Who is Aiwyn and what do we do?

Aiwyn is the first complete platform for modern Accounting Firms. Backed by top-tier investors like Bessemer, KKR, and Revolution, we’re one of the fastest-growing scale-up SaaS companies in the world. We build category-defining technology—and we’re doing it with world-class people, processes, and products.

To learn more, visit our website

Role Overview:

Our Design org sits at an inflection point: as our product surface area grows across business lines, we need designers who can operate above any single team and shape how our platform coheres as a whole.

For Staff-level roles at Aiwyn, focus shifts based on where design has the greatest impact. This role begins with a clear mandate: preparing our design system to support AI-driven prototyping and development. As AI tools take on more of the work of generating and modifying interfaces, they depend on a system that's consistent and well-structured underneath. Your initial focus will be building that foundation.

As the system matures, we'll assess where your focus can add the most value going forward. That may mean continuing to lead the system, or shifting toward a specific product area while staying connected to its direction.

Who Are You?

You're in the top tier of your craft, the kind of talent that's shaped product at companies where design is a genuine competitive differentiator, not just a support function. You've spent years solving complex B2B problems, and you've learned that the highest-leverage work often isn't the next feature. It's the underlying patterns, components, and standards that make every future feature faster and more consistent to ship, and it's also the last mile of polish that makes something feel magical rather than merely functional.

You operate with real autonomy in ambiguous situations. You don't wait for a brief; you figure out what needs to be done, make the case for it, and own the outcome, not just the mocks you produced. You care about the people around you as much as the pixels. You mentor generously, give feedback that lands, and help other designers see problems more clearly.

What Makes This Role Unique:

Design at Aiwyn increasingly sits at the intersection of craft and AI-assisted workflows. Our design system is what lets that scale: the mechanism that allows engineers and AI to produce on-system UI without a designer touching every screen. Strengthening it is how product quality scales without just adding headcount, and this role puts you at the center of that shift early.

At the same time, this isn't a purely systems role. You'll lead design on complex initiatives across product teams, hold the quality bar for the surfaces you own, and represent design's point of view directly to product and engineering leadership.

Key Responsibilities

• Quality Bar: Define what "great" looks like for the surfaces you own — not just functional, but the kind of synthesis that makes something feel magical. Build standards and systems that hold that bar even as AI generates more of the UI, so quality doesn't depend on you personally reviewing every screen.

• Design System Stewardship: Drive the strategic direction, quality, and consistency of our design system. Identify gaps across business lines, advocate for system investment, and support adoption through AI enablement.

• Strategy & Vision: Contribute directly to product strategy and drive product vision in partnership with product leads. Bring a first-principles lens to the biggest, most ambiguous problems.

• Complex System Design: Solve system-level design challenges—the kind that touch information architecture, shared components, and cross-surface consistency.

• Research Leadership: Lead quantitative and qualitative research efforts that inform decisions across your product area, not just a single feature.

• Mentorship & Guild Leadership: Coach and grow other designers. Actively lead initiatives, design reviews, and process improvements that raise the bar for the whole team.

• Storytelling & Influence: Communicate design rationale and strategy clearly to cross-functional and executive audiences. Anticipate pushback and address it before it becomes a blocker.
  

What Success Looks Like

• Our design system is a force multiplier for engineering and design because you drove its evolution.

• Multiple product teams are moving faster because you identified and solved a shared problem they couldn't see on their own.

• Designers you mentor show observable growth in their craft and confidence.

• Leadership trusts your judgment on ambiguous, high-stakes design and strategy calls.

• Design's presence and influence in cross-functional and executive conversations visibly increases.

Qualifications:

• 8+ years designing complex B2B SaaS products, with demonstrated experience operating above a single product team.

• Direct experience owning or significantly shaping a design system (component strategy, documentation, adoption, and governance).

• Experience with token-based design systems and component libraries that span design tooling (e.g., Figma) and code (e.g., Storybook).

• Background at a design-forward, product-led company recognized for design as a differentiator, or equivalent demonstrated top-tier craft.

• Proven ability to manage ambiguous, cross-team initiatives autonomously, from problem framing through execution.

• Strong track record mentoring designers and shaping team practices or standards.

• Excellent communication skills, with experience influencing product and engineering leadership.
  
  Preferred Skills and Qualifications:

• Experience in accounting, financial services, or other operationally complex B2B verticals.

• Experience leading or contributing to a design guild, community of practice, or similar cross-team design function.
  

Why Work at Aiwyn?

• You'll shape not just what we ship, but how we ship it, building the system and standards that every designer after you will build on. If you're energized by finding leverage other people miss, and you want a seat at the table where product strategy actually gets decided, this is that role.

• The big-picture value proposition of this role is simple: join us, and you'll be paid competitively to have freedom in solving worthwhile, challenging problems alongside other A-players at a fast-growing SaaS startup led by an experienced and successful team with industry experience

• AI-by-Default - you'll have access to best-in-class AI tools and work in an environment that embraces an AI-by-default mindset, where curiosity and experimentation are part of how we operate

• Remote-first organization

• Competitive compensation and benefits

• Stock options

• 401(k) matching

• Adventure Travel Stipend on each anniversary of your employment with Aiwyn

Our Values:

• Relentless by Design

• Owners not Renters

• Trust at the Core

Aiwyn is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to age, ancestry, color, family or medical care leave, gender identity or expression, genetic information, marital status, medical condition, national origin, physical or mental disability, political affiliation, protected veteran status, race, religion, sex (including pregnancy), sexual orientation, or any other characteristic protected by applicable laws, regulations and ordinances.

Candidate information will be treated in accordance with our CCPA privacy notice which can be found here: https://www.aiwyn.ai/ccpa