VP Enterprise & AI Automation

Generali Global Assistance | Travel Insurance; San Diego (CA); Hybrid; USD 150,000 - 250,000; Full time

Benefits offered by this job

Health insurance

Paid parental leave

Scholarship program for dependents

401k match

EAP

Disability insurance

Pet insurance

Travel insurance discounts

Volunteer days

Job summary

Generali Global Assistance | Travel Insurance in San Diego hosts a hybrid leadership role guiding enterprise AI and automation initiatives. The VP leads AI governance, operating models, and scalable automation across functions to improve productivity, customer experience, and growth.

The position requires 10+ years in digital transformation with AI/automation leadership, and strong collaboration with Risk, Legal, Compliance, and InfoSec. Travel and regulated-industry experience are preferred.

Qualifications

• 10+ years of experience in digital transformation including AI, automation, or enterprise tech leadership.
• Proven track record leading large-scale AI or automation programs with measurable impact.
• Experience designing and scaling enterprise AI operating models and governance.
• Hands-on leadership with AI copilots or autonomous workflow orchestration.
• Strong executive presence to influence regulated organizations.

Responsibilities

• Define and own the enterprise automation and AI strategy.
• Build a multi-year roadmap for automation and AI adoption.
• Lead governance forums (AI Steering Committee, AI Operations Council, AI Risk, Ethics & Security Board).
• Partner with Risk, Legal, Compliance, InfoSec, and Data Privacy for responsible AI deployment.
• Oversee design and deployment of automation solutions including AI agents.

Skills

Strategic leadership

Executive presence

AI governance

Automation programs

Stakeholder management

Team leadership

Education

Bachelor’s Degree or Equivalent Experience

High School Diploma or GED

Tools

RPA

Cloud platforms

AI platforms

Job description

Embark on a Journey That Makes a Difference.

At Redion, every day is an opportunity to help people explore the world with confidence. We’re not just in the business of protection—we’re in the business of adventure and peace of mind. Whether it’s a backpacker trekking through the Andes, a family cruising the Mediterranean, or a solo traveler chasing the Northern Lights, we’re there to ensure their journey is safe and supported. From assisting with emergency medical claims to guiding customers through trip disruptions or ID theft, your work helps turn travel challenges into stories of resilience.

Passport to Perks Includes:

• Generous Employer contribution for health, dental, and vision insurance
• Paid Maternity and Paternity Leave
• Scholarship Program for Employee Dependents
• Company match on 401k
• Employee Assistance Program (EAP)
• Company paid short-term and long-term disability insurance
• Voluntary Pet Insurance
• Voluntary Legal Benefit
• Discounts on travel insurance
• Time off policies including vacation days, sick days, personal days, holidays and volunteer days (VTO)
• Pay Range: $180,000-250,000/yr

Your Role on the Expedition:

The Vice President of Enterprise AI & Automation leads the enterprise-wide AI-first transformation, including AI governance, agentic automation, operating model design, and value realization. This role is accountable for defining and scaling responsible, secure, and measurable AI capabilities across Operations and non-Operations functions. The VP partners with executive leadership to embed AI into the target operating model, enabling productivity, enhanced customer experience, and AI-powered growth

Chart Your Course:

Strategic Leadership

• Define and own the enterprise automation and AI strategy aligned to corporate goals, digital transformation priorities, and operational needs.
• Build a multi-year roadmap for automation, AI/ML, agentic systems, and advanced analytics adoption across business units.
• Identify high-value opportunities for automation, generative AI, AI agents, and intelligent workflows.
• Serve as the executive sponsor for major automation and AI programs, ensuring alignment, funding, and measurable outcomes.

Enterprise AI Governance & Operating Model

• Design, implement, and own the enterprise AI operating model, including intake, prioritization, lifecycle controls, and delivery standards.
• Establish and lead AI governance forums, including AI Steering Committee, AI Operations Council, and AI Risk, Ethics & Security Board.
• Partner with Risk, Legal, Compliance, InfoSec, and Data Privacy to ensure responsible, compliant, and secure AI deployment.
• Define AI KPIs, dashboards, and reporting cadence tied to productivity, cost reduction, customer experience, and risk management.

Technology, Automation & Agentic Systems

• Oversee the design, development, and deployment of automation solutions including RPA, workflow orchestration, intelligent document processing, AI copilots, and AI agents.
• Lead the design and scaling of agentic automation, including task agents, process agents, and supervisor agents orchestrating multi-step workflows.
• Stand up an agentic orchestration layer, enabling semi-autonomous, end-to-end process automation within defined risk controls.
• Lead the evaluation and implementation of AI platforms, automation tools, and emerging technologies (e.g., Copilot Studio, third-party AI agents).
• Establish scalable architectures, reusable components, and enterprise standards for AI and automation solutions.
• Ensure solutions are secure, resilient, and integrated with enterprise systems.
• Own the enterprise AI initiative portfolio, including intake, prioritization, and roadmap governance.
• Define and track AI KPIs tied to productivity, automation rate, cost-to-serve, sales, customer experience, etc.
• Lead quarterly AI strategy reviews and ongoing value realization reporting with executive leadership.

Organizational Enablement & Adoption

• Build and lead a high-performing team of e.g. automation engineers, AI engineers, product owners, and solution architects.
• Develop a federated operating model that empowers departments while maintaining enterprise standards.
• Launch and scale an enterprise AI Academy in cooperation with the larger group, including role-based learning for leaders, operators, and technical teams.
• Establish and manage an AI Champions / Ambassadors network across departments to drive adoption and value realization.
• Drive change management, training, and adoption programs to scale AI literacy across the organization.
• Foster a culture of innovation, experimentation, and continuous improvement.

Stakeholder & Executive Engagement

• Partner with C-suite leaders to identify strategic opportunities and communicate progress, risks, and outcomes.
• Collaborate with Operations, Finance, HR, Sales, Legal, Product, Underwriting, and other teams to embed AI into core processes and workflows.
• Closely partner with other entities in the group and head office on AI initiatives.
• Represent the company in external forums, vendor partnerships, and industry events related to AI and automation.

Your Ticket to Success:

Required Qualifications:

• High School Diploma or Equivalent (GED) required
• Bachelor’s Degree or Equivalent Experience
• 10+ years of experience in digital transformation, including experience in AI, automation, or enterprise technology leadership.
• Proven track record leading large-scale AI or automation programs with measurable business impact.
• Experience designing and scaling enterprise AI operating models and governance frameworks.
• Hands-on leadership exposure to AI copilots, agentic systems, or autonomous workflow orchestration.
• Deep understanding of RPA, workflow automation, machine learning, generative AI, and cloud platforms.
• Strong executive presence and ability to influence complex, regulated organizations.
• Demonstrated ability to translate business problems into scalable, governed AI solutions.

Preferred Qualifications:

• Experience in regulated, customer-facing industries (insurance, financial services, assistance, healthcare).
• Background in data engineering, analytics, or enterprise architecture.
• Familiarity with responsible AI frameworks, AI risk management, and model governance practices.
• Experience with process mining, AI value modeling, and automation prioritization frameworks.

Position Coordinates:

This is a hybrid role based out of our San Diego, CA office. As a hybrid role, you will be working onsite 2-3 days a week and working from home 2-3 days a week. Up to 5% domestic travel may be required

California Residents -

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