Careers at Umbrella Property Services

Umbrella Property Services is hiring an Operations and Office Coordinator in Mokena, IL. Pay is $18 to $22 per hour based on experience, working 35 to 40 hours per week. You need a high school diploma and solid skills with Microsoft Office or Google Workspace. You will be the organizational hub of a commercial property maintenance company, and your work shifts with the seasons, from landscape operations in summer to snow and ice in winter. Who You Are: • You are the organized one, the person who tracks the details everyone else forgets. • You take pride in follow-through. When you say it is handled, it is handled. • You are friendly and professional, and customers feel taken care of after one call with you. • You love learning new software and picking up new skills. • You bring administrative, office, or customer service experience (preferred, not required). • You bring legal authorization to work in the US. A valid driver's license and bilingual skills are each a plus. Who We Are: • A growing commercial property maintenance company serving the Chicagoland area. • We handle year-round facility maintenance, landscape management, parking lot services, and snow and ice management for commercial, industrial, and institutional properties. • Our mission is simple, deliver dependable service and build lasting relationships. • We run on integrity, accountability, teamwork, and continuous improvement. What You Will Do Each Day: • Answer the main phone line and assist customers • Manage mail, email, digital files, and records, and order office, shop, and jobsite supplies • Coordinate subcontractors, rental equipment, and deliveries, plus fleet records, uniforms, and vendors • Assist with work orders, permits, project photos, and job documentation • Support recruiting, interview scheduling, onboarding paperwork, and employee records • Prepare proposals and customer packets, keep the CRM current, and help projects move from sale to completion Why You'll Love Working Here: • $18 to $22 per hour based on experience • Onsite role in Mokena, IL, 35 to 40 hours per week • Property maintenance experience not required. We train the right attitude. • Room to take on new responsibilities as the company grows, with a path toward the leadership team.

Commercial Business Development Manager Commercial Landscape Maintenance & Snow Management Location: Homer Glen, IL (Serving the Greater Chicagoland Area) Compensation: $60,000–$80,000 Base Salary (DOE) + Uncapped Commission + Performance Bonuses On-Target Earnings (OTE): $100,000–$150,000+ Join a Growing Commercial Landscape & Snow Company Umbrella Property Services is a growing commercial landscape maintenance and snow management company serving commercial properties throughout the Chicagoland area. We are seeking an experienced Commercial Business Development Manager to help expand our commercial client base by developing new landscape maintenance and snow management accounts. This is a true business development (hunter) position. Your primary responsibility is generating new commercial business through relationship building, prospecting, networking, and closing new contracts. This is not an account management role. Once a new client has been successfully onboarded, our internal account management and operations teams assume responsibility for the ongoing relationship, allowing you to stay focused on bringing in new business. If you thrive on building relationships, winning new clients, and controlling your income through performance, we'd love to hear from you. Responsibilities • Prospect and develop new commercial landscape maintenance accounts. • Generate new commercial snow and ice management contracts. • Build relationships with property managers, facility managers, HOA boards, municipalities, REITs, industrial properties, office parks, retail centers, schools, healthcare facilities, and commercial property owners. • Schedule meetings and perform on-site property evaluations. • Prepare and present professional proposals. • Negotiate and close commercial service agreements. • Follow up on qualified company-generated marketing leads. • Maintain an organized sales pipeline using CRM software. • Attend networking events and develop referral relationships. • Work closely with estimating and operations to ensure accurate proposals and smooth project transitions. • Meet and exceed monthly and annual sales goals. Qualifications • Minimum 3 years of commercial landscape maintenance, snow management, or commercial exterior services sales experience required. • Proven track record of developing and closing new commercial accounts. • Strong understanding of commercial landscape maintenance and snow management operations. • Existing relationships with commercial property managers, facility managers, HOA boards, municipalities, or commercial real estate professionals are highly preferred. • Excellent communication, presentation, and negotiation skills. • Highly self-motivated, goal-oriented, and organized. • Experience using CRM software is preferred. • Valid driver's license with a clean driving record. Compensation • Competitive base salary of $60,000–$80,000 based on experience. • Uncapped commission plan. • Performance-based bonuses. • Expected first-year earnings of $100,000–$150,000+ for successful performers. Benefits • Company vehicle or vehicle allowance. • Company gas card (if applicable). • Company cell phone. • Company laptop. • Paid vacation (PTO). • Paid holidays. • Health insurance. • Ongoing professional development and sales training. • Networking and industry association opportunities. • Advancement opportunities as our sales team continues to grow. Why Umbrella Property Services? At Umbrella Property Services, we're building a company known for exceptional service, professionalism, and long-term partnerships. Our marketing efforts generate qualified leads, our operations team delivers outstanding service, and our account management team maintains long-term client relationships—allowing you to focus on what you do best: developing new business. If you're an experienced commercial landscape and snow sales professional looking for an opportunity with uncapped earning potential, a supportive team, and the chance to make a meaningful impact on a growing company, we'd love to meet you. Join Umbrella Property Services and help shape the future of commercial landscape maintenance and snow management throughout the Chicagoland area.

