Director of Technology

Job Description: 

Position Title: Director of Technology 

Location: Remote (Canada) 

Reports To: President 

Team: R&D

About LilYPad

LilYPad POS is a Canadian SaaS company serving family entertainment centers—from trampoline parks to indoor play cafés—with a powerful, purpose-built point-of-sale platform. As we continue to grow, we’re entering an exciting phase of technical transformation and scalability.

We’re actively enhancing our product architecture, moving workloads to AWS, and modernizing how we deploy and manage applications. This role is central to that journey, offering a rare opportunity to shape the infrastructure, technical culture, and future direction of the business.

Why This Role Matters

LilYPad is at a pivotal point. We’re evolving from legacy infrastructure toward a modern, containerized architecture hosted on AWS. With that comes the chance to lead meaningful changes in how we deploy, secure, and scale our platform.

The technical foundation is being laid now—and this role is about building it right. You'll be the one to help us shift from reactive to proactive, from manual to automated, and from fragmented to unified across our systems and teams.

Role Overview

As Director of Technology, you will lead the charge in stabilizing and scaling LilYPad’s technology environment. This hybrid leadership role combines DevOps expertise, software architecture, and hands-on engineering with the strategic vision to guide our long-term roadmap.

You’ll collaborate closely with the President, Director of Operations, QA, Product, and Customer Success teams to ensure that our systems are robust, efficient, and built for long-term success.

This is a successor-track position, with visibility into executive decision-making and the potential to evolve into broader organizational leadership.

Key Responsibilities Infrastructure & DevOps

• Implement monitoring, alerting, and recovery systems so issues are caught internally before customers ever notice.
• Lead our AWS migration and infrastructure modernization efforts, including containerization of core services.
• Automate backups, patching, certificate renewals, and deployments across environments.
• Overhaul CI/CD pipelines with tools like GitHub Actions, supporting robust testing and rollback procedures.
• Introduce and manage Infrastructure as Code using Terraform or similar tools.
• Own platform security and PCI compliance in collaboration with stakeholders and partners

Technical Leadership

• Provide architectural direction as we modernize core services and transition toward containerized applications.
• Mentor developers and foster best practices in scalable, secure, and maintainable code.
• Partner with QA to embed performance, testing, and resiliency into our engineering lifecycle.

Strategy & Team Building

• Define and lead the long-term technology roadmap across product, infrastructure, and automation.
• Translate business goals into prioritized, actionable engineering initiatives.
• Build, grow, and manage a high-performing technical team over time.

What We're Looking For

Must-Have Experience

• 5–10 years in software development, DevOps, or infrastructure engineering.
• Proven DevOps expertise with AWS, Linux environments, CI/CD, monitoring, and automation.
• Strong PHP/Laravel and MySQL experience in a production SaaS context.
• Ability to stabilize and secure legacy environments while leading a transition to modern cloud-native infrastructure.
• Clear, confident communicator with experience across technical and business teams.
• Availability for occasional after-hours deployments or critical incident response.

Leadership Traits

• Ownership mindset—you fix what breaks, then improve the system that allowed it to break.
• Strategic and execution-oriented—you see the big picture but get the work done.
• Self-starter who creates clarity and alignment across teams.
• Leadership ambition—you’re capable of stepping into broader responsibilities over time.

Nice to Have

• AWS Certification or Kubernetes experience
• Background in POS systems or customer-facing SaaS
• Familiarity with PCI DSS and technical audit requirements
• A demonstrated interest in emerging technologies—particularly AI and automation—with a mindset for leveraging innovation to drive meaningful operational improvements and customer value

Why Join LilYPad POS?

• High-impact role: You'll make our platform more stable, secure, and scalable.
• Executive growth: This is a key succession path within the company.
• Customer relevance: What you build directly affects real businesses every day.
• Autonomy with support: You’ll have freedom to lead, backed by a collaborative team and the CSI network.
• Remote flexibility: Work where you’re most productive—with high accountability and trust.

#LI-PP1

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More About Jonas Software:

Jonas Software is the leading provider of enterprise management software solutions to the Country and Golf Clubs, Foodservice, Construction, Fitness & Sports, Attractions, Salon & Spa, Education, Radiology/Laboratory Information Systems, and Product Licensing industries. Within these vertical markets, Jonas is made up of over 65 distinct brands, which are respected and leaders within their own domain.

Jonas’ vision is to be the branded global leader across the aforementioned vertical markets and to be recognized by customers and respective industry stakeholders as the trusted provider of ‘Software for Life’ and as an ambassador for technology, product innovation, quality, and customer service.

Jonas Software is the valued technology partner of over 60,000 customers worldwide in more than 30 countries. Jonas employs over 2,000 skilled individuals consisting of a cross-section of industry experts and technology professionals.  Jonas is headquartered in Canada and also operates offices throughout North America, the United Kingdom, Europe, Australia New Zealand and Africa.  Jonas is a 100% owned subsidiary of Constellation Software Inc., headquartered in Toronto and traded on the S&P/TSX 60.