Why We Invested in Checkbox

Today, enterprise legal teams are seeing significant growth in the volume and complexity of legal work and requests. Concurrently, most enterprise legal departments have not seen proportional growth in headcount to support this demand.

While most enterprise functions run on purpose-built systems of record, legal teams still rely on email, spreadsheets, and disconnected tools to manage some of the organization’s most critical legal workflows. Requests arrive through multiple channels, are manually triaged, and often get lost in the shuffle. This creates delays, administrative burden, slower business velocity, and a poor experience for both legal teams and their business partners. Despite the myriad of tools available to lawyers today from contract review to drafting, many lawyers spend a disproportionate amount of their time on low value, administrative work.

We’re excited to back Checkbox, an AI-powered service management platform built specifically for corporate legal departments. Checkbox is the AI-first infrastructure that allows enterprise legal departments to streamline, automate, and modernize legal operations.

Checkbox serves as the autonomous legal front door for the enterprise. Checkbox’s AI ingests unstructured legal requests, intelligently routes them, and agentically automates routine work. For legal teams, this means dramatically less time spent on low-value administrative tasks. For the business, it means faster, more consistent access to legal support, improving velocity of closing deals, hiring team members, expanding into new geographies and other key business initiatives. Customers report automating 50-80% of inbound legal work, freeing lawyers to focus on higher-impact matters.

The opportunity here is significant. Corporate legal departments are undergoing a long-overdue digital transformation, particularly within mid-to-large enterprises that have growing legal complexity but limited operational infrastructure. Legal technology spending is increasing rapidly, especially among companies with $1B-$20B in revenue, as general counsels look for durable ways to improve efficiency, scale intelligence, and demonstrate value to leadership.

Checkbox isn’t just solving intake, but building the system of record for legal service delivery. As usage grows, the platform accumulates deep institutional knowledge, improves automation, and unlocks deeper AI-driven capabilities across workflows, matter management, and decision support. Over time, this creates a powerful flywheel where more data leads to better automation and outcomes for both legal teams and the broader business.

Checkbox is seeing tremendous growth in the enterprise, with customers including SAP, Pepsi, Hitachi, Elastic, Analog Devices and more. Behind the product is a team with a deep understanding of legal operations and tremendous hustle that shines through in customer love. Checkbox is building with legal teams, not around them, enabling autonomy without sacrificing AI-driven enterprise-grade functionality.

We’re proud to partner with the Checkbox team as they build the infrastructure that will define the next generation of legal work.

Priya Saiprasad

Co-Founder and General Partner

San Francisco, CA

Priya is a General Partner at Touring Capital.

Priya co-founded Touring after 13 years in venture capital, M&A and enterprise technology. She was most recently a Partner at SoftBank Vision Fund, where she led investments into category-defining software companies including Pixis, Vendr, Observe.ai, CommerceIQ, Sendoso and Skedulo. Previously, Priya was at Mayfield Fund focused on early-growth investments, and a founding member of M12 (Microsoft’s Venture Fund), where she led investments in Go1, Workboard, PandaDoc, Element AI (acquired by ServiceNow), and Bonsai (acquired by Microsoft). Prior to that, she was a Deal Lead in Square’s M&A team leading acquisitions at the intersection of software and machine learning.

Priya was recognized by Forbes in 2018 as part of their 30 under 30 in Venture Capital list. She is actively involved with All Raise, Neythri, and several prominent Women in Tech associations. Priya holds a B.S. in Business Administration from the Haas School of Business at UC Berkeley.

As a kid, Priya moved across 12 different countries before she turned 12 and has since developed a deep appreciation for entrepreneurs who are scrappy, highly adaptable, and voracious learners. In her free time, Priya is a passionate foodie with a penchant for sushi, a reformer Pilates instructor (to combat all the eating), and a proud mom of Gandalf, Katniss & Jax, two furry felines and a quick-witted pup!

Carol Yi

Business Manager, Founding Member

San Francisco, CA

Carol is Business Manager at Touring Capital, where she manages team operations and supports the fund’s general partners.

Prior to joining Touring, she spent 15 years at Microsoft and SoftBank Vision Fund, supporting various business functions and senior executives spanning Engineering, Marketing, Communications, and Venture Capital. Carol is a graduate of Guangdong University of Foreign Studies.

Originally from Guangzhou, China, Carol is fluent in English, Mandarin and Cantonese.

Outside of Touring, Carol enjoys traveling and exploring different cultures. She is a yoga enthusiast, a self-proclaimed Asian food expert and a tea lover.

Lee Feldman

Operating Partner, Founding Member

Miami, FL

Lee is an Operating Partner at Touring Capital, where he leads platform and operational efforts.

