The Top 25 Real Estate Software CEOs of 2019

The Software Report is pleased to announce this year's Top 25 Real Estate Software CEOs. The awardees were selected based on a competitive nomination process that occurred over the past several weeks. CEO nominees were evaluated across several areas including, but not limited to, integrity, drive, intelligence, company culture, growth and profitability. While numerous CEOs were clearly top performing executives and deserving of recognition, the below awardees were, in our view, the best of the best.

1. Dave Bateman, Entrata

While studying business at Brigham Young University, Dave Bateman realized he had a passion for coding and started teaching himself how to program server-side PHP applications for his internet startup company. He left school early to launch a fledgling software business, Property Solutions, in 2003 and hasn't looked back since. That start-up eventually evolved into Entrata – a comprehensive property management platform-as-a-service (PaaS) solution designed to provide users with streamlined access to online tools for payments, accounting, lease support, and resident management.

He has served as CEO since inception and has led Entrata to $100 million in annual recurring revenue without the benefit of venture capital backing. He remains very engaged with product development and architectural implementation of Entrata's platform. Today, the company provides its solutions to over 20,000 rental communities within the United States. Bateman was also awarded Ernst & Young's Entrepreneur of the Year and Utah Business' CEO of the Year. He has been featured on the cover of both Entrepreneur and Fortune Small Business magazines.

2. Rich Barton, Zillow

Business-minded Rich Barton found success as both an entrepreneur and investor from an early age. In 1989, he graduated from Stanford University with a degree in engineering and economics and a short six years later at 26 years of age, launched Expedia from inside Microsoft. He served as CEO, president, and board director of the fledgling travel tech firm from 1994 to 2003 before moving on to co-found career recruitment site, Glassdoor, in 2007.

He is currently serving as CEO of Zillow, an online real estate marketplace devoted to supporting customers who wish to sell, buy, or rent property. Barton co-founded the company with Lloyd Frink in 2005 and it's now one of the most popular real estate tech companies. In addition to his entrepreneurial undertakings, he has held board member positions with many notable companies including, Netflix, and Artsy.

3. Joe Chen, Chime Technologies

Chime Technologies, an AI powered sales acceleration platform, offers a one-stop-solution for busy brokers and real estate agents looking for a way to track leads and manage customer relationships. According to CEO Joe Chen, Chime's success is due to the company's customer-centered focus. "Our CS (Customer Success) team serves our customers by listening intently to customer feedback and strategically implementing technology changes in weeks, if not days."

Chen explains that his inspiration comes from the potential positive impact that his business can bring to his customers' working lives. In addition to being an entrepreneur with several startup projects on the go, he is a venture capitalist with investments in over 60 tech companies. Chen received his Master of Engineering from MIT in 1995 and his MBA from Stanford University in 1999. He has held several senior leadership and board member positions with companies ranging from one of China's internet pioneers,, to an investment holding company called Oak Pacific Investment.

4. Frank Martell, CoreLogic

Frank Martell is not only CEO, president, and a member of the board of directors for CoreLogic – he is also an activist for financial empowerment and an influential leader within the housing industry. With over 30 years of experience as a senior executive in the marketing, financial services, and business information sectors, he joined the company in 2011 as CFO before moving into the chief operating officer role. In March 2017, he became chief executive officer of the $3.2 billion company.

CoreLogic is a provider of consumer, financial, and property information and analytics to businesses and governments. Founded in 1991, the company has established itself as a recognized authority within the housing industry. It is also responsible for creating the largest, most comprehensive databases for information on real estate, mortgage application, fraud, and loan performance within the United States.

Martell sits on the global board of directors for Operation Hope, a provider of financial education for youth and empowerment for communities. He also serves as chair for the West Coast Scarlet & Gold Committee of the Marine Corps Scholarship Foundation.

