The contract lifecycle management (CLM) industry has undergone a total transformation over the past decade. A sector that was previously defined by clunky spreadsheets, thousands of physical files, and regimented, unwavering processes have only just begun their reinvention with the introduction of smarter, faster, leaner technology. Contract management capabilities have soared to new heights with the advent of AI. 

But as exciting as these innovations are, apprehension is natural. AI is flashy and new, but its inner workings aren’t necessarily intuitive and its legal future is still being defined. And this can make it difficult to move forward while also protecting organizations. 

Trepidation is historically par for the course — and in general, a wise decision. Benefit-of-doubt is not easy to come by when your objective is to protect an organization. Most organizations are not early adopters of any given product or innovation, and the majority fall between early and late majority categories, otherwise known as pragmatists and conservatives. When we look at the rise of intranet or ecommerce or AI-powered solutions, the data is consistent: only around 15% of companies account for the groups who are ahead of the adoption curve. The rest need a bit more time, data, or proof of tangible value before they feel ready to make the big switch. 

Discernment is crucial to helping companies succeed. We also know that, when it comes to AI, this technology doesn’t seem to be going anywhere. AI’s initial rough edges are already smoothing, it’s continuously getting smarter, and teams who have adopted it are becoming more efficient – and more dependent. 

As you evaluate your CLM strategy and the tools that support it, consider what you’re missing out on without an AI-powered component. And not just any AI, but rather one that was specially designed to simplify and streamline contract management. If missed renewals, constant bottlenecks, manual search, or disjointed processes are challenges for your team, you’re already paying the price in lost time, savings, and opportunities. The good news is, you don’t have to start all over. You just need one great CLM platform to centralize and optimize everything.  

In this eBook, we’ll cover the ins and outs of using an AI-powered CLM tool, the problems it solves(along with the repercussions of ignoring these problems), how you can turn AI from a question mark into your team’s competitive advantage, and where to start building trust.

The Never-Ending Grind of Manual Contracts

There’s a certain kind of fatigue that only contract people grasp: the bleary-eyed, double-vision stare at your third screen at 11:47 PM, where a single missing clause could turn into seven-figure regret. 

If the tools don’t evolve, the workload never ebbs. Every quarter brings new pressure: faster approvals, tighter audits, deeper visibility. But the response is still copy, paste, double-triple-check, stress out, and repeat.

Our 2020 survey, The Current State of Contract Management, demonstrated just how tedious and time-consuming outdated contract management processes can be:

• 40% spent 41+ hours per week on contract creation tasks.
• 53% reported that their teams spend the equivalent of half a day (1-5 hours) per week on the signature process. 
• 61% spent 2-20 minutes to locate a given contract 
• 49% used Excel spreadsheets to track and analyze specific contract terms, spending the hour equivalent of an afternoon conducting analyses in Excel 

While this thoroughness and attention to detail are appreciated — failure to scrutinize has a hefty associated cost  — they haven’t exactly helped legal streamline their processes. With outdated or manual workflows in place, legal remains in productivity purgatory. 

Meanwhile, sales wants to close, finance needs to reconcile, security seeks indemnification, and everyone wants to know what’s taking so long. 

With the rise and advancement of AI-driven contract management software, legal teams can lighten their workloads and speed up processes, all while retaining critical levels of accuracy. Despite the ever-growing landscape of possibilities, red tape and resistance to change have kept legal teams everywhere shackled to traditional contract review and storage methods and time-consuming manual workflows.

The manual process devil you know is better than the automated devil you don’t. But shying away from innovation and acceleration still comes at a cost — one that compounds the longer you wait. 

The Cost of Doing Nothing

Even in a profession rooted in tradition, “this is how we’ve always done things” is almost never a good reason to shirk innovation. But inaction can come at a major detriment when considering a CLM. 

There’s a growing amount of evidence to support this idea. In fact, according to the latest from PwC, top-performing organizations are now shifting from AI “use cases” to AI as a business strategy. This approach has begun permeating the contract management space, and it’s not exactly shocking, considering that Deloitte’s benchmarks now suggest an average of 26% of an organization’s workflow now touches contracts throughout the contracting process. We’ve outlined three major ways delaying AI adoption can damage your organization: 

#1: Wasted Time

Every touchpoint presents a new bottleneck to account for. Using spreadsheets and manual search may only add a few minutes to each edit or review, but over time, those precious minutes compound into hours or even days of your fiscal year. With too many cooks in the contract kitchen, things can get overly-complicated. Every delay, every pending approval, every file access request gathering dust in someone’s inbox is lost momentum that teams unfortunately can never get back. When you factor in time-sensitive deals, the lost revenue continues to build.

