Rich Hollister joins Lone Wolf as Chief Revenue Officer

Bringing more than 25 years of revenue leadership across real estate technology, legal information services, and SaaS to the company's next chapter.

Rich Hollister joins Lone Wolf as Chief Revenue Officer at a moment when how a real estate technology company grows matters as much as how fast. The next several years of growth at Lone Wolf will be measured in the strength of its customer and partner relationships, in the value those relationships create over time, and in how the company adapts as the industry around it keeps changing. Rich's career has been built on exactly that work.

Background and approach

Rich brings more than 25 years of experience scaling revenue organizations across real estate technology, legal information services, and broader SaaS. He joins Lone Wolf from LoopNet, the most-trafficked commercial real estate marketplace in the U.S., where he served as SVP of Sales and led the team through one of the most aggressive growth periods in the company's history. Before LoopNet, he spent four years at Wolters Kluwer's Legal and Regulatory U.S. business as Vice President of Sales and Business Development, building the go-to-market function for one of the most established legal technology brands in the country. His earlier work also includes senior sales leadership at Watermark, a higher education SaaS platform. Across those roles, the through-line is consistent. Rich gets brought in to rebuild sales organizations, shift transactional sales motions into consultative ones, integrate sales teams from acquired companies, and build compensation structures that align with new business strategies. He has done this work in SMB, enterprise, government, and international divisions, which gives him an unusually broad reference set for what works at different scales.

What he is being asked to build at Lone Wolf

The work ahead for Rich maps directly to what customers, partners, and the broader industry are telling the company they need. Real estate professionals are increasingly looking for partners rather than vendors, partners who understand the operational reality of their businesses and who keep showing up as that reality changes. Rich's mandate is to build a revenue function that operates from exactly that posture. In practical terms, that points to a sales organization where every conversation connects to measurable customer value, supported by partnerships with integrators, MLS organizations, franchises, and adjacent technology providers that strengthen what Lone Wolf can deliver. The end state is a growth model that compounds because customers and partners want to expand the relationship, not because the company is asking them to. The connection to the rest of the leadership group is direct. J.R. Stricker's customer experience work creates the conditions for relationship-led growth, Aaron Kardell's innovation function shapes products genuinely worth recommending, and Alan Matuszak's technical foundation enables scaled partner integration this strategy requires. Rich connects those threads to how Lone Wolf shows up in the market.

A grounding outside the work

Rich holds an MBA from the Lally School of Management at Rensselaer Polytechnic Institute and a BS from Binghamton University. He lives in New York, where he teaches with Junior Achievement, the nonprofit that brings business leaders into classrooms to introduce young people to entrepreneurship and financial literacy. This long-arc, relationship-based work has shaped his approach to building both teams and businesses over time.

Read more about Rich on his Lone Wolf bio page.