🚀 From Paper Checks to #1 in the Market: How Longstreet Property Management Scaled Fast with LeadSimple + Black Sheep

With a bold 3-month implementation plan and an ambitious growth target, Longstreet Property Management partnered with Black Sheep Global to transition off monday.com and fully build out operations in LeadSimple. The result? Streamlined processes, scalable automation, and a #1 national ranking.

Introduction

Longstreet Property Management is a growing property management company based in Oregon, operating in the Corvallis and Portland markets. Originally founded in 1992 and acquired by its current owner in 2020, the company has since undergone a complete digital transformation. With COO Ondrej Podlesak leading operations, Longstreet set out to implement LeadSimple as a core part of their scaling strategy—with Black Sheep as their implementation partner.

Before

  • Systems were heavily manual: one email address, checks delivered by hand, and no centralized digital operations.

  • Monday.com was being used as a task manager, but it lacked scalability and deep integration with property management tools.

  • Attempted a self-implementation of LeadSimple but hit roadblocks, especially with complex operational workflows.

  • Wanted to move fast—entire system built and launched in 3 months—but most vendors advised a slower pace.

After

  • Fully transitioned off monday.com and launched a comprehensive LeadSimple buildout in just 3 months.

  • Reduced onboarding time and support needs for new team members—COO no longer needed to train leasing staff directly.

  • Integrated portfolio data directly into workflows, eliminating double entry and manual cross-referencing.

  • Added automations through Zapier to further streamline processes and connect tools.

  • Ranked #1 and #4 in their respective markets on PropertyManagement.com, gaining national visibility.

Process

  • Pre-work: Ondrej mapped out business processes ahead of time to speed up collaboration.

  • Partner selection: Chose Black Sheep after meeting at LeadSimple University and assessing fit with other providers.

  • Implementation cadence: Weekly sessions with Black Sheep, supported by shared spreadsheets and Loom videos for async collaboration.

  • Training & change management: Leveraged EOS principles—hyper-focus, milestones, and team buy-in. Led weekly trainings to roll out changes.

  • Launch strategy: Hard cutover—shut off monday.com on a Friday, launched LeadSimple Monday. Minimized disruption during peak season.

  • Post-launch: Fine-tuned workflows, built dashboards (manually where needed), and expanded functionality with automation tools.

Conclusion

Longstreet Property Management didn’t just implement software—they built a platform for scale. With LeadSimple as their operational core and Black Sheep as their implementation partner, they moved fast, stayed focused, and came out ahead—literally. Ranked #1 in their market, they now have a system that supports aggressive growth, improves team onboarding, and frees up leadership time for high-level strategy.

“If you value your time, spend the extra money on a partner whose job is to be an expert in this area.”
– Ondrej Podlesak, COO