing the work.
Team Member — You are a full contributor. You execute your scope independently, you know the standard, and newer apprentices look to you when they have questions. Your pay reflects your skill.
Team Leader — You lead a small crew on active jobs. You are responsible for the output, the pace, and the quality of the people around you. This is the first leadership step — and it matters.
Crew Manager — You manage multiple crews across active projects. You own the schedule, the standards, and the performance of everyone under your watch. You are accountable to results.
Project Manager — You own a project from the day it is signed to the day a homeowner walks out and sees their finished space for the first time. You manage the crew, the client relationship, the timeline, the budget, and the quality. You are the face of Skyline on the job.
Operations Manager — You run the operational infrastructure of a company that, by the time you get here, will be operating at a scale that very few outdoor living companies in the country have reached. You are a senior leader. And you earned every bit of it.
This is not a hypothetical. This is the path that exists right now inside Skyline — and it is open to the person who is willing to take it seriously.
We are looking for people, not resumes
We are not looking for someone who has done this before. We are not asking for certifications or a portfolio of projects. We are looking for people who are built for this — regardless of where they are coming from.
You might be coming out of construction or manufacturing and want work that you can actually see and be proud of. You might be in logistics and want to use your hands. You might be fresh out of school with no professional experience at all. You might have been doing something completely unrelated and just know that sitting in an office or a warehouse is not the version of your life you want.
None of that disqualifies you. What matters:
- You show up every day, on time, ready to work
- You are coachable — you take direction and get better
- You take pride in what you build and you are not satisfied with doing something halfway
- You are physically capable of demanding outdoor work in all Chicago weather conditions
- You want a career — not just a paycheck, not just something to get you through the season
What you get from day one
- Paid on-the-job training — full trade education from experienced crew members who care about developing the people around them
- A clear, documented career path with advancement tied to real performance and real skills — not tenure
- Competitive hourly pay that grows as your role and responsibility grow
- Work that you can point to — before and after — and say that you built that
- A company that is in a genuine growth phase and wants to take you with it
- A culture where the people doing the work are respected, developed, and invested in
- A team that feels like a team — not a number on a roster
The work is hard. That is the point.
We work early mornings. We work through summer heat and fall cold. We build things that require precision and effort and physical presence. If you are looking for something easy, this is not it.
But if you are looking for something real — something that builds skills you will carry for the rest of your career, on a team that is going somewhere, at a company that started from nothing and is turning into something — this is exactly it.
The neighborhoods we work in are some of the most beautiful in the greater Chicago area. The projects we build will be there in twenty years. The career you build here is yours.
How to apply
We keep this simple. Send us a short message answering one question:
Why do you want to build a career in the trades?
No resume required. No certifications needed. No industry experience necessary. Just tell us who you are and what drives you. The right person for this role will know what to say.
Apply Here Or email: [email protected]
Skyline Exteriors is an equal opportunity employer. We hire character and develop skill. If you are serious about building something real with a company that is building something real — we want to hear from you.
Pay: $26.00 - $30.00 per hour
Benefits:
- On-the-job training
- Referral program
Work Location: In person
