Lead Engineer / Head of Engineering (CTO-Track)

Company Overview

Our client is a 25-year-old, bootstrapped SaaS company serving the property & casualty insurance industry, specializing in high-volume catastrophe claims management.

The platform is used by insurance carriers to manage residential property claims and scales during surge events from ~1,500 to 5,000+ concurrent users, supporting 250,000+ claims annually. The company is lean (~13 employees), profitable, and highly regarded for delivering the most functionally complete product in its niche.

The founder is product- and domain-driven, seeking a senior technical leader to own how the product is built, scaled, and delivered.

The Role

This is a hands-on technical leadership role, not a traditional CTO. You will be the senior-most engineering leader, responsible for architecture, code quality, delivery, and operational reliability.

You will work closely with the Founder and the small engineering team, contributing code, making technical decisions, and mentoring others. Over time, this role can evolve into a CTO-level position.

Responsibilities:

• Own and contribute to technical architecture and core codebase, acting as a hands-on senior engineer and technical authority.
• Design, implement, and maintain scalable, reliable, and secure systems.
• Lead code reviews and enforce high standards of quality and maintainability.
• Ensure technical quality, testing standards, and release readiness in partnership with Product and DevOps.
• Continuously evolve engineering practices and workflows incrementally and pragmatically.
• Champion AI-assisted development and implement best practices for AI tooling (e.g., LangChain, CrewAI, Cursor).
• Collaborate with Product leadership to translate requirements into technical solutions, identifying trade-offs and risks.
• Mentor and lead a small engineering team, primarily through hands-on contribution and example. The team is bifurcated into Product and Professional Services and made up of W2 and 1099 (supplemental capacity when needed).
• Proactively manage technical debt and risks, balancing short-term delivery with long-term maintainability.
• Lead calmly during critical incidents or surge events, ensuring system stability and clear communication.
• Adherence to departmental budgets, as well as performance KPIs for productivity and profit.
• Accurately record time worked using the company's time-tracking system.

Requirements:

• Backend: 7+ years in C#, ASP.NET, including modernizing legacy systems
• Frontend: 2+ years in Vue (or React, but you should be ready to adapt to Vue3)
• Cloud / DevOps: Extensive Azure experience, familiarity with CI/CD pipelines
• AI & Modern Development: Experience or familiarity with LLMs, AI-assisted coding tools, and establishing internal best practices
• Leadership: Previous experience leading 5-10 person engineering teams, setting standards, making technical decisions, conducting code reviews, and collaborating in sprint/product planning
• Operating Style: Pragmatic, low-ego, execution-focused; comfortable in founder-led, low-process environments; willing to be accountable during high-pressure situations

Why Join Us?

• Hands-on impact: Lead architecture, code, and product execution in a high-value, critical SaaS platform
• Not a startup: You will own a large, end-to-end enterprise, mission-critical operating system relied upon by several market-leading and rapidly growing insurance carriers
• CTO-track growth: Opportunity to evolve into a top technical leadership role with significant equity upside
• AI-driven innovation: Apply AI-assisted development and modern tooling in production
• Founder-led environment: Work directly with a product- and domain-driven founder in a low-bureaucracy culture
• Progressive mindset where innovation is critical and rewarded.
• High-responsibility, high-trust culture: Small, lean team with autonomy and direct influence
• Operational scale exposure: Gain experience with surge-heavy systems used by thousands of users simultaneously
• Competitive benefits: Health, dental, vision, life insurance, 401(k) match, flexible time off, and floating holidays

Retirement & Benefits:

• 401(k): Up to 3% company match
• Flexible Spending Account (FSA): Available
• Remote, occasional travel to New Orleans or client sites, profitable and stable company with high-impact opportunities
• Holidays & Floating Days: 12 total days
• Fixed holidays: 9 days (New Year's, Memorial Day, Independence Day, Labor Day, Thanksgiving + day after, Christmas Eve & Christmas Day)
• Floating holidays: 3 days (Mardi Gras/Fat Tuesday, Birthday, Mental Recharge Day)
• 3 weeks of combined sick and vacation time

Insurance:

• Health, Dental, Vision: 85% company-paid, 15% employee-paid
• Life Insurance: Basic coverage 2x salary (up to $250K), optional voluntary coverage available
• Disability & Accident: Employee-paid optional plans

Apply now and high-growth product journey!