brokerage-technology
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Applied Systems Built the Plumbing of Insurance - Now It Wants AI to Run the Pipes
For four decades, Applied Systems has turned the insurance agency's least glamorous chores into software. Its next bet is that the company controlling the workflow can also control where AI becomes useful.
Michael Martin
Michael Martin is the Co-Founder and CEO of Sidekick, a generative AI assistant purpose-built for real estate agents and brokerages. A Dartmouth-educated executive with a career spanning investment banking at Deutsche Bank and Apollo Global Management, digital agency leadership at Code and Theory, and proptech entrepreneurship, Martin co-founded Avenue 8 in 2020 as a tech-enabled mobile-first brokerage. When Sidekick's AI tooling proved more compelling than the brokerage itself, he made the bold call to shut down the brokerage entirely and go all-in on the software platform. Sidekick has raised $18M in funding, won back-to-back Webby Awards in 2024, and secured MLS partnerships covering over 120,000 real estate agents across the US.