Director, Technical Operations - (Infrastructure)

Accommodations Plus International•Markham, ON

1d•CA$160,000 - CA$180,000•Onsite

About The Position

The Director of Technical Ops - Infrastructure is a senior technology leader responsible for the reliability, scalability, performance, and security of API's cloud-based platform and underlying infrastructure. Operating across our New York and Pune, India offices, this leader will manage and develop geographically distributed engineering and operations teams, driving a culture of operational excellence, continuous improvement, and high availability. The Director will own governance and operational management of our AWS cloud environment, oversee system reliability and service continuity, and serve as the primary bridge between technology operations and the broader business. This role requires a seasoned technology executive who combines deep cloud expertise with strong people leadership, financial acumen, and the ability to partner with executive stakeholders to align infrastructure strategy with organizational goals.

Requirements

Proven leadership ability with experience building, scaling, and retaining high-performing technical teams across multiple geographies and time zones
Executive presence and strong communication skills; able to translate complex infrastructure and operational concepts into clear, actionable narratives for C-suite and board-level audiences
Strategic mindset balanced with operational discipline — equally effective setting a multi-year infrastructure vision and ensuring day-to-day operational excellence across distributed teams
Deep technical credibility with AWS cloud services, cloud-native application patterns, networking, and security; respected by engineering teams for substantive technical knowledge
Strong financial acumen with experience managing multi-million-dollar cloud and infrastructure budgets and driving cost optimization without compromising reliability
Culturally aware and skilled at leading geographically distributed teams; experienced navigating the logistical and interpersonal dynamics of cross-timezone collaboration between US and India-based teams
Data-driven decision maker who leverages metrics, SLOs, and operational KPIs to prioritize investments and communicate operational health to stakeholders
Commitment to engineering excellence, blameless culture, and continuous learning across the entire technical operations organization
Bachelor's degree in Computer Science, Information Technology, Engineering, or a related field; Master's degree or MBA preferred; equivalent experience will be considered
15+ years of progressive experience in technology operations, infrastructure engineering, or cloud operations, with at least 5 years in a senior director-level or equivalent leadership role managing technical teams
Demonstrated experience managing geographically distributed teams across multiple countries, with specific experience overseeing engineering or operations staff in India strongly preferred
Strong working knowledge of AWS cloud services including compute (EC2, ECS, EKS, Lambda), storage (S3, EFS, EBS), networking (VPC, Transit Gateway, Route 53, CloudFront), databases (RDS, Aurora, DynamoDB, ElastiCache), and security services (IAM, GuardDuty, Security Hub, WAF, Shield)
Proven track record overseeing highly available, multi-region production systems with aggressive uptime and performance SLAs in a cloud-native environment
Demonstrated experience managing cloud infrastructure budgets, implementing FinOps practices, and presenting financial performance and forecasts to executive leadership
Experience with security and compliance frameworks relevant to cloud environments, including SOC 2 Type II, ISO 27001, GDPR, or PCI-DSS
Experience owning and operating observability and monitoring platforms (Datadog, CloudWatch, Grafana, or equivalent) and driving a metrics-driven approach to operational health
Experience owning disaster recovery and business continuity programs for cloud-based infrastructure, including regular testing and executive-level reporting

Nice To Haves

AWS Certified Solutions Architect or equivalent AWS professional-level certification preferred
Experience leading technical operations at a SaaS or cloud-native technology company supporting enterprise customers with high availability and data security requirements
Experience with database reliability engineering including RDS/Aurora operational management, performance tuning, failover testing, and backup/recovery validation
Knowledge of networking protocols and enterprise network architecture including BGP, SD-WAN, MPLS, VPN, and zero-trust network access (ZTNA) frameworks
Familiarity with service management concepts and change management processes; experience with tooling such as ServiceNow or Jira Service Management is a plus
Experience working in travel technology, hospitality, or other high-volume, customer-facing SaaS environments
Exposure to ML/AI infrastructure considerations including data pipeline reliability and model serving infrastructure on AWS

Responsibilities

Lead, mentor, and develop distributed technical operations teams across New York and Pune, India, fostering a collaborative, high-performance culture that bridges time zones and cultural contexts
Define team structure, roles, and career development frameworks for engineers and site reliability engineers (SREs) across both locations
Establish clear goals, KPIs, and performance expectations for the technical operations organization; conduct regular performance reviews and provide ongoing coaching and feedback
Partner with HR and talent acquisition to recruit and retain top-tier technical talent in both New York and Pune; build a deep bench of operational expertise across the organization
Facilitate cross-functional collaboration between the technical operations team and product engineering, security, data, and business teams to ensure operational requirements are integrated into the software development lifecycle
Own the governance and operational management of API's AWS cloud environment, including multi-account strategy, security controls, compliance posture, and cost management
Drive cloud cost optimization efforts including Reserved Instance and Savings Plans management, rightsizing, resource tagging governance, and FinOps practices to maximize infrastructure ROI
Establish and enforce AWS security best practices including IAM least-privilege access, SCPs, GuardDuty, Security Hub, AWS Config, and CloudTrail audit logging across all environments
Oversee multi-region and multi-availability-zone operational strategies to support disaster recovery objectives, minimize RTO/RPO, and maintain continuous service availability for global customers
Evaluate new AWS services and infrastructure technologies; assess organizational fit and present adoption recommendations to senior leadership
Define and own SLAs and uptime commitments for all production systems; establish reliability targets in partnership with product engineering leadership and communicate performance against those targets to executive stakeholders
Oversee the monitoring and observability ecosystem using tools such as CloudWatch, Datadog, Grafana, or equivalent platforms to ensure proactive detection and rapid response to operational issues
Drive capacity planning efforts, ensuring infrastructure scales efficiently to support business growth without compromising performance or cost targets
Own the IT disaster recovery and business continuity plan for infrastructure systems; lead periodic tabletop exercises and failover testing to validate recovery capabilities
Develop and execute the multi-year technical operations roadmap in alignment with the company's product strategy, growth objectives, and technology vision
Provide regular operational reporting to senior leadership team, including infrastructure health dashboards, cost reports, and strategic initiative progress updates
Lead technology vendor relationships for cloud, infrastructure tooling, and managed services; oversee contract negotiations, SLA management, and vendor performance reviews
Ensure compliance with relevant regulatory and data privacy requirements (SOC 2, GDPR, PCI-DSS, ISO 27001) as they apply to infrastructure and operations; partner with the security team on audit readiness
Manage the technical operations budget, including headcount, tooling, and cloud spend; provide accurate forecasting and variance analysis to finance and leadership stakeholders