VP, Enterprise AI & Automation
Generali Global Assistance | Travel Insurance, San Diego, CA, United States
Role Overview
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.
Responsibilities
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.
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.
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 such as Copilot Studio and 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.
Build and lead a high‑performing team of 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.
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.
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 such as 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.
Internal Programs
Diversity, Equity, and Inclusion (DEI) Committee
Career pathing and Individual Development Plans
Internal training and internship opportunities
Women in Business Mentorship Program
Employee awards and recognition
Education and professional development assistance program
Benefits
Generous employer contribution for health, dental, and vision insurance
Paid maternity and paternity leave
Scholarship program for employee dependents
Company match on 401(k)
Employee Assistance Program (EAP)
Company paid short‑term and long‑term disability insurance
Company paid life 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 per year
Location & Work Arrangement This is a hybrid role based out of our San Diego, CA office. You will work onsite 2‑3 days a week and work from home 2‑3 days a week. Up to 5% domestic travel may be required.
Schedule This position will be Monday‑Friday during regular business hours (approximately 8:00 am‑5:00 pm). Occasional overtime may be required according to business need.
Equal Employment Opportunity Statement The company is committed to providing equal employment opportunity in all our employment programs and decisions. Discrimination in employment on the basis of any classification protected under federal, state, or local law is a violation of our policy. Equal employment opportunity is provided to all employees and applicants for employment without regard to age, race, color, religion, creed, sex, gender identity, gender expression, transgender status, pregnancy, childbirth, medical conditions related to pregnancy or childbirth, sexual orientation, national origin, ancestry, ethnicity, citizenship, genetic information, marital status, military status, HIV/AIDS status, mental or physical disability, use of a guide or support animal because of blindness, deafness, or physical handicap, or any other legally protected basis under applicable federal, state, or local law. This policy applies to all terms and conditions of employment, including, but not limited to, recruitment and hiring, classification, placement, promotion, termination, reductions in force, recall, transfer, leaves of absence, compensation, and training. Any employees with questions or concerns about equal employment opportunities in the workplace are encouraged to bring these issues to the attention of Human Resources. The Company will not allow any form of retaliation against individuals who raise issues of equal employment opportunity. All Company employees are responsible for complying with the Company’s Equal Opportunity Policy. Every employee is to treat all other employees equally and fairly. Violations of this policy may subject an employee to disciplinary action, up to and including termination of employment.
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Responsibilities
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.
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.
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 such as Copilot Studio and 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.
Build and lead a high‑performing team of 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.
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.
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 such as 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.
Internal Programs
Diversity, Equity, and Inclusion (DEI) Committee
Career pathing and Individual Development Plans
Internal training and internship opportunities
Women in Business Mentorship Program
Employee awards and recognition
Education and professional development assistance program
Benefits
Generous employer contribution for health, dental, and vision insurance
Paid maternity and paternity leave
Scholarship program for employee dependents
Company match on 401(k)
Employee Assistance Program (EAP)
Company paid short‑term and long‑term disability insurance
Company paid life 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 per year
Location & Work Arrangement This is a hybrid role based out of our San Diego, CA office. You will work onsite 2‑3 days a week and work from home 2‑3 days a week. Up to 5% domestic travel may be required.
Schedule This position will be Monday‑Friday during regular business hours (approximately 8:00 am‑5:00 pm). Occasional overtime may be required according to business need.
Equal Employment Opportunity Statement The company is committed to providing equal employment opportunity in all our employment programs and decisions. Discrimination in employment on the basis of any classification protected under federal, state, or local law is a violation of our policy. Equal employment opportunity is provided to all employees and applicants for employment without regard to age, race, color, religion, creed, sex, gender identity, gender expression, transgender status, pregnancy, childbirth, medical conditions related to pregnancy or childbirth, sexual orientation, national origin, ancestry, ethnicity, citizenship, genetic information, marital status, military status, HIV/AIDS status, mental or physical disability, use of a guide or support animal because of blindness, deafness, or physical handicap, or any other legally protected basis under applicable federal, state, or local law. This policy applies to all terms and conditions of employment, including, but not limited to, recruitment and hiring, classification, placement, promotion, termination, reductions in force, recall, transfer, leaves of absence, compensation, and training. Any employees with questions or concerns about equal employment opportunities in the workplace are encouraged to bring these issues to the attention of Human Resources. The Company will not allow any form of retaliation against individuals who raise issues of equal employment opportunity. All Company employees are responsible for complying with the Company’s Equal Opportunity Policy. Every employee is to treat all other employees equally and fairly. Violations of this policy may subject an employee to disciplinary action, up to and including termination of employment.
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