Director, Technical Operations - Infrastructure in Markham, Ontario at Accommodations Plus International

About Accommodations Plus International

API is the global leader in crew accommodation technology & services for the airline industry, with a strong service base in rail, cruise lines and sports teams. For more than 40 years, we have been offering a powerful combination of crew accommodation services delivered through innovative technology, unique software solutions, and a highly experienced team of service professionals, enabling our clients to maximize savings in all areas of travel operations.

Our Company is globally-supported by 794 employees and full-time dedicated consultants working from 59 locations around the world and is privately-held and headquartered in Melville, Long Island, New York.

OverviewThe 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.Essential Functions: Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.Leadership & Team Management

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 contextsDefine team structure, roles, and career development frameworks for engineers and site reliability engineers (SREs) across both locationsEstablish clear goals, KPIs, and performance expectations for the technical operations organization; conduct regular performance reviews and provide ongoing coaching and feedbackPartner 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 organizationFacilitate 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

Cloud Infrastructure & AWS

Own the governance and operational management of API's AWS cloud environment, including multi-account strategy, security controls, compliance posture, and cost managementDrive cloud cost optimization efforts including Reserved Instance and Savings Plans management, rightsizing, resource tagging governance, and FinOps practices to maximize infrastructure ROIEstablish and enforce AWS security best practices including IAM least-privilege access, SCPs, GuardDuty, Security Hub, AWS Config, and CloudTrail audit logging across all environmentsOversee multi-region and multi-availability-zone operational strategies to support disaster recovery objectives, minimize RTO/RPO, and maintain continuous service availability for global customersEvaluate new AWS services and infrastructure technologies; assess organizational fit and present adoption recommendations to senior leadership

System Reliability & Service Continuity

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 stakeholdersOversee the monitoring and observability ecosystem using tools such as CloudWatch, Datadog, Grafana, or equivalent platforms to ensure proactive detection and rapid response to operational issuesDrive capacity planning efforts, ensuring infrastructure scales efficiently to support business growth without compromising performance or cost targetsOwn the IT disaster recovery and business continuity plan for infrastructure systems; lead periodic tabletop exercises and failover testing to validate recovery capabilities

Strategy, Governance & Stakeholder Engagement

Develop and execute the multi-year technical operations roadmap in alignment with the company's product strategy, growth objectives, and technology visionProvide regular operational reporting to senior leadership team, including infrastructure health dashboards, cost reports, and strategic initiative progress updatesLead technology vendor relationships for cloud, infrastructure tooling, and managed services; oversee contract negotiations, SLA management, and vendor performance reviewsEnsure 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 readinessOwn the IT disaster recovery and business continuity plan for infrastructure systems; lead periodic tabletop exercises and failover testing to validate recovery capabilitiesManage the technical operations budget, including headcount, tooling, and cloud spend; provide accurate forecasting and variance analysis to finance and leadership stakeholders

Competencies

Proven leadership ability with experience building, scaling, and retaining high-performing technical teams across multiple geographies and time zonesExecutive presence and strong communication skills; able to translate complex infrastructure and operational concepts into clear, actionable narratives for C-suite and board-level audiencesStrategic mindset balanced with operational discipline — equally effective setting a multi-year infrastructure vision and ensuring day-to-day operational excellence across distributed teamsDeep technical credibility with AWS cloud services, cloud-native application patterns, networking, and security; respected by engineering teams for substantive technical knowledgeStrong financial acumen with experience managing multi-million-dollar cloud and infrastructure budgets and driving cost optimization without compromising reliabilityCulturally aware and skilled at leading geographically distributed teams; experienced navigating the logistical and interpersonal dynamics of cross-timezone collaboration between US and India-based teamsData-driven decision maker who leverages metrics, SLOs, and operational KPIs to prioritize investments and communicate operational health to stakeholdersCommitment to engineering excellence, blameless culture, and continuous learning across the entire technical operations organization

Position Type and Expected Hours of Work

This is a full-time, exempt position based in New York, NY. Standard hours are Monday through Friday during core business hours. Given the global nature of this role, flexibility in scheduling is expected to accommodate regular collaboration with the Pune, India team across significant time zone differences. Occasional evening availability for major deployments and scheduled maintenance windows may be required.

Travel

This position may require occasional domestic travel to support vendor meetings, industry conferences, cross-functional leadership engagements, and business unit initiatives.

Required Education and Experience

Bachelor's degree in Computer Science, Information Technology, Engineering, or a related field; Master's degree or MBA preferred; equivalent experience will be considered15+ 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 teamsDemonstrated experience managing geographically distributed teams across multiple countries, with specific experience overseeing engineering or operations staff in India strongly preferredStrong 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 environmentDemonstrated experience managing cloud infrastructure budgets, implementing FinOps practices, and presenting financial performance and forecasts to executive leadershipExperience with security and compliance frameworks relevant to cloud environments, including SOC 2 Type II, ISO 27001, GDPR, or PCI-DSSExperience owning and operating observability and monitoring platforms (Datadog, CloudWatch, Grafana, or equivalent) and driving a metrics-driven approach to operational healthExperience owning disaster recovery and business continuity programs for cloud-based infrastructure, including regular testing and executive-level reportingAWS Certified Solutions Architect or equivalent AWS professional-level certification preferred

Preferred Qualifications

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

Success Metrics

Stability, uptime, and performance of all cloud infrastructure and production systems, measured against defined SLAs and reliability targets.Successful execution of cloud cost optimization initiatives, delivering measurable reductions in AWS spend through FinOps practices and rightsizing.Reduced risk profile through strong security posture, compliance readiness, and governance frameworks across all AWS environments.High-performing, engaged distributed technical teams across New York and Pune, with clear career frameworks and low voluntary attrition.Validated disaster recovery and business continuity capabilities through regular tabletop exercises and failover testing.Infrastructure roadmap milestones delivered on schedule and in alignment with product engineering and company growth objectives.

Compensation:160,000 180,000 CAD, commensurate with experience.