Head of Engineering
Remote
Full Time
#Engineering
#Financial Services
#Artificial Intelligence
#AI
#Team Leadership
#Scalability
#Process Improvement
#Product Management
At Trellis, we are on a mission to make the process of shopping for home and auto insurance faster, smarter, and more accessible for everyone. As a profitable and rapidly expanding Series A startup, we have secured backing from prominent investors like General Catalyst, QED, NYCA, and Amex Ventures. Our platform leverages machine learning and generative AI to help people save time and reduce stress while finding the right coverage. We operate as a fully remote team, driven by a culture of speed and led by a veteran fintech founder with a proven history of building successful public companies.
About the Role
We are searching for a Head of Engineering to join us in a full-time capacity. In this executive-level role, you will lead our Conversational AI team as we scale our platform, which already processes over 100,000 phone calls every single day. You will serve as the first dedicated people leader for this group, working in tandem with our technical lead to refine our architecture and processes. This position requires a balance of hands-on coding and strategic leadership, as you will spend roughly half your time building alongside the team and the other half developing the structures and workflows necessary for our continued growth.
Key Responsibilities
- Lead and scale the team: You will be responsible for hiring top talent, coaching our existing engineers, and fostering an environment that prioritizes speed and quality.
- Architect and develop: You will remain hands-on with the code, designing and optimizing our conversational AI orchestration to ensure high performance and scalability.
- Drive product strategy: You will act as a partner to our leadership team by evaluating data, prioritizing product initiatives, and implementing workflows that allow us to experiment and improve our business outcomes consistently.
Requirements
We are looking for a leader who has successfully navigated the journey of scaling technology from early stages to significant growth. You should possess a deep technical background and a genuine passion for building, alongside the ability to think like an owner who is comfortable wearing multiple hats in a fast-paced startup environment. Strong collaborative skills are essential, as you will be working closely with our technical lead, internal teams, and external partners to push the boundaries of what our AI can achieve.
Location
This is a fully remote position available to candidates located anywhere in the United States or Canada.
Compensation and Benefits
We offer a total compensation package ranging from $300,000 to $600,000, which is determined based on your specific experience and qualifications. Our benefits package is designed to support your well-being and long-term success, including:
- Unlimited vacation time
- Medical insurance
- 401(k) retirement plan
- Home office budget
- Equity compensation
- 100% remote work environment


