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AI Pitches to Mid-Size Law Firms: A Partner’s Advice for Vendors

By The Editors

According to the latest data, there are more than 70,000 artificial intelligence companies worldwide. Approximately 17,500 of these operate in the U.S. From GenAI engines to legal platforms and niche tools, choosing which AI pitches to mid-size law firms to hear and products to test is a huge, time-consuming often frustrating exercise for mid-size law firms. How can AI companies make the process smoother? Thomas Kearns, partner at Olshan Frome Wolosky and participant in many AI pitch sessions, has some suggestions.

3D glass letters spelling "AI" with blue digital glow effects, symbolizing Artificial Intelligence technology and legal tech.

Pitching AI Products to Mid-Size Law Firms

The decision to purchase artificial intelligence technology is a big one for mid-sized and smaller law firms. The process is easier when technology companies understand their audience. To that end, here’s advice for AI companies on successful AI pitches to mid-size law firms like mine.

Review the Firm’s Practice Areas

Nothing is more frustrating to an audience of busy lawyers than spending most of a presentation on information about a platform that isn’t suited to the type of law they practice. Review the firm’s practice areas. Your approach should vary based on the practice areas and the partners participating in the pitch. Transactional lawyers will use AI products differently from litigators. Tailoring your pitch is vital for legal tech sales.

Mid-size Is not Biglaw

In midsize firms, the people involved in the buying decision will be partners, senior IT staff and tech-savvy associates. We do not have teams of “knowledge management” lawyers on staff. The good news is that the partners are in touch with the reality of day-to-day practice and the potential benefits of an AI product and will be on the front lines of the decision. It’s a much more rapid process for law firm technology adoption. The bad news is that the vendor must tailor their approach to the busy partner who is serving clients while exploring AI tools to help their firm.

Target the Right Level of Seniority

Since the products come with a significant cost, most firm partners listening to the initial AI pitches to mid-size law firms pitch will be senior. Aim at that level. Keep in mind that senior lawyers have limited non-billable time, so be succinct. This is key to pitching technology to law firm partners.

Once a vendor gets past the initial screening, more junior lawyers are typically invited to review and compare products. That second level can be more detailed and should focus on the uses and benefits for the firm’s specific practice areas.

Address Security Requirements Up Front

It’s best to have a preliminary call with the firm’s IT and cybersecurity leaders. Vendors should first address security and integrating AI with existing law firm systems. We will only schedule a meeting for an in-depth review if our team assures us the product will work with existing systems and meet law firm data security requirements.

Quick Tips for Making Your Pitch

  • Get to the point and limit the use of sales speak. Define what you do and how you do it, and explain how you differ from other vendors.
  • Focus on hallucinations and what your product does for AI hallucination mitigation. Hallucinations are poison for lawyers.
  • Detail how you can leverage the firm’s existing database of transactional and litigation documents for new matters. Most midsize firms that have been in business for a while have a treasure trove of prior transactions that could be helpful for new matters.
  • Focus on the value proposition when discussing costs with the partners, keeping in mind the typical mid-size law firm tech budget.

Finally, for trial offers, be as flexible as possible with respect to the number of trial participants, the length, and the cost.


To learn more about Tom, read his interview on the state of the legal industry and follow him on LinkedIn and at @TDKearns @OlshanLaw.

Image © iStockPhoto.com.

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