Aaron Levie: AI will create more lawyers in five years, workflows must be redesigned for AI agents, and the commercial race in AI is reshaping global dynamics | 20VC

AI-driven automation is set to boost the legal profession, creating more lawyers and new job roles.

Listen on 20VC

Share

Add us on Google by Editorial Team Apr. 20, 2026

Key takeaways

• AI and automation are predicted to increase the number of lawyers in the next five years.
• Workflows should be redesigned for AI agents rather than humans to improve efficiency.
• The AI race is primarily commercial and economic, not existential.
• Software upgrades are ongoing processes without a single moment of technological advantage.
• AI is expected to augment human work rather than replace it.
• The tech industry has a narrow focus on engineering opportunities, ignoring broader needs.
• More lawyers will emerge due to easier legal content generation, despite court system constraints.
• Automation is anticipated to create new job roles, such as agent operators.
• Automation will expose new bottlenecks in industries previously masked by manual processes.
• Effective automation in large organizations requires redesigning workflows for AI agents.
• AI advancements will continue to reshape workforce dynamics across various sectors.
• The integration of AI in enterprises demands a shift in operational design and strategy.
• The legal profession will face significant changes due to technological advancements.
• The demand for engineering skills extends beyond the tech industry into other sectors.
• New job roles will require technical expertise and deep understanding of AI.

Guest intro

Aaron Levie is the co-founder and Chief Executive Officer of Box, the enterprise cloud content management platform that surpassed $1 billion in annual revenue in its 2024 fiscal year. He launched Box in 2005 as a college project at the University of Southern California, dropping out to lead its pivot to enterprise customers and its 2015 public listing on the New York Stock Exchange. Levie now drives AI integration into enterprise workflows, including the Box AI platform.

The future of legal professions in the age of AI

• There are gonna be more lawyers in the next five years than we have today.

  — Aaron Levie

• AI will lead to a significant increase in the number of lawyers.
• Legal content generation is becoming easier, but court approval remains challenging.

• We’ve made it easy to generate legal content but it has not gotten any easier to actually get any of that approved by any court system.

  — Aaron Levie

• The legal industry will need to adapt to new technological advancements.
• Workforce dynamics in the legal profession will shift due to AI and automation.
• The legal system’s capacity to process content is not keeping pace with technological advancements.
• AI’s impact on legal professions highlights the need for strategic adaptation.

Redesigning workflows for AI integration

• The workflow needs to be redesigned for agents not for people.

  — Aaron Levie

• AI agents require a shift in operational design to maximize efficiency.
• Enterprises must adapt workflows to accommodate AI integration.
• Redesigning workflows is crucial for leveraging automation effectively.

• If we actually want to get real leverage from automation we need to start to redesign the workflow.

  — Aaron Levie

• Effective AI integration demands a strategic overhaul of existing processes.
• Large organizations face unique challenges in implementing automation.
• The redesign of workflows is essential for maximizing the benefits of AI.

The commercial and economic race in AI

• I think what we are in is a commercial and economic race obviously with safety built into that.

  — Aaron Levie

• The AI race is driven by commercial and economic factors, not existential threats.
• Competition in AI focuses on economic advantages rather than existential risks.
• Understanding the AI race requires a focus on commercial implications.
• The US and China are key players in the commercial AI race.
• Economic competition in AI shapes global technological advancements.
• The commercial race in AI emphasizes the importance of strategic investments.
• AI advancements are reshaping global economic landscapes.

The ongoing nature of software upgrades

• Upgrading software is a multi year effort… there’s not like some magical moment where you can just secure everything.

  — Aaron Levie

• Software development is a continuous process without a single breakthrough moment.
• Technological advancements require ongoing efforts and investments.
• The complexity of software upgrades challenges oversimplified views of AI progress.
• Continuous improvement is essential for maintaining technological advantages.
• The nature of software upgrades highlights the need for strategic planning.
• Enterprises must invest in long-term software development strategies.
• Understanding software upgrades is crucial for navigating technological advancements.

AI’s role in augmenting human work

• We haven’t removed humans from the loop we’ve just changed where they enter the loop.

  — Aaron Levie

• AI is expected to augment rather than replace human work.
• The integration of AI into various professions will reshape workforce dynamics.
• AI advancements provide opportunities for enhancing human capabilities.
• The role of humans in the workforce will evolve with AI integration.
• AI’s impact on job displacement is more nuanced than commonly perceived.
• Understanding AI’s role in augmenting work is crucial for strategic workforce planning.
• AI integration offers potential for improving efficiency and productivity.

The demand for engineering skills beyond tech

• We are so myopic and self interested and and we think that the entire industry is the tech industry.

  — Aaron Levie

• The tech industry’s narrow focus ignores broader engineering opportunities.
• Engineering skills are in demand across various sectors beyond tech.
• The need for engineering expertise extends to industries worldwide.
• The tech industry’s myopic view limits potential engineering advancements.
• Broader recognition of engineering roles is essential for global progress.
• Understanding the demand for engineering skills is crucial for strategic workforce development.
• The tech industry must adapt to broader engineering needs to drive innovation.

The emergence of new job roles due to automation

• There is gonna be 500,000 a million jobs created for and it’s basically some kind of agent operator.

  — Aaron Levie

• Automation will create new job roles that require technical expertise.
• The emergence of agent operators highlights the evolving job market.
• New roles will demand deep understanding of AI and technical skills.
• The job market will continue to evolve with advancements in AI and automation.
• Understanding the impact of automation on job creation is crucial for workforce planning.
• The creation of new roles emphasizes the need for strategic adaptation.
• Automation’s impact on job markets highlights the importance of continuous learning.

Automation revealing new industry bottlenecks

• Automation is gonna actually just force us to see the next set of bottlenecks that are in all of these industries.

  — Aaron Levie

• Automation will expose new challenges in industries previously masked by manual processes.
• The identification of new bottlenecks requires innovative solutions.
• Understanding automation’s impact on industries is crucial for strategic planning.
• The emergence of new challenges emphasizes the need for continuous improvement.
• Automation highlights the importance of addressing underlying industry issues.
• The identification of bottlenecks provides opportunities for innovation and growth.
• Strategic adaptation is essential for navigating the challenges revealed by automation.

Disclosure: This article was edited by Editorial Team. For more information on how we create and review content, see our Editorial Policy.