Designing software for accounting firms isn’t just about clean interfaces, it’s about clarity, trust, and helping professionals move through their day with confidence. In this edition of Behind the Build, we’re having a conversation with Joshua Rudd, VP of Product Design at Aiwyn, to explore what it means to design tools for one of the most detail-oriented professions.
From building intuitive workflows to scaling a growing design team, Joshua shares how he’s approaching design in an industry that’s often underserved by modern UX. He also offers a behind-the-scenes look at what it’s like to build at Aiwyn and the team that’s shaping a more thoughtful, user-centered future for accounting technology.
Q: Share a little bit about yourself and your role at Aiwyn.
I joined Aiwyn over four years ago where I initially served as the sole design lead, working closely on our early products, particularly in Payments and Collections, Billing, and Engagements. I had the privilege of shaping many of the early design foundations of our platform. As the company began to grow, so did my role. I transitioned into the Director of User Experience position, expanding my involvement beyond just design execution to include team building, strategy, and cross-functional collaboration.
Fast forward to today and I serve as VP of Product Design. It’s deeply gratifying to see those early ideas evolve through the leadership and creativity of others, whether by iterating on existing features or pioneering entirely new products.
While I operate as a player-coach, I’m still closely engaged with design work and have the opportunity to mentor a growing team of talented product designers. Each designer leads design in their respective product areas, and we work alongside amazing product managers and engineers every day. My responsibilities range from getting deep into the weeds of specific product experiences to thinking more broadly about team operations, cross-platform consistency, and the overall culture of design at Aiwyn.
Q: Tell us about your journey into design. Where did it start and what led you to where you are today?
I’ve been a designer for over 30 years, but my journey began back in the early-90s, specifically when I got my first Macintosh, though my fascination with computers dates even earlier to the Apple IIe days. I combined interests in art, drawing, and programming, teaching myself BASIC programming in fifth grade and diving into Pascal and C++ in high school.
By the time college came around, I initially planned to study computer science. A mentor recognized that I was spending a tremendous amount of time on design work, which I enjoyed deeply but hadn’t considered as a viable professional path. I wasn’t really aware of any structured career opportunities in design, and it hadn’t occurred to me that it could be more than a hobby. That mentor encouraged me to shift my focus and explore a design program instead of pursuing a traditional computer science degree.
It was a good time to make the shift. The early web was just beginning to take shape, and my initial work in desktop publishing and graphic design naturally evolved into web development. I gained hands-on experience with backend technologies like PHP and MySQL, and later expanded my skills significantly while working on an open-source CMS project. That project, in particular, was where I really started to focus on product design and user interface design for software. It sharpened my abilities in information architecture and content management and exposed me to the challenges of designing tools that were both powerful and easy to use.
Eventually, my family and I moved to San Francisco where I joined Pentagram Design on their interaction design team. I had already been honing my skills in semantic HTML and CSS, but had the amazing opportunity to connect with a broader community of professionals. It was a period of intense learning and collaboration, working with institutions that had complex content and navigation needs, like large universities and companies with professional product suites.
After many years of client service work, I began to feel the pull toward building and owning a product long-term. That desire to go beyond zero-to-one and keep iterating on solutions led me to transition into tech startups around 2009. I've been doing that ever since.
Q: How would you describe the design culture at Aiwyn?
The design culture at Aiwyn is rooted in the concept of being missionaries rather than mercenaries—a philosophy popularized by Marty Cagan. We don’t outsource our design or engineering tasks to simply complete a list of requirements. Instead, we deeply engage with our customers' problems, aiming for genuine ownership, pride, and impact in our solutions.
We’ve built this culture around several key principles:
- Talent and experience: We hire highly capable, seasoned professionals who bring a mix of diverse backgrounds and proven expertise. Our designers consistently deliver exceptional work and raise the bar for quality across the board. We look for those who embrace generative AI and other emerging tools to continually evolve how we work and define what’s possible in the products we deliver.
- Collaboration: We are collaborative rather than hierarchical. Designers don’t operate from an "ivory tower" issuing directives. They act as facilitators within their teams. This means regular check-ins and design workshops to share ongoing work and encourage a proactive culture of feedback and transparency. Every designer contributes to and evolves our core design systems.
- Empowerment and problem solving: Designers are empowered to determine the right solutions for the problems they encounter. We encourage self-starters who bring surprising and creative ideas to the table—people who understand our customers deeply enough to identify opportunities others might miss. Design at Aiwyn is proactive, investigative, and woven into the fabric of how we build great software.
Q: How do you ensure design supports both the firm experience and their client’s experience?
Early on, the interface designs for both audiences shared similar visual language and structure, but as our understanding evolved, we recognized the need to split them apart. This led to the development of two parallel, evolving design systems: one dedicated to firm-facing tools, and another tailored for the client-facing experience, each optimized to suit its specific user base.
