Or a VP Engineering who wants to take the next big step Our client is an established technology company with nearly 30 years of experience delivering innovative software solutions to the skilled trades sector across North America. With a strong customer base, deep industry expertise and a proven track record, the organization is entering an exciting new chapter of growth and transformation.

As the business evolves from custom software development to a scalable, product-driven SaaS model, it is investing in technology modernization, AI-driven innovation and new opportunities for growth. Its portfolio includes enterprise SaaS solutions and immersive XR training technologies, offering a unique opportunity for a technology leader to shape the company's future and make a meaningful impact.

Their business includes two core technology offerings: 1. SaaS Management Platform A comprehensive SaaS platform serving skilled trades unions, apprenticeship programs, and trade schools. The platform supports member management, dues collection, job dispatch, communications, reporting, and administrative workflows, alongside apprenticeship and education management functions such as student records, class scheduling, curriculum tracking, attendance, and evaluations.

2. XR Training and Simulation Platform An immersive training and simulation platform that uses virtual reality, mixed reality, motion capture, volumetric video, and AI to create realistic, interactive learning experiences for the skilled trades. The platform enables organizations to simulate complex work environments, safety procedures, and hands‑on technical training in a controlled virtual setting.

Our client’s customers rely on them for dependable systems that support critical operational workflows, member services,



education, and training. As they continue to scale, they are looking for a senior technology leader who can bring strategic direction, operational discipline, technical depth, and practical AI leadership to their engineering organization.

Role Summary We are seeking a CTO / VP Engineering who is as passionate about developing people as they are about technology, to lead our engineering organization through its next stage of growth. This is a hybrid executive and operational leadership role that calls for an inspirational, empathetic and collaborative leader who brings out the best in their team. They recognize that great technology is built by great teams and measure their success through the growth, performance and achievements of the people they lead.

The ideal candidate can contribute to company strategy at the leadership table while also driving execution across engineering, architecture, platform reliability, security, AI governance, and product delivery.

This person will be responsible for ensuring that our technology organization is scalable, accountable, secure, and aligned with business priorities. They will help shape the technical vision for our SaaS platforms and XR/AI products while improving delivery predictability, team structure, engineering practices, and long‑term product quality.

The successful candidate will be comfortable working in a growing,



entrepreneurial technology business where strategic thinking and hands‑on involvement go hand in hand. They should be able to move fluidly between product strategy, engineering management, customer impact, architecture decisions, AI governance, and team coaching.

Key Responsibilities

Own and evolve the overall technology strategy across the company’s SaaS and XR/AI product portfolio.

Lead the engineering organization, including software development, architecture, infrastructure, DevOps, QA, technical support escalation, and AI‑related engineering practices.

Partner with the CEO, product leadership, customer success, sales, and operations to align technology decisions with business goals.

Establish clear engineering priorities, delivery processes, accountability structures, and performance expectations.

Improve predictability of product delivery through better planning, estimation, roadmap execution, release management, and communication.

Balance recent product development, customer‑specific needs, technical debt, security, scalability, and platform reliability.

Provide technical leadership for multi‑tenant SaaS architecture, integrations, data management, reporting, automation, and platform modernization.

Guide the continued development of agentic AI features and immersive XR training capabilities.

Oversee engineering budgets, tooling decisions, vendor relationships, infrastructure costs, and AI‑related cost controls.

Build, mentor, and manage a high‑performing engineering team.

Define and track engineering performance metrics.

Ensure the company maintains appropriate standards for security, privacy, uptime,

📌 Chief Technology Officer (Winnipeg)
🏢 Ari Agency Executive Search and Digital Recruitment
📍 Winnipeg