Legal teams are running out of breathing room and billable hours.

#2: Quality Assurance

The more people go clicking around through your contracts, the higher the chances of human error:  typos, skipped clauses, and the risk incurred when your CLM is entirely manual begins to creep up in a big way. When people are reviewing potentially hundreds of pages of legalese each week, accountability for accuracy can take a backseat to hitting a deadline. Many people looped into the contract management process aren’t legal experts, were never trained to use the tools, or are too busy (maybe even embarrassed) to ask questions. It’s a recipe for noncompliance disaster.

#3 Falling Behind 

Here’s the reality: Your competitors are testing AI right now. Not next quarter, or even year. Yesterday. And their legal teams are making strides.

But just because they used it first doesn’t mean you can’t use it better. One good thing about AI-powered CLMs? If you choose the right one, you can get up and running in no time. The ROI of taking a few weeks to get the hang of things is well worth your time, especially compared to what you risk when you stick with antiquated solutions and end up lagging behind the competition. 

Chances are, most organizations are aware of all these risks and choose to delay or refuse AI adoption anyway. Why? When we consider that 39% of U.S. employees use AI to consolidate information or data and to automate basic tasks, it seems like an obvious choice to optimize the most common functions of our jobs.

A Skeptic’s Guide to AI-Powered CLMs

We hate to be the bearers of bad news, but the truth is that a lot of CLM solutions out there won’t exactly be upfront about some of these features, or decided lack thereof. Buyer beware: Without asking the right questions, you might end up with the wrong software. You don’t want that, and neither do we, so we’ve compiled a checklist to help you do your due diligence as a contract management customer and figure out which options are actually worth your time, money, and above all, trust.

What to look for:

• A user-friendly interface that’s clear, intuitive, and can be tailored to each team or user’s needs
• Customizable, smart analytics that can display information relevant to your company’s unique goals and KPIs
• Risk detection capabilities that reduce exposure to non-compliance, helping you avoid costly penalties, legal setbacks, and a damaged reputation

What to ask:

• “How does your platform keep user data safe and secure?”
• “Which compliance certifications is your organization verified with?”
• “Is your AI trained on rules and regulations specific to [your industry]?”

What to research:

• Public opinion: Look for tools from vendors with a history of successful deployments, strong case studies, and positive third-party reviews. 
• Bias detection and mitigation: A trustworthy CLM should regularly audit their models for bias and take the appropriate corrective steps.
• Human-in-the-loop (HITL): Reputable solutions are designed to support human legal professionals, not replace them. For example, the AI should always flag clauses for human review rather than making final judgments on its own.

What Trustworthy AI Actually Looks Like

Not everyone is privy to the above checklist, so the larger cultural embrace of this modern marvel has left some staunch reservations in its wake. And we get it, considering a number of current AI solutions out there don’t deserve that trust. Because if the tool was trained on performative LinkedIn posts, legal blogs, and Wikipedia articles, it probably won’t be smart enough to give you the context or the confidence you need.  

So we built ours differently than the rest.

We know firsthand that trust needs to be earned, particularly with legal teams. The risk of incomplete outputs, privacy, and uncertain decision-making is too great to incorporate a software that doesn’t leave your team feeling 100% confident in its abilities. Compliance, audit, and financial teams need to be able to verify their accuracy, and leadership’s role in the contract management process requires crystal clear visibility. All of this was top of mind when the team at LinkSquares set to work on creating AI-driven CLM that provided ROI across every vertical, and we’re proud to have set the standard.

Trustworthy CLM should look like: 

• Trained on real legal agreements. Not scraped keyword-laden blog posts or fantasy contracts from open-source graveyards. Real deal contracts that lived, breathed, and got signed.
• Clause-level intelligence. It understands nuance and context, and why failing to provide both could cause serious problems.
• Transparency you can audit. No black boxes or mystery logic. Every result has a paper trail and every suggestion has a reason.
• Built for your pace that’s actually sustainable. It doesn’t try to replace you. It just makes you faster, clearer, and better than ever.
• Built-in controls. You stay in the loop, ahead of the chaos, and capable of pulling the plug if something feels off.
• Prioritized privacy & security. You should feel like you’re in safe hands on a platform that prioritizes end-to-end privacy & security, protecting what matters most to you: your data. 

With LinkAI, you’re not ceding control — you’re gaining a co-pilot.

