The Legal Departments That Dominate the Next Decade Are Being Built Right Now

While others debate whether AI will matter, forward-thinking leaders are already gaining insurmountable advantages. The question isn’t whether your department will transform. It’s whether you’ll lead that transformation or watch it happen to you. The answer is my Legal Innovation as a Service package.

Strategic guidance for visionary legal leaders from Dennis Kennedy, the authority on Applied AI and innovation.

Your competitors aren’t standing still. As you read this, innovative legal departments are implementing AI strategies that will make traditional approaches obsolete within 18 months. The departments that cling to “proven” methods will find themselves explaining declining performance to increasingly impatient stakeholders.

This is your moment.

You have the vision to see what others miss. You understand that the AI transition isn’t just about efficiency—it’s about fundamentally redefining what legal excellence looks like. Your leadership during this transition will define your legacy and position your department as the strategic powerhouse your organization needs.

But vision without execution is just ambition. The legal departments investing in AI without strategic guidance face predictable, expensive failures: vendor lock-in costing millions in switching costs, compliance gaps requiring emergency remediation, and productivity initiatives that create more friction than value. Meanwhile, departments with strategic AI roadmaps report 40-60% efficiency gains in targeted workflows and measurable competitive advantages in client service delivery.

You’re not looking for someone to make these decisions for you. You’re looking for the strategic partner who ensures you make them flawlessly.

The Strategic Advantage of Proven Experience

Dennis Kennedy brings three decades of pioneering experience in legal technology, recognized with the American Legal Technology Awards Lifetime Achievement Award in 2024. Dennis has guided the legal profession through every major technological transition, from early internet adoption to cloud computing to today’s AI revolution.

Unlike consulting firms that assign junior teams to learn on your investment, or internal hires who lack broad market perspective, Legal Innovation as a Service (LIaaS) offerings provide direct access to the architect of legal technology strategy. You’re not getting a report about what others think. You’re getting the thinking that has shaped the industry for three decades, enhanced by Dennis’s path-breaking AI enhancements.

True Strategic Independence: No vendor relationships, no implementation revenues, no hidden agendas. My only incentive is your success. This independence allows for unvarnished assessments of vendor claims, honest evaluation of internal capabilities, and strategic recommendations based solely on your department’s best interests, not what generates the most fees or continuing engagements that drag on endlessly.

You have the vision and the team to execute. My role is to ensure you’re executing a strategy that will make you the leader others study and emulate.

The Strategic Investment Menu

These are not “packages”; they are focused advisory sprints designed for leaders who are building the future of legal service delivery. They are built to deliver maximum strategic clarity with minimum operational drag.

Tier 1: The AI Innovation Roadmap Session

The essential starting point for visionary leaders ready to move.

This is a single, intensive 2-hour virtual working session designed to stress-test a core strategic assumption or map a specific AI initiative. It’s the most valuable two hours you’ll spend positioning your department for the future.

Best For: Leaders evaluating a specific, high-stakes AI vendor; validating the business case for a transformative initiative; or pressure-testing your department’s overall AI readiness against tomorrow’s demands.

What You’ll Achieve: Clear identification of your highest-ROI AI opportunities, elimination of 80% of common implementation pitfalls before they occur, and a defendable strategic rationale for AI investments that builds stakeholder confidence and positions you as the forward-thinking leader.

Deliverable: A One-Page Strategic Blueprint outlining Red Flag/Green Flag analysis, prioritized next actions, and the critical questions you must answer in the next 30 days to maintain your competitive advantage.

Strategic Clarity Guarantee: If our initial engagement doesn’t provide absolute clarity on your next strategic move, we’ll continue working until it does, at no additional cost.

Investment: $7,500

Tier 2: LIaaS Deep Dive

For leaders building comprehensive transformation strategies.

We move beyond a single issue to assess the health and strategic fit of a larger portfolio. This is where you develop the strategic depth that separates true innovators from followers.

Choose from one of four deep dives:

AI-Enabled Reality Check: Assess your current or proposed portfolio. Are your initiatives aligned with real-world value that will drive competitive advantage, or are you at risk of “innovation theater”?

Portfolio Optimization for the AI Era: Review your innovation investments as a strategic portfolio. Is your risk/return profile aligned with your department’s goals in an AI-driven landscape where winners take all?