5. Joe Edgar, TenantCloud

Joe Edgar is a serial entrepreneur and agent of change. His latest company, TenantCloud, is a cloud based marketplace involving tenants, landlords and service professionals. The company provides an online platform for payment processing, rental advertising, accounting, tracking, information storage, and facilitation of maintenance requests. Edgar embraced his entrepreneurial spirit at a young age after buying his first real estate property at 14 years old. Three years later, he co-founded Modern Homes Inc., a Brazil-based business that he eventually sold in 2001. His first professional venture into tech was in 2005 with his startup, an online property management startup.

Edgar also has extensive experience working in government to advance business and economic growth. In 2008, he joined Texas Governor Perry’s office and managed $487 million in state authority with a focus on early stage and emerging companies and in 2011, joined Commissioner Staples in advising and operating a state venture fund focused on Texas’ early stage companies. Edgar holds a BS in economics from the University of Oregon, an MBA from Cornell University and was a Kauffman Fellow.

From Humble Beginnings, Top Software CEO Joe Edgar Persists and Succeeds

6. Marc Lefar, RentPath

As CEO of online leasing resource, RentPath, Marc Lefar is helping people find their perfect home. His unique combination of experience in strategic planning, product management, financial operations, and global marketing has made him the ideal executive for ensuring his organization reaches its full potential. RentPath was founded in 1989 and currently offers solutions to real estate professionals for rental listing and advertising, customer relationship management, and digital communication options.

Lefar attended the University of Virginia and received his BS in Commerce in 1985. He began his career with Proctor & Gamble, where he worked in brand management for the next nine years. From there, he occupied a series of senior leadership positions with the likes Verizon Wireless, Cingular Wireless, and Vonage, where he served as their CEO for six years. Lefar also acted as an advisor on the President's National Security Telecommunications Advisory Committee from 2011 to 2016.

7. Steve Winn, RealPage

Steve Winn brings together a unique blend of technological know-how and business acuity to his role as CEO with RealPage. With over two decades as CEO, president, and chairman of the property management software company, Winn is a capable leader who is known as a strong strategic and tactical thinker.

Winn spent 27 years serving as president and CEO for the Computer Language Research organization, a provider of tax compliance, tax research, and accounting software. He also served as president of the Research Institute of America, a Thomson Reuters Corp subsidiary, which offers information services to the accounting industry. He has been recognized as a leader in the multi-family real estate industry by the National Apartment Industry and as one of the top 100 most influential people by Accounting Today.

Winn graduated with a BS in electrical engineering from the University of Texas at Austin and earned an MS in management from Stanford University.

8. Eric Wu, Opendoor

Eric Wu's mission was to make moving simple, and he founded Opendoor to make that happen. A self-made millionaire, Wu bought his first property with scholarship money awarded at college. He purchased a 3-bedroom family home near his school at the age of 19 and owned over 25 properties by the time he graduated in 2005.

He started working on his first real estate tech startup after college and launched RentAdvisor, a rental and community review platform, in 2008. Shortly after, the company was acquired by Apartment List. An entrepreneur at heart, Wu continued to innovate on his original idea and founded a geo-data analytics company called Motivity that was picked up by real estate site Trulia, in 2011.

Wu led Trulia’s Geo & Social Products team before striking out on his own once again with Opendoor. The company has served more than 50,000 customers to date who wanted to make buying or selling their home a quick, seamless transaction.

9. Shahar Alster, SpaceIQ

Israeli entrepreneur Shahar Alster founded SpaceIQ, a cloud-based workplace management software company, along with co-founders Noam Livnat and Jeff Revoy in 2016. Dedicated to helping organizations optimize their workplace resources, the firm provides a suite of powerful tools for space planning, move management, real estate forecasting, and integration options. As SpaceIQ's CEO, he successfully led his company through three funding rounds and its acquisition by WeWork in July 2019.

Peers have praised Alster as a talented leader with an in-depth technical knowledge. He received his MBA in economics and marketing in 2010 and has a wide-breadth of experience with technology, business development, and service companies. Prior to starting SpaceIQ, he co-founded ASI Enter, an Israel-based IT company, and served in senior leadership positions with telecom companies Bezeq and ChooChee.

