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Head of AI - Group Strategy & Execution; Agency

Job in Morden, Winnipeg, Manitoba, Canada
Listing for: Fluent Software
Full Time position
Listed on 2026-02-20
Job specializations:
  • Software Development
    AI Engineer, Machine Learning/ ML Engineer
Job Description & How to Apply Below
Position: Head of AI - Group Strategy & Execution (Agency Application )
Location: Morden

Description

Fluent Software Group is seeking a VP of AI Enablement 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.

#Fluent Software

#J-18808-Ljbffr
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