VP of Technology / CTO

Job Description

Job Description

VP of Technology / CTO

Location:  San Ramon, CA (Some flexibility for Hybrid)
Salary Range: $200,000 – $250,000 (Annual, DOE)

Work Schedule:  Monday-Friday, 8:30-4:30 with some flexibility of start/end times

Comprehensive Benefits Package : Competitive medical, dental, and vision plans. 401(k) with employer contribution, generous PTO, wellness rewards, and additional employee support benefits.
Direct Hire

We are actively seeking a VP of Technology / CTO to join a specialized financial services organization that plays a critical role in the California insurance ecosystem. You will be the senior technology leader driving the evolution from complex legacy systems to a modern, secure, and user-friendly technology environment, while setting a clear, long-term technology vision in partnership with executive leadership. This is a high-impact role for a strategic, hands-on technology executive who enjoys shaping long-term roadmaps, partnering with executive leadership, and seeing transformation efforts through from concept to successful rollout.

If you are excited by complex environments, large-scale transaction systems, and the opportunity to modernize mission-critical platforms, this could be an excellent next chapter in your career. To explore this role, apply today and call Brett or Tiffany at View phone number on us.fitly.work to discuss details.

Reasons to Join This Team:

• Directly influence the modernization of a mission-critical technology environment that processes very high transaction volumes and supports a unique market niche.
• Partner closely with executive leadership and a dedicated technology committee to align strategy, budget, and long-term innovation priorities.
• Take ownership of the roadmap for replacing and modernizing a large, proprietary legacy system with modern, scalable platforms that improve user experience and operational agility.
• Join a stable, established organization with a clear mission and strong commitment to continuous improvement and operational excellence.

What You’ll Be Responsible For:

• Setting and executing the overall technology vision, with a strong focus on modernizing legacy platforms and migrating to scalable, intuitive systems.
• Providing strategic leadership across infrastructure, applications, security, and support functions to ensure a cohesive, future-ready technology environment.
• Owning vendor strategy, from evaluating modern platforms and overseeing implementations to managing ongoing performance, SLAs, and value delivery.
• Building multi-year technology investment roadmaps, preparing and managing the IT budget, and presenting business cases to senior leadership.
• Overseeing all core technology operations, including cloud environments (such as AWS), internal servers, networks, security, system monitoring, backups, and disaster recovery.
• Driving the full lifecycle of the legacy system migration, from gap analysis and platform selection through phased rollout, change management, and optimization.
• Establishing and maintaining technology policies and governance for data management, security, cloud adoption, and use of emerging technologies.
• Championing a forward-looking cybersecurity posture, including zero-trust principles, proactive threat monitoring, and regular risk reviews with executives.
• Acting as a strategic advisor to senior leaders, translating organizational needs into practical technology initiatives and clearly communicating complex concepts.

To Be Successful in This Role, You'll Bring:

• 10+ years of progressively responsible technology leadership experience, including leading enterprise-scale environments and multi-functional initiatives.
• Experience managing heterogeneous environments and mission-critical transaction systems, ideally including legacy platforms such as IBM AS/400, DB2, and related technologies.
• Strong background working with cloud platforms and SaaS ecosystem and evaluating modern replacements for legacy systems in complex organizations.
• Demonstrated success leading large, multi-phase technology programs, including vendor selection, implementation, stakeholder engagement, and change management.
• Experience managing blended onshore/offshore development efforts with clear governance, quality standards, and delivery discipline.
• Exceptional communication and presentation skills, with the ability to engage senior leaders, committees, and non-technical stakeholders in clear, business-focused terms.
• Highly analytical, proactive, and solutions-focused mindset, with a track record of anticipating risks, addressing issues early, and driving results in ambiguous situations.
• A collaborative, low-ego leadership style that builds trust, encourages innovation, and creates a culture of accountability and continuous improvement.

Dynamic’s benefits and leave programs for Temporary and Temp to Hire Associates are provided in our employee handbook and are reviewed during onboarding and follow state, local and federal laws. Eligibility and accrual rates may vary based on work location and employment status.

Dynamic provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state, or local laws. This policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation, and training.