Turning Legal Tech Pilots into Enterprise-Wide Deals

In the previous post in this series, we covered the basics of running successful trials that convert. Here, we focus on components that help deliver larger wins, leveraging the small wins into big, firm-wide deals.

Selling is more than just showing off the features; you need to understand your client's unique culture, navigate decision-making dynamics, and prove your solutions' value in a way that resonates with their priorities. This post is all about practical strategies to help you scale your solution across entire firms, even if you’re new to sales.

We focus on common and uncommon pitfalls. Mistakes we’ve seen being made too often, many of which are unique to selling into legal. We’ve coached reps to identify these early so they can be mitigated, and we’ve suggested what you should do to avoid learning lessons at the cost of losing deals.

It’s Not Just About the Partner Champion

Getting a partner champion on board is a great start, but it’s not enough to drive adoption across the firm, which is required for large multi-stakeholder wins. Law firms are complex organizations, and there are other key players you need to win over.

The Hidden Influencers

Some of the most important people in the adoption process aren’t the ones signing the order form. These “hidden influencers” are often the ones who keep the momentum going when your champion gets busy with client work.

Here are a few examples (this is not a complete list and will likely differ based on your product and the firm):

• Knowledge Management Professionals: These are often former lawyers or legal professionals who specialize in optimizing workflows and managing the firm’s knowledge assets. They’re deeply familiar with the pain points lawyers face and are tasked with finding tools that improve efficiency and accuracy.

• Innovation Leaders: Many firms now have dedicated innovation roles, such as “Innovation Manager” or “Chief Innovation Officer.” These professionals are responsible for evaluating and implementing new technologies that align with the firm’s strategic goals.

• Practice Group Leaders: Senior lawyers who oversee specific practice areas, such as litigation, corporate law, or real estate, often drive decisions about tools that impact their group’s efficiency. Their buy-in can pave the way for broader adoption across the firm.

• IT and Security Teams: While not directly involved in legal workflows, IT and security teams are gatekeepers for any new technology. They ensure that tools meet the firm’s security standards, integrate with existing systems, and don’t disrupt operations.

• Client-Facing Teams: Professionals who manage client relationships, such as business development managers or client service teams, are focused on tools that enhance client satisfaction and improve transparency.

These groups are critical because they:

• Have a bird’s-eye view of the firm’s technology needs

• Understand internal politics and how to navigate them

• Can translate your product’s benefits into terms that resonate with lawyers

What You Can Do: Build relationships with these influencers early. Share materials that make their lives easier, like security documentation, ROI calculators, and implementation timelines. Tailor your messaging to their specific priorities and empower them to advocate for your product internally.

Why Narrow Pilots Lead to Big Wins

It might seem like a good idea to show off every feature of your product during a pilot, but the truth is, less is more. The most successful pilots are laser-focused on solving a specific problem.

The Power of Focus

Instead of trying to demonstrate your product across multiple practice areas, pick one high-value workflow and knock it out of the park. For example, if your product helps with contract analysis, don’t try to roll it out firm-wide. Instead, focus on speeding up M&A due diligence for one specific type of deal.

Here’s why this works:

• It’s easier to measure success when you’re solving one problem.

• A small, successful pilot creates a story that other teams in the firm will want to replicate.

• You can deliver results faster, which keeps everyone engaged.

What You Can Do: Work with your champion to identify the single most valuable use case for your product. Design your pilot to deliver exceptional results in that area, and don’t try to showcase every feature.

What Really Motivates Law Firm Partners

If you’re selling to law firms, you’ve probably heard that ROI is important. And it is—but it’s not the only thing that matters to the firm. To really win over partners at the firm, you need to understand what drives them.

More than Efficiency

Partners across all law firms care about more than just efficiency. They’re often motivated by things like:

• Client Perception: How does your product make them look good to their clients?

• Competitive Edge: Can your product help them win pitches against rival firms?

• Leadership: Does using your product position them as innovators in their field?

