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Marks Baughan Advises Spellbook on its $50M Series B Financing led by Khosla Ventures

Spellbook, often described as “Cursor for contracts,” today announced a $50 million…

Spellbook, often described as “Cursor for contracts,” today announced a $50 million USD Series B funding round led by Keith Rabois, Managing Director at Khosla Ventures, with participation from Threshold Ventures, and existing investors Inovia Capital, Bling Capital, Moxxie Ventures, Path Ventures and Jean-Michel Lemieux. The capital raise values the company at $350 million post-money and brings total funding to over $80 million.

The investment comes as Spellbook surpasses 10 million contacts reviewed on its platform, with customers including Nestlé, eBay, and Kennedys, among others. On pace to triple its revenue this year, Spellbook has emerged as the leading AI solution for transactional lawyers, serving nearly 4,000 law firms and in-house legal teams across 80 countries – more customers than any comparable AI contract review product.

“We’re at the spreadsheet moment for lawyers,” said Scott Stevenson, CEO and co-founder of Spellbook. “Just as spreadsheets transformed accounting, large language models are transforming law after 20 years of technological stagnation. With $30 trillion running through contracts annually in the U.S. alone, even small efficiency gains create massive value. This funding accelerates our mission to make contracts move at the speed of commerce.”

The new capital will fuel Spellbook’s expansion beyond contract review into the full scope of transactional work, scale go-to-market teams to capture more of the $1 trillion transactional legal services market, and enhance AI capabilities with deeper contract intelligence grounded in realtime market data.

“Spellbook is using technology to make law faster, better, and more transparent,” said Keith Rabois, Managing Director of Khosla Ventures, who will join Spellbook’s board of directors. “It’s the Shopify and Square democratization story for lawyers.”

AI That Lawyers Actually Use

Unlike competitors that require multi-month enterprise rollouts, Spellbook is like Cursor for contracts: it works instantly within existing workflows – right in Microsoft Word.

“We think Cursor has been so successful because it’s like an electric bicycle for engineers. They already had a bicycle – with Cursor they are still pedalling and still steering, but they can get up hills much faster, said Stevenson. “We have the same philosophy at Spellbook. We don’t require lawyers to totally change how they work, or to give up control. We just help them ascend hills faster.”

AI Grounded in Realtime Data

Lawyers are frustrated by the contract review outputs they get from other AI tools. In order to win negotiations, they need positions that are grounded in data that they can cite, not so-called “AI slop.”

With this latest funding, Spellbook will continue to build out the most data-driven contract review tool available, providing relevant and substantive suggestions grounded in realtime market data, lawyer preferences and deal history.

The company has already begun rolling out features toward this vision, releasing Market Comparison and Preference Learning in beta, with plans to extend availability in coming months. It’s continuing to invest in Spellbook Associate, the first AI agent that can handle multi-document transactional drafting.

Marks Baughan Securities LLC served as exclusive financial advisor to Spellbook.

About Marks Baughan Securities

Marks Baughan provides investment banking services to growth companies. Our clients are software, technology-enabled services and data-intensive companies seeking shareholder liquidity or growth capital. We work tirelessly alongside our clients and excel at defensible positioning and disciplined processes that maximize shareholder value. Our professionals come from senior positions at bulge-bracket firms, giving our clients access to the relationships and experience that come from our years of interaction with the top executives and investors in companies in our fields. Our clients receive top-flight advice throughout any advisory relationship, because our boutique approach allows our senior advisors to stay deeply involved with each client on a continuous basis. No handoffs to junior staff. No preferential client relationships. No conflicts of interest.

For more information on Marks Baughan, see www.marksbaughan.com.

About Spellbook

Spellbook launched the first GenAI tool for lawyers in 2022 and continues to be the leading provider of legal AI for transactional law. It’s helped nearly 4,000 legal teams improve their contract workflows and eliminate legal drudgery. Powered by large language models like OpenAI’s GPT-5, Spellbook is optimized to use legal-specific approaches for superior contracting performance. Spellbook is backed by investors including Khosla Ventures, Thomson Reuters Ventures, Inovia Capital, The Legaltech Fund, Bling Capital, and Moxxie Ventures. For more information about Spellbook go to https://www.spellbook.legal/.

