Head of AI Enablement and Emerging Technology

Chrysalis

$120K — $180K *
Enterprise Technology
8 - 10 years of experience
Job Overview by Ladders

Qualifications

  • 10+ years in senior technology or enterprise transformation leadership
  • Proven track record of leading large-scale AI implementations
  • Expertise in shaping operating model and organizational design
  • Strong financial acumen; experience building investment cases
  • Ability to inspire and promote AI adoption
  • Deep knowledge of AI platforms and emerging technology ecosystems

Responsibilities

  • Define and execute a company-wide AI strategy
  • Align AI initiatives with long-term corporate goals
  • Serve as executive sponsor for transformation initiatives
  • Redesign workflows and team structures for an AI-driven organization
  • Identify productivity gains through AI integration
  • Collaborate on ROI models for AI investments
  • Lead pilot projects and ensure governance compliance

Benefits

  • Comprehensive benefits package for employees and families
  • Flexible hybrid working environment with generous vacation
  • Retirement plan options with matching contributions
  • Family-oriented leave policies including salary top-ups
  • Annual paid cultural days for religious or cultural observances
  • Up to 6 paid days off for volunteering or learning
  • Seven-week sabbatical after seven years of employment
Full Job Description
Reporting to: Founder & CEO

About the Role

We are seeking a Head of AI Enablement and Emerging Technology to lead enterprise-wide AI transformation across the organization. Reporting directly to the Founder & CEO, this role will shape how we integrate AI into our strategy, operating model, workforce design, and financial planning.

This is not an IT infrastructure role. It is a cross-functional executive mandate focused on enabling responsible innovation, redesigning how we work in an AI-enabled environment, and ensuring measurable business impact.

You will partner closely with ETS, Risk & Compliance, R&D, People & Culture, and Finance to embed AI into the core of how we operate and scale.

Key Responsibilities

Enterprise AI Strategy
  • Define and execute the company-wide AI and emerging technology strategy.
  • Align AI initiatives with corporate priorities and long-term growth objectives.
  • Serve as the executive sponsor for AI transformation initiatives.

Organizational Design & Operating Model Evolution
  • Partner with the Lead of People & Culture, to redesign workflows, roles, and team structures in an AI-enabled organization.
  • Identify opportunities to increase speed, autonomy, and productivity through AI integration.
  • Support leadership in workforce planning and capacity modeling.

Financial & Investment Alignment
  • Collaborate with Finance to build ROI models and investment frameworks for AI initiatives.
  • Prioritize initiatives based on measurable value creation.
  • Align AI transformation efforts with budget planning and capital allocation.

Innovation & Implementation
  • Lead enterprise AI pilots and scaling initiatives.
  • Evaluate tools and platforms in partnership with ETS and Risk & Compliance.
  • Ensure responsible, secure deployment aligned to governance standards.

Governance & Risk Partnership
  • Co-develop AI guardrails and approval frameworks.
  • Balance innovation with privacy, compliance, and security requirements.
  • Reduce shadow AI risk through structured enablement.

Adoption & Cultural Enablement
  • Build executive and organizational AI literacy.
  • Develop internal playbooks and best practices.
  • Foster a culture of experimentation and continuous improvement.

Qualifications
  • 10+ years in senior technology, innovation, or enterprise transformation leadership.
  • Demonstrated knowledge in leading AI implementation at scale.
  • Experience influencing operating model and organizational design decisions.
  • financial acumen with experience building investment cases.
  • Ability to inspire others and champion AI adoption
  • Deep understanding of AI plat1forms, automation, and emerging technology ecosystems.

What Success Looks Like
  • AI strategy embedded into strategic planning.
  • Measurable productivity, revenue, or cost optimization gains.
  • AI integrated into workforce and operating model decisions.
  • Clear governance model with reduced risk exposure.
  • Metric of number of AI agents in production creating measurable impact
  • Strong cross-functional alignment across Technology, People, and Finance.

What We Offer:
  • Begin your journey with a competitive starting salary!
  • Enjoy peace of mind with a comprehensive benefits package for you and your entire family.
  • Embrace work-life harmony with a flexible hybrid working environment, generous vacation and trusted sick leave program.
  • Invest in your future with our RRSP/401K/PF and Share Ownership plans. What's even better? We offer a match program!
  • We care about your family, offering maternity, adoption, and paternity leave salary top ups as well as ten "New Baby Days" for all parents welcoming a new child into their life.
  • Enjoy a "Cultural Day" off annually to celebrate a day of religious or cultural significance.
  • Give back with up to 6 days of paid time off annually for volunteering or personal learning.
  • We believe in the value of taking time to refresh, re-energize, and reflect on your career journey. Employees are granted a seven-week sabbatical after every seven years of employment!

We are a hybrid work environment, remote and in-office for all employees in an office city.

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