LinkSquares

LinkSquares

Subscription-based contract lifecycle management platform

Overview

LinkSquares offers a cloud-based contract lifecycle management platform for in-house legal teams. It helps draft, review, and approve contracts in one system using customizable templates and dynamic workflows. The platform also includes legal project management to track tasks and ownership, accessible to both legal and non-legal users. Its goal is to standardize contract operations, shorten cycle times, and scale with a subscription model.

About LinkSquares

Simplify's Rating
Why LinkSquares is rated
B-
Rated B on Competitive Edge
Rated B on Growth Potential
Rated C on Differentiation

Industries

Enterprise Software

Legal

Company Size

201-500

Company Stage

Series C

Total Funding

$161.5M

Headquarters

Boston, Massachusetts

Founded

2015

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Simplify's Take

What believers are saying

  • June 16, 2026 general availability expands LinkSquares' agentic platform to all customers.
  • August 11, 2026 Inc. 5000 recognition confirms growth momentum despite a crowded CLM market.
  • The July 21, 2026 OCR rebuild strengthens data quality, improving downstream AI outputs and renewals.

What critics are saying

  • Docusign launched AI agents and contract review on May 21, 2026, compressing LinkSquares' differentiation window.
  • The April 2026 overtime settlement and pending Caicedo case keep employment exposure visible.
  • If agentic CLM disappoints on accuracy, customers will revert to Docusign or Icertis within 2027.

What makes LinkSquares unique

  • May 2026 rebuilt LinkAI into an all-agentic CLM platform from drafting through execution.
  • July 2026 Smart OCR improves contract text quality for search, extraction, and analytics.
  • 1,200-plus customers and six straight Inc. 5000 appearances signal durable product-market traction.

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Funding

Total Funding

$161.5M

Above

Industry Average

Funded Over

5 Rounds

Series C funding is usually for startups that are doing well and are looking for more money to fuel major growth, such as acquiring other companies, expanding into global markets, or launching new product lines. Investors typically include larger venture capital firms and private equity.
Series C Funding Comparison
Above Average

Industry standards

$50M
$50M
Medium
$62M
SeatGeek
$100M
Oura
$100M
LinkSquares

Benefits

Stock options

Medical and dental plans with flex spending and dependent care

Matching 401k plan

Unlimited vacation

Health & wellness programs

Paid parental leave

Growth & Insights and Company News

Headcount

6 month growth

0%

1 year growth

2%

2 year growth

1%
SalesTech Star
Aug 20th, 2026
LinkSquares names Lyle McCutcheon-Schour SVP of Revenue to drive Agentic CLM growth.

LinkSquares names Lyle McCutcheon-Schour SVP of Revenue to drive Agentic CLM growth. Veteran LinkSquares leader brings a decade of industry experience and revenue growth track record to new role. LinkSquares, the leading Agentic contract lifecycle management (CLM) platform, proudly announces the appointment of Lyle McCutcheon-Schour as Senior Vice President of Revenue. McCutcheon-Schour has spent over a decade at LinkSquares in various customer-facing roles. Most recently, McCutcheon-Schour served as Vice President of Account Management for LinkSquares, where he led significant revenue growth. "Lyle was here at the beginning of LinkSquares and bleeds orange," says Bill Hewitt, CEO of LinkSquares. "Starting as a Business Development Representative ten years ago and rising through the ranks, he brings passion, knowledge, and desire to the job. His leadership will continue to fuel our success as the only fully-Agentic CLM solution available today." LinkSquares' new agentic platform is the first of its kind. Designed to act on contracts by handling repetitive tasks automatically, the LinkSquares platform keeps legal teams in full control of review and strategic decision-making. Agents draft, redline, research and generate communications in minutes, while contract data automatically triggers workflows, tracks obligations and connects insight to execution in a single flow. Non-legal teams can use the platform within legal guardrails, accelerating deal cycles without introducing risk. And with citation-backed research, structured data and built-in governance, organizations can trust every output. "I am thrilled to be stepping into this new role at LinkSquares at such an exciting time in our history," said McCutcheon-Schour. "As employee #1, I've seen how our platform has delivered significant value for our customers, their businesses, and the market. I'm excited to be at the forefront of driving this next phase of strategic growth with such a dedicated and talented team." LinkSquares has recently been named to the Inc. 5000 list of fastest-growing private companies in America for the sixth straight year. This recognition highlights the company's commitment to growth and delivering value to customers.