For the firm experience, we collaborate closely with accounting professionals through regular contextual inquiry. These sessions, often conducted through virtual calls and in-person visits, help us understand their environment, daily workflows, pain points, and strategic objectives. Our software is often seen as an assistant helping them get their work done, so it's critical that we understand what their goals are and how our tools can best support them. The interfaces we create for firms are often more dense, professional, and information-rich, providing the high visibility and control they need to navigate complex and fast-moving work.
In contrast, the client experience requires a much more consumer-friendly approach. These users typically engage with our platform infrequently, perhaps only once a year, and don't have access to training or internal support. Their priorities are ease of use, minimal friction, and clear guidance. For this audience, we are actively working to move away from rigorous registration processes or complex logins, using approaches like magic links and one-time-passwords to create lightweight and intuitive experiences.
We regularly test our firm-facing products directly with our customers, refining the experience based on firsthand feedback. For client-side testing, where we don't always have direct access to end users, we rely on tools like Ballpark to test with analogous populations. These are users who reflect the demographics, expectations, and behavior patterns of our clients. This ensures we're not just relying on secondhand interpretations of what clients want, but are actively validating those experiences with real users or relevant stand-ins.
Q: How do you incorporate user research and customer feedback into product design at Aiwyn?
User research and customer feedback are foundational at Aiwyn. We maintain regular, direct interactions with customers through virtual meetings, on-site visits, and annual user conferences. These direct engagements ensure firsthand understanding of our customers' daily challenges and needs.
Our approach has evolved as we've scaled, employing sales and customer success teams who help amplify the voice of the customer across the organization. We systematically record and analyze customer interactions using AI-driven tools to surface actionable insights. Our research encompasses both generative phases, where we deeply explore user processes and pain points, and evaluative phases, where we validate and iteratively improve solutions. Frameworks like Teresa Torres’s Opportunity Solution Trees help us visualize connections between customer pain points and strategic opportunities.
Q: Can you share an example of incorporating feedback into the product?
One clear example of how generative research has directly informed product development was during early discovery work around billing processes.
In one call with a billing manager, we kept hearing a rhythmic clicking sound in the background. When we asked what it was, they explained they were using a ten-key adding machine alongside their computer to track and manually write up or write down specific WIP line items.
This insight was powerful. It surfaced an inefficiency we wouldn't have uncovered without observing their real-world workflow. That observation helped shape our cascading write-ups and write-downs feature in the billing product, ultimately resulting in a significant reduction in time and a measurable increase in accuracy for billers preparing draft invoices.
Q: What’s your approach to scaling design across a growing suite of products?
As Aiwyn has expanded into a multi-product platform, we’ve structured our design approach accordingly. Each designer leads design for specific product areas, paired with a dedicated product manager and tech lead. Our centralized design system maintains consistency and coherence across products, supporting efficient scaling.
To maintain alignment between design and engineering, we host regular "GUI Guild" meetings, a nod to graphical user interfaces, ensuring coordinated development between design and front-end engineering. Additionally, we implement oversight through design and product leads, who ensure strategic alignment and integration across the entire suite of products, keeping our designs cohesive and consistent as our platform grows.
Q: What excites you about the team you’re building at Aiwyn right now?
I'm particularly energized by the camaraderie and culture of psychological safety and radical candor we've fostered within the design team. This environment encourages designers to openly share feedback, collaborate spontaneously on overlapping problems, and engage proactively with new tools and methodologies, such as generative AI.
Our team’s diverse backgrounds and experiences contribute to rich, varied perspectives, enhancing our problem-solving capabilities. I love seeing the genuine enthusiasm when team members proactively organize workshops or collaborative sessions to tackle challenges together. This initiative and ownership are what elevate our outcomes. Above all, our team views itself as a deeply integrated part of Aiwyn, actively partnering with stakeholders rather than functioning in isolation.
Q: What are you most excited about building in the next 6–12 months?
The next 6–12 months at Aiwyn promise significant developments as we launch three major products: Aiwyn Practice, our new client experience portal, Aiwyn Experience, and a transformative product, Aiwyn Tax. Each of these innovations addresses substantial needs within the accounting profession, promising to deliver major efficiencies and user experience improvements.
But even more than the products themselves, what excites me is the opportunity to build them with this team. There's something incredibly fulfilling about getting to work every day with people you respect. People who genuinely care not just about the craft, but about our customers and the bigger picture.
I've often told others that there are three things that make a job truly great: the people you work with, the problems you're solving, and the product you're building. If you can find a place where two out of those three are great, you’re doing pretty well. At Aiwyn, I genuinely believe we’ve found all three. And that’s what makes this next chapter so exciting. It’s not just the technology, but the human and strategic alignment behind it.
