Chief Technology Officer

About The Job

The Chief Technology Officer will serve as a strategic business partner and operational leader responsible for transforming technology into a durable competitive advantage. This executive will modernize core systems, elevate cybersecurity and data capabilities, and build a disciplined, high-performing technology organization.

Beyond technical leadership, the CTO will shape culture—establishing clear expectations, measurable performance standards, and a team-oriented environment that attracts and retains top talent. The ideal candidate leads with clarity, builds trust across functions, and develops leaders within the organization.

This role is ideal for a technology leader from insurance, fintech, banking, payments, or other regulated B2B industries who understands how to scale platforms in complex compliance environments. Direct title insurance experience is welcome but not required.

Key Responsibilities

Strategic Technology Leadership

• Develop and execute a multi-year technology roadmap aligned with growth and value creation objectives.
• Translate business strategy into clear technology priorities and organizational goals.
• Modernize core operational and underwriting platforms to improve scalability, automation, and user experience.
• Lead cloud transformation and architect API-driven, modular systems.
• Identify opportunities to leverage data, automation, and AI to drive efficiency and risk insight.

Operational Excellence & Financial Discipline

• Implement KPI-driven technology management (uptime, velocity, cost per transaction, ROI on tech spend).
• Establish rigorous capital allocation and vendor management processes.
• Build structured SDLC, release management, and change governance frameworks.
• Drive measurable improvements in system reliability, scalability, and operating leverage.
• Foster a culture of accountability where commitments are clear and outcomes are measurable.

Cybersecurity, Risk & Compliance

• Ensure enterprise-grade cybersecurity controls and regulatory compliance.
• Strengthen business continuity and disaster recovery capabilities.
• Partner with legal and compliance teams to support regulatory requirements.
• Provide transparent reporting to executive leadership and the Board.

Data & Analytics

• Develop enterprise data architecture supporting actionable business intelligence.
• Enhance reporting, underwriting insights, and operational dashboards.
• Introduce automation and analytics tools that improve risk management and decision-making.
• Promote data literacy and insight-driven decision-making across the organization.

Team Leadership & Culture

• Build, mentor, and scale a high-performing engineering, infrastructure, security, and data organization.
• Recruit and develop strong leaders who can operate with autonomy and accountability.
• Establish succession planning, talent development pathways, and performance management standards.
• Encourage collaboration across underwriting, operations, finance, and compliance functions.
• Serve as a visible, engaged executive who reinforces company values and promotes a culture of ownership and continuous improvement.

Required Experience

• 10–15+ years of progressive technology leadership experience.
• Experience in financial services, insurance, fintech, payments, banking, regulated SaaS, or similarly complex B2B environments.
• Proven track record leading digital transformation or platform modernization initiatives.
• Experience managing cybersecurity, compliance, and risk frameworks.
• Demonstrated success building and scaling high-performing teams.
• Strong financial acumen and comfort operating in a performance-driven or PE-backed environment.
• Demonstrated success integrating AI and intelligent automation into core business operations, delivering measurable gains in speed, accuracy, and decision quality at scale.

Preferred (But Not Required)

• Exposure to insurance underwriting or transaction-based business models.
• Experience integrating acquisitions and rationalizing technology stacks.
• Cloud transformation leadership (AWS, Azure, or GCP).
• Familiarity with workflow-intensive, document-heavy operational environments.

Leadership Characteristics

• Strategic Builder: Sees technology as a growth enabler and competitive differentiator.
• Disciplined Operator: Brings structure, metrics, and predictable execution.
• People Developer: Invests in talent, builds strong leadership benches, and fosters accountability.
• Value-Creation Oriented: Connects technology investments directly to enterprise outcomes.
• Collaborative Executive: Builds trust across departments and aligns teams around shared goals.
• Board-Ready Communicator: Clear, concise, data-driven storyteller.
• Change Leader: Comfortable modernizing legacy systems and evolving culture.

About TRG

TRG is one of the nation’s largest and fastest-growing title insurance underwriters, delivering trusted solutions to a broad range of customers and protecting property ownership rights across America. At TRG, we don’t just underwrite title insurance policies – we build partnerships that last.

As part of our broader network, we proudly serve leading affiliate partners, including Anywhere Real Estate, Inc. a subsidiary of Compass, Inc. (d/b/a Compass International Holdings) (NYSE: COMP), HomeServices of America (a Berkshire Hathaway affiliate), Lennar (NYSE: LEN and LEN.B), and Opendoor Technologies Inc. (NYSE: OPEN) – and a large network of strong independent agents.

We are powered by our people—their expertise, dedication, and passion drive everything we do. As a Great Place to Work®-certified company, we believe our employees are our greatest asset. Your success drives ours, and at the core of our company is a commitment to help you own, develop, and nurture your career.

Why Work with Us?

• Lead in the Industry: Join one of the nation’s largest and fastest-growing title insurance underwriters.
• Powered by Our People: Be part of a team where your talent and ideas fuel innovation and success.
• Innovate for Impact: Create solutions that solve real problems and deliver value to customers.
• Culture Where Every Voice Counts: Work in a positive, inclusive, and collaborative environment where your ideas matter.
• An Edge for Your Career: Access tools, resources, and training designed to help great talent become even stronger.
• Advancement Opportunities: Take on new opportunities to expand your skills and grow.
• Flexibility That Fits: Enjoy remote and hybrid options (role-dependent) to support work-life balance.

For more information, visit www.TRGUW.com.

Key skills/competency

• Strategic Technology Leadership
• Operational Excellence
• Cybersecurity and Compliance
• Data and Analytics
• Team Leadership
• Digital Transformation
• Platform Modernization
• Cloud Transformation
• AI and Automation
• Risk Management