From Pilot to Scale: Embedding AI Into Contract Workflows

As in-house legal teams move beyond experimentation, the real challenge is scaling generative AI responsibly, embedding it into contract workflows without introducing risk or friction.

In this Future Contracts Miami interview, Daniel Di Maria, CRO & Co-Founder of Spellbook, shares his perspective on governance, workflow fit, and how legal teams can move from pilots to measurable, scalable adoption.

Enjoy the interview below.

---

Q1: As AI becomes more embedded in contract work, what key considerations should in-house legal teams keep in mind to use it responsibly and effectively?

Security and governance have to come first. That's non-negotiable. Teams need to be clear on what data can be used, where it's processed, what's retained, and when human review is required. From there, the biggest thing is consistency. AI should be guided by playbooks and approval thresholds so it's accelerating work without introducing variability or new risk.

---

---

Q2: How do you see digitalisation changing expectations around speed, consistency, and decision-making across the contract lifecycle?

It's raising expectations across the board, and honestly, that's a good thing. Businesses are going to expect faster turnaround on routine agreements and more consistency in how terms get negotiated, which means efficiency gains for both legal and the commercial teams they support. It also brings more visibility into the process, where deals stall, which clauses cause friction, and whether the terms you're actually closing on match what your playbook says they should.

---

Q3: From your perspective, how important is it for technology to fit into lawyers' existing ways of working rather than requiring them to change how they work?

Fitting into existing workflows is everything, really. Lawyers are already deep in live negotiations and managing a high volume of contracts, so tools that add friction just don't get adopted. Products with clean, intuitive design that fit naturally into how people already review and redline will be the ones that become part of daily work. A great example of how we manage this is by incorporating Spellbook directly into Microsoft Word. Our CEO, Scott, recently joked that he wants us to think about our product like a toaster; how do we build something super reliable that does exactly what it promises? That's the bar. It just works, and it fits right into how you already operate.

---

Q4: As legal teams move beyond initial trials, where do you see the most practical opportunities for advanced technologies in contract management and commercial operations?

The clearest wins are in repeatable work. Faster first drafts, playbook-based review, stronger intake and routing, interacting with the latent business legal knowledge in their existing database, and equipping business users with in-house team configured playbooks. Beyond that, I think data-driven term analysis will be a major unlock because it’ll help teams negotiate from real market standards, improving speed and consistency while keeping decision-making grounded and defensible.

---

Q5: What are you hoping to contribute at Future Contracts Miami, and which conversations are you most looking forward to?

I'm excited to share a practical perspective on what it takes to get these tools adopted in-house. That's something we think about a lot at Spellbook. We build specifically for in-house teams, so things like design, workflow fit, and measurable outcomes are central to how we approach the product. We've also built a Compare to Market feature that lets teams see how their contracts stack up against thousands of similar agreements at the click of a button, so I'm excited to dig into that. I'm also looking forward to talking with legal and commercial leaders who are past the pilot stage and figuring out how to scale these programs across their operations.

---

Join Daniel on Stage on 25 February

Daniel will be delivering a keynote presentation and live product demonstration at Future Contracts Miami on 25 February, exploring how generative AI can be embedded into everyday contract workflows, responsibly, securely, and at scale.

His session will focus on practical adoption: governance first, workflow fit, and measurable outcomes that matter to in-house teams.

February 24 - Opening Reception | 6pm - 8pm

February 25 - Conference Day | 8.30am - 7.25pm

Newman Alumni Center, University of Miami

Secure Your Pass to Future Contracts Miami