About the Role

Mine & Yours is at a pivotal stage of growth. We’ve built a strong foundation as a leader in luxury resale, and we’re now scaling into our next phase. Technology - particularly AI, automation, and modern systems design - will be a core unlock in how we get there.

We’re looking for a Fractional Chief Technology Officer (CTO) who doesn’t just advise from the sidelines, but actively builds, ships, and drives execution.

This is a hands-on leadership role for someone who can translate business problems into technical solutions, architect scalable systems, and directly drive the implementation of AI-powered workflows and automation across the company. You will be responsible for reimagining how Mine & Yours operates through technology, with a strong focus on AI, automation, and modern systems design.

From day one, you will identify inefficiencies, manual workflows, and missed opportunities — then design and implement solutions that unlock speed, scale, and intelligence across the business. A core mandate of this role is to build and scale an AI-enabled operating system for the company, leveraging AI agents, automations, and intelligent workflows to reduce manual effort, improve operational efficiency, and accelerate decision-making.

You will also define and evolve the long-term technology architecture of the business, ensuring our systems are scalable, well-integrated, and built for continuous innovation.

This position can be completed remotely.

Responsibilities:

Technology Vision, AI Strategy & Roadmap

• Define and own the end-to-end technology and AI strategy
• Build a roadmap that prioritizes high-impact automation and system improvements
• Identify where AI, automation, and data can create competitive advantage
• Serve as the senior technology voice within the leadership team
• Translate business goals into scalable technical solutions

AI Systems, Agents & Automation (Core Focus)

• Design and implement AI-powered workflows and agent-based systems across the business
• Build, integrate, and deploy internal AI solutions
• Identify opportunities to reduce manual work through automation
• Build systems that improve:
• Inventory decision-making intelligence
• Pricing optimization
• Client personalization and clienteling
• Marketing efficiency and targeting
• Operational execution speed and accuracy
• Continuously test, iterate, and scale high-ROI AI use cases

Internal Tools & Custom Software Development

• Design and oversee development of custom internal tools where off-the-shelf solutions are insufficient
• Bring systems from concept to production
• Improve workflows across:
• Buying and inventory management
• Retail operations
• E-commerce operations
• Finance and reporting
• Ensure tools are intuitive, adopted, and actively used by teams

Systems Architecture, Integrations & Optimization

• You will own the full technology ecosystem - from audit to optimization to transformation.
• Conduct a full audit of current systems and workflows
• Identify underused, redundant, or limiting platforms
• Define a clear “future state” architecture for the business
• Optimize existing systems before introducing new ones
• Ensure teams are fully enabled to use systems effectively

You will be responsible for ensuring our ecosystem is:

• Fully integrated (not fragmented)
• API-first and scalable
•Designed for both operational efficiency and innovation

Key systems include:

•Shopify and e-commerce stack
• POS, RFID, and inventory systems
• CRM and clienteling tools
• Marketing and analytics platforms

E-Commerce & Client Experience Innovation

• Improve digital shopping experience end-to-end
• Drive conversion improvements through data and experimentation
• Explore AI-driven personalization and recommendation systems
• Enhance omni-channel and clienteling capabilities
• Identify new ways to elevate the customer experience through technology

Data, Reporting, & Decision Intelligence

Build a stronger, more reliable data foundation across the business
Improve reporting, dashboards, and visibility for leadership and teams
Enable faster, higher-quality decision-making through data systems
Develop models and frameworks for:
Inventory health
Pricing strategy
Customer behaviour and segmentation

Qualifications

10+ years of experience in technology leadership, software engineering, or systems architecture roles
Proven experience building and shipping production systems (not just advising or consulting)
Hands-on experience designing and implementing AI-driven solutions, automation, or agent-based systems
Strong background in modern software architecture, APIs, and system integrations
Demonstrated ability to translate business problems into scalable technical solutions
Experience working in fast-paced, high-growth environments (startup or scale-up strongly preferred)
Strong understanding of data systems, analytics, and decision-support infrastructure
Experience with e-commerce, retail, inventory, or multi-channel consumer businesses is an asset
Comfortable operating in environments with ambiguity, speed, and evolving priorities
Ability to balance strategic thinking with hands-on execution
Strong communication skills and ability to influence senior leadership without formal authority
Proven track record of delivering measurable operational or revenue impact through technology