Business Details
20 Years
experience
Emergency
services
Your Trusted Property Management Partner in Chicago
Westward360 was founded in 2006 with a vision to revolutionize property management by combining technology, in-house expertise, and a client-centric approach. Starting with a small Chicago condo building, we recognized the need for innovation in an industry dominated by mom-and-pop operations. Over the years, weve grown to manage over 50,000 homes and $16 billion in real estate assets, driven by our core values of GRIT (Glass-ful, Responsive, Innovative, Team). Our acquisition of 360PROS in 2008 allowed us to offer in-house services like plumbing, painting, and HVAC, ensuring quality control and accountability.Technology has always been a priority, with a custom tech stack developed in 2010 to streamline billing, communication, and operations. Our team of 450+ employees, including certified property managers, is the backbone of our success, enabling us to serve communities nationwide. Weve expanded through strategic acquisitions, including six companies in 18 months in 2018, and now operate in major markets like Houston, Las Vegas, and Portland. Our mission remains unchanged: to simplify property ownership through transparency, expertise, and relentless dedication to client satisfaction.
Services
Community Management
Rental Management
Real Estate Brokerage
Maintenance Services
Property Inspections
Details
- Year established: 2006
Highlights and features
- 20+ years of combined leadership experience in property management
- In-house services (plumbing, HVAC, painting) via 360PROS for faster response
- 24/7 emergency support and client-responsive task system
- Custom technology stack for real-time financials and communication
- Proven track record managing 50,000+ homes and $16B in assets
What people say
24-hour responses
Plumbers on point
Responsive process
Well-organized meetings
Best team experience
Services
Community Management
We provide comprehensive community management for HOAs and condominium associations. Our services include budget planning, vendor coordination, property inspections, and board meeting facilitation. With low manager-to-building ratios, we ensure personalized attention while maintaining operational efficiency through proprietary tools like Property Journals. Our team handles day-to-day operations, capital projects, and emergency response to protect community assets.
Rental Management
Our rental management covers tenant screening, lease creation, and maintenance coordination for single-unit condos and multi-family properties. We handle rent collection, eviction processes, and property marketing through MLS listings and major platforms. With 24/7 emergency maintenance support and preventive service calendars, we maximize rental income while minimizing owner involvement across Chicago and surrounding markets.
Real Estate Brokerage
Our full-service brokerage assists with property sales and rentals, offering professional photography, market analysis, and tenant placement. We leverage extensive local market knowledge and digital marketing channels to optimize property exposure. From lease negotiations to closing coordination, our agents provide end-to-end transaction support for residential and commercial real estate clients.
360PROS Maintenance
360PROS delivers prompt maintenance solutions including plumbing, HVAC, painting, and pest control. Our licensed technicians use route optimization technology for efficient service calls, while emergency teams respond immediately to critical issues. This internal division ensures quality control, faster turnaround times, and cost savings compared to third-party vendors for both community associations and rental properties.
Property Inspections
We conduct detailed property inspections with digital documentation of structural and mechanical systems. Annual and seasonal reports identify maintenance needs and long-term repair planning. Our inspectors use standardized checklists to evaluate common areas, building systems, and compliance with association rules, helping prevent costly emergency repairs through proactive maintenance scheduling.
People
Brent Straitiff
Principal & Chief Executive Officer
Brent leads Westward360's strategic growth initiatives, leveraging 15+ years of property management experience. He oversees operations across 10 states while maintaining focus on client satisfaction and technological innovation.
Travis Taylor
Principal & Chief Operating Officer
Travis manages daily operations and process optimization, ensuring service consistency across 50,000+ managed units. His leadership drives the company's expansion into new markets and service verticals.
David Westveer
Principal & Financial Chair
David oversees financial strategy and risk management, maintaining fiscal responsibility across $16 billion in managed assets. He ensures compliance with accounting standards and investment protocols.
Brawley Reishman
Principal & Chief Technology Officer
Brawley leads technology development, maintaining our proprietary systems that power real-time financial reporting and client communication platforms used by 450+ employees.
Nathan Brown
Principal & Chief Investment Officer
Nathan directs acquisition strategy and portfolio growth, having integrated ten competing firms since 2018. His expertise in market analysis drives strategic expansion into high-growth regions.
Questions
How many years have you been in business?
We were founded in 2006 and have grown to manage over 50,000 properties nationwide.
Do you offer 24/7 emergency services?
Yes, our team responds to emergencies 24/7 with live support and customized protocols.
What technology platforms do you use?
We utilize Vantaca for real-time financial reporting and client portals with automated billing features.
Can owners use their preferred vendors?
Yes, while we have a vetted network, you may choose your own licensed and insured vendors.
How are maintenance requests tracked?
All tasks are time-stamped and documented in our system for board reporting and accountability.
