Founder Monesh Jain on speed, simplicity, and the tech reshaping wholesale insurance

The specialty insurance industry is long overdue for a digital transformation, and Monesh Jain, Founder and CEO of SquareRisk, is leading the charge. With a mission to bring speed, transparency, and automation to a traditionally manual and difficult-to-navigate process, Jain has built a digital marketplace that is reshaping how brokers and carriers interact.

“Traditional wholesalers are slow, opaque, and overly manual—relying on PDFs, emails, and phone calls,” says Jain. “We knew the industry needed a better way.”

Jain’s journey into insurtech began long before SquareRisk. In 2002, he was an early engineer at SquareTrade (later acquired by Allstate), then went on to found NorthOut, a digital transformation agency for P&C carriers and brokerages. But the inspiration for SquareRisk came from a frustrating personal experience.

“We had an eight-figure revenue deal delayed by two weeks just because we couldn’t get the necessary specialty coverage fast enough,” he recalls. “At that point, whether the policy cost $800 or $8,000 didn’t matter—all I wanted was speed and ease of doing business.”

That moment revealed the critical gaps in how brokers access specialty insurance—and led to the creation of SquareRisk.

What Makes SquareRisk Different?

SquareRisk is a purpose-built marketplace for retail brokers to discover, quote, and bind specialty MGA products across more than 45 carriers—all through a single, modern interface. Unlike competitors that are tackling outdated workflows, SquareRisk reimagines the entire process with automation at its core.

“We’re not just digitizing outdated processes—we’re automating and optimizing them,” Jain explains. “That means brokers can move faster, carriers get cleaner data, and deals close sooner.”

Some of the features include:

• MGA Discovery Module: Instantly checks market appetite and eligibility.
• Multi-Carrier Quoting: One portal to generate quotes from numerous markets.
• Smart Forms: Auto-map client data to each carrier’s requirements.
• Submission Automation: Full visibility into status, quote timelines, and underwriter feedback.
• Concierge Support: Managed follow-ups for complex or non-standard risks.

This approach helps brokers eliminate redundant manual work and focus on selling. “SquareRisk helps brokers win more business—faster and with less friction,” says Jain.

Innovation at the Core

SquareRisk isn’t just another SaaS tool. It’s built on an API-first architecture and includes AI-powered enhancements like automated risk classification, PDF data extraction, and appetite intelligence. These innovations enable seamless integration with agency management systems (AMS) like Applied Systems and support both broker and carrier efficiency.

“Our Appetite Intelligence Engine and AI-assisted workflows are changing how submissions are matched, quoted, and bound,” Jain says. “We’re building tech that actually understands the complexities of specialty insurance.”

Despite its technological strength, Jain admits SquareRisk had to overcome early resistance from an industry steeped in tradition.

“Specialty insurance is relationship-driven and resistant to change,” Jain notes. “We didn’t ask brokers to change everything at once—we designed SquareRisk to fit into their existing habits—but with immediate timesaving benefits, that naturally expands usage.”

Carrier integration also posed challenges due to the varying workflows and submission preferences. SquareRisk overcame this with flexible tooling and strong underwriter partnerships, which in turn built trust and traction.

Traction and Testimonials

SquareRisk has already processed hundreds of submissions and is actively used by dozens of retail brokers. Jain highlights a few standout success stories:

• A benefits broker launched a P&C insurance agency and bound over $600k in premium in just a few months. 
• An agency network enhanced its revenue from specialty insurance products by 20% by offering digital access to specialty markets to its agents. 
• A specialty MGA improved submission quality and reduced processing time by 30%.
• A mid-size agency scaled their operations and started closing six-figure deals—without hiring new staff.
  
  

“SquareRisk gives us the speed and efficiency we need to compete with the big players,” shared one agency owner. “It’s like having technology perform operational work for us so that we can spend more time with our clients.” 

What’s Next?

Looking ahead, SquareRisk plans to:

• Expand AI capabilities to support matching individual risk with right markets, smart document generation, and further automation.
• Grow its carrier network, adding even more market options for brokers.
• Launch analytics tools for marketplace insights, risk profiling, and trend tracking.
• Deepen AMS integrations, building on its Applied Systems partnership and adding more platforms.

“We’re building the infrastructure for a more connected, tech-driven future of insurance,” says Jain. “SquareRisk will continue to lead the charge in transforming how specialty insurance is distributed, with a focus on reducing friction and empowering brokers to close more business.”

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Contact Information:

Monesh Jain is the Founder and CEO of SquareRisk, a digital wholesale insurance marketplace helping brokers and specialty MGAs streamline commercial coverage. He can be reached at mjain@squarerisk.com. Learn more at www.squarerisk.com.

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