AI Special Assistant to the Chief Legal Officer

About the Role 

Alumni Ventures (AV) is pioneering the use of AI Pods — compact, high-velocity teams where an executive, cutting-edge technology, and an AI-native operator collaborate to produce outsized results. As an AI Special Assistant to the Chief Legal Officer (CLO), you’ll be a force multiplier—expanding the CLO’s capacity across legal strategy, risk management, and operational execution. You’ll work side by side with the CLO, senior legal team members, and cross-functional leaders, operating as part of a high-trust, high-performance inner circle.

This is a unique opportunity for a legally savvy, detail-oriented professional eager to apply their expertise in a fast-paced, venture-backed environment. You’ll partner closely with cross-functional teams to support key business initiatives, streamline legal operations, and prototype AI-assisted workflows that improve compliance, contract management, and risk mitigation across the organization.

What You’ll Do 

Strategic Legal Support & Execution

• Integrate AI models and other forms of automation into scalable, repeatable processes

• Evaluate complex, high-scale workflows for opportunities to enhance efficiency through automation or specialized training for AI models

• Evaluate the efficacy of existing automation and AI resources and suggest improvements

• Evaluate existing automation and AI resources for potential risk areas, gaps in functioning, or errors.

AI-Driven & Process-Enhanced Legal Operations

• Use Gen-AI tools and custom GPTs to streamline document review, research, and reporting.

• Prototype automations for contract management, compliance tracking, and legal workflows.

• Continuously identify efficiency gains in legal operations and decision support.

• Sensitivity to risk areas including data privacy, AI misdeployment, hallucination risk, and training gaps

Project Management & Cross-Functional Alignment

• Integrate automation and AI interfaces with other departmental users and stakeholders; ensure accessibility

• Work with Technology and Data Privacy personnel to limit risks from integration and deployment of AI models. Apply risk evaluation to models used within the Legal Department and others in use more broadly across the organization.

• Integrate with other AI-native personnel and oversee development, implementation, and deployment of other automated and AI resources in other departments, with view towards risk management

Research & Communication

• Research and analyze emerging capabilities for new AI resources and report on potential applications for the organization

• Advise and educate stakeholders, particularly Legal stakeholders, on training, implementation, and deployment of AI tools to maximize efficacy and reduce risk areas.

Who You Are 

• 0 to 1 year of experience

• Educational and practical experience with leading AI resources and platforms

• Exceptional intellect and work ethic

• Specific background in use of cutting-edge AI tools, ideally in advancing process optimization or otherwise integrating automation into complex workflows.

• Familiarity with low-code automation and scripting (Python a plus), and ideally document management systems and workflow processes to edit marketing and customer-facing communications

• Exceptional writing and communication skills

• Self-motivated and self-directed professional comfortable with hands-off supervision and bringing initiative to seek out new opportunities to contribute

• Absolute discretion and sound judgment in handling sensitive legal matters.

• Willingness to be based in Manchester, NH or Boston, MA 

Compensation includes a starting base salary of $60,000. - $65,000.