SpaceIQ’s Shahar Alster, A Top Real Estate Software CEO

10. Doug Chang, Calyx Software

Doug Chang is the founder and CEO of Calyx Software, a provider of streamlined mortgage loan application solutions, which is used by mortgage professionals to connect with over 200 integrated partners offering closing documents, compliance services, and more.
Chang understands the complexity involved in creating simplicity. “Developers of a user-friendly LoS (loan-origination software) work hard to not overcomplicate the interface and workflow,” he wrote in a 2016 Scotsman Guide article.

It was a chance encounter between Doug Chang and mortgage software reseller Dennis Boggs in 1990 that gave Calyx Software its start. In an interview, Boggs recalled his first meeting with Chang. They exchanged business cards, and six months later, Chang called Boggs about marketing a new mortgage software program he had created. His fledgling tech firm had a total of six clients at the time, and he asked Boggs if it was possible to sell his product to 1,000 more. Calyx Software was formally launched in 1991 and eventually reached 40,000 clients.

11. Robert Reffkin, Compass

Compass was founded by Robert Reffkin in 2012 with the mission to help everybody find their place in the world. Touted as the first modern real estate platform where property professional meets the best of technology, the New York-based real estate brokerage offers in-person and online services for residential buyers, sellers and renters.

Reffkin credits his mother, Ruth, for the beginning of Compass. As a seasoned real estate professional, his mother introduced him to the possibilities the property industry could offer, and he was hooked. Reffkin obtained a BA and MBA from Columbia University and spent his early career working in finance and investments. He has served as a White House Fellow with the Department of Treasury and held positions with Goldman Sachs, Lazard, and McKinsey & Company.

12. Vance Loiselle, Propertybase

Propertybase was founded in 2010 to provide real estate professionals with a better option for managing the complicated business of buying and selling property. In December 2017, Vance Loiselle stepped up to lead the company into its future and was recognized for his success a short year later. He was included in both the 2019 Swanepoel Power 200 and 2019 REAL Trends Game Changer lists – both acknowledgments if the impact he has had on the real estate industry.

Propertybase boasts a full-service, tightly integrated platform that engages clients, manages transaction details, and streamlines otherwise time-consuming tasks. Loiselle's leadership helped the company achieve its goals through the acquisition of two new businesses and its transition from a real estate CRM to a comprehensive suite of solutions geared towards teams and brokerages. Prior to joining Propertybase, Loiselle held leadership positions with SaaS-based businesses including Boston Logic, Sumo Logic, and BMC Software.

13. John Borgerding, Accruent

Accruent's CEO John Borgerding has a proven track record for leading tech teams, expanding businesses, and managing mergers and acquisitions. He has 23 years of experience with leadership tenures at top tech companies including Ventex, SumTotal Systems, and WebSense.

Under his leadership, Accruent has doubled its revenue performance and grown through its acquisitions, product innovation, strong organic growth, and expansion into new international markets. Borgerding holds a bachelor of arts in political science from the University of Missouri-Columbia and currently serves as a board member with cybersecurity firm Gigamon.

14. Anant Yardi, Yardi Systems

Anant Yardi was one of the first to create software specifically for the real estate industry. His entry to the space goes back to 1984 when he recognized the need for integrated accounting and property management software for the residential marketplace. At the time, he was the director of systems development for Burroughs Corporation (now Unisys) and with 14 years of programming experience, he knew he had the background to design such a product. Yardi created what was then dubbed “Basic Property Management” for the Apple II computer. The software solution was sold to Yardi’s first customer, Sabaco Realtors.

Since that time, Anant has directed the company through over 30 years of steady growth, remaining the President and sole owner as Yardi Systems became a leader in real estate asset and property management solutions. He has been recognized as one of the early pioneers in the commercial real estate automation industry, a “visionary in respect to automation systems and the resultant benefits in property operations,” according to Realcomm, when they honored him with the 2004 “Digie” award. Anant has an M.A. in Engineering from the University of California at Berkeley.