LinkSquares
Aug 11th, 2026
LinkSquares ranks on the 2026 Inc. 5000 List of America's fastest-growing private companies for 6th straight year.

LinkSquares ranks on the 2026 Inc. 5000 List of America's fastest-growing private companies for 6th straight year. This recognition solidifies LinkSquares' position as a leading performer in one of the economy's most rapidly evolving sectors LinkSquares has been ranked No.2532 on the 2026 Inc. 5000 list, the annual list of the fastest-growing private companies in America. As the leading AI-powered contract lifecycle management platform, LinkSquares earns its place on the Inc. 5000 for the 6th consecutive year. The list is the most prestigious ranking of the nation's most successful independent and entrepreneurial businesses, recognizing companies that have achieved remarkable growth while driving innovation, creating jobs, and shaping the future of the economy. Past honorees include companies such as Microsoft, Meta, Chobani, Oracle, and Patagonia. "Being recognized on the Inc. 5000 for the sixth straight year reflects more than our growth - it reflects the transformation happening across the legal technology market," said Bill Hewitt, CEO of LinkSquares. "Organizations are moving beyond systems that simply manage contracts to AI that actively executes work to deliver business outcomes. At LinkSquares, we're proud to be leading that shift with our all-agentic AI platform. We're grateful to our customers, partners, and employees for making this milestone possible, and we're just getting started." This year's Inc. 5000 recognizes a new class of companies redefining what growth looks like. From AI and advanced manufacturing to healthcare, consumer products, and professional services, these businesses are expanding their impact, creating jobs and proving that entrepreneurial ambition continues to fuel the U.S. economy. Among the 5,000 companies on the list, the median three-year revenue growth rate was 130%, and those companies have collectively added more than 627,208 jobs to the U.S. economy over the past three years. "Every company on the Inc. 5000 has a story of perseverance, smart decision making, and a refusal to sit still," says Mike Hofman, editor-in-chief of Inc. "Their growth reflects more than strong financial performance-it reflects creativity, resilience, and the customer focus required to build companies that make a lasting impact. We congratulate all honorees on this significant achievement." For the full Inc. 5000 list, honoree company profiles, and a searchable database by industry and location, please visit: www.inc.com/inc5000. Inc. 5000 List Methodology Companies on the 2026 Inc. 5000 are ranked according to percentage revenue growth from 2022 to 2025. To qualify, companies must have been founded and generating revenue by March 31, 2022. They must be U.S.-based, privately held, for-profit, and independent - not subsidiaries or divisions of other companies - as of December 31, 2025. (Since then, some on the list may have gone public or been acquired.) The minimum revenue required for 2022 is $100,000; the minimum for 2025 is $2 million. As always, Inc. reserves the right to decline applicants for subjective reasons. About Inc. Inc. is the leading media brand and playbook for the entrepreneurs and business leaders shaping its future. Through its journalism, Inc. aims to inform, educate, and elevate the profile of its community: the risk-takers, the innovators, and the ultra-driven go-getters who are creating the future of business. Inc. is published by Mansueto Ventures LLC, along with fellow leading business publication Fast Company. For more information, visit www.inc.com. Justin McGetrick is a Sr. Marketing Campaign Associate at LinkSquares.

PR Newswire
Jul 21st, 2026
LinkSquares advances Contract Intelligence with rebuilt Smart OCR engine.