Umbrella Property Services is hiring a dependable Fleet Mechanic to maintain and repair our fleet and equipment. You will work on diesel pick up trucks, gas trucks, trailers, commercial mowers, 2 cycle engines, plows, skid steers, and salters. Our fleet is 60% gas and 40% diesel , so we need someone comfortable supporting both. We have all Ford diesel and gas trucks and multiple brands of skid steers. WE DO NOT HAVE SEMI'S. DO NOT APPLY IF YOU ONLY WORK ON SEMI'S. This role also includes responsibility for warehouse organization and parts inventory, plus fleet documentation and maintenance tracking. Snow work is mandatory. We are a faith driven company and our values guide how we work and how we treat people: Faith First, Honesty Integrity and Respect, Exceptional Service, and Reliable Quality. What you will do • Diagnose and repair diesel and gas engines • Maintain and repair: • Diesel Pick Up trucks and gas trucks • Trailers (lights, wiring, brakes, hubs, bearings, tires, general repairs) • Commercial mowers and 2 cycle equipment • Snow equipment (plows and salters) • Skid steers and small equipment • Preventative maintenance: fluids, filters, belts, batteries, brakes, basic hydraulics, seasonal inspections • Troubleshoot electrical and mechanical issues using scan tools as needed • Train team members on proper equipment use and basic maintenance • Fleet documentation and tracking • Log repairs and maintenance completed • Track PM schedules (oil changes, inspections, seasonal readiness) • Note parts used and upcoming needs • Warehouse responsibility • Receive parts, organize inventory, keep shop stocked and clean, track usage and reorder needs • Snow work is mandatory • Be available during snow events for fleet readiness and repairs • Support snow operations as needed during events What we are looking for • Experience with fleet vehicles and equipment (diesel and gas) • basic diagnostics and problem solving skills • Reliable, organized, and takes ownership • Valid drivers license • Must have own tools • Willing to work extended hours during snow events when required Pay and Benefits: • Pay is $36–$40. • Benefits: Health insurance, paid time off, company vehicle, and overtime.