Lee joined Touring after spending his career in various technology operating and strategy roles. Prior to Touring, Lee led the thesis-driven investment strategies in emerging technology areas for M12 (Microsoft’s Venture Fund), including autonomous systems, national security technology, MLOps, gaming infrastructure and blockchain. Lee also built a machine learning tool for the fund to bolster data-driven sourcing and diligence strategies. Prior to M12, Lee led strategic initiatives for Corporate Strategy, Core Services Engineering and Operations, and was on the Corporate Strategy & Development team at Microsoft where he developed go-to-market and M&A strategies. Lee is a graduate of University of Michigan where he studied Economics and Entrepreneurship.

In his free time, Lee enjoys spending as much time as he can outdoors, especially with his Husky-Poodle named Uni, and tinkering with tech-enabled human performance. He’s an avid skier, golfer and aspiring tennis player. Lee is also involved in non-profit work, including as an Executive Board Member of Globally.Org, a public-policy organization with a mission to build communities of impact that solve global challenges

Evan Wijaya

Principal, Founding Member

San Francisco, CA

Evan is a Principal at Touring Capital, where he focuses on global software investing.

Prior to Touring, Evan was at SoftBank Vision Fund, where he primarily focused on growth-stage software investing. At SoftBank, Evan invested in companies including Pixis, CommerceIQ, Go1, Fountain, Cloudbeds, Observe.ai, Standard AI, Blockdaemon, Vuori, and Picsart. Before SoftBank, Evan worked in growth equity and investment banking at The Raine Group, a global TMT-focused merchant bank; at Raine, Evan’s investments included Foursquare, Voi Technology, and Robin.io (acq. Rakuten). Evan is a graduate of the Wharton School at the University of Pennsylvania.

Outside of Touring, Evan enjoys surfing around California (although he much prefers the warmer waters of his native Indonesia) and searching for the best street food around the world. Evan spent many of his younger days on the rugby pitch and remains a massive rugby fan.

Samir Kumar

Co-Founder & General Partner

Menlo Park, CA

Samir is a General Partner at Touring Capital.

Before co-founding Touring, Samir was a Managing Partner at M12 (Microsoft’s Venture Fund), where he led investment activities in horizontal / vertical AI, deep tech, and hardware-enabled software companies. Samir’s notable investments include Applied Intuition, Psi Quantum, Wandelbots, Syntiant, D-Matrix, Regrow, and Netradyne. Samir previously held senior product and strategic business development roles at Qualcomm, Samsung, and Microsoft. He developed a strong passion for AI after delving deep into neural networks a decade ago; this ultimately paved his path to becoming a venture investor. Samir is a graduate of Cornell University.

Born in New Delhi and raised in New York, Samir has been inspired throughout his life by the future envisioned in Star Trek. This has been a driving force in shaping his technologist perspective throughout his career, both as an operator and a venture capitalist. At Touring, Samir is excited to partner with entrepreneurs building companies with a strong technical vision and potential to reshape our future.

When not with founders or reading up on the latest research trends in AI and the sciences, Samir enjoys his deep love for electronic music, which he can already see is shared by his 17-month-old daughter! Samir also dabbles in flight simulation and amateur astronomy.

Nagraj Kashyap

Co-Founder & General Partner

San Francisco, CA

Nagraj is a General Partner at Touring Capital.

Nagraj co-founded Touring after a 20+ year career in venture capital. Nagraj previously founded and served as Global Head at M12 (Microsoft’s Venture Fund), was a founding partner and Global Head of Qualcomm Ventures, and most recently a Managing Partner at SoftBank Vision Fund. Nagraj’s notable investments include Zoom, Outreach, Livongo, Kahoot!, Waze, Fitbit, Airvana, Loggi, and Innovaccer. Nagraj is a graduate of the Kellogg School of Management at Northwestern University and the University of Texas, Austin.

Originally from New Delhi, Nagraj is an accidental venture capitalist who has still yet to receive formal training. Nagraj initially began his career as a software engineer, product manager, and management consultant before landing in venture capital in 2003. At Touring, Nagraj looks to partner with entrepreneurs who are highly adaptable, deeply people-oriented and product-obsessed.

Nagraj is active in the academic community, serving on the Advisory Council of the University of Texas Department of Computer Science and the Dean’s Advisory Board at SDSU Fowler College of Business. Nagraj was also formerly a board member of the National Venture Capital Association. In his free time, Nagraj enjoys meticulously planning family vacations (the most recent of which was a three-week long biking trip in the Balearic Islands), road biking, and studying political history.