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Gaurav Oberoi, the CEO and co-founder of Lexion, a tech startup that uses artificial intelligence to extract insights from legal documents, has had success in building and selling companies. Lexion was recently acquired by Docusign in a $165 million deal, marking the third company co-founded by Oberoi to be acquired. Despite not being a household name, Oberoi is highly respected in the Seattle startup community for his technical talent, business judgment, and emotional intelligence. His ability to deeply understand customer problems and evaluate startup ideas has led to his success as a company builder.

Oberoi’s entrepreneurial journey began in his youth when he created computer games that received positive feedback from his classmates. His experience in founding and selling companies such as BillMonk and Precision Polling, as well as his time at SurveyMonkey, helped him develop the skills necessary to successfully launch and grow startups. Oberoi has a playbook for evaluating ideas that involves understanding the problem, talking to customers, conducting tech diligence, and building prototypes. This rigorous approach has enabled him to sift through countless startup ideas and identify those with potential for success.

Lexion was born out of Oberoi’s dedication to solving complex legal document challenges faced by companies. Through hundreds of calls with various stakeholders, including lawyers and contract managers, Oberoi identified a gap in the market for a solution that could efficiently extract key terms from contracts. Lexion’s innovative AI-powered text-mining capabilities, developed at the Allen Institute for Artificial Intelligence, set the startup apart in the legal tech space. Initial successes with law firm Wilson Sonsini led to them becoming not just a customer, but also an investor in Lexion.

One of the key factors in Lexion’s success has been its focus on listening to customers and building products that address their needs. Oberoi and his team created a smart repository for contracts that evolved into a suite of products for contract creation across various functions within organizations. The company’s ability to recruit and hire talent, including bringing on Jessica Nguyen as chief legal officer early on, has also been crucial to its growth. Despite not following the typical venture capital-funded growth trajectory, Lexion has maintained a pragmatic culture and avoided layoffs during tough times.

Oberoi’s leadership style, characterized by humility, thoughtfulness, and a focus on listening, has been instrumental in shaping Lexion’s success. The company’s acquisition by Docusign further validates the impact of its technology and the team’s dedication to solving customer problems. Oberoi’s advice to other entrepreneurs is to focus on understanding the problem deeply, ensuring alignment among team members, and prioritizing customer feedback. As a finalist for CEO of the Year at the 2024 GeekWire Awards, Oberoi’s track record of building successful companies and creating value for customers has solidified his position as a respected entrepreneur in the Seattle startup ecosystem.

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