Director, AI

Role: Director, AI
Location: Toronto
Department: Exa Enterprise Support Group - EESG
Reports to: CEO, Exa Capital

About Exa Capital
Exa Capital is a permanent capital holding company focused on acquiring and building vertical market software businesses. We take a long-term, stewardship-driven approach – buying and holding companies forever, and empowering leaders through a decentralized operating model.

Position Overview
The Director of AI will serve as Exa Capital's strategic leader in artificial intelligence implementation across our portfolio of enterprise software companies. Reporting to the Exa CEO, this role combines deep technical expertise with business acumen to identify, develop, and deploy AI solutions that enhance product competitiveness, operational efficiency, and long-term value creation. This position requires someone who can influence, working collaboratively with Exa and portfolio company leadership teams to integrate AI capabilities that align with each company's unique market position while advancing Exa's stewardship philosophy.

Operating in Exa's decentralized model, the Director of AI will act as both strategist and enabler—building trust with portfolio company executives, assessing AI readiness and opportunities, and providing hands-on guidance for implementation. This role demands someone who thinks in decades rather than quarters, understanding that sustainable AI transformation requires cultural buy-in, thoughtful change management, and solutions tailored to each company's trajectory.

Key Responsibilities
Strategic AI Leadership

• Develop and maintain Exa's AI strategy framework, establishing principles and standards that respect portfolio company autonomy while ensuring technological competitiveness

• Conduct comprehensive AI readiness assessments across portfolio companies, identifying high-impact opportunities for product enhancement and operational optimization

• Serve as Exa's primary advisor on AI-related M&A considerations, evaluating target companies' AI capabilities and integration opportunities

• Monitor AI technology landscape and emerging trends, translating developments into actionable insights for portfolio company application
  
  
  

Portfolio Company Collaboration

• Build trusted relationships with portfolio company CEOs, CTOs, and product leaders, earning the right to influence through expertise and results rather than mandate

• Partner with portfolio company technical teams to design and implement AI solutions tailored to their specific products, customers, and competitive contexts

• Facilitate AI knowledge sharing across portfolio companies, creating communities of practice and enabling cross-portfolio learning

• Provide hands-on technical guidance and problem-solving support for complex AI implementation challenges
  
  
  

Product & Market Competitiveness

• Identify opportunities to integrate AI features into portfolio company products that enhance customer value and competitive differentiation

• Lead development of AI-powered capabilities that create defensible moats and expand addressable markets for portfolio companies

• Ensure portfolio companies remain at the forefront of AI application within their respective industries and customer segments

• Guide product teams in responsible AI development, including ethical considerations, bias mitigation, and transparency
  
  
  

Operational Efficiency & Cost Reduction

• Assess portfolio company operations to identify processes suitable for AI-driven automation and optimization

• Design and implement AI solutions that reduce operational costs while maintaining or improving service quality

• Develop ROI frameworks for AI investments, ensuring disciplined capital allocation and measurable returns

• Lead initiatives in AI-powered customer support, sales enablement, marketing optimization, and back-office automation
  
  
  

Technical Implementation & Governance

• Establish AI development standards, security protocols, and governance frameworks applicable across diverse portfolio companies

• Guide build vs. buy decisions for AI capabilities, evaluating third-party tools against custom development

• Ensure AI implementations align with data privacy regulations, security requirements, and compliance obligations

• Develop talent assessment frameworks to help portfolio companies build and retain AI/ML capabilities
  
  
  

Thought Leadership & External Relations

• Represent Exa Capital's AI capabilities and philosophy in industry forums, conferences, and with prospective portfolio companies

• Build relationships with AI technology vendors, research institutions, and industry experts that benefit the broader portfolio

• Contribute to Exa's investment thesis development by identifying AI-driven market opportunities and threats
  

Required Experience

• 10+ years in AI/ML roles with at least 5 years in leadership positions overseeing AI strategy and implementation

• Proven track record of successfully deploying AI solutions in enterprise software environments that delivered measurable business outcomes

• Experience working across multiple business units or companies, demonstrating ability to influence diverse stakeholders without direct authority

