Principal Technical Program Manager

Accountabilities: Lead the end-to-end planning, coordination, and delivery of complex technology programs, ensuring alignment with strategic objectives, product roadmaps, and engineering priorities. Partner with Engineering, Product, Architecture, and business stakeholders to define program scope, objectives, milestones, dependencies, and measurable success criteria. Provide senior leadership with clear, data-driven updates on program health, delivery progress, risks, resource requirements, and strategic trade-offs. Apply Agile methodologies and program management best practices to improve delivery predictability, operational efficiency, accountability, and time to market. Proactively identify and mitigate program risks, resolve cross-functional blockers, manage competing priorities, and facilitate timely decision-making. Work with functional leaders to coordinate team capacity, address resource constraints, and optimize resource allocation across strategic initiatives. Build strong relationships across departments and organizational levels, facilitating collaboration, negotiating priorities, and driving alignment toward shared outcomes. Establish effective program governance, reporting structures, and communication processes to maintain visibility into milestones, deliverables, dependencies, and business impact. Identify opportunities to improve delivery processes, operational performance, and organizational execution through data analysis, stakeholder feedback, and industry best practices. Ensure program decisions balance customer needs, technical requirements, product quality, scalability, reliability, and long-term business value. Leverage AI-powered tools to synthesize program data, identify risks and dependencies, improve reporting, support scenario analysis, and streamline documentation while maintaining appropriate human oversight, data security, and accountability. Drive successful delivery of scalable, reliable SaaS solutions that meet business objectives and create measurable value for customers. Requirements Bachelor's degree in Computer Science, Engineering, Information Technology, or a related discipline. 12+ years of experience in technical program management, software delivery, engineering program management, or a related field, with a proven track record of delivering complex technology programs in SaaS environments. Strong knowledge of software development lifecycles, Agile methodologies, Scrum, SAFe, Lean Portfolio Management (LPM), and DevOps practices. Demonstrated experience managing multiple concurrent programs, cross-functional dependencies, delivery milestones, risks, and commitments. Solid technical understanding of software architecture, system integrations, and scalable cloud-based platforms. Proven ability to translate business strategy into actionable program plans, priorities, and measurable outcomes. Excellent stakeholder management, communication, negotiation, and influencing skills, with the ability to engage effectively with senior executives and technical teams. Strong analytical and problem-solving abilities, including the capacity to navigate ambiguity, assess trade-offs, and facilitate data-driven decisions. Proficiency with program management and collaboration tools such as Jira, Confluence, and Power BI. Strong customer-centric mindset and the ability to balance customer expectations, technical considerations, product priorities, and business objectives. Experience improving program delivery frameworks, governance practices, operational efficiency, and organizational performance. Ability to collaborate effectively with geographically distributed, cross-functional teams across multiple time zones. Additional qualifications that would be an advantage: Master's degree in Computer Science, Engineering, Business, or a related field. Experience leading large-scale, multi-team technology initiatives involving complex architectures, platform integrations, or enterprise SaaS products. Background in restaurant technology, customer loyalty and engagement platforms, or digital offers solutions. Relevant professional certifications such as PMP, PgMP, PMI-ACP, Certified ScrumMaster (CSM), or Lean Portfolio Management (LPM). Experience using AI tools to improve program analysis, reporting, risk management, and delivery processes. Benefits Competitive annual salary ranging from CA$160,000 to CA$190,000 . Equity participation, offering an opportunity to share in the company's long-term growth. Performance-based bonus opportunities. Fully remote working arrangement within Canada. Full-time position within an engineering organization focused on technology innovation and scalable SaaS solutions. Opportunity to collaborate with senior leadership and influence strategic technology initiatives. Exposure to complex, large-scale programs and cross-functional international teams. Professional growth opportunities through involvement in strategic projects and continuous improvement initiatives.