Articles by Preston
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7 things I learned about building a business in the Peace Corps
7 things I learned about building a business in the Peace Corps
Imagine getting dropped off at 22 years old in a small village on a volcano in a foreign country. By yourself.
24 Comments -
Going upmarket or downmarket in software is harder than people think
Going upmarket or downmarket in software is harder than people think
Going upmarket or downmarket in software is harder than people think, but the reasons are non obvious. If you’ve…
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How to build a user conference (SaaS edition)
How to build a user conference (SaaS edition)
Before we dive into the topic of building a user conference, let me give you some quick context into why writing this…
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The Rise of the Silent Sales Floor
The Rise of the Silent Sales Floor
With the rise of the sales stack, there is a ton of great activity that can happen without ever picking up the phone…
150 Comments -
Your first SDR job looks like this...
Your first SDR job looks like this...
You know that awkward moment at the end of an interview, where you're asked if you have any questions? Don't let that…
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The Magical SaaS Sales Quadrant
The Magical SaaS Sales Quadrant
So it’s the year of the SDR, huh? If that’s true, then it must also be the year of the Account Executive. After all…
18 Comments -
How to become a (SaaS) VP of Sales
How to become a (SaaS) VP of Sales
This is the only way I know how to do it… Behind every great SaaS success story, there’s a great VP of Sales. From Jim…
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Twitter for Business Owners Who Don't Get Twitter
Twitter for Business Owners Who Don't Get Twitter
In the words of the late Notorious B.I.
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The Lawyer Who Became the King of SaaS
The Lawyer Who Became the King of SaaS
Post originally published via Law Insider (here) From lawyer to tech start-up guru, and the undeniable thought leader…
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Preston Clark reposted thisPreston Clark reposted this𝗩𝗼𝗶𝗰𝗲𝘀 𝗼𝗳 𝗙𝘂𝘁𝘂𝗿𝗲 𝗖𝗼𝗻𝘁𝗿𝗮𝗰𝘁𝘀: Preston Clark As a valued speaker at Future Contracts London 2025, Preston Clark, CEO of SimpleDocs, shared a thought-provoking perspective on what legal teams will expect from legal AI as adoption continues to grow. As Preston highlighted, the challenge is not simply getting AI to respond, but identifying, surfacing, and integrating the right context into legal workflows to deliver greater precision, trust, and adoption. We appreciate Preston sharing these insights with our community and look forward to continuing the conversation this year! Want to be in the room with us at Future Contracts London 2026? 👉 Pre-registration is now open: https://lnkd.in/gKNkyjw4 #FutureContractsLondon #FCLondon #LegalTech #AIinLaw #Contracting
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Preston Clark shared thisA quick Friday story about Law Insider. A couple of years ago, we recognized that our legacy value proposition as a public contract database where lawyers could search and compare clauses would eventually erode with the adoption of AI. The decision to evolve to an AI-first platform may seem obvious now. But as a self-funded company, it carried real risk. Could we convert an audience that trusted us for contract language into one that would trust us for drafting and review? The creation of #SimpleAI and the merging of SimpleDocs and Law Insider were all part of that pursuit: transforming a legacy database business with thousands of subscribers and millions of monthly visitors into an AI-first platform. Today, our identity looks like this: SimpleDocs is our enterprise brand, serving global in-house legal departments at companies including Menzies, Ferrovial and Herbalife, along with hundreds of others. Law Insider serves law firms and individual lawyers with easy-to-use AI drafting and review tools used by thousands of legal professionals around the world, including firms like Vorys and Pierson Ferdinand. And most importantly, we're growing. 100% organically. No outbound sales. No digital advertising. We expect to cross $10 million in ARR within the next few months, driven by a combination of enterprise growth at SimpleDocs and accelerating momentum at Law Insider. The customer message I received earlier this week (below) captures our transformation perfectly. They came to Law Insider to compare clauses. Now they’re using us to draft, review and redline documents. The contract database remains an incredible asset. But its greatest value is no longer simply helping lawyers find language. It’s combining that data with AI to help lawyers put the language to work. This is what the transition from a legacy search database to an AI-first legal platform looks like. Thanks to all of our customers, users, partners, and team members. We're just getting started.
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Preston Clark shared thisVC-backed founders build toward a narrow set of acceptable outcomes. Once you raise enough capital, a good business may no longer be considered a successful one. Profitability is not enough. A modest acquisition is not enough. Sometimes even a strong exit (see Airtable acquisition) is not enough. The company has to produce a return large enough to satisfy the fund economics, the liquidation stack, and the expectations created in the last financing round. That’s how the spoon gets bent so to speak. You lose the ability to: • Sell when the timing is right • Run the company for cash flow • Accept a smaller but life-changing outcome for you and employees • Change direction without protecting an inflated valuation • Build patiently instead of chasing venture-scale growth Venture capital can be an incredible accelerator. But it is not just money. It is a commitment to a specific kind of destination. Founders should understand the exit math before they celebrate the valuation. Right Raymond Blyd ? The best financing strategy is often the one that preserves the greatest number of good outcomes. It’s not always easy but we remain profitable and privately funded at SimpleDocs to preserve this optionality for ourselves, our customers and employees.
