Chief Technology Officer 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 new 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, auditability, and customer trust.
- Represent the technology function in executive planning, customer conversations, strategic partnerships, and board or investor discussions as needed. AI Leadership and Governance AI is already an important part of both our internal development practices and our customer-facing product strategy. This role will be responsible for ensuring that AI is used effectively, securely, and responsibly.
- Define the company’s practical AI strategy across internal operations and external product features.
- Establish governance for AI-assisted software development, testing, documentation, support, and engineering workflows.
- Ensure internal AI tools are used in ways that improve productivity without compromising intellectual property, customer data, security, or code quality.
- Lead the architecture and governance of agentic AI features in the company’s SaaS and XR products.




- Create standards for AI model selection, prompt management, evaluation, logging, observability, cost management, and human oversight.
- Ensure AI-enabled features are designed for reliability, transparency, auditability, and customer trust.
- Partner with product leadership to identify high-value AI use cases that solve real customer problems rather than pursuing AI for novelty.
- Implement guardrails for privacy, data access, hallucination risk, permissions, workflow automation, and customer-specific data boundaries.
- Evaluate vendors, models, frameworks, and AI infrastructure options pragmatically.
- Establish internal policies for the safe use of generative AI, agentic workflows, code generation, and customer data.
- Help the organization distinguish between experimental AI capabilities and production-grade AI features. The ideal candidate understands that AI adoption requires more than enthusiasm. It requires governance, testing, security, user experience design, operational monitoring, and clear business value. People Management The CTO / VP Engineering will be responsible for developing a strong, accountable, and collaborative engineering culture.
- Lead, coach, and mentor software developers, technical leads, QA resources, DevOps/infrastructure personnel, and other technology team members.
- Clarify roles, responsibilities, decision rights, and expectations within the engineering organization.
- Build career development paths and performance management practices for technical staff.
- Hire, onboard, and retain strong engineering talent.
- Create a culture of ownership, accountability, continuous improvement, and practical problem-solving.
- Support technical leads and managers in improving estimation, delivery planning, code quality, and team communication.
- Identify skills gaps and make recommendations for hiring, training, outsourcing, or team restructuring.
- Foster collaboration between engineering, product, customer success, implementation, and support teams.
- Encourage high standards without creating unnecessary bureaucracy.
- Address underperformance directly and constructively.
- Promote a low-ego, high-trust environment where people can challenge ideas, improve systems, and deliver meaningful outcomes. Technical Leadership This role requires enough technical depth to make sound architectural decisions, challenge assumptions, evaluate trade-offs, and guide the team through complex product and platform decisions.
- Own the technical architecture and long-term scalability of the company’s product platforms.
- Provide leadership across SaaS architecture, cloud infrastructure, APIs, integrations, data models, security, reporting, performance, and system reliability.
- Guide architectural decisions for multi-tenant SaaS environments, customer-specific configurations, and integration-heavy workflows.
- Lead modernization efforts where appropriate, while avoiding unnecessary rewrites or over-engineering.
- Establish standards for code quality, automated testing, CI/CD, observability, documentation, and production readiness.
- Ensure systems are maintainable, secure, performant, and cost-effective.
- Manage technical debt through clear prioritization and business-aligned trade-off decisions.
- Provide technical guidance for the XR development platform, including immersive content workflows, AI-enabled training scenarios, data capture, and platform extensibility.
- Evaluate build-versus-buy decisions and vendor/platform choices.
- Ensure engineering practices support both innovation and operational stability. The ideal candidate does not need to be the strongest individual contributor in every technology area, but must be technically credible, architecturally sound, and able to lead senior technical staff effectively. Product and Customer Partnership The CTO / VP Engineering will work closely with product, customer success, implementation, and sales teams to ensure that technology supports customer value and business growth.
- Partner with product leadership to translate business priorities and customer needs into achievable technical plans.
- Help prioritize roadmap items based on customer value, revenue impact, technical complexity, risk, and strategic importance.
- Support customer conversations where senior technical credibility is required.
- Help evaluate large customer requests, custom development opportunities, integrations, and implementation risks.
- Balance the needs of individual customers with the long-term health of the core product.
- Ensure technical teams understand the operational realities of unions, trade schools, apprenticeship programs, and skilled trades training environments.
- Improve communication between engineering and customer-facing teams.
- Help define product capabilities that are scalable, configurable, and repeatable rather than overly customized.
- Support go-to-market efforts for AI-enabled and XR-based training capabilities.
- Ensure that customer commitments are realistic, well-understood, and aligned with engineering capacity. Security, Risk, and Compliance Our customers rely on us to manage sensitive operational, member, training, and organizational data. This role will be responsible for maintaining and improving the company’s security and risk posture.




