Alex Kenis has been a key part of the Aiwyn story for years, evolving from senior roles in implementation and customer success to now serving as our Transformation Lead, which makes him uniquely positioned to shape Aiwyn’s consultative, transformation-first approach.
In this edition of Behind the Build, Alex shares what transformation looks like in practice - how he partners with firms to define success, align stakeholders, and bring scalable execution to life in areas like payments, practice management, CRM, and data integration.
Q: You’ve been with Aiwyn for 4 years. What’s different about your new role as Transformation Lead?
In my new role, my team and I serve as navigators on a firm’s journey from constrained legacy systems to empowered, intelligent operations. Our goal is to take them from zero to one, not just implementing tools but reimagining what’s possible with the right technology ecosystem.
What’s unique is our focus on reducing complexity to unlock potential. Technology transitions are tough, especially when it involves replacing foundational systems like practice management. But we approach each engagement with a tailored, human-centric lens: understanding a firm’s vision, mapping where they fall on the change-readiness spectrum, and architecting a transformation plan rooted in that understanding.
Over time, we’ve become great at “map-building,” creating paths that account for cultural nuances, user behavior, and scalable execution. Firms aren’t the problem. Their systems are. Accountants are inherently adaptive. Our job is to remove ceilings so firms can realize their full potential.
Q: How did your previous roles in implementation and customer success prepare you for this next chapter?
Implementation gave me boots-on-the-ground insight into how firms operate, how workflows are structured, and how to embed new tools with minimal disruption. It was about fitting into the fabric of the firm without unraveling it.
Customer success helped me develop a persona-based lens, understanding how different roles perceive and respond to change. This empathy allows me to lead transformations that not only succeed on paper but are adopted in practice. Transformation isn’t one-size-fits-all. It’s about aligning success with the human realities inside the firm.
Q: What does “transformation” mean in the context of your work with accounting firms?
Transformation is often mistaken for just a tech upgrade, but at its core, it's a mindset and behavior change. Yes, we bring in cutting-edge systems, but without addressing how people work, think, and adapt, the tech will fall flat.
It’s a human journey. Transformation succeeds when we earn trust, co-create the path, and support users through each phase. Technology sets the stage. People power the play.
Q: What’s your process when working with a firm that’s just beginning their transformation journey?
We begin by defining the destination: what does success look like?
Then, we identify key stakeholders, their roles, and their pain points. What do they do, how do they do it, and what’s standing in their way?
Throughout the journey, we help firms maintain focus without losing imagination. It’s easy to be seduced by big ideas, but transformation fails when you try to solve everything at once. We balance visionary thinking with disciplined execution, capturing ideas for later while keeping the project activity rooted in purpose.
Q: How do you help firms move from ideas to execution, especially when there are multiple systems and stakeholders involved?
We rely on the right tech stack. Tools like Monday.com help keep moving parts visible and manageable. But our true lever is collaboration.
We partner closely with Product and Engineering to translate ideas into reality, and we set the expectation that progress is incremental, consistent, and measured.
We’ve learned that the future firm is built in sprints, not marathons. Each step compounds, and we celebrate those wins along the way.
Q: How do you hope this role will elevate Aiwyn’s overall approach to helping firms modernize?
Aiwyn already offers powerful technology. But tech alone doesn’t move the needle. Transformation does.
Our role is to ensure firms don’t just buy potential. They activate it. We’re building a services layer that bridges innovation with adoption. Over time, we aim to use data from these journeys to predict change-readiness, personalize onboarding, and offer smarter pathways to success.
By blending platform and partnership, we help firms not only modernize but stay ahead of the curve.
Q: Are there specific signs that a firm is ready for real change?
Absolutely. The first is awareness. Are they asking questions, seeking demos, or benchmarking against peers? That shows they’ve recognized a gap.
The second is imagination. Do key stakeholders envision a better version of their operations? Do they welcome change or resist it? When leaders have the courage to reimagine, not just react, they’re ready to co-author transformation.
Fear can stall progress. Belief in a better future unlocks it. We look for firms that are ready to partner not just with our tools but with our process.
Q: What guidance do you have for a firm who wants to learn more about a transformation with Aiwyn?
Let’s get on a call right away. Please email me (alex.kenis@aiwyn.ai) or Chad Osgood (chad.osgood@aiwyn.ai), and we’ll coordinate with your account manager and customer success manager to schedule a meeting as soon as possible.
To all our firm partners: there is never a perfect time to start a transformation. Sending that one email to learn more is a huge first step, and you can take that today. We look forward to hearing from you.
