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Role Description

Trusty is building the modern Estate Binder — helping families organize assets, clarify wishes, and align advisors around what matters most. We’re live, have raised capital, and have early traction. Now we’re looking for a Head of Product to turn direction into disciplined execution. This is not a corporate PM role; it is a hands-on, AI-native builder role.

You will own the product roadmap end-to-end and be responsible for turning company priorities into shipped features. You are expected to:

• Bring structure to ambiguity
• Translate ideas into clear specs
• Prioritize decisively
• Drive sprint execution
• Maintain high product quality

You won’t manage layers of PMs; you will be in the details.

What You’ll Own

• End-to-end product roadmap and prioritization
• Sprint planning and execution rhythm
• Clear specs and tight collaboration with engineering
• Bug tracking and release management discipline
• UX clarity across consumer + advisor experiences
• Converting advisor and client feedback into shipped improvements
• Always defining the next 2–3 sprints

We operate in short cycles. We value shipping over theorizing.

AI-First Expectation (Important)

We are building an AI-native product organization. You should have hands-on experience experimenting with tools such as:

• Cursor
• Claude Code
• Lovable
• OpenAI APIs
• Prompt architecture and structured outputs

You don’t need to be a full-stack engineer, but you must be comfortable prototyping, testing ideas, and using AI tooling to increase velocity and reduce dependency. We are looking for someone who actively tinkers — not someone who outsources experimentation.

Operating Beyond Product

We are a lean, pre-seed team. That means this role will occasionally extend beyond traditional product boundaries. You should be comfortable:

• Joining advisor calls to hear objections firsthand
• Translating GTM feedback directly into product changes
• Helping shape positioning when product and messaging intersect
• Reviewing onboarding and CX flows
• Rolling up your sleeves when something needs fixing

This is not a “stay in your lane” role; it’s a “do what the company needs to win” role.

Tooling & Operating Discipline

You should be comfortable owning and organizing:

• Figma (design systems, scalable components, file hygiene)
• Jira (epics, sprint planning, backlog discipline)
• Bug tracking and prioritization workflows
• Roadmap documentation
• Release coordination
• Cross-functional feedback loops

We expect clean systems — not scattered knowledge.

What Success Looks Like

In 90 days:

• In tune with Product and ICP with ability to guide next sprints and ideas
• Clear, ranked roadmap aligned to company priorities
• Tight sprint cadence
• Organized Figma and scalable design system
• Documented AI architecture and workflows

In 12 months:

• A differentiated, polished product experience
• Strong AI-native workflows
• Clear advisor dashboard direction
• Faster iteration cycles and stronger engagement signals

Who You Are

• 0→1 product builder
• Comfortable in ambiguity
• Strong product instinct + UX judgment
• Structured but not bureaucratic
• Energized by early-stage pace
• High ownership, low ego

Important Bonus

• Fintech / wealth / estate / insurance planning experience
• Experience shipping AI features in production

Team & Structure

You will work directly with:

• Founder (product-oriented, vision-driven, expects thoughtful challenge and clear ownership)
• Head of Engineering
• Revenue and Marketing resources
• Contractor design and development support as needed

This is a high-ownership role with real influence over the product and direction of the company. If you want to manage a large team, this isn’t the role. If you want to build alongside a founder, own the roadmap, wear multiple hats, and use AI as leverage — we should talk.