Chief AI Office

10 hours ago


Toronto, Ontario, Canada Elumini Outdoing IT Full time

About the Client

The customer is a long-term owner and operator of established software companies serving specialized vertical markets. The organization focuses on acquiring resilient and proven products, with clear opportunities for sustained expansion, supporting them in strengthening their competitive position and leadership in their respective niches.

Its portfolio spans multiple categories of enterprise software, including human capital systems, fleet and mobility technologies, asset and infrastructure management platforms, digital healthcare solutions, document and workflow management tools, and other purpose-built software that serves regulated and mission-critical environments. The client is backed by experienced investors and advisors with a track record of building and expanding software businesses to significant levels of recurring revenue and driving lasting value creation.

About the Opportunity

As Chief AI Office, you'll be responsible for identifying, deploying, and scaling practical AI initiatives across a portfolio of vertical-market software businesses. The position is focused on driving measurable economic impact through AI, enhancing products, improving internal efficiency, and creating reusable AI approaches that can be adopted by multiple operating companies while preserving their autonomy.

This is not a centralized role of research or experimentation. Success is defined by speed to value, real-world adoption, and tangible business results achieved at the operating enterprise level.

Main Responsibilities

AI Strategy and Value Creation

  • Develop and execute a portfolio-wide AI strategy, aligned with long-term value creation, customer retention, and operational efficiency.
  • Identify high-impact AI applications across internal products and workflows, including pricing optimization, customer support, forecasting, data abandonment mitigation, compliance processes, and workflow automation.
  • Prioritize initiatives based on return on investment, technical feasibility, data readiness, and repeatability across industries.

Product and Platform Enablement

  • Partner with product leaders in operating companies to embed AI capabilities into existing software products, rather than rebuilding platforms.
  • Create shared AI frameworks, reusable patterns, and reference architectures that can be leveraged across the portfolio.
  • Support build-vs-buy decisions related to AI tools, models, and infrastructure.

Operating Enterprise Support (Decentralized Model)

  • Act as a trusted advisor to CEOs, CTOs, and product leaders across the portfolio.
  • Enable adoption through practical frameworks, manuals, and proven results, rather than centralized mandates.
  • Provide hands-on guidance during early pilots and support transitions from prototype to production.

Data, Governance and Risk Management

  • Establish pragmatic governance standards for AI covering data privacy, security, model risk, and regulatory requirements such as SOC 2 and GDPR, where applicable.
  • Ensure that AI-enabled solutions are transparent, auditable, and suitable for critical software environments.
  • Promote the responsible and sustainable use of AI, aligned with customer trust and long-term ownership principles.

Talent and Capacity Development

  • Build AI literacy across the portfolio through training programs, manuals, and shared best practices.
  • Support operating companies in hiring, assessing, and developing AI-related talent.
  • Collaborate closely with existing engineering and analytics teams, rather than creating a large, centralized AI organization.

Measures of Success

  • Demonstrable EBITDA improvement or cost savings driven by AI initiatives
  • Customer adoption and value gained from AI-enabled product capabilities
  • Reusable AI solutions successfully implemented across multiple operating companies
  • Speed from idea to pilot to production
  • Operational company satisfaction and voluntary adoption

Ideal Candidate Profile

Basic Qualifications

  • At least five years of experience in software, data, analytics, or AI roles, ideally in B2B SaaS software environments or vertical markets.
  • Proven experience in delivering production AI solutions with clear and measurable impact to the business.
  • Strong understanding of modern AI and machine learning approaches, including large language models, predictive analytics, and automation, without relying on use cases based on hype.
  • Experience working in decentralized, multi-company or private equity-backed contexts.
  • Ability to translate technical concepts into business value for non-technical stakeholders.

Preferred Experience

  • Experience in vertical market software such as ERP, industry-specific SaaS, or mission-critical systems.
  • Experience in product management, platform engineering, or analytics leadership roles.
  • Familiarity with long-term ownership or investment models of purchase and conservation.
  • Exposure to regulated or compliance-oriented industries.