• Recruiting and Retention: Will your product help them attract and keep top talent?

What You Can Do: Frame your product’s benefits in terms of these prestige factors. For example, if your product improves efficiency, explain how that frees up time for higher-value work that impresses clients. If it helps with collaboration, show how it can make the firm look more modern and innovative.

Should You Charge for Pilots?

The question of whether to charge for pilots comes up a lot, and the answer depends on your goals. Offering free pilots can help you get your foot in the door, but charging for them can signal value and weed out firms that aren’t serious.

A Tiered Approach

Here’s a simple framework you can use:

Pilot Type	Duration	Cost	Scope	Goal
Discovery Pilots	2-4 weeks	Free	5-10 users, minimal setup	Prove concept, secure next stage commitment
Validation Pilots	1-3 months	30-50% of license cost	15-25 users, success metrics tracking	Demonstrate measurable value, prepare for implementation
Implementation Pilots	3-6 months	Fully paid, credited toward enterprise agreement	Department-wide deployment, full integration	Establish foundation for firm-wide adoption

This approach lets you qualify prospects based on their commitment level while giving them a clear path to scale.

What You Can Do: Define your pilot tiers with specific deliverables, timelines, and pricing. Use the progression from free to paid as a way to identify serious prospects.

How to Get Clients Involved

Depending on your product, one of the fastest ways to get a law firm to adopt your product is to involve their clients or show how it might help to deliver greater value to their clients. When a firm’s key client endorses or participates in a pilot, adoption tends to skyrocket.

Why This Works

• It turns your product into a client development tool, not just a cost.

• It creates external accountability for adoption.

• It gives the firm a compelling story to share with other clients.

What You Can Do: Research your prospect’s key clients and their priorities. Position your product as a way to help the firm meet client needs. For example, if a client is pushing for more transparency, show how your product can provide better reporting.

Keep It Simple: Managing Stakeholders

Law firms have a lot of decision-makers, and it can feel overwhelming to keep track of everyone’s priorities. The key is to keep it simple and focus on what matters most to each group.

A Quick Guide to What Stakeholders Care About

Stakeholder Type	What They Care About	How to Win Them Over
Partners	ROI, client perception	Show how your product helps them impress clients and win business.
IT Teams	Security, integration	Provide detailed documentation and address concerns early.
End Users	Ease of use, time savings	Focus on how your product makes their day-to-day work easier.
Innovation Leaders	Success stories, adoption metrics	Share pilot results and help them champion your product internally.

What You Can Do: Tailor your messaging to each group. For partners, focus on client impact. For IT, focus on security. For end users, focus on ease of use.

Turning Pilot Success into Firm-Wide Adoption

A successful pilot is just the beginning. To scale your product across the firm, you need to communicate the results clearly and keep the momentum going.

How to Share Success

1. Document Results: Track metrics like time saved, error reduction, and user feedback during the pilot.

2. Tell a Story: Frame the results in a way that resonates with the firm. For example, “20% faster document review” becomes “capacity to handle 3 more deals per quarter.”

3. Create Materials: Develop case studies, ROI analyses, and client-facing materials that partners can use to pitch your product internally.

What You Can Do: Make it easy for your champion to share the success of the pilot. Provide them with clear, compelling materials that highlight the value of your product.

Final Thoughts

Scaling legal tech adoption is all about understanding the unique dynamics of law firms and proving your value in a way that resonates. It’s not about hard selling or flashy pitches, it’s about solving real problems, earning trust, and showing how your solution fits into their world.

The key is to focus on the pain points that matter most, engage the right people at the right time, and frame your product as a tool that helps the firm achieve its goals. Small wins, like a successful pilot, can open the door to bigger opportunities if you approach them strategically and build momentum.

Selling to law firms takes patience. Position yourself as a trusted partner in their long-term success. By applying the strategies in this guide, you’ll be better equipped to scale your product, grow your business, and make a meaningful impact in the legal industry.