Product & Commercial Lead at Chestnut

At Chestnut, we are on a mission to modernize the massive insurance industry by building the first AI-native operating system for distribution. We believe the way insurance companies allocate their sales and distribution spend is ripe for a transformation, and we are using agentic AI to replace legacy systems with a flexible, intelligent platform. Backed by a16z, we are already working with major insurers to automate complex workflows and unlock significant growth. We operate as a small, high-context team that values 10x productivity, and we are looking for someone who shares our urgency to reshape this essential industry.

The opportunity

As our Product & Commercial Lead, you will serve as the primary bridge between our technology and our customers. This is a high-impact role where you will own the end-to-end success of our deployments, acting as both a strategic partner to our clients and a product visionary. You will embed yourself within customer organizations to understand their unique workflows, identify critical pain points, and translate those insights into scalable product features. By blending product management with commercial operations, you will help us move faster and deliver measurable value while shaping the future of our platform.

A day in the life

• Manage the full customer lifecycle, serving as the main point of contact from initial kickoff through successful deployment and ongoing partnership.
• Conduct deep discovery sessions to map out complex organizational workflows, identifying the most effective areas to implement AI-driven automation.
• Collaborate with engineering and design teams to turn real-world customer feedback into high-impact product improvements and platform features.

Who you are

You are a seasoned professional with at least 5 years of experience in product management, consulting, or a similar leadership role. You possess strong technical acumen and are comfortable navigating complex systems. You are an expert at building trust with both technical and non-technical stakeholders, and you excel at driving execution even when you have to work with imperfect information. You are naturally curious, a fast learner, and deeply motivated by the challenge of solving real-world business problems. While not required, experience working with SQL, large datasets, or within the insurance and finance sectors will help you hit the ground running.

Why you'll love it here

We are a remote-first company that prioritizes autonomy and high performance. We offer a comprehensive package designed to support your well-being and long-term success:

• Equity compensation with a 10-year exercise window for stock options.
• A flexible, unlimited vacation policy so you can take the time you need.
• Comprehensive medical, dental, and vision insurance plans.
• Regular company retreats to build connections with the team.
• The opportunity to work remotely from anywhere.