Personal Attributes

  • Highly pragmatic, execution-focused, and ROI-oriented.
  • Comfortable influencing outcomes without formal authority.
  • Long-term thinker aligned with models of permanent ownership of capital.
  • Low-ego employee who respects the autonomy of the operating company.
  • Trend toward simplicity, maintainability, and durability rather than experimentation with no clear business value.


  • Toronto, Ontario, Canada The Mirillion Group Full time

    Chief Financial OfficerOur client is a well established Canadian professional services organization in the consulting engineering and infrastructure space. They are hiring a Chief Financial Officer to partner closely with the executive leadership team and board and help lead the next phase of growth.This is a high impact CFO role with meaningful influence...


  • Toronto, Ontario, Canada Klass Full time

    Role: CFOReports to: CEOLocation: GTA (Toronto office 3-4 days per week)Company: Rightsline, Type: Full Time / PermanentTravel: Up to 15%CompanySince 2012, Rightsline has been revolutionizing rights and royalties management with its leading IP Commerce SaaS platform. Trusted by global innovators like Disney, Amazon, Spotify, and the NFL, our solutions...

  • Chief Talent

    4 days ago


    Toronto, Ontario, Canada Manulife Full time

    Manulife Financial Corporation is a leading international financial services provider that helps people make their decisions easier and lives better. With our global headquarters in Toronto, Canada, we provide financial advice and insurance, operating as Manulife across Canada, Asia, and Europe, and primarily as John Hancock in the United States. Through...


  • Toronto, Ontario, Canada Moneris Full time $72,000 - $85,000

    Your Moneris Career - The OpportunityAs the Executive Assistant to the Chief Human Resources Officer (CHRO), you will be accountable for providing highly confidential administrative support and co-ordination to the CHRO ranging from routine to complex matters, managing the day-to-day administrative and confidential activities such as board materials,...


  • Toronto, Ontario, Canada SoundHound AI Full time

    Your Career, our Future—Together.Ready to join something big? At SoundHound AI, we bring voice, generative, and conversational AI together to transform how people interact with products and services. From voice-enabled vehicles to food ordering and customer support, our multilingual, omnichannel technology already impacts hundreds of millions worldwide.The...

  • Office Manager

    3 hours ago


    Toronto, Ontario, Canada Borderless AI Full time

    CompanyWe are on a mission to transform HR for everyone.Borderless AI builds AI agents for HR departments. The company leverages the power of generative AI to automate and accelerate routine tasks for HR teams such as employee onboarding, payroll, and paying international team members. Borderless AI's AI agents allow users to access the world's HR knowledge...


  • Toronto, Ontario, Canada LCBO Full time

    Established in 1927 as a provincial government agency, the LCBO is the largest retailer and wholesaler of beverage alcohol in the world. With a stellar local, national and international reputation as a best-in-class, customer-first, socially-responsible retailer and wholesaler, the LCBO prides itself in its commitment to supporting the local beverage alcohol...

  • Chief Legal Officer

    3 hours ago


    Toronto, Ontario, Canada Kingsdale Advisors Full time

    About Us: WeShall Investments is a premier mid-market private equity firm with a portfolio of investments across Canada, the U.S.A, and the Caribbean. WeShall does not just invest; we build bridges with a diverse range of leaders, investors, lenders, and entrepreneurs who share our passion for making a difference.  WeShall pursues profits with principles....


  • Toronto, Ontario, Canada LCBO Full time $56,430 - $93,414

    Location Address:100 Queens Quay East, 9th Floor, TorontoNumber of Openings:1Pay:$56, $93,414.00Job Posting Description:This is an onsite role #LI-OnsiteAre you interested in supporting the Chief People Officer during a unique and transformative time at the LCBO? Reporting to the CPO, you will provide a variety of confidential, accurate and efficient...


  • Toronto, Ontario, Canada RioCan Full time

    Who We Are For over 30 years, our entrepreneurial mindset and strategic vision have fueled our growth into one of Canada's largest and most successful REITs. Our retail-focused and mixed-use portfolio reflects our commitment to creating vibrant community spaces where people want to shop, live, work, and play. We take pride in our strong legacy while...