Accounting technology strategist shaping Dext’s Canadian fintech products and North American market strategy. Translating accounting regulations and workflows into compliant, market - leading software solutions.
About the role
- Chief Technology Officer modernizing Innovative Computer Solutions’ retail POS, ecommerce, and payments platform. Leading AI-driven engineering transformation, cloud modernization, cybersecurity, and distributed teams.
Responsibilities
- Own technology strategy, software engineering, architecture, infrastructure, DevOps, and delivery across the organization
- Set product direction and roadmap prioritization aligned with commercial priorities
- Lead platform modernization and migration off the legacy platform
- Evaluate rewrite, replatform, refactor, and phased-modernization options and recommend target architecture and delivery path
- Establish CI/CD pipelines, observability, automation, cloud and hosting modernization, migration controls, and rollback readiness
- Embed AI tooling into development, including automated testing, code review, and faster iteration cycles
- Own cybersecurity, IT general controls, compliance, business continuity, disaster recovery, and technology risk governance
- Document institutional knowledge through documentation and runbooks
- Lead, develop, and retain a distributed 14-person engineering organization
- Evaluate and prioritize commercially viable customer-facing AI capabilities
- Maintain selective involvement in strategic customers, major escalations, product advisory discussions, and technically complex opportunities
- Provide periodic Board and executive exposure on modernization, technology investment, strategy, cybersecurity, and risk
- Establish AI-DLC maturity baselines, target timelines, and AI-enabled workflows
- Assess and prioritize customer-facing AI opportunities on commercial merit
- Model disciplined AI-enabled decision-making and verify outputs
- Complete technology, product, and delivery assessment within 60 days
- Deliver target architecture and funded modernization roadmap by 120 days
- Deploy CI/CD and observability infrastructure and establish predictable weekly releases
- Make AI-assisted development standard practice within the first 120 days
- Reduce tribal knowledge through documentation, runbooks, and cross-training
- Demonstrate measurable modernization progress and increased resilience within 12 months
Requirements
- Prior Chief Technology Officer, VP of Engineering, or equivalent executive accountability for a software organization
- 15+ years of progressive technology experience, including 10+ years leading software development teams
- Hands-on experience modernizing legacy systems, including demonstrated leadership of a POS or eCommerce platform modernization and/or a migration off legacy platforms
- Track record building or deploying CI/CD pipelines, observability systems, and automation in resource-constrained environments
- Experience leading distributed teams across internal, offshore, and external partner resources
- Executive oversight of cybersecurity, technology risk, operational resilience, and business continuity
- Technical depth paired with business fluency
- Preferred: Retail technology, point-of-sale, eCommerce, or payments experience
- Preferred: Beverage-alcohol, grocery, or specialty retail industry experience
- Preferred: Cloud modernization leadership on AWS, Azure or Google Cloud
- Preferred: Adjacent experience in vertical SaaS, fintech, ERP, or other high-availability transaction environments
Benefits
- Base salary plus revenue sharing
- Long-term incentive: 20% stock option match, subject to the applicable plan terms and vesting schedule
- Medical, dental, and vision coverage
- Retirement program
- 4 weeks PTO
- Flexible work arrangements
- Fully remote work across the United States and Canada
- Annual corporate leadership training (global)
Job title
Job type
Experience level
Salary
Not specified
Degree requirement
No Education Requirement
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