VP, Engineering & Operations

The Vice President, Engineering & Operations is a transformative technology executive responsible for defining and delivering the next generation of enterprise engineering, operations, cloud, and infrastructure capabilities. Reporting directly to the CITO, this leader will set a bold vision for modern technology adoption, operational excellence, and organizational maturity. The ideal candidate is a visionary who embraces new technologies and approaches to accelerate technical capability, elevate skill sets, strengthen culture, and evolve operating models. This role requires a dynamic people leader who excels at building high-performing teams and designing organizations that scale with the business.

How You Will Contribute:

• Develop and execute multi-year engineering, operations, teammate (employee) experience, and cloud strategy aligned with enterprise goals.

• Shape and evolve the operating model to improve agility, scalability, and organizational maturity.

• Serve as a strategic advisor to the CITO on technology trends, organizational design, and operational transformation.

• Lead workforce transformation to uplift technical skills, leadership capabilities, and team effectiveness.

• Build, inspire, and develop high performing teams across cloud engineering, infrastructure, teammate experience, operations, and command center functions.

• Define and lead the enterprise cloud strategy, including architecture, workload placement, modernization, and migration roadmaps.

• Build and mature a FinOps capability to optimize cloud spend, improve forecasting, and drive cost efficient engineering practices.

• Drive cloud performance optimization, automation, and operational efficiency across all environments.

• Oversee cloud engineering, platform engineering, and infrastructure modernization initiatives.

• Implement modern DevOps, SRE, automation, and continuous delivery practices.

• Establish engineering standards, governance, and reusable frameworks that improve quality, speed, and reliability.

• Build out the Operations & Command Center, ensuring proactive monitoring, incident response, and operational resilience.

• Drive operational excellence through automation, observability, and data driven decision making.

• Ensure high availability, performance, and reliability across all critical systems and services.

• Build and scale AI infrastructure support for AI driven agent monitoring, automated inventory and asset intelligence, and AI enabled management and observability.

• Partner with data, security, and engineering teams to ensure AI infrastructure is secure, scalable, and aligned with enterprise strategy.

• Oversee enterprise infrastructure strategy across networks, compute, storage, and end user technologies.

• Champion a modern, frictionless teammate (employee) experience through intuitive tools and reliable services.

• Partner with HR, Security, and Business Units to ensure technology enhances productivity and engagement.

• Bold, forward-thinking leader who challenges the status quo and embraces emerging technologies.

• Ability to translate complex technology trends into actionable strategies that accelerate business value.

• Empathetic, people first leader who builds trust, psychological safety, and strong team culture.

• Proven ability to build high performing teams and develop future leaders.

• Skilled at organizational design, talent development, and capability uplift.

• Strong executive presence with the ability to influence business units and senior leadership.

• Highly collaborative, adept at aligning diverse stakeholders around shared goals.

• Comfortable navigating ambiguity and driving clarity in complex environments.

• Strong focus on measurable outcomes, continuous improvement, and operational resilience.

Technology Competencies

• Experience developing and executing cloud modernization strategies, including workload optimization, migration planning, and architectural evolution.

• Demonstrated ability to implement and scale FinOps practices to drive financial accountability, cost transparency, and cloud efficiency.

• Proven track record building automated, scalable cloud environments that support rapid delivery and operational excellence.

• Hands on experience applying AI and automation to operational domains such as monitoring, asset intelligence, and predictive issue detection.

• Ability to design and scale AI infrastructure that supports enterprise-wide adoption, security, and performance requirements.

• Deep experience leading teams in modern engineering disciplines such as DevOps, SRE, and platform engineering.

• Strong background implementing automation, CI/CD pipelines, and reusable engineering frameworks to accelerate delivery.

• Expertise designing resilient, high availability infrastructure across networks, compute, storage, and end user technologies.

• Demonstrated ability to modernize infrastructure environments with a focus on performance, security, and operational efficiency.

• Experience building observability, monitoring, and proactive issue prevention capabilities into complex technology ecosystems.

• Implement modern DevOps, SRE, automation, and continuous delivery practices.

• Establish engineering standards, governance, and reusable frameworks that improve quality, speed, and reliability.

• Build out the Operations & Command Center, ensuring proactive monitoring, incident response, and operational resilience.

• Drive operational excellence through automation, observability, and data driven decision making.

Skills & Experience to be Successful:

Required:

• 15+ years of progressive experience in data, analytics, engineering, or related fields, including 5+ years in a senior executive or Chief Engineering and Operations-level role.

• Proven success building and scaling enterprise data platforms and modern data architectures.

• Deep expertise in data governance, data engineering, cloud modernization strategies, and ability to implement and scale FinOps practices to drive financial accountability, cost transparency, and cloud efficiency.

• Demonstrated ability to operate in a fast-paced, outcomes-driven environment with a strong bias for action.

• Strong business acumen with a track record of enabling measurable business value through data.

• Exceptional communication, leadership, and stakeholder-management skills.

• Experience driving organizational change and building data-driven cultures.

• Strong understanding of regulatory, ethical, and security considerations related to data and AI.

Preferred:

• Experience in the insurance industry, including risk, and regulatory considerations.

We go beyond standard benefits, focusing on the total well-being of our teammates, including:

• Health Benefits: Medical/Rx, Dental, Vision, Life Insurance, Disability Insurance
• Financial Benefits: ESPP; 401k; Student Loan Assistance; Tuition Reimbursement
• Mental Health & Wellness: Free Mental Health & Enhanced Advocacy Services
• Beyond Benefits: Paid Time Off, Holidays, Preferred Partner Discounts and more.