Our all-in-one CLM platform can eliminate friction across every stage of the contract lifecycle, from drafting and review to approval, signature, and beyond. And when it comes to intelligence, know that AI isn’t some new add-on feature at LinkSquares. It’s in our DNA. From day one, we engineered our platform with artificial intelligence in mind for the sole purpose of making legal work faster, smarter, and more confident. While competitors scramble to bolt AI onto legacy systems, we’ve spent years training our AI-powered platform, LinkAI, on millions of real legal contracts. The result? A system that doesn’t just keep pace with your work. It anticipates, accelerates, and elevates it — all while you maintain the level of visibility and security your organization requires.

Introducing Your New Legal Partner: LinkAI

Meet a machine that actually knows what you’re looking for and why it matters if you miss it.

If generic AI is like asking a stranger for directions, LinkAI is like working with a guide who’s walked your exact route hundreds of times. It knows the shortcuts, the roadblocks, and the best way to get you where you need to go. You can immediately tell the difference, because LinkAI wasn’t trained on random PDFs or synthetically-generated legal jargon. It was trained on real contracts. Thousands of them. The good, the bad, and the redlined. And unlike most tools, it shows its work.

How LinkAI Works

In a world where a new AI-driven platform is launched nearly every day, it’s important to remember: not all CLM platforms are created equally. Like humans, Jack-of-all-trades generative AI (like ChapGPT and Gemini) have too broad of a database for legal-specific tasks. They can be a fabulous place to start, but not a strong enough solution to store and review thousands of contracts when they are also considering the rest of the internet simultaneously. That’s why LinkAI was built intentionally, methodically, and with one express purpose: to optimize the existing CLM experience. Here’s how it earns the right to become part of your process:

• Purpose-built for contracts: LinkAI doesn’t have to guess what a liability cap is. It’s seen thousands of them.
• Thinks like a lawyer, but moves like a machine: Risk scoring. Clause tagging. Metadata extraction. LinkAI can do all this and more in minutes, not hours-long meetings. So your team can focus on what moves the needle while maintaining compliance.
• Post-signature alerts: Because you never know what might happen, even after digital signatures are submitted.
• Audit-ready by default: No retroactive justifications. Just a breadcrumb trail clean enough for Legal Ops, Finance, and whoever’s buying you next.
• No black boxes or uncertainty: You can click into every recommendation, see the logic, and decide for yourself because your team is the real expert, LinkSquares is just here to help.

Where LinkAI Strikes the Balance

The best CLMs were made to be functional, not frilly. We’ve all seen what happens when tech overpromises and under-explains. Or even worse, when the AI gets a little too “smart” for its own good and starts making things even more complicated than they were before.

With trust (and an unbeatable user experience) in mind when developing Link AI, our developers made sure that legal teams and beyond would always feel supported, not superseded, by the tool’s functionalities. 

So, here’s what LinkAI doesn’t do:

• It doesn’t override your judgment.
• It never files or makes changes to an agreement without your approval.
• It doesn't rely on live contracts to adapt, ensuring it maintains consistency with your risk profile.

We’re passionate about this technology, but we’re also strong believers in nuance, collaboration, and critical thinking. We created LinkAI to make people’s jobs easier, but never redundant. Like a suped-up sportscar, it can only cross the finish line with a skilled driver behind the wheel.

Who LinkAI Helps

We may have designed LinkAI with legal in mind, but its capabilities were actually created to help the entire organization. If a person or department needs to access a contract in any way, at any stage, LinkAI can help improve the process, period.

• Legal: Automates reviews, redlines, and risk assessments while preserving full, human-powered oversight. Nothing gets signed off on until the right person says so. 
• Finance: Provides easy visibility into obligations, value, and spend. Know what’s owed, what’s committed, and where the risks live, making audit season a lot less chaotic.
• Procurement: Ensures compliance language is embedded from the first draft. No more clean-up at the end of the process.
• IT & Security: Add an armored layer to your risk mitigation strategy. LinkSquares AI is built securely, with privacy-first design and data governance at every layer.

FAQs

We know that legal experts want proof, not promises. And if you haven’t implemented AI into your CLM process, you may have some concerns. Here’s what to expect from LinkAI:

“Will it make decisions for me?”

No. It just makes them visible. Your team decides, always.

“Is my data secure?”

Yes. More secure than your inbox, and with better version control than your DMS.

“Do I have to throw away what I already use?”

No. With 12 integrations (and counting), LinkAI plugs into your workflow like it’s been waiting there all along.

