Originally aired October 30, 2025 on Extropy On AIr.
Contracts are the connective tissue of the business, and if you aren’t managing them with precision, you are leaving value and risk on the table. In this episode of our Raindrop partner series, Kevin Zirkle of Extropy Advisors and Ward Karson, COO of Raindrop, dig into contract lifecycle management (CLM): why scattered contracts are a CFO problem, how Raindrop CLM and its built-in RainSign e-signature cover the full lifecycle, how trainable AI earns legal’s trust, and why CLM isn’t just for big companies.
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Key takeaways
- Most companies still manage contracts across email, shared drives and desktops, so renewals and risk terms get missed.
- Raindrop CLM covers the full lifecycle in one system, from request and AI authoring to redlining, approval, RainSign e-signature and obligation tracking.
- Transparent, trainable AI lets legal and procurement stay in control while the model learns their preferences.
- Contracts are the largest creator of obligations in a company, which makes CLM a CFO tool, not just a legal one.
- CLM isn’t just for big companies. It is for smart companies, and starting early builds resilience.
What does contract management look like at most companies?
Ward says most companies are still stuck in fragmented processes. Contracts live in email threads, shared drives, file cabinets or individual desktops. Legal and procurement don’t speak the same language, approvals take weeks, and risk terms like auto-renewals and price uplifts are routinely missed. It is painful, and it is costly.
Kevin has seen it firsthand. A Fortune 500 client couldn’t find 200 active vendor contracts during a Q3 audit, and had five different versions of a contract for a single vendor stored in different departments. Ward’s point: it isn’t about storage, it is about visibility and control. If you can’t see it, you can’t govern it, and if you can’t govern it, you expose the business to financial and compliance risk.
What does a full contract lifecycle include?
Raindrop CLM includes:
- Contract intake with metadata tagging.
- Generative AI authoring that drafts contracts from your clause library and legal-approved templates, plus the suggestions or concerns you raise as you draft.
- Collaboration with single or multi-party in-app redlining, internal and external comments and complete version control.
- AI-powered risk assessment that identifies contract risk in real time and suggests how to resolve it.
- Approval routing through automated, rules-based workflows.
- RainSign, Raindrop’s built-in e-signature.
- Obligation tracking with extracted terms, expiration alerts and compliance dashboards.
- One-click NDAs, so legal doesn’t have to get involved in every high-volume, low-value agreement.
RainSign is a key differentiator. It provides audit-ready, legally binding digital signatures without a third-party tool, so a business request can move from contract creation through redlining, approval and signature in one system.
How do you standardize contracts across departments?
Kevin sees many clients where sales uses one MSA and procurement uses another. In Raindrop, you can lock down clause types, associate them with specific use cases or regions, and set fallback language for negotiable terms. Version control shows which templates are being used and who changed what. That matters when legal teams are lean and can’t manually approve every contract.
How does AI help with contracts without becoming a black box?
Raindrop uses AI to extract terms, flag risk language, recommend clauses based on context and summarize contract obligations. AI-driven search lets users ask questions like “show me all contracts expiring in the next 90 days with indemnification clauses over $1 million” and get real answers.
Ward stresses that it is transparent and trainable. Legal and procurement can accept or override suggestions, every change is tracked so you know what was suggested and why, and the model gets smarter based on user preferences. He compares it to a junior analyst learning on the job, except it is consistent, scalable and never forgets. Teams can also turn it off. Kevin notes that legal’s first question about AI is usually whether they can really control it, and this approach answers that.
Why should CFOs care about CLM?
Ward says contracts are the largest creator of obligations in any company. They define revenue, risk and cost. With good CLM, you reduce leakage, catch renewal hikes and make sure you aren’t paying for things you didn’t agree to. Contract data also feeds spend forecasts, supplier performance and compliance metrics, so it is foundational.
It matters in M&A too. Kevin has supported due diligence efforts where CLM, or the lack of it, became a deal breaker. When you are acquiring a company, you need to know what obligations and exposure you are taking on and what rights you can assign, right away, not after a six-week contract review. Raindrop surfaces that by entity, geography, term, termination rights and risk exposure in a click or two. As Kevin puts it, contract visibility is foundational to enterprise value.
What results can CLM deliver?
Ward described a client that uses Raindrop CLM to manage contracts from supplier onboarding through commitments, renewal and offboarding, while its Oracle ERP handles the supplier master, orders and payments. Information flows between the two systems. With Raindrop, the client improved contract process efficiency by about 75% and now has 90% of its spend under management, making Raindrop its source of truth for commitments across the organization.
How do you drive CLM adoption?
Ward’s answer is to keep it simple: a modern UI and no-code workflows that are easy to configure, with Raindrop’s implementation team partnering with firms like Extropy on change management. Kevin says the biggest hurdle is often internal skepticism, the assumption that CLM tools are hard to use or just a legal project. Extropy helps reframe it as a business enabler, not just a control mechanism, by redesigning workflows, retraining teams and showing stakeholders the value.
And if you think you are too small for CLM, think again. Kevin has seen fast-growing clients start with 50 contracts and use the visibility to scale faster, reduce leakage and pass audits. Ward’s closing advice: if you are managing contracts in email and shared drives, it is time to upgrade.
In their words
CLM is not just for big companies. It’s for smart companies.
Ward Karson, Raindrop
Contract visibility really is foundational to enterprise value.
Kevin Zirkle, Extropy Advisors
About the speakers
Kevin Zirkle is Director of Business Development at Extropy Advisors, where he works across Extropy’s partner ecosystem, matching organizations with the right technology and the right people to move transformation from the whiteboard into production.
Ward Karson is Chief Operating Officer at Raindrop, a spend management platform covering sourcing, contracts, supplier management, e-procurement and analytics.
FAQ
What is contract lifecycle management (CLM)?
CLM centralizes, digitizes and manages contracts from the initial request through authoring, negotiation, approval, signature, obligation tracking and renewal. It replaces contracts scattered across email threads, shared drives and desktops with one governed system.
Why should CFOs care about CLM?
Contracts are the largest creator of obligations in any company: revenue, cost and risk. Good CLM reduces leakage, catches renewal hikes and auto-renewals, ensures you only pay for what you agreed to, and feeds contract data into spend forecasts, supplier performance and compliance metrics.
Can legal teams control how AI is used in contracts?
Yes, when the AI is transparent and trainable. In Raindrop, legal and procurement can accept or override AI suggestions, every change is tracked so you know what was suggested and why, the model learns from those preferences over time, and AI can be turned off.
How does CLM help in M&A due diligence?
In an acquisition you need to know right away what obligations, exposure and assignable rights you are taking on. CLM surfaces that contract intelligence by entity, geography, term, termination rights and risk exposure in a click or two, instead of a weeks-long manual review.
Is CLM only for large companies?
No. Companies starting with as few as 50 contracts gain visibility that helps them scale faster, reduce leakage and pass audits. Building CLM into operations early builds resilience from day one.
Keep exploring
- More from our partner series on Extropy On AIr
- Previous in the Raindrop series: Raindrop + Extropy: Strategic Partnership Driving Financial Transformation
- Next in the Raindrop series: Know Your Suppliers: Streamlined, Smart, and Secure with Raindrop + Extropy
- Why Extropy
Ready to get your contracts under control? Book a discovery call with our team.
