Head of Engineering
Remote
Full Time
#Engineering
#Financial Services
#Artificial Intelligence
#AI
#Team Leadership
#Scalability
#Process Improvement
#Product Management
Trellis is a profitable, fast-growing Series A startup backed by top investors like General Catalyst, QED, NYCA, and Amex Ventures.
Our mission: make shopping for home and auto insurance faster, smarter, and easier for everyday Americans. Powered by ML and GenAI, we help people find better insurance — saving them time, money, and stress.
We’re fully remote, built for speed, and led by a third-time fintech founder with a track record of building public companies.
If you move fast, take ownership, and care about your craft, you’ll thrive here.
About the Role:
We’re looking for a Head of Engineering to lead our Conversational AI team, and help us level up what we’ve already built. In just a year, we’ve gone from zero to 100,000+ phone calls a day through our conversational AI platform, and now we’re looking to add someone who’s hungry to scale, optimize, and push it even further.
You’ll be the first dedicated people leader of this team, working closely with our current technical lead, who’s shifting into a more focused development role (Hi, Chuong 👋🏼), meaning you’ll have a strong technical partner from day one.
You’ll spend about 50% of your time in the code and 50% building the team, processes, and structure that we need to grow fast and smart. We’re looking for someone who loves solving tough problems, scaling systems, and leading from the front; not just managing from a far.
This is a fully remote position, based in the US or Canada, and will report directly into the CEO, Daniel Demetri.
Your Goals:
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- Own and grow the Conversational Engineering team: Hire smart people, coach existing talent, and help us move faster without breaking what’s working.
- Architect and build: Hands on keyboard, you’ll help design, build, and optimize our conversational AI orchestration with a focus on performance, quality, and scalability.
- Be a pinch hitter for product: We need someone who can evaluate data, prioritize MVPs, draft concept docs, and keep projects moving across a lot of moving parts.
- Solve problems with process: Build lightweight workflows and QA systems that help us react faster, find opportunities, and stay ahead of issues.
- Think strategically: Partner with leadership to design experiments, improve the business by 5% every week, and push the limits of what conversational AI can do (hint: dynamic sales conversations, not just triage).
- Own and grow the Conversational Engineering team: Hire smart people, coach existing talent, and help us move faster without breaking what’s working.
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- Evangelize and collaborate: Work closely with vendors, affiliates, internal teams. You're someone who can herd cats when needed without breaking a sweat.
Who you are:
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- You’ve scaled tech before: You've been part of the 10 → 100 journey and know how to safeguard what works while adding what’s needed.
- You still love getting your hands dirty: You enjoy leading but you love building.
- You think like an owner: You can spot opportunities to improve, ship experiments quickly, and constantly push for better.
- You’re startup tough: You’re flexible, fast, and comfortable wearing multiple hats.
- You can riff with a strong tech partner: Chuong will stay hands-on with the tech stack, you’ll have the advantage of working closely together, complementing each other's strengths.
- You’ve scaled tech before: You've been part of the 10 → 100 journey and know how to safeguard what works while adding what’s needed.
Compensation
Total compensation will be between $300-600K, dependent on experience and other factors.
Trellis is a fantastic place to work
Join a talented, passionate team:
- Flat, collaborative, transparent culture; get in at the ground floor and be a true business partner
- Opportunities for growth and development within your role and all areas of the organization
- 75th-percentile (competitive!) compensation
- 100% remote work environment
- Quarterly, fun team bonding events
Trellis additionally offers competitive benefits:
- Unlimited vacation time
- 100% employer-paid Platinum-tier health insurance for employee, 65% for dependents
- Flexible Spending Accounts (FSAs)
- 401(k) retirement savings plan
- Bonuses and equity opportunities
- Budget for home office equipment
