About Trellis

Trellis is rewriting the insurance experience from the inside out. We’re the tech company behind Savvy, our licensed insurance agency, and we’re bringing clarity and ease to a space known for… the opposite. With powerful tools, clean design, and a customer-first mindset, we’re making insurance shopping refreshingly effortless.

We’re a profitable, fast-growing Series A startup backed by General Catalyst, QED, NYCA, and Amex Ventures. As a remote-first team, we move quickly, experiment boldly, and build with intention.

If you’re craving meaningful impact, energized by ambiguity, and are ready to build alongside exceptional teammates, you’re going to love doing your best work at Trellis.

Position Overview

As a Senior Principal Software Engineer on the Conversational AI team at Savvy (Trellis), you’ll play a critical role in shaping the future of our AI-driven customer experiences. You’ll architect and build intelligent systems that power natural, engaging conversations between users and our platform. Working closely with cross-functional partners, you’ll transform high-level product initiatives into scalable, well-tested technical solutions.

You’ll lead the way on complex projects by defining scope, setting technical direction, and mentoring teammates along the way. You’ll guide the team through tough challenges, offer thoughtful code reviews, and contribute to a culture of continuous learning and collaboration. Whether you're onboarding new teammates or refining our LLM-driven infrastructure, you’ll be a key force behind our AI innovation.

You will report directly into John Hartley, Head of Conversational AI.

What You’ll Do

• Own the ideation and execution of high-impact projects that directly influence the user experience and business outcomes

• Flesh out and evolve the Conversational AI Engineering roadmap alongside product and technical leadership

• Incept projects: identify opportunities, design solutions, and lead implementation

• Guide integration efforts with external agencies and insurance carriers

• Normalize, rank, and evaluate results using ML-based predictions to determine optimal user paths

• Work closely with our Data Science team to leverage MLMs in tools like DataRobot for retention forecasting and decision logic

• Ensure scalability and performance across the platform as we continue to grow

What You’ll Need

While you don’t need all of these to be successful in this role, we think you’ll be more successful the more you have.

• 7+ years’ experience developing software in a production environment

• 4+ years’ experience in a senior engineer role

• Ability to lead projects from conception through execution

• Production experience with Node.js and Typescript

• Proven experience working in backend systems, designing RESTful APIs and codifying business logic on top of data stores

• Familiarity with GCP, Looker, BigQuery are a plus

• Exceptional ability to communicate clearly and concisely, particularly in Slack and technical documents

• Experience in product development where you were a key decision maker

• Cross-functional leadership and collaboration experience

Who You Are

• Meticulous: You pay attention to detail and take pride in what you deliver

• Articulate: You succinctly and effectively communicate verbal and written technical and non-technical ideas and topics

• Kind, not (just) nice: You provide tough feedback in a clear and concise manner that does not diminish or belittle the recipient

• Opinionated: You bring strong opinions to discussions but are willing to change your mind when presented with new or better information

• Product-minded: You focus on the “why” just as much as the “what” or “how”

• Collaborative: You work within your team and cross-functionally to build consensus and achieve results

• Autonomous: You are self-motivated, able to hold yourself accountable, and can generate high-value work with little direct supervision

Why Trellis? Because you deserve a career that’s exciting, meaningful, and surrounded by people who lift you up.

We’re a group of curious, mission-driven humans rewriting the insurance experience and having a lot of fun along the way. At Trellis, you’ll make a real impact on a product millions rely on, and grow alongside a company that’s scaling fast.

What sets Trellis apart:

✨ A transparent, collaborative culture where ideas win, not titles
🚀 Big opportunities to take ownership and chart your growth
💰 Competitive compensation (75th+ percentile)
🏡 Fully remote across the US & Canada
🎉 Quarterly virtual and/or in-person events that keep us connected

Plus, the benefits are built to support your whole life:

🌴 Flexible vacation (yes, actually flexible)
🩺 Health insurance starts day one

🧘 Wellness programming, because balance matters
💸 401(k) and HSA contributions, FSAs, bonuses & equity opportunities
🐣 Paid parental leave

👉 If you want a role where you’ll grow, be trusted, and build something that genuinely improves people’s lives, Trellis is the place. Join us.

We are an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.

Note: all employees must complete a background check prior to starting employment with Trellis or its subsidiaries