Director, Technical Operations

Who We Are

Accommodations Plus International (API) is a technology and services company focused on driving innovation across the travel and transportation industry. We partner with organizations in the airline, cruise, and rail sectors to deliver solutions that improve layover operations, enhance customer experience, and support long-term growth. Our mission is to make layovers simpler and more efficient for crew members - and we bring that to life through deep industry expertise and a practical, results-driven approach. Today, API’s platform powers over 18 million crew room nights each year for 100+ airlines and travel operators worldwide. Our Global Reach ensures that airline crews are rested, transported, and connected so global aviation runs on time. At API, we’re building a culture rooted in succeeding and thriving together. It’s a place where people are encouraged to take ownership, develop their skills, and contribute to work that matters. If you’re looking to grow your career in a company that values steady progress, real impact, and long-term development, we’d like to meet you!

Summary/Objective

The Director of Technical Operations is a senior IT leader responsible for the reliability, performance, and continuous improvement of API's internal technology environment. This leader oversees all aspects of corporate IT operations, including helpdesk and end-user support, employee hardware lifecycle management, corporate systems administration, enterprise AI tooling ownership, and the tools and processes that keep our global workforce productive every day. Operating across teams in Canada, India, Brazil, and the United States, the Director will lead a team of approximately [X] employees, including [X] direct reports, and manage and develop geographically distributed IT support and systems teams, setting clear service standards and fostering a culture of responsiveness, accountability, and employee-first service delivery. This role requires a seasoned IT operations leader who brings deep experience in enterprise support environments, strong people management skills, and the ability to align internal technology services with the needs of a growing, globally distributed organization.

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 IT operations teams across Canada, India, Brazil, and the US, fostering a collaborative, service-oriented culture that bridges time zones and delivers a consistent employee experience globally
• Define team structure, staffing levels, roles, and career development frameworks for helpdesk technicians, desktop support engineers, and systems administrators across Canada, India, Brazil, and the US
• Establish clear goals, KPIs, and performance expectations for the IT operations organization; conduct regular performance reviews and provide ongoing coaching and feedback
• Partner with HR and talent acquisition to recruit and retain skilled IT support professionals in Canada, India, Brazil, and the US; build a team capable of scaling to meet growing organizational demand
• Foster a customer-service culture within the IT team, setting expectations for responsiveness, communication quality, and employee satisfaction across all support interactions
• Facilitate cross-functional collaboration between IT operations and HR, Finance, Legal, and business teams to anticipate technology needs and deliver solutions proactively

Helpdesk & End-User Support

• Own the global helpdesk function end-to-end, including service desk operations, ticket management, escalation procedures, SLA definitions, and performance reporting for teams in Canada, India, Brazil, and the US
• Administer the helpdesk ticketing and knowledge management tools used by the global support team, ensuring workflows, categorization, and reporting meet organizational needs
• Define and enforce helpdesk SLAs and response time targets; monitor queue performance, ticket aging, and resolution rates, and drive continuous improvement initiatives to reduce mean time to resolution (MTTR)
• Establish and maintain a comprehensive, searchable knowledge base and self-service portal to reduce repeat ticket volume and empower employees to resolve common issues independently
• Oversee Tier 1, Tier 2, and Tier 3 support workflows, ensuring clear escalation paths and effective knowledge transfer between support levels
• Develop and report on helpdesk metrics and employee satisfaction scores (CSAT) to executive leadership; use data to identify systemic issues and prioritize improvements
• Manage on-call and after-hours support coverage across time zones to ensure critical support needs are addressed outside standard business hours

Employee Hardware & Asset Management

• Own the full lifecycle of employee hardware including procurement, provisioning, deployment, tracking, maintenance, refresh, and secure decommissioning for laptops, desktops, mobile devices, peripherals, and other end-user equipment
• Develop and maintain a hardware refresh strategy and multi-year capital plan, ensuring employees in Canada, India, Brazil, and the US are equipped with current, standardized, and reliable devices
• Administer mobile device management (MDM) and endpoint management platforms (such as Jamf, Microsoft Intune, or equivalent) to enforce security policies, manage configurations, and support remote provisioning and wipe capabilities
• Maintain accurate and up-to-date IT asset inventory using asset management tooling; ensure all hardware and software assets are tracked, auditable, and compliant with licensing and security requirements
• Work with the procurement function to manage hardware vendor relationships and purchasing programs; partner on pricing negotiations, warranty and support evaluations, and timely fulfillment for new hires and hardware replacements
• Define and enforce hardware standards for different employee roles and personas (office-based, remote, executive, field); maintain an approved hardware catalog that balances performance, cost, and supportability
• Coordinate onboarding hardware readiness in partnership with HR and People Operations, ensuring new employees in Canada, India, Brazil, and the US receive fully configured, ready-to-use equipment on or before their first day

