Head of AI - Group Strategy & Execution (Agency Application Canada)

Role Overview 

Fluent Software Group is seeking a Head of AI to define and operationalize a group-wide AI strategy across 30+ companies. This is a high-impact leadership role designed for a hands-on builder who can move from strategy to execution and ship real AI capabilities into production environments. 

Core Mandate 

• Define and execute a group-wide Agentic AI strategy across 30+ SaaS businesses, focused on deploying autonomous, decision-capable systems that drive measurable revenue growth and operational efficiency. 

• Design and operationalize production-grade agent architectures, including multi-agent systems, orchestration layers, tool use, memory frameworks, and secure LLM integrations. 

• Own ROI accountability for agent deployments, prioritizing high-impact use cases where autonomous agents meaningfully reduce cost, increase speed, or unlock new product value. 

• Establish scalable infrastructure standards, including data pipelines, evaluation frameworks, guardrails, monitoring, and MLOps for agent lifecycle management. 

• Embed agents directly into products and internal workflows, moving beyond copilots to systems that can execute, reason, and act within defined boundaries. 

• Create cross-portfolio leverage, developing repeatable agent frameworks that can be adapted across heterogeneous tech stacks and business models. 

• Build and scale a central Agentic AI capability, influencing CEOs and product leaders while shaping long-term competitive advantage at the group level. 

Profile 

• Proven experience implementing AI/ML solutions in production SaaS environments. 

• Hands-on technical capability (comfortable reviewing architecture, models, and code-level decisions). 

• Experience shipping AI features that drive measurable commercial impact. 

• Builder mindset: executes, prototypes, and drives implementation. 

• High agency and self-starter; comfortable operating in ambiguity. 

• Creative and systems-level thinker who identifies leverage opportunities. 

• Strong problem solver with commercial acumen. 

• Confident influencing senior stakeholders and driving alignment across organizations. 

Agency RFP Requirements 

Agencies responding to this mandate should demonstrate: 

• Access to passive, high-caliber AI talent. 

• Clear search strategy including target geographies and company profiles. 

• Compensation benchmarking insights. 

• Defined timeline and success fee structure. 

• Replacement guarantee terms. 

Why Fluent?  

• High Autonomy, High Impact: Own your work from Day 1  

• Serious Career Growth: Exposure to M&A, integration, and scaling operations  

• Learning-Driven Culture: We invest heavily in talent development  

• Entrepreneurial Energy: No two days look the same  

• Competitive Offer: Compensation, Health, dental, vision, PTO, and more  

• Team-First Mindset: Regular events, collaboration, and global connections  

Join Us  

Help us scale incredible software companies—without losing their entrepreneurial edge. At Fluent and Valsoft, you’ll make a real impact from Day 1.  

#FluentSoftware