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Preston Clark shared thisLegal Tech Investors: “Aren’t you just a wrapper?”… “Why can’t ChatGPT just do this?”… “I bet I can rebuild this in a weekend.”… “Have you heard of MikeOS?”… “What’s your proprietary data moat?”… “Why aren’t you growing like Harvey?” Legal Tech Founders:
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Preston Clark shared thisBrett Trembly and I went to law school together at UM (Go Canes!). Since then, Brett has built Trembly Law Firm into one of Miami’s leading business law firms. He also co-founded Get Staffed Up, a successful legal staffing company serving law firms around the country. Last year, I approached Brett and his partner Elias Correa Menendez to see if the firm could benefit from an AI-powered contract solution. Brett and Elias weren't sure, so we set them up with an extended trial and a few training sessions. To Brett and Elias' pleasant surprise—and our delight—lawyers across the firm started using SimpleAI daily for complex drafting and contract review. I'll tell you, there's something especially gratifying about building a product that becomes indispensable to the work of someone you started your legal career alongside. Thank you, Brett, for your friendship, partnership, and trust in SimpleDocs. And, hey, if we went to law school together and you want an extended free trial, hit me up. Looking at you Sarah Alexander Tayson Gaines Gregory d'Incelli Christopher Lomax Sharlene Gonzalez Kristofor Nelson Tommy Wang Billy Hildbold Jillian Brevorka Alex M. Ramon Trujillo Aaron Blumberg Joycelyn Brown Marco D. Britt Forton Wimbush Seriously! 😎 Law Insider (by SimpleDocs)
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Preston Clark shared thisLinde (Nasdaq: LIN) is one of the world's largest industrial gases and engineering companies, with operations in more than 80 countries, and a workforce of more than 65,000 employees. Supporting a business of that scale means legal and procurement teams must navigate multiple languages, jurisdictions, business units, and contracting standards every day. Building software and systems to support large, global in-house legal teams has become our North Star at SimpleDocs. The future of Legal AI isn't just producing faster draft or redlines. It's helping multinational legal and procurement teams establish consistent standards across regions, languages, and legal systems—while still giving local teams the flexibility they need. We're grateful that Linde selected SimpleDocs to support that vision, and even more grateful for the partnership throughout the evaluation process. The best enterprise products are built alongside customers who push you to solve harder problems. Thank you, Felicitas Forchheim, for your partnership, thoughtful feedback, and trust. We're excited about what we'll build together in the months and years to come. George Homer Jacqueline Mezzetta Jordan Trevino Electra Japonas Law Insider (by SimpleDocs)
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Preston Clark shared thisI never like losing star talent. And we're losing an absolute star today in Dory Lord But Dory is leaving us for the absolute best reason. She's going off to build her own #legaltech startup, CounselPro. Over the past two and a half years, Dory has built the SimpleDocs marketing function into a well oiled machine. From webinars, newsletters, podcasts, conferences, product launches, and just about every major marketing initiative we undertook, she was in the middle of it. She helped us build a growth engine that reaches hundreds of thousands of legal professionals around the world every month. But more importantly, she made our company better. Dory is smart, relentlessly curious, and the kind of teammate every founder hopes to have. Today she's taking that experience into her own startup, CounselPro, an AI platform built for litigators, forensic accountants, investigators, and other professionals who need to analyze financial records, trace transactions, identify patterns, and build stronger cases. As much as I'd selfishly rather keep her on our team, I believe the best companies produce builders. When talented people leave to create something new, that's something worth celebrating. Dory, thank you for everything you built here. I couldn't be more excited to watch what you and Ian O'Brien build at CounselPro. Go follow her journey— and keep an eye on CounselPro. I have a feeling this won't be the last time you hear about it. #legaltech Alex Denne Electra Japonas Ali W. Jordan Trevino
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Preston Clark shared thisHow are transactional lawyers actually using AI in 2026? Today, Law Insider is publishing the first in a series of research reports, beginning with a survey of 534 legal professionals across 75 countries on how they use AI for contract drafting, review, and negotiation. This report benchmarks #ChatGPT, Microsoft #Copilot, #Claude, #Gemini, #SimpleAI, and #Spellbook across usage, trust, workflow integration, and the capabilities lawyers want AI vendors to build next. 