15. Anthemos Georgiades, Zumper

Like many great Silicon Valley startups, Zumper came about as an answer to a painful problem that Anthemos Georgiades saw play out over and over again when trying to rent an apartment. Despite the ease of reserving a hotel room online, there was nothing out there that made the apartment leasing process simple.

In 2012, Georgiades left a budding career in politics and, along with three other co-founders, launched Zumper to make renting an apartment as easy as booking a hotel. The company provides a full-service rental platform that connects renters with landlords and assists with prequalifying potential tenants, lease signing, and payment processing. Amongst his earlier achievements, Georgiades studied classics at Oxford, worked with the Boston Consulting Group, and graduated with distinction from Harvard Business School.

16. Amit Haller, Reali

As a real estate tech company, Reali strives to change the way people experience buying and selling their homes. Co-founded by Amit Haller and Ami Avrahami in 2015, Haller is the company's CEO and has blended the best of his real estate experience with his knowledge of technology to build a platform that makes home buying and selling almost fully mobile. Users can search for homes, communicate with their Reali agent, and place offers within the app. Their agents can negotiate on a buyer or seller's behalf and make closing arrangements.

Haller started out serving four years in the Israeli Defense Force. Assigned to a research and development unit, he led teams in the development of mission-critical systems during times of crisis. After his military service, he founded Butterfly Communications, a Bluetooth tech development company. Texas Instruments acquired the company five years later, and Haller moved on to launch IXI Mobile, a mobile data device and services firm in 2001 and then Veev, a proptech startup in 2009. He has almost three decades of leadership and entrepreneurial experience and brings this to bear as he leads Reali.

17. Grier Allen, BoomTown

BoomTown, an end-to-end sales and marketing platform for the discerning property professional, was co-founded by Grier Allen in 2006 as part of his mission to connect home buyers and sellers with the right real estate talent. As CEO and president, he has led the company to become one of the fastest-growing companies in 2011, 2012 and 2013 – as recognized with its inclusion on the INC. 500 list.

He also helped secure $20 million in funding in 2015 and was a driving force behind the company's launch of its open platform project – providing an API as part of an initiative to build an ecosystem with their partners. Allen received his BS in computer science from Clemson University. He has worked as an in-house marketing & technology consultant with O’Shaughnessy Real Estate and as a CTO with Slant Media.

18. Jan Poulsen, thinkstep

thinkstep is leading the charge on supporting organizations that want to become more sustainable. Jan Poulsen joined the company in 2007 as a managing director and stepped into the role of CEO in 2016. The German-based thinkstep is a market leader in sustainability software, data, and consulting services and helps their clients incorporate environmentally-friendly options throughout the building and construction process. The organization also offers similar options for those in energy & mobility, consumer goods, chemicals & life sciences, metals, mining & manufacturing, and the services & public sector industries.

Poulsen is a well-rounded senior executive with a strong background in the software, content, and consulting industries. He has worked primarily with multinational organizations with a B2B focus, including dk-Teknik Energy & Environment, FORCE Technology, and Send24. He received an MS Engineering (Sustainability & Process Optimization) from Danmarks Tekniske Universitet, and completed course work in business administration from the Copenhagen Business School.

19. Drew Uher, Homelight

Drew Uher is CEO and co-founder of Homelight, a platform provider that matches home buyers and sellers with the top-performing real estate agents based on area of expertise. As the first of its kind, HomeLight analyzes millions of real estate transactions to find the best agent according to how well they sell homes similar to the buyer's property or the seller's stated preferences.

Prior to launching his proptech, Uher received his bachelor’s degree in management information systems from Texas A&M University and his MBA from Stanford. He began his career with hedge fund Q Investments before moving on to work as an Associate with Morgan Stanley. He co-founded Gameyola, a distribution and monetization platform for Flash games, in 2009 and grew daily users to 250,000 during his time there. Currently, Uher is also a venture partner with 1984 Ventures.

