Capitalizing on the Right Resources to Transform Your Business

How PayLease gained the support and guidance needed to achieve more rapid growth.

Between billing, tenant contracts, maintenance requests, utilities, and other day-to-day tasks, property managers have a hectic job. Collecting and processing checks from residents only adds to their duties.

In 2003, PayLease was founded to create a better, more convenient way to pay and collect rent. Today, it supports over 4,500 property management companies and homeowners associations with online payment and utility expense management tools. The company’s solutions simplify property managers’ workflows, increase their net operating income, and enhance the way they connect with tenants.

Dirk Wakeham joined PayLease as CEO after gaining experience as an executive at other Vista companies, including Kibo Software and Cvent. From his perspective, it was refreshing that Vista put such a strong emphasis on talent, culture, and people development. In particular, Wakeham has found Vista has the ability to bring in strong hires, provide training, measure satisfaction both quantitatively and qualitatively, and improve employee productivity over time.

In Vista’s partnership, Wakeham has gained value that reaches beyond capital investment. With guidance from Vista Consulting Group (VCG) and the support of a professional network of executives who have dealt with similar situations, he’s developed greater confidence in moving quickly and driving business transformation. Wakeham found that VCG understands and aligns with PayLease’s vision and provides specialized skills and additional expertise to supplement its management team. In his own words, VCG gives his team “bench depth” and helps the executive team make data-driven decisions for the business.

For added support, Wakeham reaches out to the Vista network of executives for advice in areas like talent strategy and process development. Through his experience at different Vista companies, Wakeham has built a strong trust in Vista’s approach to growth and value creation. Now, he’s focused on implementing best practices that he knows can lead to success for PayLease.

Please see the “Case Studies” section of the Disclosures page for important information about these Case Studies.

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In my experience, the probability of success as a Vista CEO is much higher because of the network and assets they bring to the table.
–Dirk Wakeham, CEO, PayLease


Year of Investment: 2017
Portfolio Status: Current
Headquarters: San Diego, CA

Online payment solutions for property management companies and tenants.

PayLease provides online payment, billing, and utility expense management tools to property management companies, HOAs, and residents. PayLease provides tenants with convenient online payment options that are easy to use and are bolstered by the highest levels of security and customer support. PayLease simplifies property manager workflows through seamless integrations, increases net operating income, and enhances resident relationships. The Company has over 4,500 clients, supporting in excess of 12 million residents.

PayLease was founded in 2003 and is based in San Diego, CA, with operations in Chicago, IL.

Vista Foundation Fund III completed the acquisition of PayLease in July 2017.

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