Job description

ABOUT TAXWIRE Taxwire is building an AI-native global sales tax engine & managed service for finance teams. We handle sales tax and VAT from end to end for hundreds of mid-market companies and dozens of accounting / tax firms. We’ve raised ~$25M in venture capital from firms like Headline, XYZ, Vinyl, and dozens of CFOs, founders, and tax practitioners. Indirect tax is high-stakes, fragmented, and unforgiving. Rules change constantly, vary by product and location, and create real financial risk when companies get them wrong. We hire people with high ownership, strong judgment, and low ego. Everyone at Taxwire is expected to understand the customer, solve messy problems end to end, and build systems that scale. We move quickly because our customers depend on us to get it right. Death and taxes are forever. If you want to operate in one of the largest markets in the world and sovle a massive, enduring problem with a team of people playing to win, Taxwire is the place to do it. ABOUT THE ROLE We’re looking for a skilled, experienced, and motivated Founding Product Designer to join our team. This role is focused on product design and UX, with opportunities to shape both product and brand from the ground up. Experience owning product work is a plus. You’ll work closely with our founders, engineers, and tax SMEs to design intuitive, fast, and powerful user experiences. Our product spans self-serve onboarding, data visualization, integrations, and interfaces that help customers configure and automate compliance across hundreds of jurisdictions. You’ll play a central role in shaping the core UX of our platform and making complexity feel simple and trustworthy. This is a great role for someone who craves impact and ownership, and loves turning gnarly, abstract workflows into clear, polished software. WHAT YOU’LL DO - Lead the end-to-end design of Taxwire’s core product surfaces — from user onboarding and dashboards to workflow tools and internal ops interfaces. - Translate complex compliance logic and tax rules into intuitive interfaces that users can trust and understand. - Partner with engineers to rapidly prototype and ship polished features. - Develop a product design system that’s scalable, accessible, and consistent across use cases. - Collaborate with tax specialists to understand the real-world edge cases and regulatory nuance our product must support. - Help evolve and define the company’s visual identity and voice across product, marketing, and internal tools. - Create UX that balances speed, clarity, and trust — especially for workflows involving financial and regulatory risk. - Contribute to product strategy, roadmap planning, and customer research alongside the founders. WHAT YOU NEED 5–10 years of professional product design experience, with a strong portfolio of shipped work (especially B2B, fintech, or data-heavy tools). Experience designing for complex workflows, backend systems, or enterprise use cases. Strong systems thinking — you’re comfortable designing scalable, reusable components and patterns. Excellent interaction design and visual design skills. You know what great UX looks and feels like. Ability to prototype quickly and work closely with engineers to get things built right. Clear, thoughtful communicator — especially in writing. We’re a writing-first company. A deep sense of ownership. You’re proactive, biased toward action, and don’t need to be told what to do. Bonus: experience designing for regulated or trust-critical domains (e.g. finance, healthcare, payroll, tax). Bonus: comfort doing light brand design (e.g. decks, website, marketing assets) in the early days. NICE TO HAVE - Experience designing for regulated or trust-critical domains such as finance, healthcare, payroll, or tax - Comfort doing light brand design—including decks, website, and marketing assets—in the early days WHY WORK AT TAXWIRE - As our first designer, you’ll set the ground work for the role of both design and product in this company. You’ll also work extremely closely with our founders and have the chance to have a major voice in the direction of the product and business. We expect the person that takes this role to grow into a leader in the company. - We’re solving a complex problem that affects companies globally, with a clear path to becoming a large, enduring business. We literally can’t build fast enough to onboard the volume or magnitude of customer inbound we have. - You’ll be earning early-stage equity in a business that’s been significantly de-risked. We’re in execution mode, not will people give a fuck mode. Our market is large with material tailwinds. And we’ve proven we can build great software, sell customers, win against competitors, and recruit talented, senior people from our industry. - We’re an anti-hype-cycle company. Customers will have to solve these problems regardless of what changes with technology or investor sentiment. - Our team is leveraging years of experience building several of the most successful products in our space from 0 to 1 and beyond. - We’re creating trustworthy products that leverage modern technology, in that order. No half-measures. No shortcuts where it matters. We do right by our customers or go home. - If Taxwire succeeds, our goal is to help our team achieve life-changing financial and career outcomes. We’ll work closely with you to make sure you understand and can reap the benefits of your equity (including things like taxes). - We care deeply about serving our people, whether those people are our customers or our team. - We’re well funded by respected institutional VCs and angels. - You’ll work with some of the most talented engineers and tax experts in this domain. - Competitive salary and company-covered benefits package. WHY YOU SHOULDN’T WORK AT TAXWIRE - You love lots of structure and want to be closely managed. - You want to be handed a playbook instead of building one. - You want to ship pretty screens, not solve hairy real-world workflows. - Don’t get excited about serving our customers or find this problem space boring. - You hate the idea of talking to a customer. - You lack conviction or taste. - You’ve never written a PRD and would be against doing so. - Shipping lots of high-quality design and product, fast… scares you. - Confronting and navigating uncertainty intimidates you. BENEFITS - Company-covered benefits - Meaningful equity

Requirements

Must-haves

This is a great role for someone who craves impact and ownership, and loves turning gnarly, abstract workflows into clear, polished software.
Lead the end-to-end design of Taxwire’s core product surfaces — from user onboarding and dashboards to workflow tools and internal ops interfaces.
Translate complex compliance logic and tax rules into intuitive interfaces that users can trust and understand.
Partner with engineers to rapidly prototype and ship polished features.
Develop a product design system that’s scalable, accessible, and consistent across use cases.
Collaborate with tax specialists to understand the real-world edge cases and regulatory nuance our product must support.
Help evolve and define the company’s visual identity and voice across product, marketing, and internal tools.
Create UX that balances speed, clarity, and trust — especially for workflows involving financial and regulatory risk.
Contribute to product strategy, roadmap planning, and customer research alongside the founders.
5–10 years of professional product design experience, with a strong portfolio of shipped work (especially B2B, fintech, or data-heavy tools).
Experience designing for complex workflows, backend systems, or enterprise use cases.
Strong systems thinking — you’re comfortable designing scalable, reusable components and patterns.
Excellent interaction design and visual design skills. You know what great UX looks and feels like.
Ability to prototype quickly and work closely with engineers to get things built right.
Clear, thoughtful communicator — especially in writing. We’re a writing-first company.
A deep sense of ownership. You’re proactive, biased toward action, and don’t need to be told what to do.
We’re an anti-hype-cycle company. Customers will have to solve these problems regardless of what changes with technology or investor sentiment.
Our team is leveraging years of experience building several of the most successful products in our space from 0 to 1 and beyond.
We’re creating trustworthy products that leverage modern technology, in that order. No half-measures. No shortcuts where it matters. We do right by our customers or go home.
We care deeply about serving our people, whether those people are our customers or our team.

Nice-to-haves

Bonus: experience designing for regulated or trust-critical domains (e.g. finance, healthcare, payroll, tax).
Bonus: comfort doing light brand design (e.g. decks, website, marketing assets) in the early days.
Experience designing for regulated or trust-critical domains such as finance, healthcare, payroll, or tax
Comfort doing light brand design—including decks, website, and marketing assets—in the early days

Application prep

Use the role’s language and application details while tailoring your materials.

Keywords to mirror

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Platform: ashby
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