Senior Product Designer

Our mission

The trucking and logistics industry provides the backbone of the economy. But the payments infrastructure on which it runs is broken. For the hard-working men and women of this sector, the existing suite of payment tools is outdated, difficult to use, prone to fraud, and saddled with shady fee structures. The incumbent players in this space often overlook the economic and practical needs of this user base.

Our history and background

Our founding team has backgrounds in payments, working on autonomous vehicles at Cruise Automation, leading ops and growth for Uber, and building apps that were featured on the Apple app store. We have staff and senior engineers from Google, Uber, Meta, Shopify, Stripe, Chime, and other leading technology companies.

We have raised $125 million+ from investors such as General Catalyst, Elad Gil, Bloomberg Beta, Y Combinator, XYZ; founders and CEOs of companies such as Google (Eric Schmidt), Salesforce (Marc Benioff), Coinbase (Brian Armstrong), DoorDash (Tony Xu), Instacart, Gusto; strategic investors like Mastercard, Flexport and Samsara.

We were named to Forbes annual Next Billion-Dollar Startup List, and have just recently been selected to join the World Economic Forum as a Global Innovator.

You'll be the second product designer on the team, reporting to our Staff Designer and partnering closely with a PM, an engineering team, and — on the right problems — directly with our CEO. You'll own meaningful surface area end-to-end: shaping the problem, exploring solutions, pressure-testing assumptions, and ensuring the solution actually ships.

This is real ownership over a large product surface area at a fast-growing fintech platform, in a small senior team where you'll set the bar rather than inherit one.

Take ambiguous problem areas and turn them into simplified, well-considered solutions. Inject product thinking into fast-moving conversations and challenge assumptions with clear rationale. Design flows across payments, underwriting, capital, and fintech infrastructure. Build the connective tissue between flows so the product feels like one thoughtful thing, not a collection of features. Raise the visual and interaction bar across the product, including motion and the moments between states. Help us evolve our design system from "what we have now" toward something that scales — comfortable working without it when needed, and building toward it when possible. Use modern AI-native tools (Claude Code/Design, v0 etc.) to explore interactive ideas, while keeping your design fundamentals sharp.

You can go from messy whiteboard idea → structured flow → polished solution. You can explain why something should exist, not just how it should look. You care more about product clarity than visual flourish — and your portfolio still has the visual and interaction craft to back it up. You design fast without sacrificing coherence. You've been the lone or near-lone designer before (or wish you had been). You have senior-level scope and judgment from a modern, design-forward product environment — ideally fintech or fintech-adjacent, though caliber of work matters more than the logo on your résumé. You have a working relationship with AI tools that's neither dismissive nor dependent.

This isn't a role for someone who wants a mature design system, a full research org, and clearly scoped tickets. It's also not a pure visual or pure systems role — if either of those is what you love most, we may not be the best fit for you.

Based in the San Francisco Bay Area (3-4 days/week in our SF office), or remote from a close metro like Los Angeles with monthly trips to SF (Tues-Thurs, expenses covered). Relocation supported for the right candidate.