VP, Technology & Digital Services

Preferred

Location:

Candidates must reside within four (4) hours of New Berlin, NY at the time of employment or be willing to relocate within that geographic area. Relocation assistance may be offered as part of an employment offer for qualified candidates. Employment opportunities for this position are limited to residents of the following states:
Connecticut, Delaware, Massachusetts, Maryland, Maine, New Hampshire, New Jersey, New York, Pennsylvania, Rhode Island, and Vermont.

At Preferred, we understand the importance of holistic health. To meet the diverse needs of our employees, we offer a comprehensive set of benefits:

• Short-term disability, long-term disability, and life insurance coverage are provided at no cost
• Optional benefits include enhanced life insurance and critical illness plans
• 401k plan with an employer contribution that you will receive regardless of your own contribution to the plan
• Student Loan Repayment Assistance
• A short-term incentive plan for all employees

• Generous paid time off, offering of 25 days at hire (prorated based on start date for the first year)
• 7 days of paid sick leave
• 10 paid company holidays
• Personalized paid time off after 3 years!

• Access to 26 sessions with a Better Help therapist each year for you and up to 5 dependents, as well as access to all of Better Help’s group and digital resources
• Access to Family First, a team of care experts who can provide you and your loved ones 1:1 assistance with a variety of caregiving solutions, from elder care to legal and financial challenges, insurance and Medicare navigation, and more!

• Medical, dental, and vision coverage options begin on the first day of employment
• Health Savings Accounts (with a generous employer contribution!)

The Vice President, Technology & Digital Services is a technology executive responsible for defining and executing enterprise technology strategy. This role also serves as the organization’s designated Chief Information Security Officer (CISO) and AI Governance Officer.

This high-impact role provides strategic leadership and operational oversight across five core pillars: networking, hybrid infrastructure, application development, cybersecurity, and artificial intelligence (AI) governance. As a key member of the IT leadership team, the VP collaborates closely with executive leadership, the Board of Directors, and external partners to ensure that technology investments drive operational excellence, business growth, and modern application delivery, all while maintaining rigorous regulatory compliance within the insurance industry.

The CISO designation carries formal regulatory accountability under NYDFS 23 NYCRR 500, requiring regular updates to the Audit & Risk Committee and the Board of Directors on cybersecurity posture and program maturity.

• Enterprise
  
  Roadmap:
  
  Develop and execute a multi-year technology and application roadmap aligned with corporate business objectives and P&C digital transformation initiatives.
• Executive Partnership: Partner with business leaders to identify technology opportunities that align with the organization’s strategic priorities including improvement in underwriting efficiency, claims processing, customer experience, and competitive advantage.
• Financial & Capital Planning: Lead enterprise technology planning, budgeting, and investment prioritization, ensuring strict ROI accountability for both infrastructure and software development projects.
• Innovation vs. Security: Balance innovation velocity with security and risk management obligations, enabling the organization to modernize rapidly without compromising its regulatory standing.