World's 20 Inspiring Women to Follow in 2025
Company: Charlee.ai, AI Certifications Group
Designation: Founder & CEO
Country: United States
Sri Ramaswamy is a pioneer at the intersection of artificial intelligence and insurance, with a career that spans hospitality, technology, banking, and ultimately, insurtech innovation. As the Founder & CEO of Charlee.ai, she has built a flagship claims intelligence platform rooted in her belief that insurance is fundamentally a business of risk, and that AI can transform hidden risks into measurable, actionable intelligence. Her work has earned recognition across the insurance and AI ecosystem, not only for the products she has built, but also for the philosophy of empathy, responsibility, and ethical leadership she weaves into every venture.
Sri’s journey began far from insurance. With a degree in hotel management, she spent her first year working in hospitality before moving into sales and administration at Samsung India. It was there that she spotted an overlooked opportunity: a showroom full of unsold microwaves. She pitched her manager on an idea, Saturday cooking demos using the microwave, complete with postcards sent to customers and a friend preparing recipes live. Within a month, the inventory was sold out. That experience revealed two things that would define her career: a talent for creative problem-solving and an instinct for using data to unlock growth. Her manager was the first to tell her she had a future in analytics.
That seed of advice shaped her path. She went on to earn her Master’s in Information Technology with a specialization in database administration from Griffith University in Australia. While there, she tested her entrepreneurial chops by setting up a small branding venture. One of her first projects was for a restaurant tucked inside a train station. By mapping train schedules and targeting morning and evening commuters with flyers, she helped the owner outsell his mainstay product, a chicken tikka wrap, through data-driven marketing. Once again, she was encouraged to pursue analytics seriously, this time within banking and CRM.
Her career in data and analytics accelerated from there. Sri became a CRM consultant on large banking projects and eventually relocated to San Diego, where she entered the insurance industry through a workers’ compensation carrier. Leading a legacy transformation project, she saved the company millions of dollars and proved her ability to modernize complex systems. From there, she was recruited by a software company building vertical solutions in analytics. She successfully launched two analytics products in underwriting and claims, collaborating with early adopters and system integrators.
It was during this phase that Sri had the insight that would change her career trajectory. Conversations with claims managers revealed a shared frustration: the most important insights about risk were locked inside unstructured claims data, notes, documents, adjuster files. Determined to understand the problem, Sri read more than a thousand claim files in a single month. Her conclusion was simple but profound: if unstructured risks could be converted into structured, measurable risk attributes, insurers could finally act on them proactively. Coupled with her earlier Associate in Risk Management (ARM) certification, this realization gave her both the conceptual and technical grounding to launch Charlee.ai.
Today, Charlee.ai applies a patented claims language model, a proprietary exposure intelligence database trained on more than 60 million claims, and a suite of agentic AI tools to help carriers, brokers, MGAs, and self-insureds predict litigation, manage reserves, identify fraud, and mitigate risk before it escalates. The platform doesn’t just process data, it decodes the language of risk itself.
Sri is also a storyteller and educator. Through her popular Two Tuesday Taglines series, she distills lessons about AI and leadership into short, memorable reflections, drawing inspiration from nature, history, and everyday life. She has authored widely read articles including Patterns, Pivots & Purpose: The Road to Charlee.ai and The Litigation Storm Is Here: Agentic AI vs. Insurance Litigation. She is frequently invited to speak on podcasts and panels about AI in insurance, ethics, and the future of risk management. In parallel, she founded the AI Certifications Group, offering domain-specific training such as Fundamentals of AI in Claims and Fundamentals of AI in Policy Management to upskill professionals across the insurance value chain.
For Sri, the mission goes beyond technology. She believes that AI must be built on empathy, transparency, and responsibility. Just as she once turned unsold microwaves into a success story through creativity and customer focus, she now helps insurers transform overwhelming claims data into foresight and resilience. Her journey, spanning hotel kitchens, train-station branding campaigns, banking systems, and insurance claims, demonstrates that at the heart of every innovation lies the same principle: find the hidden patterns, and use them to create impact.
