The Role
Who is Aiwyn and what do we do?
At Aiwyn, we’re revolutionizing the accounting industry with sophisticated, AI-powered solutions designed to transform practice management, payments and collections, client experiences, and tax workflows. Our mission is to automate end-to-end processes—from data ingestion and computation to validation and correction—dramatically enhancing efficiency, accuracy, and productivity for accounting professionals and their firms.
Founded in 2020, Aiwyn has quickly become the fastest-growing software provider serving the accounting profession. Today, we partner with over 150 of the largest CPA firms globally, delivering solutions that accelerate cash flow, save valuable partner time, and create best-in-class client experiences.
Led by seasoned entrepreneurs with multiple successful exits, and supported by a top-tier fintech VC, our team is committed to long-term innovation and collaboration. We value curiosity, agility, and a supportive culture where everyone’s voice matters. At Aiwyn, we’re building for the future—together.
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, prototype, and test designs, but to foster alignment, enable rapid iteration, and validate critical user workflows early and often.
What makes this role unique:
At Aiwyn, you’ll join one of the fastest-growing SaaS companies transforming an accounting industry long burdened by legacy software—an industry now eager for innovation. Leveraging advancements in AI and LLMs, you’ll pioneer entirely new experiences that fundamentally reimagine how tax professionals interact with deeply complex workflows. Your designs won’t just improve existing processes; they’ll set new standards for clarity, usability, and intuitive interaction, shaping the future direction of our entire platform.
You won’t be part of a feature factory here. Instead, you’ll join an empowered product team, collaborating closely with product managers and engineers to deeply understand customer needs and directly shape product decisions. You’ll engage firsthand with customers—conducting research, testing concepts, and rapidly iterating—ensuring your designs genuinely solve user problems rather than just checking off requirements.
Beyond your own product area, you’ll partner with a supportive community of talented designers and cross-functional experts to build a cohesive, innovative platform. Together, we’re moving the industry towards automated online solutions that delight clients and dramatically improve efficiency for firms.
At Aiwyn, our design system is robust but continuously evolving. You’ll not only leverage it, you’ll actively contribute to shaping its future alongside your peers in our design guild. Here, nothing is considered sacred; every idea is open to refinement, innovation, and improvement.
If you’re an experienced product designer who thrives in a fast-paced environment—one that offers genuine ownership, direct customer engagement, and the freedom to continually rethink and refine how an entire industry operates—this is your role.
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.
- Rapid identification and resolution of usability challenges through iterative design and research cycles.
- Reduction in user error rates and support tickets tied to your product area.
- Shortened onboarding and task‑completion time for both accounting professionals and their clients, verified through analytics or usability testing.
- Consistent alignment with cross‑functional partners, ensuring smooth hand‑offs and on‑time delivery of intuitive experiences.
- Development of adaptive, scalable design methodologies and tools that accelerate innovation and iteration.
What Success Looks Like:
Required Skills and Qualifications:
- 5+ years designing complex B2B SaaS products in high‑cognitive‑load, operationally demanding environments.
- Demonstrated ability to turn intricate workflows into intuitive, user‑centered experiences that reduce errors and speed up task completion.
- Deep collaboration track record with product managers and engineers—you co‑own outcomes, not just screens.
- Mastery of rapid prototyping and iterative design in Figma (and similar tools), validating concepts early through research and testing.
- Exceptional communicator who clearly and persuasively explains design rationale to technical and non‑technical stakeholders.
- Expert UX writer who crafts concise, clear microcopy that enhances every interaction.
- Solid grasp of cross‑device browser behavior and core web tech (HTML, CSS, JavaScript); you partner closely with engineers to ship designs as intended.
- High level of comfort using LLMs and modern AI tools.
- Experience or strong interest in accounting, financial services, or tax compliance software.
Preferred:
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.
- 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
Other benefits include:
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
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The Company
What We Do
Aiwyn helps leading accounting firms automate and optimize critical revenue processes by unlocking client data from existing practice management and CRM systems with our Practice Automation platform. With Aiwyn's Practice Automation platform, high-value firm executives, partners, and staff are liberated to deliver more value to clients and work at the highest end of their professional expertise. Benefits of Practice Automation to accounting firms include: - save time, bill faster - eliminate tedious back office tasks - reduce days-in-WIP and days-in-AR, - speed up client payments - smooth out cash flow - protect financial health with predictive insights and controls - offer a best-in-class experience to both employees and clients
