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Executive Interview: Sid Singh, CEO at Rectangle Health

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The Executive Interview Series provides readers with exclusive insights from movers and shakers in the payments industry. The payments industry is under continuous transformation. This series offers diverse perspectives on everything from strategy to payments technology and the industry’s future.  

In this interview, TSG marketing team member Rachel Hartley spoke with Sid Singh, CEO of Rectangle Health, to discuss recent M&A activity and the future of healthcare technology as it relates to payments. 

Sid Singh, CEO of Rectangle Health, has over two decades of experience in the FinTech industry, specializing in SaaS, Data and Analytics, and Technology. He most recently served as President of the U.S. Information Solutions at Equifax and prior, spent 14 years at Global Payments, where he held the role of Group President of Integrated Solutions & Vertical Markets. Sid has also held various executive leadership positions at GPN, including Chief Product Officer and Vice President, in addition to serving as the regional head of Asia Pacific. Before these roles, Sid held senior management positions with HSBC and Citibank in the Asia Pacific region.

Q. Rachel H

How have your past experiences shaped how you approach your role as CEO of Rectangle Health?

A. Sid Singh

I’ve been in the FinTech industry for over 20 years, with focus and experience in SaaS technology. My first encounter with Rectangle Health was in 2014 at Global Payments. At the time, Rectangle Health was known as Retriever Medical/Dental Payments, and even though they were a relatively small company, we recognized that their technology and expertise were powerful and could compete with the major players. 

At Global Payments, I grew the software division beyond payments, combining multiple areas into a single platform, which was also the direction Rectangle Health was taking with Practice Management Bridge. 

Rectangle Health’s exclusive focus on healthcare and its offering of digital tools to modernize and transform today’s practice is particularly compelling. When the opportunity to lead the company came up in 2023, I knew I couldn’t pass it up. 

Q. Rachel H

How does Rectangle Health’s technology compare to competing technologies in the healthcare industry?

A. Sid Singh

What makes Practice Management Bridge unique is that it is a comprehensive solution that truly simplifies the administrative, operational, and financial side of healthcare. Many of our competitors focus on one or two things, and most of them do those things very well. But with Rectangle Health, you get the whole package. 

Our goal is to provide a solution that doesn’t just encompass multiple areas; it leads in all of them. That’s why when we’ve expanded the platform into new territory, we’ve done so by acquiring industry-leading companies who have expertise in those areas. 

That said, there’s still a lot of work left to do. Overall, technology providers have only solved about 25% of the challenges that healthcare practices face. There are many pain points that providers and their staff face, and their current practice management systems can only do so much. As we continue to grow and enhance Practice Management Bridge, we’ll be looking to solve those challenges as well. 

Q. Rachel H

What has Rectangle Health gained through recent acquisitions?

A. Sid Singh

We’ve acquired several software companies over the past few years —RavePoint, ReminderCall, and PCIHIPAA. Each of these organizations brings efficiencies to healthcare practices – from streamlining how they engage with customers to making it easier to remain PCI, HIPAA, or OSHA compliant. We have integrated each software acquisition into Practice Management Bridge, making the features available to all our healthcare practice customers. 

Furthermore, what we found with each of these acquisitions is that many of the verticals we were targeting—chiropractors, optometry and ophthalmology, physical therapy—were already using these products. So, by bringing these companies under the Rectangle Health umbrella, we have been able to serve the broader healthcare community. 

Q. Rachel H

How does M&A fit into Rectangle Health’s growth strategy in the upcoming years? 

A. Sid Singh

M&A is a critical component of our growth strategy.  We acquire for specific products, skill sets or to accelerate time to market.


Contact TSG, Rectangle Health’s preferred provider, to learn about M&A and partnership opportunities.


Q. Rachel H

What is the most attractive aspect of joining Rectangle Health from an M&A perspective? 

A. Sid Singh

As our platform has expanded to include more products and our profile has grown, healthcare technology companies have come to see what Rectangle Health can offer providers. And they want to be a part of that. Especially now that we’ve moved beyond just payments and into software such as patient engagement and compliance, companies that might not have thought about teaming up with us are taking notice. 

As I said earlier, we have a lot of competitors, and they are very good at what they do. But so many of them are only focused on one thing. We want to be the solution that relieves healthcare providers of all of their financial and administrative burdens. That way, they can focus on what matters most—their patients. 

Q. Rachel H

How does Rectangle Health leverage its technology in bridging the gap between healthcare providers and patients?

A. Sid Singh

Practice Management Bridge is carefully crafted to enhance the relationship between provider and patient. The staff at a healthcare practice is stretched thin. Our platform enables them to work efficiently and allows for more time in their day to manage the office by eliminating the manual work that they must do, such as calling patients to remind them of appointments or sending paper statements to request payment. 

Additionally, our technology creates a digital workflow that integrates into any practice management system. Being system agnostic enables our platform to flex and grow with healthcare organizations. As we expand Practice Management Bridge’s capabilities, we maximize the full revenue cycle and provide critical integration into the provider’s technology stack, allowing them to consolidate systems and vendors. This is a major benefit for organizations who want to offer a convenient, digital experience to their patients. 

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Q. Rachel H

What trends in healthcare technology do you expect to see grow in the next 5 years?

A. Sid Singh

There are no signs that the next few years will be easier for the healthcare industry—high staff turnover rates, continued physician burnout, and rising patient demand substantially impact teams and administrations. Creating a sustainable workforce and consumer-centric patient experience is how and where technology can play a significant role. 

Technology adoption in the administrative and financial sectors of the healthcare experience is still in the early stages. Over the next few years, organizations that rely heavily on their practice management software will be overburdened as they struggle with long Accounts Receivable cycles, maintaining a full patient schedule, and managing office security compliance. 

Technology that can absorb, consolidate, and relieve strain will prove valuable to offices. 


Related: Rectangle Health Drives SaaS Expansion Through M&A and Partnerships