Staff Product Manager, Conversational AI

About the role

We run one of the largest conversational AI platforms in insurance, powering millions of calls and texts each week through our AI assistant, Abby. The system is strong, but the conversations themselves haven't had a dedicated owner, until now. We're hiring a Staff Product Manager to own how and when those conversations happen. You'll dive into transcripts and call flows, leveraging AI to mine them for insight and making sharp product decisions that improve quality and conversion. You'll also shape Abby's next chapter as we extend her reach into new products and customer journeys, with the same obsession for quality and conversion. This role is for someone with strong product instinct and analytical rigor, able to diagnose where conversations break down, run experiments, and drive impact. If you're excited to leverage AI and voice at scale, you'll own a high-volume, revenue-critical surface and be given the autonomy to move your metrics. This is a fully remote position, based in the US, reporting directly to the Head of Conversational AI, John Hartley.

Responsibilities

• Own conversation quality . Review transcripts, calls, and SMS across sales, voice AI, and CS. Identify where conversations break: dead ends, confusion, tone issues, missed intent.
• Own the metrics. You'll be given targets (e.g. answer rate, conversion, time to monetization) and the autonomy to create projects and experiments that shift the metrics.
• Run experiments. Test prompts, messaging, timing, and flows. Define success, analyze results, and ship what works.
• Use AI as a real tool, not a buzzword. Leverage tools like Claude to surface patterns, draft prompts, and validate ideas.
• Partner with Analytics. Work with Analytics to answer key questions (who to call, when, and why) and act on insights.
• Define success. Establish and track metrics like completion, escalation, sentiment, and time-to-resolution.
• Expand Abby. Extend Abby across Gen Digital - Help bring conversational AI into new products and partners.
• Be the user's voice. Ground decisions in real conversations, not abstractions.

Requirements

• 7+ years in product . Experience with conversational AI, messaging, or adjacent (MarTech, CRM, lifecycle).
• Strong experimentation skills . You've run A/B tests and know how to separate signal from noise.
• Lifecycle/engagement background . Experience with SMS, voice, email, or similar channels.
• LLM familiarity . Comfortable with prompts, evals, and conversational design.
• Data fluency . Can work in SQL/Looker and use data to make decisions.
• AI-native workflow. Tools like Claude are part of how you think and work.
• Strong product instinct . Especially for real-time, multi-step interactions.
• Excellent written and verbal communication. You can distill complex conversation patterns into clear, actionable insights for engineering, design, and leadership.
• Proven senior IC. Comfortable owning outcomes in fast-moving teams.
• Bonus Points
• Experience in insurance, fintech, or another regulated industry.
• Background in conversational design, UX writing, or CX operations.
• Familiarity with evaluating ML outputs to guide user flows.
• Light Python or notebook experience.
• Obsessively curious . You spot patterns others miss.
• Methodical . You test, measure, decide.
• Opinionated but adaptable . Strong views, guided by data.
• A clear communicator. Across eng, design, and execs.
• Autonomous. You find problems and drive solutions.
• Product-minded. Focused on user outcomes, not process.
• 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 fle

Benefits

Additional Information

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.

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