About Artemis Insurance
Artemis Insurance is an independent insurance brokerage on a mission to modernize and automate legacy insurance processes. We’re leveraging AI, automation, and scalable cloud infrastructure to improve quoting, sales, service, customer retention, and the employee experience. As we evolve our technology roadmap, we’re seeking a
Fractional CTO
to lead strategy and execution — bringing a blend of technical leadership, AI expertise, and insurance domain experience.
About the Role
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.
Prioritized 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
Additional Detail:
Data Quality, Governance & Reporting
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
Technology Strategy & Leadership
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
Technology Stack & Architecture
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.)
AI & Automation
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
[C2]
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
System Integration
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
Insurance Tech Expertise
Bring a strong understanding and background in insurance related to:
Customer experience
UI
UX
Align technical strategy with industry-specific regulations and user needs
Team & Vendor Leadership
Mentor and guide engineering resources (internal or external)
Evaluate and manage third-party vendors or dev partners
Set development standards and implement best practices
Security & Compliance
Review and improve data security, privacy, and compliance policies
Ensure all systems align with standards such as HIPAA, SOC 2, and applicable insurance regulations
Qualifications
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
Physical Requirements
This role may require sitting for extended periods, working at a computer, and occasionally lifting or moving items up to 10 pounds.
Work Environment and Schedule
This position may operate in an in-office, hybrid, or fully remote environment depending on the role, department, and business needs.
Standard business hours at Artemis Insurance are typically Monday through Friday; however, schedules may vary by department, office location, or operational requirements.
Specific work arrangements, schedules, and location expectations will be discussed during the interview process.
Equal Opportunity Employer
Artemis Insurance is an equal opportunity employer and is committed to creating an inclusive workplace. We consider all qualified applicants without regard to race, color, religion, sex, national origin, age, disability, veteran status, or any other protected characteristic under applicable law.
Work Authorization
Applicants must be legally authorized to work in the United States. Artemis Insurance does not currently sponsor employment visas.
Ready to Join Our Team?
If you are interested in building your career with Artemis Insurance, we encourage you to apply today.
As part of our hiring process, applicants must complete the Culture Index Assessment listed above.
We look forward to learning more about you and how you can contribute to our growing team.