Outdoor Living Apprentice Umbrella Property Services is looking for an Outdoor Living Apprentice to join our growing outdoor living and construction division. This role is designed for someone with a strong construction foundation who wants to grow into a Foreman position and over time, an Outdoor Living Manager. The Outdoor Living Apprentice will work hands-on with our team to build high-quality outdoor living spaces, including paver patios, outdoor kitchens, decks, pergolas, gazebos, and water features. This person must be dependable, hardworking, teachable, and willing to take on increasing responsibility as they learn our standards, systems, and leadership expectations. This is not just a labor position. This is a training opportunity for someone who wants to build a long-term career, develop leadership skills, and grow with Umbrella Property Services. Position Overview The Outdoor Living Apprentice will assist with the construction and installation of outdoor living projects from start to finish. This includes site preparation, material handling, layout assistance, installation support, cleanup, tool use, and learning how to manage quality, safety, efficiency, and crew communication on job sites. This position is intended to develop into a Foreman role over time. The right candidate will show leadership potential, strong work ethic, attention to detail, and the ability to learn and follow direction. Key Responsibilities • Assist with the installation of outdoor living projects, including: • Paver patios • Outdoor kitchens • Decks • Pergolas • Gazebos • Water features • Assist with site preparation, demolition, grading, base preparation, installation, finishing, and cleanup • Load, unload, move, and organize materials, tools, and equipment • Assist with measurements, layouts, cuts, installation, and finishing work • Operate hand tools, power tools, and small equipment safely • Follow project plans, Foreman direction, and company quality standards • Maintain clean, organized, and safe job sites • Learn proper construction methods, project sequencing, and job site leadership • Communicate clearly with team members and supervisors • Show up on time, prepared, and ready to work each day • Participate in snow removal operations during the winter season • Represent Umbrella Property Services with professionalism, integrity, and respect Training & Growth Opportunity This position is designed to train and develop the right person into a future Foreman. During the winter months, Umbrella Property Services plans to invest in additional training, schooling, or industry-related classes to help the right candidate continue building their skills in outdoor living construction, leadership, safety, and job site management. The ideal candidate should be eager to learn, willing to grow, and serious about turning this opportunity into a long-term leadership role within the company. Requirements • Minimum 1 to 2 years of construction experience required • Outdoor living, hardscape, deck building, landscaping, or exterior construction experience preferred • Indoor construction experience will also be considered • Must have or be willing to provide their own basic hand tools • Must be willing and available to participate in snow removal during the winter season • Must be willing to participate in winter training, schooling, or industry-related classes as part of the Foreman development path • Must be physically able to lift, carry, dig, bend, kneel, and work outdoors in various weather conditions • Must be dependable, teachable, and willing to learn • Must have strong attention to detail and pride in quality workmanship • Must be able to follow instructions and work well with a team • Must be interested in growing into a leadership or Foreman role • Valid drivers license preferred Ideal Candidate The ideal candidate is someone who already has basic construction experience but wants to build a long-term career in outdoor living construction. This person takes pride in doing things the right way, wants to learn leadership, and is excited about helping build beautiful, high-quality outdoor spaces. We are looking for someone who is not only willing to work hard, but also wants to grow. The right person will be dependable, coachable, detail-oriented, and motivated to take on more responsibility over time. Compensation • $21 - $26 per hour • Pay based on experience. About Umbrella Property Services Umbrella Property Services is a faith-based company committed to serving clients with honesty, integrity, respect, exceptional service, and quality work that earns trust. We take pride in doing things right, treating people well, and building a team culture where hard work, character, and growth matter.

Umbrella Property Services is hiring a Hardscape Installer in Mokena, IL, with pay of $22 to $25 per hour on W-2 or $25 to $28 per hour on 1099. You will work on a crew building paver patios, retaining walls, walkways, and outdoor living features for commercial properties across the Chicagoland area. Who You Are • You take pride in laying pavers that sit perfectly level, with crisp lines and clean joints. • You believe a properly prepped base is the foundation of work that lasts for years. • You love working outdoors and seeing finished hardscape that property owners actually use every day. • You are the kind of teammate others want next to them when the install gets demanding. • You take ownership of the small details (drainage, grading, joint sand) because you know those are what separate work that holds up from work that fails. • You bring at least one year of experience in hardscape, masonry, concrete, or landscape construction, and reliable transportation. Who We Are • Umbrella Property Services provides dependable property services across Chicago and the wider Chicagoland area. • We support commercial properties with coordinated service across multiple operational categories. • We help clients reduce vendor complexity, maintain consistent standards, and protect long-term property value. • We run year-round work, with hardscape construction in the build season and snow services through the winter. What You Will Do Each Day • Install paver patios, walkways, steps, and retaining walls for commercial properties. • Perform base prep, grading, and drainage work to set every install up to last. • Use tools like plate compactors, cut-off saws, and laser levels. • Operate equipment such as skid steers or mini skids. • Work with paver products including Unilock, Belgard, and Techo-Bloc across different jobs. Why You Will Love Working Here • Pay of $22 to $25 per hour on W-2, or $25 to $28 per hour on 1099, based on your preferred employment structure. • Full-time seasonal Hardscape Installer role based in Mokena, IL, with steady construction work in the build season and snow work opportunities in winter. • Health, dental, and vision insurance after 90 days, plus paid time off after 90 days. • Time and a half holiday pay, plus additional pay for snow work. • Spring Return Bonus of $500 to $1,000. • 401(k) with 3 percent company match after one year, plus paid training for certifications and classes. Next Steps If you take pride in clean hardscape work and want steady year-round opportunities, apply for the Hardscape Installer role and our team will be in touch.