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What Do Legal Tech Startups Need to Know Before Raising Capital? (A Banker’s Perspective)

Legal tech companies raised $1.83 billion in the first quarter of 2025…

Legal tech companies raised $1.83 billion in the first quarter of 2025 — an 80% year-over-year increase.1 It’s a good time to be a founder or CEO of a growth-stage legal tech company as the market sees continued momentum. Innovation is high, and investor interest is higher — ushering many startup founders into financing rounds at a gallop.

Whether a transaction is on your immediate horizon or in the planning stages, it’s critical to avoid common mistakes and keep a few must-dos in mind if you want to make the smartest pre-financing moves. As an investment bank with a finger on the pulse of the legal tech market, Marks Baughan has a tried-and-true set of tips and tricks for companies at this critical juncture. Here’s what seasoned bankers want legal tech CEOs to understand before they raise a dollar.

Avoid these pre-financing missteps

In our 25+ years of experience working with legal tech companies, we’ve seen these all-too-common sentiments hinder founders from making the right moves before raising capital.

“It’s too soon for my business to engage a banker.”
Many founders believe a couple of months or so is enough time to get a banker to help them launch a financing process. While eight weeks isn’t a rush per se, it’s better to spend more time developing a stronger degree of comfort with your future advisor and collaborating with them to hone the full — sometimes nuanced — picture of your story and value. A good banker will sink their teeth into your data and grasp your financial model in short order, but a great banker will become your advisor who understands the deeper details, advocates for your business, and functions as an extension of your team. The more time you invest in developing your banker relationship, the more seamless and efficient the process will be when it comes time for you to transact.

Furthermore, should you discover that your data isn’t up to snuff or requires some revamping, you’ll need time to work with your banker to get it investor-ready. The due diligence process for these transactions can be grueling — and will be all the more so if an investor finds that your data doesn’t hang together. With this risk in mind, there is no “too soon” moment to begin working with a banker. The sooner you get your data in order — and instill processes to keep it in order — the better prepared you’ll be for raising capital and reporting on your business the way investors want to see it done. Founders that start this process months, or even years, in advance lose no time when it comes to launching fundraising efforts.

“I’ve done this before, and I can do it on my own again.”
DIY-ing may be a fine approach for earlier or smaller fundraising rounds, but for more significant rounds, it’s a full-time job to do it right. The goal is to get a maximum market check with minimum executive bandwidth commitment, and the more positive response you receive from your outreach, the more difficulty you’ll have keeping your ducks in a row and addressing that demand.

Pro tip: even if you’re embarking on an early or small round, get a banker to sanity-check your presentation. A banker worth their salt will do so for “free” — viewing it as an investment into building the relationship with you.

“I know how to get the best deal for my business out of this transaction.”
Going without a banker also means you miss the creative, out-of-the-box thinking they provide and the market intel they have about what investors find exciting. As the CEO, you may be focused on the transaction at hand, but you may lack the time and brain space to contemplate a bigger-picture approach that earns you more down the line.

A banker has the know-how and market intel to see and propose more options such as acquiring a competitor, exploring an adjacent technology, or pursuing a complementary platform that may be for sale. By taking different creative steps ahead of the next round, you could potentially raise more at a synergized valuation and give your company a bigger market profile — all while adding real value to your offerings. CEOs who tackle transactions singularly may miss what a banker sees: the opportunity to upsize a financing round.

What financial sponsors really care about

Every financial sponsor, whether it be a private equity or venture capital firm, wants to see proof of growth and a large total addressable market (TAM) — these are table stakes. Beyond these basics, they prioritize similar-but-different elements.

How Investment Criteria Differ Between Venture Capital and Private Equity

Private equity firms look at larger, somewhat scaled platforms to identify opportunities for more growth. They also look ahead — almost from day one — to begin positioning the platform for the next buyer. For these reasons, future exit strategy is of greater consideration when positioning your company’s value to private equity investors. It’s never too early to start thinking about your approach to these funds. A banker gives you a strategy framework, and potentially actionable targets, that will resonate with private equity investors.