- Establish and maintain security standards across application development, infrastructure, data management, AI usage, and vendor selection.
- Ensure appropriate controls are in place for access management, authentication, authorization, data privacy, backups, disaster recovery, and incident response.
- Oversee secure software development practices, including code review, dependency management, vulnerability remediation, and penetration testing where appropriate.
- Implement governance for the use of customer data in AI systems, analytics, testing, support, and development workflows.
- Ensure customer data boundaries are respected across multi-tenant SaaS environments.
- Support compliance with contractual, privacy, and security requirements.
- Develop policies for data retention, audit logging, administrative access, and production support access.
- Maintain practical incident response and business continuity plans.
- Communicate clearly with customers and internal stakeholders about security, risk, and technical controls.
- Balance appropriate governance with the needs of a growing, pragmatic software company. Qualifications / Experience The ideal candidate will have many of the following

qualifications:
- Prior experience as a CTO, VP Engineering, Head of Engineering, Director of Engineering, or similar senior technology leader.
- Experience leading technology teams in a SaaS, product software, or platform company.
- Proven ability to manage both strategy and execution in a growing company environment.
- Strong understanding of modern software architecture, cloud infrastructure, application security, APIs, data platforms, and DevOps practices.
- Experience managing engineering teams through scale, process improvement, modernization, or product growth.
- Demonstrated ability to improve delivery predictability, engineering quality, release processes, and team accountability.
- Experience with multi-tenant SaaS products, configurable platforms, customer-specific workflows, and enterprise integrations.
- Practical experience applying AI tools within the software development lifecycle.
- Understanding of generative AI, agentic workflows, model evaluation, AI governance, and responsible AI implementation.
- Experience with immersive technologies, XR, VR, MR, simulation, motion capture, volumetric video, or training platforms is a strong asset but not required.
- Ability to work effectively with executive leadership, product managers, engineers, customer-facing teams, and external stakeholders.
- Strong business judgment, including comfort with budgets, trade-offs, vendor decisions, and resource allocation.
- Experience in workforce development, education technology, labor unions, skilled trades, associations, or member-based organizations is an asset.
- Excellent communication skills, including the ability to explain complex technical concepts to non-technical stakeholders.
- Track record of building high-performing teams and developing technical leaders. Leadership Traits We are looking for a leader who is:
- Strategic and practical — able to define long-term direction while making realistic near-term decisions.
- Commercially minded — understands how technology choices affect revenue, margins, retention, customer satisfaction, and company growth.
- Operationally disciplined — values planning, accountability, metrics, followthrough, and delivery predictability.
- Technically credible — can engage deeply enough with architecture and engineering decisions to guide the team effectively.
- AI-aware and governance-oriented — understands both the chance and the risks of AI.
- Low ego and collaborative — listens well, builds trust, and works effectively across departments.
- Clear and direct — communicates expectations, risks, trade-offs, and decisions plainly.
- Customer-aware — understands that technology exists to solve real customer and business problems.
- Accountable — takes ownership of outcomes and expects the same from the team.
- Balanced — knows when to move fast, when to reduce risk, and when to invest in long-term platform health.
- Comfortable in a growing company — able to operate without excessive structure while helping create the right amount of structure. Success Measures Success in this role will be measured by improvements in engineering execution, product quality, team performance, and strategic technology alignment.
- Improved roadmap predictability and delivery reliability.
- Clearer engineering priorities and better alignment with business goals.
- Reduced technical debt in high-risk or high-friction areas.
- Improved system stability, uptime, performance, and incident response.
- Stronger release management, testing, QA, and deployment practices.
- Better visibility into engineering capacity, progress, risks, and trade-offs.
- Increased productivity through effective and responsible use of AI tools.
- Clear governance for AI-assisted development and customer-facing AI features.
- Improved security posture and customer confidence.
- Stronger collaboration between engineering, product, customer success, and implementation teams.
- Better team structure, role clarity, performance management, and career development.
- Successful scaling of SaaS platforms and XR/AI product capabilities.
- Improved ability to evaluate, prioritize, and deliver customer-requested enhancements without compromising core product strategy.
- Effective management of technology spend, cloud infrastructure costs, AI usage costs, and vendor relationships. The company offers a competitive executive compensation package, including base salary, bonus and equity participation, providing an opportunity to share in the long-term success of the business.

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