Staff Product Designer - Aiwyn Tax

Who is Aiwyn and what do we do?

At Aiwyn, we're revolutionizing the accounting industry across multiple dimensions—including payments and collections, practice management, and client experience solutions. With Aiwyn Tax, we’re harnessing cutting-edge artificial intelligence to fundamentally transform tax compliance and preparation. Our vision is bold: build sophisticated, AI-powered tax engines that automate the end-to-end processes of ingestion, computation, validation, and correction. We're at a pivotal inflection point, shifting from validation-heavy workflows to fully automated, SME-empowering systems, drastically elevating efficiency, accuracy, and productivity for tax professionals and firms alike.

To learn more, visit our website

Who Are You?

You’re the type of designer who finds deep satisfaction in transforming complex challenges into elegantly simple user experiences. Driven by curiosity, you dissect intricate workflows with first-principles clarity, consistently questioning assumptions and uncovering the underlying user needs that others might overlook. For you, great design is less about aesthetic perfection and more about intuitive interactions—making the complex not just accessible, but obvious.

Comfortable in ambiguity, you see uncertainty as a creative opportunity, always seeking to iterate rapidly towards clarity and simplicity. Your designs don’t just look good—they feel intuitive. You measure success not just by user delight, but by tangible improvements in user efficiency and error reduction. You're eager to shape intuitive, transformative user experiences at a critical moment in our company's journey.

Your strength comes from collaboration within an empowered trio alongside a Product Lead and Tech Lead, each equally accountable and working cohesively toward shared outcomes. You leverage tools like Figma not merely to mock up designs but to foster alignment, enable rapid iteration, and validate critical user workflows early and often.

What makes this role unique:

At Aiwyn Tax, our success hinges on mastering the delicate balance between two interconnected yet distinctly different user experiences—internal SMEs managing our tax engine and external CPAs preparing and reviewing returns.

Internally, you’ll design experiences for SMEs who test, validate, and manage our advanced tax engine. This involves streamlining complex tasks such as creating test cases, identifying discrepancies, and making precise corrections. The SME workflows mirror actual tax return processes but with heightened emphasis on testing, validation, and iterative refinement. Your goal will be creating interfaces that not only simplify but accelerate their essential work.

Externally, you’ll craft intuitive journeys for CPAs and firm partners navigating the full lifecycle of tax preparation—from initial form completion through detailed partner reviews, corrections, and final approval. You’ll carefully design each interaction to clearly guide users, significantly reduce cognitive burden, and effortlessly prevent common errors.

The exciting complexity arises from the innovative ways we generate and manage these experiences. Your design approach must remain adaptable, intuitive, and flexible—enabling our SMEs and CPAs to efficiently refine and optimize forms and workflows. Collaborating closely with product and engineering, you’ll continually push the boundaries of what’s possible.

This role isn’t just about improving existing experiences; it’s about fundamentally reimagining how tax professionals interact with deeply complex workflows. Your designs will define entirely new standards of clarity and usability, influencing every user interaction and shaping the future direction of our products.

Key Responsibilities:

• Intuitive Flow Design: Develop and champion user experiences that dramatically simplify complex tax workflows, ensuring intuitive interactions that minimize errors and cognitive load.
• Empowered Collaboration: Work as a cohesive unit with a Product Lead and Tech Lead, equally accountable for shared outcomes, fostering seamless alignment from strategic vision through execution.
• Rapid Prototyping & Validation: Quickly create, iterate, and validate designs using tools like Figma, ensuring alignment with user needs and swift feedback loops.
• Flexible and Adaptive Solutions: Innovate design solutions that allow efficient workflow adaptation based on real-time context and user interactions.
• Strategic Documentation: Clearly articulate the "why" behind every design decision through robust documentation, storytelling, and visual communication to keep teams aligned and informed.
• Design Culture Influence: Actively shape our design team's culture, methodologies, and standards, mentoring colleagues to elevate our collective design capability and approach.

What Success Looks Like:

• Measurable improvement in internal SME productivity and external user satisfaction.
• Rapid identification and resolution of usability challenges through iterative design.
• Clear, continuous alignment with cross-functional partners, ensuring seamless implementation of intuitive user experiences.
• Development of adaptive, scalable design methodologies and tools that accelerate innovation and iteration.

Required Skills and Qualifications:

• 7+ years designing complex B2B SaaS products with high cognitive complexity and demanding operational environments.
• Proven ability to simplify complex interactions through intuitive, user-centered design.
• Deep collaboration experience within cross-functional teams, particularly alongside product managers and engineers in empowered team structures.
• Expertise with rapid prototyping, iterative design processes, and collaborative design tools, especially Figma.
• Exceptional ability to communicate design rationale clearly and compellingly.
• High level of comfort using LLMs and modern AI tools.

Preferred:

• Experience or strong interest in accounting, financial services, or tax compliance software.
• Demonstrated experience mentoring other designers and shaping design team practices.

Benefits and Perks:

• 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 co-founding team with industry experience.

Other benefits include:

• Adventure travel stipend - you receive a $1,000 travel reimbursement on your work anniversary each year. We encourage our team to recharge and explore the world beyond their home office walls.
• Remote, work-from-anywhere culture
• Flexible PTO
• World Class health benefits - we believe in fostering flourishing teams by providing benefits that go beyond the usual standards - Health, vision, dental, HSA/FSA, and mental health support.
• Stock options - every Full Time Employee has ownership in Aiwyn's future and success.
• 401(k) matching

Our Values:

• Trust - We champion transparency, welcome differing perspectives, uphold accountability, and trust that others have good intentions
• Courage - We have the courage to take calculated risks and embrace change, knowing what worked in the past won’t always work in the future
• Impact - Rooted in determination and innovation, we chase extraordinary outcomes and impactful results
• Relentlessness - We approach challenges with an unwavering resolve, never settling for mediocrity, and always striving to surpass expectations

Learn more about Aiwyn:

• **About us
• **Why Aiwyn
• **YouTube page

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