Strategic Sounding Board: In-depth analysis and counsel on your highest-potential ideas to improve your odds of investing in the initiatives that will define your department’s future.

Law Firm Innovation Partnership Review: Evaluate the innovation promises and AI capabilities of your outside counsel to ensure you’re driving maximum value from your most critical partners—and aren’t falling behind their other clients.

Enhanced Value: Every engagement includes access to proprietary frameworks developed over three decades of legal technology leadership, including the Kennedy AI-Opportunity Scorecard and the Strategic Innovation Readiness Assessment. These are iagnostic tools available exclusively through LIaaS that give you insights your competitors don’t have.

Knowledge Transfer Focus: You’ll receive not just recommendations, but the analytical frameworks and decision-making processes that generated them—ensuring your team can continue applying these insights independently and building on your strategic foundation.

Deliverable: A comprehensive Execution Blueprint, a Stakeholder Alignment Plan, and the proprietary Kennedy AI-Opportunity Scorecard.

Investment: $18,500

Tier 3: The Innovation Partner Retainer

For leaders who will define the future of legal service delivery.

This is a true partnership designed to provide sustained momentum and competitive advantage for leaders who understand that the AI transformation isn’t a project—it’s an ongoing strategic evolution that will determine who leads and who follows.

Best For: General Counsel and Chief Innovation Officers at large corporations or Am Law 100 firms who see AI as their opportunity to fundamentally redefine their department’s strategic value and competitive position.

Deliverable: Includes one LIaaS Deep Dive of your choice per quarter, a scheduled monthly Strategy & Momentum call, and priority access for ad-hoc strategic questions, ensuring that you stay ahead of the curve as the landscape rapidly evolves.

Partnership Commitment: Tier 3 partnerships are limited to eight active clients maximum, ensuring dedicated focus and immediate responsiveness. This limitation reflects the reality that meaningful strategic partnership requires dedicated attention and immediate availability. When you face a critical decision that could define your department’s future, you need your strategic advisor available, not managing an overloaded client roster.

Investment: $35,000 per quarter

A Partnership of Visionaries

This service is for you if:

You are a senior leader (GC, DGC, CLO, Head of Legal Ops/Innovation) who sees this AI transition as your opportunity to build something historic.

You have budget authority for technology investments exceeding $100K annually and face board-level expectations to demonstrate AI strategy.

You lead teams of 10+ legal professionals and view AI as strategic transformation that will redefine competitive advantage, not just efficiency tooling.

You have the authority to make strategic decisions with resources to implement recommendations, and you’re ready to be the leader who positions your department for the future.

You value incisive, candid advice over voluminous, cookie-cutter reports and densely-packed slide decks because you understand that strategic advantage comes from superior thinking, not more documentation.

My role is to:

Serve as your confidential, behind-the-scenes strategic partner as you build the future of legal service delivery.

Provide unbiased, unvarnished strategic guidance based on decades of unique experience helping legal leaders navigate transformative change.

Help you see around the corner, anticipate risks, and seize opportunities that others will miss.

Ensure the credit for the successful outcomes belongs entirely to you and your team—because history will remember you as the leader who transformed your department.

Comparing Approaches: The Value of Incisive Expertise

The Process is Designed for Clarity and Momentum

Engage: Schedule a quick introduction Zoom meeting to answer any questions you have. I’ll then send you a simple, pre-scoped agreement for your chosen advisory tier. for you to sign.

Discuss: We hold a focused kickoff discussion to frame the strategic question and your vision for transformation.

Synthesize: I analyze the situation based on my decades of experience and proprietary frameworks developed for forward-thinking leaders.

Deliver: You receive the concise, high-impact deliverable for your tier designed to position you for strategic success.

Align: We hold a follow-up conversation to ensure you have total clarity on the path forward and the confidence to lead your department’s transformation.

The decisions you make in the next 90 days will define your department’s (and even more importantly,  I believe, your own) trajectory for the next decade. You have the vision to see what others miss and the opportunity to build something that will be studied and emulated.

Join the select group of legal leaders who seized this moment.

[Schedule a confidential exploratory call to begin your department’s transformation.]

All client engagements are held in strict confidence. Your strategic discussions and transformation outcomes remain completely confidential.