Pro tip: If you’re looking for a custom integration to a platform your team leverages, LinkSquares has you covered with the help of our API and Tech Services team.

“Will I need a certification to use it?”

No. We know lawyers don’t have that kind of time on their hands. While we offer robust onboarding resources, most companies are up and running in less than 90 days.

Sure, generic AI can skim the surface of a contract. But LinkAI goes deeper. By learning from real legal work, it understands what each clause means for your business and your risk profile. It’s scalable, ultra-secure, and slots in easily to your existing CLM practices. Best of all, it has the kind of rich understanding that can only come from experience.

Teams that Made the Leap

Since 2015, legal teams have been using LinkSquares to speed up their contracting process, uncover insights in their contracts, and collaborate with other teams. Since then, our platform has only expanded, offering powerful analytics, risk reduction, and streamlined contract approvals to over 1,000 customers worldwide. 

Still not sure if LinkAI can do what your team needs it to? Here are some firsthand accounts of what happens when companies changed their CLM strategy from complacently inefficient to powerfully effective. 

Omnitrax: Cutting Compliance Workflows from Hours to Minutes

OmniTRAX, a leading rail and transportation company, needed to replace manual compliance tracking and contract management under a six-week deadline. LinkSquares’ AI-powered platform centralized thousands of contracts, automated compliance, and streamlined drafting with Salesforce integration.

• Built 40+ templates enabling contracts in as little as five minutes
• Integrated with Salesforce for seamless initiation and approvals
• Accessed compliance and reporting data in seconds

“Now I can get what I need in seconds. The system is easy to use and everything’s at my fingertips.”

—Jennifer Presnall, Senior Director of Internal Controls, OmniTRAX

TIME Magazine: From Fragmented Tools to Data-Driven Alignment

TIME had a contract management crisis with over 130 agreements per month and no visibility, control, or audit trail. LinkAI unified drafting, approvals, tagging, and e‑signatures into a single platform, transforming how contracts flow through operations. 

• Managed 130+ contracts per month with a lean legal team of six 
• Set up pre‑approved templates in Finalize for self‑service drafting, complete with audit trails 
• Centralized legacy and new contracts in Analyze, tagged by project/type/department and retrieved documents in under five minutes 

"With LinkSquares, we filtered the whole portfolio by the contract type and project name tags and surfaced all the necessary documents in less than five minutes."

—Zahreen Ghaznavi, Assistant General Counsel, TIME

Esusu: Trading Bottlenecks for Accelerated Sales Cycles

Esusu, a lean and fast-growing fintech leader in rent reporting, needed to keep pace with surging contract volume, compliance demands, and cross-team reporting requests. LinkAI centralized agreements, automated reporting, and integrated with Salesforce and DocuSign to speed drafting, reviews, and execution.

• Reduced contract turnaround time by 2 days, saving ~5 hours/week locating agreements
• Cut manual reporting by 10 hours/month with automated renewal and expiration updates
• Enabled sales to request, track, and sign contracts entirely within Salesforce

“The amount of manual effort [LinkSquares] eliminates and the time it saves is incredible, while keeping documents from slipping through the cracks.” —Melissa Snyder, Corporate Counsel, Esusu

What Should You Do Next?

The gap between teams that adopt AI now and those that wait is only getting wider. LinkAI gives you a way to close this gap without sacrificing control, security, or accuracy. Our team of legal experts created this turnkey solution to eliminate bottlenecks, surface insights instantly, and make your entire CLM process audit-ready by default. Once you make the switch, the time and money savings start trickling in. Risk analysis gets simpler and more effective. The entire organization starts viewing legal as a partner rather than a barricade. And your team, empowered by this newfound confidence and reduced busywork, is more productive than ever. 

If you’re ready to transform your company’s CLM strategy, know that it doesn’t take much once you implement the right system. Start small (or go all in, if you like — but baby steps are just fine.) 

Pick one thing:

• Your vendor NDAs
• Your renewal cycle
• That one contract type you’re convinced is a skinwalker

Plug it into LinkAI and watch what happens. You’ll see the clutter clear and cycles tighten. You’ll likely wonder why you didn’t do this sooner. But there’s never a bad time to start optimizing, and it’s never too late to let AI supercharge your team’s capabilities. 

You just need a CLM that connects possibilities to real progress. Let LinkAI do that.

• Our Risk Scoring Agent flags issues proactively
• Our Analyze tool breaks down contracts at scale
• Our Customer Success team guides every AI transition

No pressure. Only proof. See for yourself in a free demo from one of our experts, or reach out to the LinkSquares team to learn more.