ML/AIWork

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

  • Operate as a hands-on player-coach, partnering directly with CTOs and engineering teams

  • Build trust through deep technical contribution and delivered outcomes, not authority

  • Embed within teams to unblock execution, accelerate delivery, and improve engineering effectiveness

  • Drive AI adoption with a clear focus on business outcomes (revenue, cost, efficiency) and engineering efficacy (velocity, quality, reliability)

  • Translate business priorities into executable engineering outcomes while standardizing best practices across companies

Implement AI Powered SDLC across portfolio companies

  • Drive adoption of modern AI-assisted development tools (coding copilots, prompt-driven workflows, automated testing and debugging)

  • Establish Human + AI collaborative development workflows across engineering teams

  • Improve engineering velocity through faster iteration cycles, automated documentation, and intelligent debugging

  • Architect and build AI coding agents for code generation, testing, code review, and workflow automation

  • Deliver AI-native developer experiences that materially improve productivity and engineering output

  • Design and enforce guardrails for AI-generated code including validation, security, compliance, and policy controls

  • Implement static and dynamic validation, security scanning, and vulnerability detection

  • Ensure compliance with data protection standards (PII, secrets management, data leakage prevention)

  • Define and enforce policy workflows, approvals, and governance controls

  • Implement human-in-the-loop systems for critical decision points and risk management

  • Ensure systems meet enterprise standards for reliability, auditability, and traceability

  • Build evaluation frameworks to measure code correctness, test coverage, performance, and regression risk

End-to-End Delivery (Prototype Production) and M&A support

  • Own end-to-end delivery from prototype to production, ensuring real-world impact

  • Execute rapid 30–90 day cycles with production-grade outcomes

  • Build systems that are scalable, observable, and maintainable by design

  • Make clear scale / iterate / stop decisions based on measurable impact

  • Evaluate AI and engineering maturity during acquisitions to inform investment decisions

  • Define standards for AI-powered development, coding agents, and engineering platforms

  • Accelerate post-acquisition integration through shared systems, playbooks, and reusable patterns

Technical Governance, Data Readiness & Responsible AI

  • Establish AI development standards, security protocols, and governance frameworks

  • applicable across diverse portfolio companies

  • Partner with IT and data teams to assess data readiness and enable responsible access and

  • integration for AI use cases

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

  • development with disciplined cost-benefit analysis

  • Establish and enforce responsible AI and data-handling guidelines, including clear governance

  • processes for approvals, risk review, and human-in-the-loop controls

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

  • compliance obligations

  • Maintain documentation to support audit and regulatory readiness

Team Building, Change Management & Capability Development

  • Build and lead a small, high-impact AI enablement team; coordinate with external specialists and vendors as needed

  • Drive adoption through structured change management, training, and communications alongside solution delivery

  • Build repeatable AI playbooks, frameworks, and documentation that enable portfolio company self-sufficiency over time

  • 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

  • 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

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