Startup Spotlight #108: Office & Dragons
O&D is building a Transaction Development platform to help lawyers and their clients.
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I got the chance to speak with Sam Smolkin, founder and CEO of Office & Dragons, about what he’s working on at his startup, and any advice he has for emerging entrepreneurs.
Office & Dragon is pioneering Transaction Development: helping lawyers and clients develop bespoke contracts for complex deals efficiently. Document Automation is great for your thousandth NDA but has limited application to bespoke deals with many moving parts. O&D provides a termsheet-like command center for creating and editing contracts, letting you simultaneously update multiple suites of documents, or automatically spin out new documents from previous work. O&D works with any document and continues to work beyond first drafts. The structured data in the “termsheets” is retained beyond the deal, so deal experience captured therein can be applied to future deals.
Smolkin is the founder and CEO of Office & Dragons. He is passionate about applying frameworks and technology to transform lawyers from document craftspeople into deal engineers. Before O&D, Sam was an M&A lawyer at Kirkland & Ellis in London and New York and an avid open-source software developer working on projects in blockchain and Linux.
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Startup Spotlight: Office & Dragons
Problem: Deals like financings, M&A, and IPOs are getting faster and more complex, yet lawyers draft contracts as they did a century ago, leading to toil and confusion, the tension between lawyers and clients on fees, and missing 0s and other mistakes in the contracts. Document Automation doesn’t help, because the deals and the contracts are bespoke.
Market: In the legal sector, our beachhead market, we see a $5B total addressable market, of which $1B is obtainable for O&D. In addition to the lawyers, however, fund managers, bankers, accountants, and consultants all work on deals, and bringing them onto our platform to collaborate and capture data is how we’ll grow beyond legal and into a much larger market.
Solution: O&D provides a termsheet-like command centre for creating and editing contracts, speeding up alignment on deal terms and letting you simultaneously update multiple suites of documents, or automatically spin out new documents from previous work. The structured data in the “termsheets” is retained beyond the deal, so deal experience captured therein can be applied to future deals.
Team: From a team of 1 in January 2020, we’ve grown to 6 people across our go-to-market and product teams, and we’ve been supported by some awesome interns as well.
Recent Success:
Smolkin: Category Design. We used to have a really hard time explaining what our product did. At first, we called O&D a Document Automation app, but we learned that Document Automation has a really specific meaning -- generating first drafts from templates using decision trees and questionnaires. Whereas we spent most of our time talking about the gaps and barriers to adoption associated with those kinds of products, and how our approach to the problem addresses them -- i.e., all the things about O&D which are not Document Automation. You can imagine how a “Document Automation” company (as they call themselves) talking about how their product isn’t Document Automation (as you understand it) would be a confusing conversation for everyone involved.
Investing in the Category Design process (it’s a lot more than just making up a name!) was a real game-changer for us. It forced us to reflect on why we started or joined this company in the first place, nail down the core elements of our value proposition, and develop our key metaphors (like “frameworks” and “3D printing”), all of which allowed us to tell our story, as Transaction Development company, in a way that others could understand. It’s also become our north star for product development, around which our roadmap has taken shape.
Recent Struggle:
Smolkin: Making decisions was my biggest struggle when I first launched O&D. As a lawyer, I was trained to be highly risk-averse. That’s fine for a lawyer, as my job was to analyze each situation in great depth and explain the various considerations and possible outcomes to my clients and leave them to make the decisions. As a CEO, I had to make the decisions, and I found myself facing decision paralysis as I overanalyzed everything and tried to consider every possible outcome.
Coming to grips with the fact that I need to make decisions quickly based on limited data and without the benefit of prior experience was a major roadblock, and I probably lost weeks, if not months, of time due to this. Luckily, necessity has beaten the risk aversion out of me now, we’ve built a great team and collected mentors whose experience we can draw on, and we’ve gotten more clever about how to test assumptions and gather data quickly.
Founder Advice:
Smolkin: How many prospective customers have you talked to? How big is the market for this? “I talked to my friends in the industry and they think it’s a great idea” and “It’s hard to put a number to it, but it’s gotta be huge” are not good answers, especially if you’re about to quit your corporate job and spend your savings to hire engineers (or salespeople, if you’re a technical founder) to try to build (or sell) something you don’t know there’s any market for. The best way to find out is to sell the product before you pay anyone to build or sell it.
That may sound a bit odd, but the vast majority of the sales process doesn’t involve the product -- you should be able to get on a Zoom with the decision-makers at your target customer, identify their pain points and what would solve them, understand their budget for investing in said solution and the decision process for evaluating that investment before you deliver any product to them. If you do that with enough people, you should have a pretty solid idea of whether or not your product is worth building (bad news: it probably isn’t; good news: through these conversations, you’ve discovered something that is!).
Three Cool Founders You Should Know About:
Smolkin: Here are three founders you should check out next!
Tunji Williams, Founder of ShareThing: ShareThing is a mobile-first, peer-to-peer resource-sharing platform, for communities.
Dane Shell, Founder of Valla: Valla is helping the legal industry make legal decisions faster, fairer, and more accurate.
Rafie Faruq, Founder of Genie AI: Genie AI is a research-led machine learning and NLP company, with a mission to give everyone access to the law.
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