Private equity firms are also looking for concrete, defensible projections. They aren’t interested in seeing the so-called “BHAG” (Big Hairy Audacious Goal) financial models that often resonate with venture capital investors. Your models need to strike the proper balance between prudently aggressive, attainable, and substantiated. Sometimes it’s even strategically advantageous to “sandbag” your growth projections so you’re outperforming during critical negotiation stages of the transaction. The right banker helps you achieve this balance and design your model to speak to this audience.

Venture capital investors, on the other hand, tend to focus entirely on the “organic” aspects of the investment — product-market fit, the ability to scale and build an organic go-to-market machine, and more. They want to understand the BHAG and are more accustomed to lofty projections that reflect your fundamental mission in a broader way and usually over a longer horizon or hold period. But don’t discount the value of communicating a longer-term M&A strategy with these investors. It’s still critical to demonstrate that you are thinking about M&A and have it in your roadmap. This is where a banker helps you augment your positioning to make it clear that you have strategic options on your radar.

Your pre-transaction checklist

If you’re looking ahead to a financing process, consider these your five must-dos:

  • Cleanse your data: Ensuring your data — especially your customer queue — is clean and ready for investor scrutiny is non-negotiable. Doing so ultimately requires your organization to adopt an internal discipline to be able to report certain metrics in an auditable fashion.
  • Know your metrics: Familiarize yourself with the key metrics your investors care about so you can present them with confidence and in formats those investors expect.
  • Start developing sponsor-ready reporting: Once you’ve cleansed your data and internalized important numbers, you can create reports fit for the eyes of your financial sponsors. Developing board reporting and dashboarding sooner rather than later gives you a leg up.
  • Build a bulletproof transaction model: Investors don’t want “finger-in-the-air” projections; they want financial models grounded in reality. Be prepared to present a thoughtfully constructed model built from credible, defensible core assumptions — especially for private equity investors
  • Develop the right investor relationships early: It can be tricky for founders to detect which potential investors are just kicking the tires and which are serious. Your banker should act as your investor relations firm — triaging the interest in your company, honing high-potential opportunities, and weeding out false overtures.

The banker advantage: guardrails, guidance, and deal certainty

These five must-dos are part of a broader strategy founders should apply to any transaction process. Savvy founder CEOs realize that the full scope and intensity of work required to run a highly competitive transaction process is too great to take on alone. Having a banker at your side is a win-win; you’ll get further price discovery and maintain the bandwidth to run your business while closing a successful transaction.

You’ll also get a bad cop to your good cop at the negotiating table. A banker like Marks Baughan provides the guardrails for the discussions — strategically deciding when to give over certain information and when to withhold it. They act as an advocate for your company, ensuring the transaction is completely de-risked and has maximum certainty and clarity to close.

Marks Baughan is experienced in helping growth-stage legal tech companies scale toward greater valuations and bigger transactions. We widen the lens for CEOs — enabling you to tell a more powerful growth story and set a trajectory for significant financing in years to come. We leverage our unique market intel in the legal tech space to guide both your immediate transaction and your roadmap for long-term value and opportunities. Learn more about our services and team on our website, or get in touch with us here.

Sources:

  1. 1 Legal tech sees 80% funding surge amid AI boom – Law360 Pulse. (n.d.). https://www.law360.com/pulse/articles/2321847/legal-tech-sees-80-funding-surge-amid-ai-boom
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How to Achieve a Premium Valuation in Legal and Compliance Technology

You’ve built a strong company in the legal and compliance technology space.…

You’ve built a strong company in the legal and compliance technology space. You have product-market fit, great traction and momentum, and your metrics tick all the boxes.

You see strategics and sponsors pouring into this large, dynamic space. They’re looking for a company like yours that sits at the intersection of legal and regulatory,  corporate governance, and digital transformation. They’re looking for their next growth engine.

It’s not enough to just capture their attention. To hold it and position your organization for a premium multiple requires a special blend of storytelling, number-crunching, market knowledge, negotiating finesse, and creativity. With the right banker, you’ll have all that — and more — in your arsenal. Here’s what you need to command a premium valuation in the legal and compliance tech sphere.

A Narrative That Drives Strategic Impact

You have to do more than present your revenue and growth metrics; you need to tell a sophisticated, credible story that resonates with your specific buyer.