LinkSquares advances Contract Intelligence with rebuilt Smart OCR engine. Jul 21, 2026, 11:24 ET Improved document understanding helps organizations turn agreements into reliable business intelligence that supports stronger decisions, relationships, and outcomes BOSTON, July 21, 2026 /PRNewswire/ - LinkSquares, the leading AI-powered contract lifecycle management platform, today announced a rebuilt Smart Optical Character Recognition (OCR) engine designed to strengthen the foundation of Contract Intelligence. Every agreement represents an active business relationship, but organizations can only act on it when the contract is transformed into reliable data. As companies invest more heavily in AI, the quality of the outcome depends on how accurately that technology can read, interpret, and understand the agreements behind the business. LinkSquares rebuilt Smart OCR to produce cleaner, more structured contract text for AI, search, and data extraction. By preserving more of the context, hierarchy, and relationships within complex documents, the new engine helps organizations turn contract data into actionable intelligence, manage commitments, make better decisions, and keep business moving. "Contracts are more than documents. They are the foundation of relationships between businesses," said Andrew Leverone, Chief Product Officer at LinkSquares. "Rebuilding Smart OCR strengthens that foundation enabling more accurate search, more reliable data extraction and more meaningful contract intelligence." The rebuilt Smart OCR engine improves the quality of the contract data that powers LinkSquares' Contract Intelligence. With a clearer understanding of each agreement, organizations can better manage current commitments and relationships, then apply those insights to improve future decisions, workflows, and contract terms. The rebuilt Smart OCR engine is now available as part of the LinkSquares platform. To learn more about LinkSquares Contract Intelligence and its all-agentic AI platform, visit the LinkSquares' website. About LinkSquares LinkSquares is the leading AI-powered contract lifecycle management platform, trusted by more than 1,200 customers, including DraftKings, ProPharma, and TIME. Built on more than a decade of experience partnering with general counsel and legal operations leaders, LinkSquares' all-agentic AI platform sets a new standard for how AI operates across the contract lifecycle. LinkSquares revolutionizes contract management by transforming them from static documents into dynamic, AI-driven business assets - delivering deeper insights and analytics, minimizing organizational risk, unlocking greater efficiency and reliability, and driving more strategic value for teams across the business. SOURCE LinkSquares, Inc.

LinkSquares
Jul 21st, 2026
LinkSquares advances Contract Intelligence with rebuilt Smart OCR engine.

LinkSquares advances Contract Intelligence with rebuilt Smart OCR engine. Improved document understanding helps organizations turn agreements into reliable business intelligence that supports stronger decisions, relationships, and outcomes LinkSquares, the leading AI-powered contract lifecycle management platform, today announced a rebuilt Smart Optical Character Recognition (OCR) engine designed to strengthen the foundation of Contract Intelligence. Every agreement represents an active business relationship, but organizations can only act on it when the contract is transformed into reliable data. As companies invest more heavily in AI, the quality of the outcome depends on how accurately that technology can read, interpret, and understand the agreements behind the business. LinkSquares rebuilt Smart OCR to produce cleaner, more structured contract text for AI, search, and data extraction. By preserving more of the context, hierarchy, and relationships within complex documents, the new engine helps organizations turn contract data into actionable intelligence, manage commitments, make better decisions, and keep business moving. "Contracts are more than documents. They are the foundation of relationships between businesses," said Andrew Leverone, Chief Product Officer at LinkSquares. "Rebuilding Smart OCR strengthens that foundation enabling more accurate search, more reliable data extraction and more meaningful contract intelligence." The rebuilt Smart OCR engine improves the quality of the contract data that powers LinkSquares' Contract Intelligence. With a clearer understanding of each agreement, organizations can better manage current commitments and relationships, then apply those insights to improve future decisions, workflows, and contract terms. The rebuilt Smart OCR engine is now available as part of the LinkSquares platform. To learn more about LinkSquares Contract Intelligence and its all-agentic AI platform, visit the LinkSquares' website.

PR Newswire
Jun 25th, 2026
LinkSquares wins Decision Management Solution of the Year with all-agentic CLM platform

LinkSquares, an AI-powered contract lifecycle management platform, has won the "Decision Management Solution of the Year" award in the 9th annual AI Breakthrough Awards programme. The recognition follows the launch of its all-agentic CLM platform, the industry's first system transforming contracts from static records into dynamic execution systems. Powered by LinkAI, the platform uses proprietary predictive and generative AI models trained on millions of legal contracts to analyse and extract metadata from thousands of agreements simultaneously. The AI agents automate workflows across the contract lifecycle, enabling organisations to streamline reviews, accelerate negotiations and identify risks whilst reducing manual effort. LinkSquares serves over 1,200 customers including DraftKings and TIME. The AI Breakthrough Awards received thousands of nominations from more than 20 countries this year.

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