[Hiring] Director of Engineering @Recruiting From Scratch

Role Description

The Director of Engineering – Core Product will:

• Lead and grow the Core Product engineering organization, owning both technical direction and team performance.
• Partner closely with the executive team, Product, and other cross-functional leaders to translate company strategy into an engineering roadmap.
• Define the architectural roadmap for a platform powering AI-assisted and increasingly autonomous insurance workflows.
• Bridge product vision and technical execution, ensuring engineering investments translate directly into customer and business impact.
• Establish engineering frameworks, standards, processes, and operating cadences that allow the organization to scale effectively.
• Drive complex, large-scale engineering initiatives from strategy through execution.
• Develop a high-performance engineering culture with clear accountability for quality, reliability, velocity, and outcomes.
• Recruit, retain, coach, and develop exceptional engineering talent, including engineering managers and senior technical leaders.
• Raise the bar for architecture, system design, code quality, operational excellence, and engineering execution.
• Establish and use engineering metrics to identify bottlenecks, improve execution, and make better technical and organizational decisions.
• Oversee the evolution of distributed, cloud-based systems utilizing serverless technologies and asynchronous workflows.
• Help rethink how software gets built as AI agents become increasingly embedded within the engineering lifecycle.
• Balance speed and experimentation with the reliability and quality requirements of software used by major enterprise customers.

Qualifications

• 10+ years of professional software engineering experience.
• 3+ years of full-time engineering people management experience.
• Experience leading substantial full-stack product engineering organizations.
• Ideally has experience managing engineering managers and scaling engineering teams beyond a single IC team.
• Remains deeply technical and can credibly engage in architecture, system design, infrastructure, and engineering trade-off discussions.
• Proven track record leading complex, large-scale engineering initiatives.
• Strong experience connecting technical strategy to company-level product and business objectives.
• Deep architectural expertise across distributed systems, scalable infrastructure, and modern cloud environments.
• Experience overseeing platforms using technologies such as AWS Lambda, EC2, serverless architectures, and asynchronous workflows.
• Track record of building high-performing, results-oriented engineering organizations.
• Strong recruiter who can consistently attract exceptional engineering talent.
• Experience establishing engineering standards, operating rhythms, and metrics as an organization scales.
• Able to make pragmatic trade-offs between speed, technical quality, reliability, and longer-term architecture.
• Comfortable operating with significant autonomy in a fast-growing environment.

Requirements

• Experience managing managers and multiple engineering teams.
• Background scaling a technically complex B2B or enterprise SaaS product.
• Experience with AI-native products or engineering organizations incorporating AI agents heavily into software development.
• Strong point of view on how AI changes engineering productivity, development processes, and team structure.
• Experience building systems where correctness, reliability, security, and customer trust are critical.
• Experience scaling distributed and serverless architectures.
• Strong metrics orientation around engineering velocity, reliability, quality, and organizational performance.
• Experience partnering directly with founders, executives, and senior Product leadership.
• Comfortable remaining technically involved while operating at Director-level organizational scope.
• Insurance or insurtech experience can be valuable, but is not presented as a requirement.

Compensation and Benefits

• Base salary: $230,000–$350,000, depending on experience, interview performance, and geographic location.
• Equity: Significant equity options package.
• Location: Remote within the United States.
• 401(k) with employer contribution regardless of employee contribution.
• 100% covered medical insurance for individuals and families.
• 100% covered dental and vision insurance for individuals and families.
• 20 days of PTO annually.
• Healthy living/gym stipend.
• Mobile phone stipend.
• Continuing education credits.
• Global company offsites.
• Opportunity to shape both the technical architecture and engineering organization behind an AI platform tackling a massive, highly complex industry.
• Best suited for a technical engineering leader who wants meaningful organizational scope without becoming disconnected from architecture, product, and how software is actually built.