Director, AI - Software Engineering
— · Remote · Toronto
Job description
Role: Director, AI – Software Engineering
Location: North America - Remote
Department: Exa Enterprise Support Group - EESG
Reports to: CEO, Exa Capital
Role Type: Player-Coach
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
We are seeking a Director of AI – Software Engineering who is fundamentally a strong software engineer first, AI leader second.
This role is responsible for defining and executing AI strategy across a portfolio of companies, with a focus on building production-grade AI systems that materially improve software development, operational efficiency, and product competitiveness.
You will work directly with CEOs, CTOs, and VP Engineering leaders, operating as a hands-on player-coach—earning trust through execution, not authority—and driving adoption of AI solutions that deliver clear business outcomes and measurable engineering impact.
A core mandate of this role is to redefine the Software Development Lifecycle (SDLC) using AI, including building and deploying coding agents, developer copilots, and AI-powered automation systems with strong guardrails, governance, and reliability, especially in regulated enterprise environments.
In this role, you will will be responsible for following areas:
AI Strategy & Portfolio Execution
- Define and execute AI roadmap at speed, aligned to enterprise priorities and each portfolio company’s competitive context
- Identify and prioritize high-impact AI use cases across: Software development Product innovation Operational efficiency Revenue enablement
- Maintain a portfolio-wide AI backlog with clear ROI targets, success metrics, and prioritization frameworks
- Redesign and operationalize an AI-powered Software Development Lifecycle across all stages
- Continuously evaluate emerging technologies and make clear adopt / scale / defer decisions
- Build and lead a lean, high-impact AI engineering team with strong hands-on capability
- Develop and scale reusable playbooks, frameworks, and architecture patterns across teams
- Strengthen internal capability to reduce reliance on external vendors and consultants
- Drive adoption through structured training, change management, and AI champion networks
Hands-On Engineering Leadership
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Operate as a hands-on player-coach, partnering directly with CTOs and engineering teams
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Build trust through deep technical contribution and delivered outcomes, not authority
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Embed within teams to unblock execution, accelerate delivery, and improve engineering effectiveness
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Drive AI adoption with a clear focus on business outcomes (revenue, cost, efficiency) and engineering efficacy (velocity, quality, reliability)
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Translate business priorities into executable engineering outcomes while standardizing best practices across companies
Implement AI Powered SDLC across portfolio companies
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Drive adoption of modern AI-assisted development tools (coding copilots, prompt-driven workflows, automated testing and debugging)
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Establish Human + AI collaborative development workflows across engineering teams
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Improve engineering velocity through faster iteration cycles, automated documentation, and intelligent debugging
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Architect and build AI coding agents for code generation, testing, code review, and workflow automation
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Deliver AI-native developer experiences that materially improve productivity and engineering output
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Design and enforce guardrails for AI-generated code including validation, security, compliance, and policy controls
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Implement static and dynamic validation, security scanning, and vulnerability detection
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Ensure compliance with data protection standards (PII, secrets management, data leakage prevention)
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Define and enforce policy workflows, approvals, and governance controls
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Implement human-in-the-loop systems for critical decision points and risk management
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Ensure systems meet enterprise standards for reliability, auditability, and traceability
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Build evaluation frameworks to measure code correctness, test coverage, performance, and regression risk
End-to-End Delivery (Prototype Production) and M&A support
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Own end-to-end delivery from prototype to production, ensuring real-world impact
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Execute rapid 30–90 day cycles with production-grade outcomes
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Build systems that are scalable, observable, and maintainable by design
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Make clear scale / iterate / stop decisions based on measurable impact
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Evaluate AI and engineering maturity during acquisitions to inform investment decisions
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Define standards for AI-powered development, coding agents, and engineering platforms
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Accelerate post-acquisition integration through shared systems, playbooks, and reusable patterns
Technical Governance, Data Readiness & Responsible AI
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Establish AI development standards, security protocols, and governance frameworks
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applicable across diverse portfolio companies
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Partner with IT and data teams to assess data readiness and enable responsible access and
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integration for AI use cases
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Guide build-vs-buy decisions for AI capabilities, evaluating third-party tools against custom
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development with disciplined cost-benefit analysis
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Establish and enforce responsible AI and data-handling guidelines, including clear governance
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processes for approvals, risk review, and human-in-the-loop controls
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Ensure AI implementations align with data privacy regulations, security requirements, and
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compliance obligations
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Maintain documentation to support audit and regulatory readiness
Team Building, Change Management & Capability Development
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Build and lead a small, high-impact AI enablement team; coordinate with external specialists and vendors as needed
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Drive adoption through structured change management, training, and communications alongside solution delivery
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Build repeatable AI playbooks, frameworks, and documentation that enable portfolio company self-sufficiency over time
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Develop talent assessment frameworks to help portfolio companies build and retain AI/ML capabilities
Required Experience
- Advanced degree in Computer Science
- 10+ years of software engineering experience with recent hands-on experience
- 2+ years of engineering director experience, including managing managers
- Deep experience with AI infrastructure and LLMs
- Experience building large-scale query processing or distributed systems
- Strong track record of recruiting and growing technical teams
- Excellent collaboration and communication skills across global organizations
Strongly Preferred Experience
- Experience building coding agents or developer copilots
- Familiarity with: RAG (retrieval-augmented generation) Agent frameworks Prompt engineering and evaluation
- Experience in regulated industries (finance, healthcare, etc.)
- Experience in private equity, venture capital, or multi-company environments
- Background in: Developer productivity platforms Platform engineering or internal tooling
- Experience building AI centers of excellence or transformation programs
What You’ll Learn & Gain
- Ownership of AI strategy across multiple real businesses
- Direct influence with CEOs, CTOs, and investors
- Exposure to M&A and post-acquisition transformation
- Ability to define next-generation AI-powered software development
- Tangible, measurable impact on engineering and business outcomes
Who You Are
- A hands-on builder who writes code and ships systems
- Equally credible with engineers and executives
- Focused on real outcomes, not experiments or hype
- Strong in both system design and business impact
- Pragmatic—balances speed with safety and quality
- Comfortable operating across multiple companies simultaneously
- A change leader who drives adoption through trust, clarity, and results
What Success Looks Like (First 3–6 Months)
- AI-powered SDLC implemented across multiple teams
- Coding agents and copilots adopted in real developer workflows
- Measurable improvements in: Engineering velocity Code quality Test coverage
- 3–5 production-grade AI systems deployed per company
- Demonstrated ROI through: Cost reduction Productivity gains Revenue impact
Why Exa
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Permanent capital: build AI capabilities designed to last decades, not optimized for exits
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Decentralized model: portfolio CEOs own outcomes—you act as a strategic force‑multiplier, not a control layer
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Direct access to the CEO on AI strategy, acquisitions, and portfolio priorities
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The opportunity to shape what “great AI” looks like across an entire software portfolio
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A culture of high standards, low ego, discipline, and intellectual honesty
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Visible, tangible impact—your work will influence products, margins, and competitiveness in real time
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A chance to help build a new kind of software holding company, with AI as a core advantage
ML/AI Work links you to the employer's original posting — always verify the details there before applying.
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