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.

Financial

• 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
• A cash-balance pension plan
• Student Loan Repayment Assistance
• A short-term incentive plan for all employees

Social

• 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!

Emotional

• Access to 26 sessions with a BetterHelp therapist each year for you and up to 5 dependents, as well as access to all of BetterHelp'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!

Physical

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

YOUR PURPOSE AND FUNCTION IN OUR COMPANY:

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.

The Vice President of Technology Digital Services will be responsible for:

Strategic Leadership & Technology Vision

• 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 organizations' 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.

Infrastructure & Networking Services

• Hybrid Environments: Direct the design, implementation, and operation of enterprise infrastructure environments, including hybrid cloud (Azure/AWS), IaaS, PaaS, and storage/backup services.
• Network Operations: Oversee robust enterprise network operations ensuring high availability, business continuity, and adherence to strict SLAs.
• Service Delivery: Manage strategic relationships with cloud and telecom providers while overseeing service desk operations for continuous improvement in end-user support.

Engineering & Core Systems

• Modern Software Delivery: Drive DevSecOps and continuous integration/continuous deployment (CI/CD) methodologies, embedding automated security, testing, and compliance checks directly into the software delivery lifecycle.
• Architecture & Integration: Oversee enterprise architecture, API strategies, and legacy modernization efforts to support scalable digital capabilities and advanced business analytics, specifically prioritizing Guidewire environments.

Cybersecurity & Information Security (CISO Governance)

• Program Ownership: Serve as the designated CISO, owning the enterprise Information Security program, threat detection, incident response, and forensics capabilities.
• Board Engagement: Provide regular assessments and status reports directly to the Audit & Risk Committee and Board of Directors on the organization's cybersecurity posture, risk metrics, and program maturity.
• Risk & Vulnerability Management: Own cybersecurity risk assessments, penetration testing, vulnerability management, and third-party risk programs for vendors, MGAs, and insurtech partners.
• Security by Design: Ensure infrastructure and application deployment environments are designed according to security-by-design principles.

Artificial Intelligence Governance

• Responsible AI Policy: Lead enterprise AI governance, establishing policies aligned with the NIST AI Risk Management Framework and evolving state insurance AI regulations (including NAIC model bulletin guidance).
• Compliance & Explainability: Ensure AI workloads meet security, privacy, and regulatory auditability requirements, particularly regarding explainability obligations for adverse underwriting or claims decisions.

Regulatory Compliance

• Compliance Frameworks: Ensure technology, application, and security environments support compliance with NYDFS 23 NYCRR 500, PCI DSS, GLBA, and emerging insurance-specific AI laws.
• Executive Communication: Translate complex technical strategies, software release metrics, and risk postures into clear briefings for non-technical executives and the Board of Directors

Team Leadership:

• Talent Development: Lead, mentor, and develop a high-performance, cross-functional team of engineers, architects, developers, and security professionals.
• Current Team Size: 11 Direct Reports

KEY CAPABILITIES FOR SUCCESS:

• Demonstrated leadership through complex organizational changes, agile development adoptions, and digital technology transformations.
• Ability to drive rapid solutions and innovation velocity while maintaining rigorous security discipline and regulatory obligations.
• Exceptional verbal and written communication skills, with a proven ability to translate application architecture and technical risks into business outcomes for Board-level audiences.
• Strategic thinker with strong operational, procurement, contract negotiation, and financial management instincts.
• Collaborative cross-functional leader exhibiting high integrity and sound judgment under pressure.
• Ability to work collaboratively with an executive team in the formulation of enterprise strategy that aligns with short and long-term plans.
• Demonstrated leadership competencies such as: building effective teams, developing others, having strong peer relationships, managing and executing innovations, and organizational agility.
• Exceptional ability to develop departmental strategic plans that align and support the enterprise strategic plans.
• Strong leadership skills in the development of quality leaders capable of successfully executing strategic plans through the formulation and execution of operational plans and strategies.
• Results-oriented leader who is highly motivated, self-directed and passionate about creating business value for the organization.
• Ability to articulate the IT strategy to all levels within the organization and to present ideas in a business-friendly and user-friendly language.
• Keep current with trends and issues in the IT industry, including current technologies and cost, advising/counseling/educating executives and management on their competitive or financial impact.

QUALIFICATIONS:

• Bachelor's degree in Computer Science, Information Technology, Information Systems, Engineering, or a related technical field, required.
• Master's degree in Business Administration (MBA), Computer Science, or a related discipline Preferred
• 15+ years of progressive technology leadership experience.
• 7+ years in a leadership role with demonstrated accountability across infrastructure, application development, and information security.
• CISM (Certified Information Security Manager) Preferred
• Direct experience serving in or alongside a CISO function, with exposure to cybersecurity program ownership, Board reporting, and regulatory examinations (specifically NYDFS 23 NYCRR 500).
• Experience with Microsoft Azure Solutions required
• Demonstrated experience within the Property & Casualty insurance industry is strongly preferred.
• Hands-on experience supporting, implementing, or migrating core insurance suites-specifically Guidewire or similar-is highly preferred.
• Proven track record of leading cloud transformation initiatives, scale AI/ML platform deployment, and DevSecOps transitions.

Compensation: Our target base compensation for this role is approximately $200,000 per year paid on a salaried basis. Any offer made to a candidate will be based on the candidate's experience and may be more or less than this target. This position is also eligible for our short-term incentive plan, eligible to defer earnings through our Non-Qualified Deferred Compensation Plan. This position is also eligible for all other benefits including the 401(k) and Pension Plan.