Director of Technology & Operations

The Opportunity:

The Director of Technology & Operations provides overall leadership for Wakestream IT and is accountable for a secure, reliable, responsive, and forward-looking technology environment supporting family members, household teams, marine operations, offices, properties, and affiliated Family Services functions. This role sets strategy, aligns resources, develops leaders, and ensures consistent service delivery while balancing high-touch client needs with sound technology governance and operational discipline.

What You'll Do:

Strategy, Governance, and Architecture

• Develop and maintain the Technology Services strategy and multi-year roadmap in alignment with family priorities and broader Family Services objectives.
• Establish technology standards, architecture principles, policies, and decision frameworks that create consistency while allowing appropriate personalization across residences, vessels, offices, and travel environments.
• Evaluate business and technology trends; translate emerging capabilities, risks, and tradeoffs into clear recommendations for senior leadership.
• Lead major technology initiatives and ensure intended outcomes, risks, dependencies, adoption needs, and ongoing support requirements are understood before commitments are made.

Service Delivery & Operational Excellence

• Own the overall Technology Services operating model and ensure reliable, timely, discreet, and high-quality support across all supported locations and user groups.
• Define, monitor, and continuously improve operational metrics, service-level expectations, escalation practices, documentation, change management, and quality standards.
• Use service data, family feedback, recurring incident patterns, and business needs to identify improvement opportunities and allocate resources effectively.
• Ensure clear accountability for issue resolution and effective coordination across technical teams, vendors, property staff, marine teams, and other Family Services functions.

People & Organizational Leadership

• Lead, coach, and develop a multidisciplinary team; clarify roles, set priorities, assess performance, and create development and succession plans.
• Build a collaborative, service-oriented culture grounded in trust, accountability, proactive communication, sound judgment, and continuous learning.
• Assess organizational capacity and capabilities; recommend staffing, sourcing, structure, and process changes necessary to meet current and future needs.
• Create strong partnership between technical delivery teams and the Director of Family Technology Experience so family needs inform priorities, standards, and service improvements.

Financial, Vendor & Portfolio Management

• Develop and manage the department budget; oversee forecasting, purchasing, invoice approval, resource allocation, and cost stewardship.
• Set vendor strategy and oversee vendor selection, contract negotiation, performance, risk, and relationship management.
• Establish a transparent process to evaluate and prioritize projects, support demand, lifecycle investments, security needs, and urgent family requests.
• Provide concise portfolio, budget, risk, and service updates to senior leadership and other key stakeholders.

Infrastructure, Cybersecurity & Resilience

• Provide strategic oversight for infrastructure, connectivity, networks, systems, devices, applications, data protection, and cybersecurity.
• Ensure cybersecurity risks are identified, communicated, and addressed through appropriate controls, awareness, monitoring, incident response, and third-party oversight.
• Maintain business continuity, disaster recovery, crisis response, and critical-technology readiness plans; test and improve them regularly.
• Ensure technology environments remain supportable, resilient, well documented, and appropriately standardized across diverse and mobile locations.

Partnership & Communication

• Serve as the senior Technology Services partner to Family Services leadership and coordinate closely with Talent Services, Finance, Security, Property, Marine, and other related functions.
• Present options, consequences, expected outcomes, and risks to support informed decision-making.
• Maintain productive relationships with technology leaders and support professionals across affiliated organizations, sharing practices and coordinating when beneficial.

What You'll Bring:

• Bachelor's degree in information technology, business, or a related field, or equivalent combination of education and experience.
• 12 or more years of progressive technology experience, preferably in a professional services organization, including significant leadership responsibility in a complex, service-intensive environment.
• Demonstrated experience leading technology strategy, service operations, infrastructure, cybersecurity, budgets, vendors, and cross-functional initiatives.
• Experience supporting executives, private clients, family offices, hospitality, residential technology, marine operations, or similarly high-touch environments is strongly preferred.
• Enterprise thinking with the ability to translate strategy into disciplined execution.
• Proven ability to lead leaders and build a high-performing, collaborative team.
• Exceptional judgment, discretion, integrity, and commitment to confidentiality.
• Strong financial, vendor, project portfolio, analytical, and risk-management capabilities.
• Clear and influential communication; able to explain complex issues and tradeoffs to technical and nontechnical audiences.
• Calm, responsive, and decisive when managing competing priorities, sensitive situations, and technology incidents.
• Visible commitment to the organization's Standards of Excellence and to exceptional service.
• Ability to work outside standard business hours when significant incidents, projects, or family needs require leadership attention.

Equal Opportunity Employer
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