At Omegro, we believe that the strength of our portfolio is a direct reflection of our people. As part of a global ecosystem (CSU:TSX), we offer the stability of a permanent home combined with the agility of a decentralized network. We are looking for experts who are passionate about operational excellence and eager to contribute to a culture that prioritizes professional development, flexible collaboration, and the shared success of our global network of businesses.
Position Overview:
The AI Enablement & Communities Lead drives AI capability development across the Omegro portfolio and ensures AI thinking is embedded throughout the Omegro Operating System (OOS). This role combines genuine technical depth with strong facilitation and adult learning instincts — credible with R&D and product teams, equally effective running workshops with executive leaders. The role owns the functional community network, builds the AI playbook and training curriculum, and ensures that AI adoption compounds over time through people and programmes rather than requiring the CoE to touch every initiative directly.
Duties & Responsibilities:
Capability Development & Training
- Design and deliver AI-first methodology training for technical and non-technical staff across the portfolio, covering prompting, agentic workflows, AI tool adoption, and AI-first software development practices.
- Build role-specific learning pathways for engineering, product, finance, M&A, people, and customer success functions.
- Manage AI learning content on Percipio and Omegro SharePoint, ensuring content remains current as the AI landscape evolves.
- Develop and maintain the Omegro AI Playbook: best practices, templates, reusable frameworks, and success stories from across the portfolio.
Omegro Operating Systems Integration
- Embed scalable AI capability development into existing OOS programmes, aligning technical enablement with our broader learning, development, and talent management framework to support a people‑first, continuous‑learning culture.
- Work with Group Leaders and Portfolio Chief People Officers to integrate AI-first thinking into performance management and development conversations.
- Develop AI-specific modules and content assets that can be deployed across all Omegro learning and collaboration events including Leaders' Summit, Thrive, and P2P sessions.
Community Management
- Own and manage the Omegro functional AI community network across nine functions and two portfolios — coordinating one community lead per function per portfolio.
- Facilitate fortnightly drop-in sessions across time zones, ensuring sessions are recorded and accessible.
- Identify, develop, and support AI Champions within each BU — ensuring they have the skills, resources, and mandate to drive adoption in their own teams.
- Drive inter-functional knowledge sharing, surfacing cross-BU opportunities and connecting teams working on similar problems.
AI Maturity Assessment
- Design and administer the Omegro AI maturity assessment framework across BUs and functions.
- Track capability progression over time, identifying where BUs are excelling and where targeted support is needed.
- Produce monthly capability and community reports for Omegro leadership and Volaris reporting cadence.
Cultural Change
- Champion the AI-first mindset across Omegro, working with the VP of AI Transformation to inspire and motivate leaders and teams.
- Identify and address cultural barriers to adoption — making space for the productivity J-curve and building psychological safety around AI experimentation.
- Curate and amplify success stories from across the portfolio to build belief and competitive energy.
Required skills and experience:
- Technical fluency in modern AI tools, frameworks and practices: LLMs (Claude and CoPilot in particular), prompt engineering, AI agents, and workflow automation — enough to build credibly with R&D teams, not just present to them. Working knowledge of SharePoint for content management and community delivery is expected.
- Demonstrable experience in capability building, L&D, or technical enablement at scale, ideally across multiple business units or in a consulting or portfolio context.
- Proven track record designing and delivering training and change programmes that drive measurable behaviour change. You should be able to point to specific educational campaigns or enablement programmes you have executed and their measured results.
- Strong facilitation skills — able to run a hands-on technical workshop in the morning and an executive strategy session in the afternoon.
- Experience designing maturity assessments or capability frameworks, including measurement and reporting.
- Understanding of software development practices and the SaaS product lifecycle — sufficient to engage R&D leads meaningfully.
- Strong written communication skills for playbook development, content creation, and reporting.
- Experience working across multiple business units or in a portfolio, consulting, or transformation context is highly desirable. Candidates who can demonstrate coordination of large multi-programme efforts across distributed teams will stand out. Programme management certifications (PMP, SAFe, CSM, or equivalent) are a strong asset.
Requirements
- The role can be performed via hybrid or remote in Toronto (or greater surrounding area) requiring you to have the right to work, and additionally the ability to travel domestically and internationally.
Values
These values are important to us in the Omegro Portfolio:
- Humble: At Omegro, we define success collectively and work without ego. We share credit and put the company and team before ourselves. We believe in being learn-it-alls rather than know-it-alls, and we avoid any form of arrogance or ego-driven behaviour.
- Hungry: We are tenacious and personally accountable, always playing to win and learn. We believe in hard work and continuous improvement, constantly seeking more and striving for excellence. Our intrinsic motivation drives us to achieve high standards and always aim for better.
- Smart: We are great listeners and have the right people on the bus. We embrace a growth mindset, ask questions, read the room, and view feedback as a gift. We make data-driven decisions and are self-aware, ensuring that we can look back and be proud of our actions.
We welcome applicants with a wide range of experiences and perspectives. We hire based on qualifications and job-related criteria and do not discriminate on legally protected grounds. Accommodations are available throughout the recruitment process upon request.
As part of our commitment to transparency, we use artificial intelligence (AI) tools to assist in various stages of our recruitment process. These tools are designed to improve efficiency, reduce bias, and enhance candidate experience. All decisions regarding hiring are made by qualified human professionals, and we continuously monitor our AI systems to ensure fairness and compliance with applicable regulations.
The total remuneration package for this role is circa $105K - $120K.
The salary range provided is intended as a general guideline. Final compensation will be determined based on the successful candidate’s skills, experience, and alignment with the role.
If this role sounds well aligned with your experience and values, please apply through LinkedIn.
