Fractional Chief Technology Officer - 1099 Position
About The Position
As our Fractional CTO, you will act as our strategic technology partner — evaluating and evolving our tech stack, identifying automation opportunities, and guiding AI-driven innovation. You will assess our existing infrastructure (including an Agency Management System, CRM, SQL database, phone system), recommend scalable solutions, and help us build a future-ready architecture. A first-order priority is to replace the existing phone system and then second, tackle data quality: establishing trustworthy, single-source-of-truth reporting and the data-entry standards to sustain it, so leadership can run the business on numbers it trusts. Additionally, you will partner with executive leadership to complete an annual budget for the IT department. You will work closely with the executive team and collaborate with internal and external engineering resources to turn business goals into technical execution. When submitting your resume, please also include relevant project experience and/or case studies.
Requirements
- 10+ years in a CTO, VP of Engineering, or equivalent leadership role
- Proven success working in or supporting insurance or InsurTech organizations
- Deep knowledge of AI/ML tools and platforms (e.g., NLP, document AI, GPT models, etc.)
- Demonstrated experience building data-governance and data-quality programs (data standards, validation, and duplicate/master-record management) — not only AI/ML
- Hands-on with BI/reporting tools and data modeling (e.g., Power BI, Tableau, SQL) to deliver dashboards leadership can trust
- Hands-on experience with SQL databases, AMS systems, CRM and data integration strategies
- Strong cloud architecture knowledge (AWS, GCP, or Azure)
- Familiarity with agile product development and DevOps practices
- Excellent communication skills and ability to work closely with non-technical stakeholders
- U.S.-based or strong understanding of U.S. insurance regulatory landscape preferred
- Applicants must be legally authorized to work in the United States.
Responsibilities
- Evaluate phone system replacements
- Build a data integrity remediation plan
- Assess AMS alternatives or middleware solutions to work around Hawksoft's API limitations
- Evaluate integration platforms (Zapier, Make, or custom middleware) to connect the tech stack
- Design a carrier payment reconciliation workflow
- Establish a single source of truth for core operating metrics (new business, retention, cancellations, and cross-sell) across all offices and systems
- Define, document, and enforce data-entry standards and field-level data adherence in the AMS and CRM
- Build and maintain a data dictionary so every report uses the same definitions company-wide
- Implement data-quality monitoring, validation rules, and exception reports to catch incomplete, duplicate, or inconsistent records
- Deliver trustworthy, automated dashboards leadership can use to run the business day-to-day
- Establish data ownership/stewardship and a remediation process, with a clear handoff to an internal owner for ongoing upkeep
- Define and evolve the company’s technical vision and product architecture by documenting and creating a technical roadmap with key objectives, deliverables, due dates, estimates and owners assigned
- Align tech decisions with business objectives, growth plans, and market needs
- Advise on key build-vs-buy decisions
- Create an annual IT budget
- Evaluate the current technology stack and infrastructure
- Identify technical debt, security gaps, and architectural limitations
- Design a scalable and secure future-state IT architecture (cloud, DevOps, APIs, etc.)
- Prioritize use cases by ROI and sequence them after core data is reliable — AI and predictive analytics are only as good as the data feeding them
- Lead the identification and development of AI/ML use cases across the business
- Oversee design and potential buildout of AI-powered user interfaces, such as: Voice AI, chatbots, and/or virtual agents, Predictive analytics dashboards for sales and service core processes, Document ingestion and intelligent automation tools
- Ensure all AI solutions are aligned with industry regulations and data handling standards
- Ensure AI and new front-end tools integrate seamlessly with existing systems or replace the following: Agency Management System (AMS), SQL-based databases and reporting tools, CRM
- Recommend and guide implementation of APIs or middleware for interoperability
- Bring a strong understanding and background in insurance related to: Customer experience, UI, UX
- Align technical strategy with industry-specific regulations and user needs
- Mentor and guide engineering resources (internal or external)
- Evaluate and manage third-party vendors or dev partners
- Set development standards and implement best practices
- Review and improve data security, privacy, and compliance policies
- Ensure all systems align with standards such as HIPAA, SOC 2, and applicable insurance regulations
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What This Job Offers
Career Level
Executive
Education Level
No Education Listed