🔗 Link to full report in comments. With millions of legal professionals utilizing Law Insider each month and hundreds of thousands subscribing to our newsletters, we have a unique window into how transactional lawyers work. So, what did we learn from this first report? The big story isn't AI adoption. Among lawyers already using AI, 86% use AI on contracts at least weekly, and nearly half use it every day. The real story is what happens after adoption. Key findings from the study: • General-purpose AI tools lead in adoption—but purpose-built Legal AI leads in trust and reliance. (Shout out to our competitors at Spellbook, as well as our own #SimpleAI platform). • Lawyers are looking beyond general AI recommendations and toward AI that understands precedent, playbooks, and organizational knowledge. • Despite widespread use, no AI tool earned "very confident" ratings for output from even 20% of its users-- but purpose-built tools are leading that race by a wide margin. Adoption is high. Usage is high. Trust is a work in progress. That trust gap will become the defining challenge—and opportunity—for the next generation of Legal AI tools. 📖 Download the full report: Link in the comments Law Insider (by SimpleDocs) SimpleDocs Electra Japonas Alex Denne Jordan Trevino Ali W. Mark Pike Dory Lord George Homer Anthropic OpenAI
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Preston Clark shared thisWe asked 534 legal professionals across 75 countries how they're using AI for transactional work. Next Tuesday, we'll publish our findings that benchmark ChatGPT, Microsoft Copilot, Claude, Gemini, SimpleAI, and Spellbook across adoption, trust, reliance, workflow preferences, and more. If you'd like a copy of the 30-page study, please put "Law Insider" into the comments. Shout out to Electra Japonas Alex Denne and Dory Lord for your tireless support in bringing this first edition of Law Insider Studies together. Law Insider (by SimpleDocs) SimpleDocs
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Preston Clark reacted on thisPreston Clark reacted on thisTaking shortcuts with your legal AI prompts is a false economy. Last week I hosted a webinar on PromptMaxxing to show you how to get the most out of your legal AI tools. In case you missed it, you can catch the full webinar on our YouTube channel. #legaltech #legalai #promptmaxxing
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Preston Clark reacted on thisPreston Clark reacted on thisHere's what we covered in last week's webinar on PromptMaxxing for Legal Teams. If you missed it, you can still catch it. Link in comments 👇 #promptmaxxing #legaltech #legalai
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Preston Clark liked thisA quick Friday story about Law Insider. A couple of years ago, we recognized that our legacy value proposition as a public contract database where lawyers could search and compare clauses would eventually erode with the adoption of AI. The decision to evolve to an AI-first platform may seem obvious now. But as a self-funded company, it carried real risk. Could we convert an audience that trusted us for contract language into one that would trust us for drafting and review? The creation of #SimpleAI and the merging of SimpleDocs and Law Insider were all part of that pursuit: transforming a legacy database business with thousands of subscribers and millions of monthly visitors into an AI-first platform. Today, our identity looks like this: SimpleDocs is our enterprise brand, serving global in-house legal departments at companies including Menzies, Ferrovial and Herbalife, along with hundreds of others. Law Insider serves law firms and individual lawyers with easy-to-use AI drafting and review tools used by thousands of legal professionals around the world, including firms like Vorys and Pierson Ferdinand. And most importantly, we're growing. 100% organically. No outbound sales. No digital advertising. We expect to cross $10 million in ARR within the next few months, driven by a combination of enterprise growth at SimpleDocs and accelerating momentum at Law Insider. The customer message I received earlier this week (below) captures our transformation perfectly. They came to Law Insider to compare clauses. Now they’re using us to draft, review and redline documents. The contract database remains an incredible asset. But its greatest value is no longer simply helping lawyers find language. It’s combining that data with AI to help lawyers put the language to work. This is what the transition from a legacy search database to an AI-first legal platform looks like. Thanks to all of our customers, users, partners, and team members. We're just getting started.
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Preston Clark reacted on thisPreston Clark reacted on thisJoin our Playbook Building Masterclass today to learn how to build your own playbooks, whether that’s for the review of third party agreements, mark-ups to your own templates or how to leverage standard playbooks. Registration link in comments 👇 #legalai #playbooks #legaltech
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Preston Clark reacted on thisPreston Clark reacted on thisDay one (for me) done at #ILTACON in Nashville. If anyone is up for a beer, a bite or coffee anytime, just holler. The beer would come in the evening. May look crazy to be throwing out invites on LinkedIn like this, but did so all the time on Twitter, and before that on my blog as there was no social media back then. Met some wonderful people. Maybe get a little press for yourself, to boot, as the International Legal Technology Association (ILTA) has me here on a press pass. ;) Have a great evening.