Tailor your narrative to answer four key questions that buyers are asking — and that help drive premium valuations:

  1. How does your platform uniquely address the product and solution gaps that strategic acquirers are desperate to fill? Where’s the whitespace—geographically, functionally, and by end-market—that your solution fills?
  2. What are the near-term or incremental growth initiatives that will accelerate your organic growth? The goal is to position the upside and ROI for these initiatives  and show the operating leverage that will emerge from them.
  3. What is the platform potential for financial sponsors? Private equity funds looking to stake a claim in this market don’t just want a standalone asset. They need a “string of pearls” roadmap for future M&A. They need to know your business can serve as the cornerstone for bolt-on acquisitions that deploy more capital efficiently and accelerate their return horizon.
  4. What emerging trends and buying behaviors are shaping the space? Your banker should understand the pain points of corporate legal departments and compliance officers to help you craft a narrative that explains how regulation is creating tailwinds and why product integration is driving consolidation.

Developing a story that subtly yet clearly answers these questions is a tall order for any CEO, which is where your banker comes in. Some investment banks might run an auction and slap some comps on a slide, but ones with deep expertise in the legal and compliance tech fields know how to communicate the explicit value of your organization to a buyer in more than just numbers. 

As the most active banker globally focused in legal and compliance tech, Marks Baughan has perfected this approach. Our multi-decade track record of obtaining premium valuations for our clients includes landmark transactions with the leading SaaS, workflow, content, and AI players in the sector.

Market Fluency to Navigate Nuances

The legal and compliance solutions sector is no sleepy backwater; it is a massive and accelerating market shaped by complexity and specialization. Each subsegment requires fluency and a granular understanding of competitive dynamics.

Generalist bankers simply can’t bring this knowledge to the table. Only dealmakers who are steeped in this market can offer specialized expertise and experience in:

  • The nuanced motivations of corporate, strategic buyers like Thomson Reuters, Litera, Onit, Mitratech, and Wolters Kluwer.
  • The ambitions of major private equity funds eager to enter the space but lacking either the initial platform or a clear acquisition roadmap.
  • The global competitive landscapes where emerging players, vertical solutions, and geographic differences all matter.
  • The potential bluebird buyers. Strategics from adjacent — or even seemingly unrelated — sectors may have interest in entering your subsegment or have gaps you may fill.

This type of sector intimacy is unique to Marks Baughan whose bankers have 20+ years of dedicated coverage in these markets under their belts. In fact, Marks Baughan has completed three times as many deals in this space as our nearest competitor. Our bankers’ prowess and expertise translate directly into superior positioning that drives premium valuations for our clients. After all, buyers pay more when they believe they are buying not just a business but a position of strength and future potential.

Creative Transaction Ideas to Open up Opportunities

One of the most valuable — yet least-appreciated — advantages of working with a specialist investment bank is your access to a treasure trove of unique potential transaction ideas.

These bankers don’t just show up for the marquee deal. They’re continuously engaged with companies across the entire spectrum of legal and compliance tech to hone strategic intel that supports out-of-the-box thinking during a transaction.

For example, when a private equity firm is looking to build a platform investment, an investment bank like Marks Baughan doesn’t just identify a flagship asset. We quickly map out dozens of smaller, actionable bolt-on acquisitions that allow a buyer to deploy additional capital, accelerate scale, and create multiple arbitrage opportunities that can generate massive value and accelerate return horizons.

We help you create more value to drive a higher premium by assembling smaller, strategic pieces — put together using our deep sector knowledge.

The Bottom Line About Your Banker

Choose a banker that not only ensures your company is expertly positioned for a premium valuation but runs your entire process with precision — from the opening kick-off call to the closing wire and beyond.

Why? Because high-valuation exits in legal and compliance technology don’t just happen. They’re engineered by bankers who understand the sector’s complexities, maintain relationships with all the right buyers, and position your business as the must-have platform that fits perfectly into a buyer’s strategic puzzle or a private equity sponsor’s platform vision. 

As the leading advisor and investment bank in legal and compliance, Marks Baughan is embedded in this market’s ecosystem. We bring insight, creativity, and connectivity that are nonpareil to global transactions. Learn more about our work here.

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