20. Jason Hoback (co-CEO), CINC

Jason Hoback is passionate about bringing cutting-edge tech to his customers. As co-CEO of CINC, a lead acquisition and client management platform provider, he will do whatever it takes to make that happen for the real estate clients he serves. Commissions Inc (CINC) was founded in 2011 and within a few short years, became one of the fastest-growing real estate solutions on the market. Fidelity National Financial purchased the company in 2016 and the technology was leveraged to expand their offerings and better serve clients.

Hoback joined the company in 2014 and stepped into the role of co-CEO in January 2017. In his role, he oversees the cultivation of the company's workforce, client satisfaction, and overall revenue growth. He has over 20 years' sales experience in the tech industry and served as senior vice president & group publisher for the Best Media Group and as VP of Sales for Thomasnet before coming to CINC. Hoback graduated from the University of Memphis with a BA in advertising.

21. Jamie Clymer, FrontSteps

Jamie Clymer is a results-oriented leader with a mission to transform the way communities come together. He can do just that as CEO of FrontSteps, a platform provider designed to help home builders, leasing companies, realtors, and other professionals manage and secure their communities.

Clymer has built a strong reputation as a senior executive through his work with several property-tech companies over the last two decades, including industry leaders like Dominion Enterprises, Zillow, Zumper, and RealPage. He has extensive experience with startups and has excelled in company building through data analysis and discussions with both the team and their customers. Those who've worked with Clymer describe him as being open and honest with an uncanny ability to recruit and cultivate a world-class workforce. Clymer received his bachelor of science in marketing from Kent State University.

22. Nate Baker, Qualia

No one can argue that CEO Nate Baker hasn't been a boon for proptech business, Qualia. He joined the real estate cloud company 4 years ago, and under his leadership, it has tripled in size and expanded its platform's availability from 15 to 50 states. Marketed as the software for the closing industry, Qualia's solutions make it simple for agents to buy and sell property.

Before joining Qualia, Baker founded and led a company called Nebu and worked with investment firm Bienville Capital. He completed a BSE in mechanical engineering from the University of Pennsylvania in 2014.

23. Caren Maio, Nestio

Caren Maio is the real deal when it comes to being a business tycoon, and her company, Nestio, is taking the New York property market by storm. She launched the company with co-founder Mike O'Toole in 2011 after slogging through her painful hunt for the perfect apartment. The site caters to property owners, managers, and brokers that wish to advertise, track and manage their residential rentals and boasts a 20 percent reduction in the amount of time client listings languish on the market.

Maio attended New York University, where she received her BA in Publishing/Branding and made a name for herself in sales at companies like Nike, the Wall Street Journal, and MetaProp NYC.

24. Ryan Whitlock, Title Holdings

Ryan Whitlock is an experienced senior executive with a passion for transforming up-and-coming tech startups into fast-growing, profitable companies. In 2019, he started as CEO with Title Holdings, a Salt Lake City-based company that provides an automated, integrated solution called SecureSync for those in the title, escrow, mortgage lending, and related real estate industries. Previously, Whitlock served in various leadership roles with companies ranging from fintech, to proptech, SaaS, and digital marketing.

One of his longest-term commitments was with Z57, an online provider of tools and training for real estate agents. He joined the company in 2004 and was eventually promoted to the position of CEO in 2012. After the company was acquired by Constellation Software, he also took on CEO duties of another portfolio proptech company, Zurple. He eventually moved on to join Agent Squared as CEO before starting Title Holdings. Whitlock received his BS in finance and MBA from Westminster College.

25. Gary Barker, Reapit

Gary Barker is CEO of UK-based Reapit – a CRM platform provider geared toward sales, rentals, property management, and client accounts – and is responsible for the company's vision, direction, and strategy. Since joining the company fifteen years prior, he has helped transform it into the market-leading real estate tech firm they are today.

Previously, Barker held various leadership roles in both finance and IT with Countrywide Estate Agents. In addition, he served as a European business analyst and consultant for Ingram Micro. He was also a member of the accreditation and lobby organization NAEA Propertymark.

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