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Preston Clark reacted on thisPreston Clark reacted on thisGrateful and humbled to be recognized in The National Law Review as a Top 50 Legal Innovator in Academia! At Emory School of Law, our goal has always been to bridge technology and legal doctrine, and more recently, to equip students with practical AI literacy skills. Seeing that work recognized on a national stage is deeply meaningful. Proud to be listed among so many colleagues and friends doing groundbreaking work across the country. Thank you to the selection committee members: Neel Sukhatme, Stefanie Lindquist, Joshua Deahl, Bridget Mary McCormack, Robert Ambrogi, Sara Miro, Evan Shenkman, Pablo Arredondo, Darby Dickerson, Phil Saunders, Andrew Woolf, and Stephanie Goutos. I am deeply grateful for your time, thoughtful evaluation, and commitment to elevating academic innovation. A sincere thank you Wickard and Oliver Roberts for your leadership and support of legal innovation! https://lnkd.in/ePCzdqfv
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Preston Clark reacted on thisAdvantage: YOU! Come see the team if you are in Nashville booth 773... Or ping me and let's volley some thoughts.... Ready to ....serve you. (I mean - its endless....!) Ed Boal Tim Follett Neal Chatrath Karen Tuschak B.A., CHRL Rupinder M. Kari (Lukovics) HughesPreston Clark reacted on thisDay one of #ILTACON2026. Let's do this! See you at booth 773. 🎾
Experience
Education
Volunteer Experience
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Volunteer
Peace Corps
- 2 years 4 months
Poverty Alleviation
I lived and worked in a small village on the volcano of Conchuaga in eastern El Salvador. I focused on building potable water systems and agricultural development. I was also editor of the Peace Corps El Salvador Newsletter.
I continue serving the communities of Conchagua through infrastructure development projects.
Publications
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Spanish
Full professional proficiency
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3 people have recommended Preston
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My Learning Centre
Law firms spend hours creating client-friendly guides — explaining legal procedures, compliance steps, or basic rights. But with AI-generated legal guides, that entire process can now be automated. Tools like Jasper, ChatGPT, and LegalEase AI can analyze statutes, case summaries, and firm expertise to generate easy-to-understand, client-facing guides — customized for practice areas like family law, real estate, or employment. This helps firms educate clients, build trust, and enhance online visibility, all while saving valuable research and writing time. Remember — AI is a productivity enhancer, not a replacement for human expertise. Learning to use these tools wisely is key to transforming and future-proofing your practice. If you found this helpful, like, subscribe, and hit the bell for more AI and legal insights — and click the link below to download your AI Side Hustle Starter Kit and start applying what you’ve learned! 👉 https://cutt.ly/7r5ROKqJ Learn AI Agents Mastery: Build, Automate & Scale Smart Systems That Think for You 👉 https://bcns.link/TzisGT 📘 Prefer to read? Grab the eBook: 👉 https://bcns.link/qUiaC8
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The LegalTech Fund
A lot of litigation tech founders build from the top of the funnel. They focus on intake, automating how law firms bring in new clients. That’s important for high-volume firms, but it’s just the beginning. Here’s what gets overlooked: optimizing case outcomes is what drives a firm’s revenue. It's not enough to make the intake smoother. The firms that win financially are the ones that: Select the right cases Settle them smartly Use their own historical data to drive those decisions And that’s where most tech products fall short. If your product doesn’t touch how a firm gets paid, either by helping them choose better cases or shortening time to settlement, you’re likely solving a workflow problem, not a revenue one. Founders: Before you write a single line of code, ask yourself — how will this change my customer’s financial profile?
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Cleveland Metropolitan Bar Association
The conversation around AI in legal practice continues to evolve. With the release of ABA Formal Opinion 512, technological competence is now recognized as an ethical obligation for attorneys under Model Rule 1.1. CMBA Affiliate Partner Above the Bar Marketing, LLC shares practical guidance on how law firms can responsibly integrate AI into their workflows, covering everything from building custom GPT tools to efficiently capturing institutional knowledge. Legal professionals interested in exploring AI applications in legal practice may find this resource helpful. Read the full blog: https://lnkd.in/gHVmA5S4 #LegalTech #AIinLaw #EthicsInLaw #LawPracticeManagement #LegalInnovation #LawFirms #ClevelandLaw #ProfessionalCompetence #CMBA #AffiliatePartner
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Squary AI
"The legal market is document-heavy — documents in, documents out. AI is perfectly suited for that." Our CEO, Sanjay, shared why we're seeing incredible traction with mid-tier law firms at the Florida Venture Forum. The legal industry is ripe for transformation, and we're leading the charge. Watch the full clip 👇 #LegalTech #AI #FloridaVentureForum #LawFirms #FutureOfLaw
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