Corporate Systems Administration

• Oversee the administration, availability, and performance of Microsoft 365, including Exchange Online, SharePoint, Teams, OneDrive, and associated services; ensure the platform is well-governed, properly licensed, and continuously optimized for employee productivity
• Manage identity and access management (IAM) infrastructure, including Ping Identity and Microsoft Entra ID, ensuring employee access is provisioned accurately, reviewed regularly, and deprovisioned promptly at offboarding
• Administer and maintain corporate SaaS application portfolio in coordination with business stakeholders; manage license assignments, user provisioning, vendor relationships, and renewal cycles
• Ensure endpoint security standards are enforced across all corporate devices, including antivirus/EDR, patch management, disk encryption, and security baseline configurations
• Manage corporate file storage, backup, and data retention systems; ensure business data is protected, recoverable, and compliant with relevant data governance policies
• Maintain business continuity and disaster recovery plans for corporate IT systems, including regular testing and documented recovery procedures
• Support security incident response for corporate systems and endpoints in coordination with the security team
• Support audit readiness and compliance requirements (SOC 2, ISO 27001, GDPR, or equivalent) as they relate to internal IT systems, access controls, and asset management

AI Tooling & Ownership

• Serve as the business owner of the company's enterprise AI tools (such as Microsoft Copilot, Claude, or equivalent), accountable for tool selection, rollout, configuration, and ongoing performance
• Define and maintain the AI tooling strategy and roadmap, aligned with business priorities and in partnership with executive leadership and the security team
• Establish AI usage governance, including acceptable-use policy, access controls, data-protection and confidentiality standards, and an approval process for new AI tools, integrations, and use cases
• Administer AI platform licensing, user provisioning, and tenant or workspace settings; manage AI vendor relationships, contracts, renewals, and spend
• Partner with Security, Legal, and Compliance to assess AI tool risk, data handling, privacy, and regulatory requirements before and after deployment
• Drive employee adoption through training, enablement, documentation, and internal champions; help teams identify and prioritize high-value AI use cases
• Measure and report AI adoption, usage, cost, and productivity impact to executive leadership; use the data to refine tooling and enablement priorities
• Track the evolving AI tooling landscape; evaluate new tools and capabilities and recommend changes to the AI tool stack

Strategy, Governance & Stakeholder Engagement

• Develop and execute the multi-year IT operations roadmap, aligning internal technology capabilities with the company's growth plans, workforce needs, and executive priorities
• Provide regular reporting to the SVP Corporate Technologies and executive leadership team on IT service performance, helpdesk metrics, hardware spend, system availability, and strategic initiative progress
• Manage the IT operations budget, including headcount, hardware procurement, software licensing, and vendor spend; provide accurate forecasting and variance analysis to finance and leadership stakeholders
• Lead technology vendor relationships for hardware and corporate software; oversee contract negotiations, SLA management, and vendor performance reviews
• Establish and maintain IT policies, standards, and procedures covering acceptable use, hardware standards, access management, data handling, and support processes; ensure policies are current, communicated, and enforced
• Lead IT components of new office build-outs, office moves, and facilities technology upgrades, ensuring hardware and systems are ready for occupancy
• Partner with the security team to ensure internal IT practices align with the company's information security program and that corporate systems are appropriately protected and monitored Competencies
• Proven leadership ability with experience building, scaling, and retaining high-performing IT operations teams across multiple geographies and time zones
• Strong service-delivery orientation with a genuine commitment to employee experience; sets high standards for helpdesk responsiveness, communication quality, and issue resolution
• Executive presence and communication skills; able to translate IT operational metrics and investment needs into clear, compelling narratives for C-suite stakeholders and non-technical audiences
• Skilled at leading geographically distributed teams; experienced navigating the logistical and interpersonal dynamics of cross-timezone collaboration across North America, South America, and Asia
• Data-driven approach to operations management; uses helpdesk metrics, asset data, and service performance KPIs to identify trends, prioritize investments, and report on team effectiveness
• Strong financial acumen with experience managing IT operations budgets covering hardware procurement, software licensing, and staffing, with a track record of cost-effective resource allocation
• Highly organized with strong process discipline; skilled at building repeatable, scalable IT workflows that reduce manual effort and improve consistency across a growing organization
• Collaborative partner who works effectively across HR, Finance, Legal, and business teams to ensure internal IT services anticipate and meet organizational needs
• Practical working knowledge of enterprise AI tools; able to translate AI capabilities into business use cases and measurable outcomes

Position Type and Expected Hours of Work This is a full-time, exempt, hybrid position based in either our Melville, NY or Markham, Ontario, Canada office, with a combination of in-office and remote work ([X] days per week in the office). 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 teams in Canada, India, Brazil, and the US across significant time zone differences, including scheduled early-morning or late-day calls to overlap with the India team. Occasional availability outside standard hours may be required to support critical system outages, major IT projects, or after-hours maintenance.

