Lead AI-Native Software Engineer
- Hiring from
- United States
- Work type
- Hybrid
- Posted
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Guardian Service is hiring a Lead AI-Native Software Engineer to build and scale technology that transforms how we deliver insurance quotes to customers.
This role will focus on developing backend systems, integrations, and automations that streamline complex quoting workflows, improve agent productivity, and create a faster, more seamless customer experience. You'll work directly with Marketing, Sales, and business leadership to translate operational challenges into reliable, scalable software.
This is a hands-on leadership opportunity for someone who enjoys building quickly, solving complex technical problems, and developing a high-performing engineering team in a fast-growing business.
Why This Role Matters
Guardian Service is building a technology-enabled insurance agency that combines the choice and personalized service of an independent agency with the efficiency of a scaled operation.
Technology is central to our ability to simplify the insurance shopping experience, eliminate manual work, and help agents serve more customers effectively.
You'll have the opportunity to lead one of Guardian Service's highest-priority engineering initiatives, shape our technical foundation, and build the team and systems that will support our next phase of growth.
Your Day-to-Day
- Lead the design, development, and deployment of technology that improves insurance quoting workflows, speed, and accuracy
- Build backend systems, APIs, integrations, and automations that reduce manual work and improve agent productivity
- Partner directly with Marketing, Sales, and business leadership to identify high-impact engineering opportunities and prioritize development based on business results
- Rapidly prototype, test, and deploy solutions, incorporating feedback from frontline teams
- Leverage AI-native development practices and LLM tooling to accelerate engineering delivery and enhance workflow automation
- Own production reliability, monitoring, debugging, and ongoing improvements to ensure systems meet performance and quality standards
- Establish reusable engineering patterns, technical standards, and deployment processes that support faster, more reliable development
- Lead and develop an initial team of two engineers, providing technical direction, coaching, and clear ownership of workstreams
- Help define the technical roadmap and talent strategy to scale the engineering team as business needs evolve
About You
- Strong proficiency in Python, backend engineering, API development, and systems architecture
- Experience building and maintaining production software involving complex integrations or transaction-heavy workflows
- Proven ability to take ambiguous business problems from initial concept through production deployment and measurable results
- Strong engineering judgment, balancing execution speed with reliability, scalability, and long-term maintainability
- Experience leading or mentoring engineers while remaining hands-on in technical execution
- Strong business instincts and ability to work directly with commercial teams to prioritize solutions based on measurable impact
- Fluency with AI development tools and LLM APIs, with sound judgment around output quality, cost, and reliability
- Familiarity with cloud infrastructure and deployment environments, ideally Google Cloud
- Comfortable operating independently in a fast-moving, entrepreneurial environment with significant ownership and accountability
Nice to Have
- Experience building insurance quoting, rating, or carrier integration systems
- Familiarity with personal lines insurance or insurance distribution technology
- Experience integrating with Salesforce or other CRM platforms
- Experience with asynchronous workflows, distributed systems, and third-party APIs
- Experience hiring and scaling engineering teams in high-growth environments
- Background in insurance, fintech, or direct-to-consumer technology businesses
Why You Should Join Us
- Results: Guardian Service is scaling rapidly, doubling booked premium month-over-month.
- Opportunity: Personal lines insurance is a massive market ripe for transformation, and we’re investing $100M+ over the next three years to build Guardian Service into a leader.
- Ownership & Impact: You’ll own initiatives that directly affect company performance, with leadership fully aligned around growth.
- Exposure & Learning: Work alongside leaders who have built and scaled businesses, led large teams, and driven results at Fortune 500 companies.
- Career Growth: No cap on advancement or the ability to own high-impact projects.
- Stability: Privately owned, debt-free, and financially strong.
- Culture: High standards, but also a team that values fun and camaraderie.
The Package
We offer a competitive base salary based on experience. As a full-time team member at Guardian Service, you'll also enjoy a comprehensive benefits package, including health, medical, and vision insurance, a 401(k) match, flexible PTO, and a cell phone reimbursement. Additionally, we support your well-being and growth with a bi-annual $500 Relax & Recharge bonus, a learning and development stipend, and a Charity Match program to give back to causes you care about.
EEOC Statement
All applicants are considered without regard to race, color, religion, sex, national origin, age, disability, veteran status, gender identity, or any other discriminatory factors. Please note that we do not provide immigration sponsorship for this role. All offers are subject to a background check.