• Deep technical expertise in modern AI/ML technologies including large language models, computer vision, predictive analytics, and recommendation systems

• Hands-on experience with AI development frameworks, cloud-based AI services (AWS, Azure, Google Cloud), and MLOps practices

• Background in enterprise software business models, with understanding of SaaS metrics, product development cycles, and competitive dynamics

• Experience assessing and managing AI-related risks including bias, security, privacy, and regulatory compliance
  
  
  

Strongly Preferred Experience

• Private equity, venture capital, or portfolio company operating role experience

• Track record working in decentralized or matrixed organizations where influence must be earned

• Experience with AI implementation across diverse technical stacks and industries

• Background in change management and technology adoption within established organizations

• Consulting or advisory experience serving multiple clients or business units simultaneously

• Experience building and mentoring AI/ML teams
  
  
  

Education

• Master's degree in Computer Science, Artificial Intelligence, Machine Learning, Data Science, or related technical field strongly preferred

• Undergraduate degree in Computer Science, Engineering, Mathematics, or related quantitative field required

• Ongoing professional development in AI through research, certifications, or advanced coursework valued
  

What You’ll Learn & Gain

• Ownership of AI strategy and execution across multiple enterprise software businesses, each with real customers, revenue, and data—not labs or side projects

• The opportunity to turn modern AI (LLMs, automation, predictive systems) into durable product advantage and cost leverage, not hype or demos

• Deep experience building AI in a permanent‑capital environment, where decisions are optimized for long‑term value, resilience, and compounding

• Direct partnership with CEOs, CTOs, and product leaders, influencing roadmaps and architecture without bureaucracy

• Hands‑on involvement in AI diligence and post‑acquisition transformation as part of Exa’s M&A strategy

• The chance to define portfolio‑wide AI standards, patterns, and governance that scale across companies and years

• A rare seat to build AI systems that matter over decades, not quarters
  

Who You Are

• A senior AI leader who can move fluidly between strategy and hands‑on problem solving

• Credible with engineers and executives alike—you earn influence through expertise

• Experienced translating AI into measurable business outcomes in enterprise software environments

• Comfortable operating across multiple companies at once, balancing standardization with context

• Long‑term oriented by default—you care about durability, stewardship, and compounding advantage

• Clear‑thinking, direct, and pragmatic—able to cut through noise and make disciplined tradeoffs

• Grounded in responsible AI, bringing maturity around risk, ethics, privacy, and security
  
  
  

Why Exa

• Permanent capital: build AI capabilities designed to last decades, not optimized for exits

• Decentralized model: portfolio CEOs own outcomes, you act as a strategic force‑multiplier, not a control layer

• Direct access to the CEO on AI strategy, acquisitions, and portfolio priorities

• The opportunity to shape what “great AI” looks like across an entire software portfolio

• A culture of high standards, low ego, discipline, and intellectual honesty

• Visible, tangible impact, your work will influence products, margins, and competitiveness in real time

• A chance to help build a new kind of software holding company, with AI as a core advantage
  
  
  

Perks & Benefits

• Unlimited PTO

• Lifestyle Spending Account up to $1,250

• $500 home office setup allowance

• Comprehensive medical, dental, and vision benefits from day 1

• Hybrid work model (2 days in-office: Tuesday & Thursday)

• Toronto HQ at First Canadian Place with direct PATH and transit access

• Monthly team socials
  
  

Compensation
Salary Range: $150,000 – $190,000 per year

Accessibility & Accommodations
Exa Capital is committed to providing equal access to employment opportunities. Accommodation is available for applicants with disabilities throughout the recruitment and selection process. If you require accommodation or support, please reach out to us at HR@exacapital.co , we are happy to help.

Equal Opportunity Employer
We are an equal opportunity employer and are committed to fostering a diverse and inclusive workplace. We value diverse perspectives and are committed to building an inclusive environment where everyone can do their best work.

Artificial Intelligence Disclosure
Exa Capital may use artificial intelligence–based tools to support certain aspects of the applicant screening and assessment process.

Canadian Experience
This role does not require Canadian work experience. Applicants must be legally eligible to work in Canada.