Travel This position may require occasional domestic and international travel, including to Canada, India, and Brazil, to support team visits, vendor meetings, industry conferences, cross-functional leadership engagements, and business unit initiatives.

Required Education and Experience

• Bachelor's degree in Information Technology, Computer Science, Business Administration, or a related field; Master's degree or MBA preferred; equivalent experience will be considered
• 12+ years of progressive experience in IT operations or corporate technology roles, with at least 5 years in a leadership role (manager, senior manager, or director level) managing IT support and systems teams
• Demonstrated experience managing geographically distributed IT teams across multiple countries and time zones
• Extensive hands-on experience owning and managing corporate helpdesk operations, including SLA management and service performance reporting
• Demonstrated experience owning enterprise AI tools (such as Microsoft Copilot or Claude), including deployment, configuration, access controls, usage governance, vendor management, and driving employee adoption
• Deep experience managing employee hardware lifecycle programs including procurement, asset tracking, MDM/endpoint management, and hardware refresh planning at scale
• Strong expertise in Microsoft 365 administration, including Exchange Online, SharePoint, Teams, and OneDrive, as well as identity management with Ping Identity and Microsoft Entra ID in an enterprise environment
• Proven track record administering and managing a corporate SaaS application portfolio, including license management, user provisioning workflows, and vendor oversight
• Experience enforcing endpoint security standards including patch management, EDR platforms, disk encryption, and device configuration management
• Demonstrated experience managing IT operations budgets covering hardware, software licensing, and staffing, with a track record of accurate forecasting and cost management
• Experience supporting compliance and audit requirements (SOC 2, ISO 27001, GDPR, or equivalent) as they relate to internal IT systems and access controls

Preferred Qualifications

• Experience leading IT operations at a SaaS or cloud-native technology company supporting a globally distributed workforce
• Experience overseeing IT support staff in India and Brazil
• Familiarity with AI risk, data protection, and responsible-use frameworks, and experience building AI training and enablement programs for a non-technical workforce
• Experience leading office build-outs or large-scale office technology refresh projects across multiple locations
• Experience with identity management platforms, with Ping Identity (PingOne, PingFederate, or PingAccess) and Microsoft Entra ID preferred; experience with Okta also considered
• Familiarity with procurement and vendor management processes, including hardware purchasing programs (Dell, Apple, Lenovo, or equivalent) and software licensing agreements
• Experience working in travel technology, hospitality, or other high-growth, customer-facing SaaS environments
• Demonstrated experience building or maturing IT onboarding and offboarding programs in partnership with HR and People Operations teams

Compensation

The good faith compensation for this position is

United States: $130,000 - $140,000 USD

Compensation is determined based on several factors, including the candidate’s experience, qualifications, and skill set, geographic location, as well as internal alignment and external benchmarks.

Other Duties Duties, responsibilities and activities may change at any time according to business needs. The performance of additional responsibilities if you are designated as a Data Protection Champion (DPC), Senior Information Risk Owner (SIRO) or Information Assurance Accounting Officer (IAAO). Work Environment This position operates in a professional office environment. This role routinely uses standard office equipment such as computers, phones, photocopiers, filing cabinets and fax machines. Physical Demands The physical demands described here are representative of those that must be met by an employee to successfully perform the essential functions of this job. While performing the duties of this job, the employee is regularly required to talk or hear. The employee frequently is required to stand, walk; use hands to finger, handle or feel; and reach with hands and arms. AAP/EEO Statement Accommodations Plus International is an Equal Opportunity Employer that does not discriminate on the basis of actual or perceived race, creed, color, religion, alienage or national origin, ancestry, citizenship status, age, disability or handicap, sex, marital status, veteran status, sexual orientation, genetic information, arrest record, or any other characteristic protected by applicable federal, state or local laws. Our management team is dedicated to this policy with respect to recruitment, hiring, placement, promotion, transfer, training, compensation, benefits, employee activities and general treatment during employment. Privacy Statement API may use the contact information you provide to communicate about this role, including via text message. See our [Privacy Policy] for details. By clicking "Apply" you agree to Rippling's Terms of Service / User Privacy Notice.