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It takes 20 to 30 days for a company to create, negotiate, and finalize a contract, according to Aberdeen Research. This situation spurred Chris Combs and Vishal Sunak, a former Raytheon software engineer and director of sales operations at InsightSquared, to found LinkSquares, whose platform allows legal and finance teams to automate the search and reporting process for company contracts. Today, the company announced it has raised $14.5 million in a round led by Jump Capital, coinciding with the expansion of its data set — Smart Values — that lets organizations extract contract data, trends, and patterns via pretrained algorithms in reports.

“This investment is a testament to the power of our product, incredible growth in 2019, and the innovation of our team. With LinkSquares, customers are tackling universal contract management problems that historically have kept their legal teams buried in countless manual tasks,” said CEO Sunak. “With our new and existing venture partners, I’m confident that today’s investment will enable us to help even more companies move beyond contract management struggles and realign their priorities, processes, and outcomes.”

LinkSquares’ platform, which is web-based and hosted on Amazon Web Services, can perform full-text searches for keywords, phrases, and contract terms across documents in “seconds” using AI. It taps multi-query and filtering to extract key bits of data from contracts, including parties, effective and termination dates, payment terms, governing states, limitation and liability, and 30 other commercial terms, to the tune of 5 million data points extracted over the last five years. Meanwhile, its email-based notification function automatically reminds team members of important dates and obligations, and its clause library enables searches for contract clauses.

LinkSquares’ optical character recognition (OCR) tech transforms scanned PDFs into a searchable format, and its custom user roles let admins manage contracts while controlling data access. Users can set permissions for different people and teams in an organization while ensuring the LinkSquares platform plays nicely with existing customer relationship management, enterprise resource planning, and other business systems (e.g., DocuSign, Oracle Sales Cloud, and ServiceNow).


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There’s no shortage of startups developing AI-driven contract creation and management tools, which isn’t surprising — 40% of legal departments have an automated contract management tool, according to an Apptus survey. Others in the $2.9 billion market include Concord, which raised $25 million for its digital contract visualization and collaboration tools last October. That’s not to mention Icertis, which recently snagged $115 million; DocuSign, which invested $15 million in AI contract discovery startup Seal Software; and Evisort, which nabbed $15 million to further develop its solutions.

But Sunak asserts that LinkSquares’ efficiency sets it apart. The company claims the quality assurance process backing its OCR delivers the fastest turnaround time available while its platform cuts down on report generation by 60% overall. Moreover, it has over half a million contracts under management across hundreds of customers, including DraftKings, Wish, Twilio, Asurion, VMWare, and Pendo.

“LinkSquares is a great example of an enterprise AI use case leveraging advances in natural language processing technology to replace tedious and labor-intensive processes with elegant automation. Its world-class team developed a sophisticated AI-powered tool that is impressively accurate, fast, and intuitive,” said Jump Capital partner Saurabh Sharma. “The potential for LinkSquares is huge as in-house counsel and operational leaders begin to leverage LinkSquares to address pain points felt across the organization, from M&A to financing, sales and beyond.”

New investor First Ascent Ventures, MassMutual Ventures, and Hyperplane also participated in this latest round, which brings Boston, Massachusetts-based LinkSquares’ total venture capital raised to $21.4 million.

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