Founding Product Designer

About Ollive AI agents are creating a new class of enterprise risk — hallucinations, bias, data leakage, IP infringement, unsafe autonomous actions — that existing insurance (cyber, E&O, CGL) was never built to cover. Ollive is building the risk layer for the agentic economy: we measure and monitor the liability risk of AI agents today, and we're building the purpose-built insurance to cover it. We're a seed-funded team building two products on one mission, in sequence: a risk-assessment / GRC and continuous-observability platform that shows AI companies exactly how their agents fail and create liability — and the insurance product that backstops it. Customers run our assessments to prove their agents are safe to deploy, pass enterprise security reviews, and close their own deals. That same risk signal becomes the underwriting engine for coverage no one else can offer. You'd be our first design hire owning the product's look, feel, and experience end to end. The Role We're answering a question almost no one has answered well: what does risk, compliance, and insurance software look like when it feels as good as a consumer app — without losing the gravitas the category demands? This is the heart of the role, and it's genuinely hard:

• One product, very different users. AI/ML engineers who live in the data. Security and compliance leaders who need defensible proof. CFOs, GCs, and risk owners who buy the coverage. Each needs a surface built for how they think — inside one coherent product.
• Make dense data legible, even beautiful. Eval results, real-time risk posture, behavioral drift, spiking-risk alerts, accumulation. The raw material is complex and technical; your job is to make it instantly understandable and a pleasure to use.
• Design for trust. People make high-stakes, regulated decisions on this software. It has to feel authoritative and earned — premium, not flashy; confident, not loud.
• 0→1, then 1→n. Define the design language now, then evolve it as we layer in continuous observability and, later, an insurance experience — without it ever feeling bolted together.

What you'll work on - The core risk-assessment / GRC evals experience — from raw test results to a story a user can act on. - Real-time risk posture dashboards and the alerting experience — surfacing what matters the moment it matters, without overwhelming. - Procurement-ready reports that an enterprise buyer or GC will trust and accept. - The design system — we have a starting palette; you'll shape it into a language with real depth. - Later: the coverage / insurance experience, designed so it feels like the natural extension of everything before it. - Brand and marketing surfaces as needed — including the website — since you'll define how Ollive looks to the world.

What we're looking for

Must-haves - A strong portfolio of shipped, modern product design — ideally complex or data-dense B2B software you made feel simple and premium. - End-to-end range: research, information architecture, interaction, visual craft, and prototyping. - Fluency designing for multiple personas and complex workflows in a single product. - Fluent in AI-native design and prototyping tools — you move from idea to high-fidelity, interactive prototype fast. - A high craft bar paired with product and strategic thinking — you push back on the what and why, not just execute the how. - Comfort with ambiguity and the energy to own design as our first designer. Bonus - Experience in a "serious" category — fintech, insurtech, security, compliance, devtools — that you made feel genuinely great. - Comfortable taking designs into code (front-end fluency). - Genuine interest in AI, AI safety, or risk evals, insurance. - You've built and owned a design system from scratch.

Why join

- A founding design seat. You define the product experience and the brand — not inherit them. - A novel, important problem in a new category at the center of the AI buildout, with real users and real urgency. - A small, senior team that ships fast and gives you direct ownership and a direct line to the founders. - Meaningful equity and competitive compensation. Sign-in to access assignment link! - Assignment (portfolio submission process) is accessible after you sign-in and onboard onto brank.ai - After Sign-in, in the Jobs section, in the side bar please open the job opening and click on "Open Assignment" to access the same