Umbrella Property Services is hiring a Landscape Laborer in Mokena, IL, with pay of $16 to $21 per hour on W-2 or $17 to $22 per hour on 1099. You will work on our landscape crew, keeping commercial properties across the Chicagoland area sharp through mowing, planting, mulch and bed installs, and seasonal cleanups. Who You Are • You take pride in seeing the visible difference your work makes by the end of every day. • You believe a sharp lawn edge and a clean cut line are details worth caring about. • You love being outdoors and prefer hands-on work to a desk. • You are friendly with customers and easy to work with on a crew. • You are the kind of teammate who shows up ready to work no matter the season. • You bring at least one year of landscape crew experience and a valid driver's license. Who We Are • Umbrella Property Services provides dependable property services across Chicago and the wider Chicagoland area. • We support commercial properties with coordinated service across multiple operational categories. • We help clients reduce vendor complexity, maintain consistent standards, and protect long-term property value. • We run year-round work, with landscape and grounds care in the warm seasons and snow removal through the winter. • We treat each other and our customers with respect and integrity, and we look for teammates who do the same. What You Will Do Each Day • Mow, trim, and edge lawns to keep commercial properties looking sharp. • Plant flowers, trees, and bushes, lay mulch, and install garden beds. • Help with fall and spring cleanups, plus snow removal during winter when needed. • Operate commercial landscaping equipment and report any issues promptly. • Use our digital app to log completed work and stay coordinated with the team. • Follow safety protocols to keep yourself and your crew safe on every job. Why You Will Love Working Here • Pay of $16 to $21 per hour on W-2, or $17 to $22 per hour on 1099, based on your preferred employment structure. • Full-time onsite Laborer role based in Mokena, IL, supporting commercial properties across the Chicagoland area. • Steady year-round work, with landscape work in the build season and snow removal opportunities in winter. • Hands-on experience with modern equipment and a clear path to develop your skills as the team grows. Next Steps If you take pride in clean landscape work and want steady year-round opportunities, apply for the Laborer role and our team will be in touch.

Umbrella Property Services is hiring a Crew Lead in Mokena, IL to run a two-person landscape maintenance crew across our commercial route in the Chicagoland area. Pay is $20 to $25 per hour on W-2 or $22 to $27 per hour on 1099, your choice. You will be the senior person on the truck, setting the pace, calling the shots on quality, and making sure every property looks right before you pull off. Who You Are • You take pride in being the senior person on the truck, the one your crew looks to for the pace and the standard. • You believe a property is not finished until everything looks right at the curb. • You love the kind of leadership that gets done by example, not by lecturing. • You are the kind of person who can run a clean lawn route in summer and confidently plow a commercial site in a winter storm. • You are friendly and professional with customers, and reliable with the crew behind you. • You bring prior experience leading landscape crews, snow plowing experience, comfort towing 20-foot trailers, and a valid driver's license. Who We Are • Umbrella Property Services provides dependable property services across Chicago and the wider Chicagoland area. • We support commercial properties with coordinated service across multiple operational categories. • We help clients reduce vendor complexity, maintain consistent standards, and protect long-term property value. • We run year-round, with landscape maintenance through the warm season and snow operations through winter. • We are a growing company that values teammates who lead with quality workmanship and reliability. What You Will Do Each Day • Lead and coordinate a small landscape crew across assigned commercial properties. • Oversee lawn maintenance, shrub and tree trimming, and bed and mulch installation. • Run fertilization and turf care applications on schedule. • Manage spring and fall cleanups across the route. • Take on snow plowing, salting, and winter site management when the season turns. • Document work, photos, and site notes using our company systems. Why You Will Love Working Here • Pay of $20 to $25 per hour on W-2, or $22 to $27 per hour on 1099, based on your preferred employment structure. • Full-time onsite Crew Lead role based in Mokena, IL, with travel to commercial properties across the Chicagoland area. • Year-round work, with landscape maintenance in the warm season and snow operations through winter. • Health insurance and paid time off. Next Steps If you are ready to lead a route and take ownership of how every property looks, apply for the Crew Lead role and our team will be in touch.