The gap between buying software and actually using it successfully is where most technology initiatives fail. In this edition of Behind the Build, we’re talking with Megan Sims, Implementation Manager at Aiwyn, who brings a perspective most software companies can’t replicate: she’s lived the reality of working inside accounting firms.
With over a decade of experience at firms like Frazier & Deeter and Bennett Thrasher – spanning roles from computer support to database management to project leadership – Megan understands what it takes to introduce new technology into an environment where busy season waits for no one and every workflow disruption has downstream consequences.
Now at Aiwyn, Megan leads end-to-end implementations, serving as a strategic advisor to firm leaders as they accelerate cash flow, elevate client experience, and streamline operations. She shares what makes implementations succeed or stall, why the technical setup is only half the equation, and how her firm experience shapes the way she approaches every engagement.
On building partnerships with accounting firms
Q: You spent years working inside accounting firms before joining Aiwyn. When you were on the other side implementing technology at firms, what made the difference between a smooth rollout and one that struggled?
A: Having a team that’s empowered to make decisions and trusted with the authority to execute across the entire project is what sets smooth rollouts apart. That means giving your implementation lead the ability to make calls on workflows without needing three approval layers, and ensuring they have direct access to the partners who can move things forward.Layer in clear goals, consistent communication, strong documentation, and active support from leadership, and the difference is noticeable.
Q: A lot of software companies treat implementation as a checklist: install, configure, train, go live. How do you think about implementation differently, and where does that perspective come from?
A: Accounting firms all do very similar work, but contrary to popular belief, they’re not all the same when it comes to their business processes and needs. At Aiwyn, I try to approach every implementation with that in mind. Improvement isn’t one-size-fits-all, so our implementations aren’t either.
Some firms need more support defining the right business rules within Aiwyn, while others want to place a heavier emphasis on training their teams. Neither approach is “right” or “wrong.” What matters is that we tailor the implementation to the firm and stay aligned on shared goals and timelines.
Q: You’ve worked in various technical roles at firms from IT support to database administration to project management. How does that range of experience influence the way you guide firms through implementation today?
A: After spending more than 10 years in accounting operations, I’ve been part of a wide range of projects and many busy seasons. I’ve also been fortunate to work alongside some incredibly intelligent and creative people along the way.
Across those projects, I was exposed to every service line, which gave me a deep understanding of what teams do day to day and where their real pain points live. That experience makes me very aware of what firms are trying to solve during implementation because I’ve been in the trenches working through those same challenges myself.
Sometimes that means applying solutions that worked well in the past, and other times it means steering clear of approaches that didn’t. Most importantly, it allows me to advocate for firms and translate their needs to our engineers in a clear, practical way – something I never take for granted.
Q: When you’re working with a firm in the early stages of implementation, what are the signals that tell you this is going to be a successful engagement? What do the best firms do differently?
A: You can usually tell early on when a firm is excited and motivated to get to the finish line. That’s when the work is not only productive, but genuinely fun, and it’s a strong indicator of success.
The best implementations are the ones where firms stay engaged, are open to change, and are willing to roll up their sleeves alongside us. They keep their eye on the end goal, which makes go-live even more rewarding because they get to see the metrics and results from the effort they put in. I’ve also seen staff step into leadership roles through this process. A successful implementation builds confidence, creates trusted subject matter experts, and gives teams real data to show the impact of their work.
Q: Firms are often nervous about disruption, especially during busy season or when workloads are already stretched. How do you help leadership balance the urgency of modernization with the reality of operational constraints?
A: It may sound counterintuitive, but busy season is actually one of the best times for our support teams to implement our payments and collections solution, Aiwyn Payments.
We work behind the scenes with the teams assigned to the project so that once busy season wraps up, everyone gets a post-season breather, and then the firm is ready to hit the ground running on learning the new tool and then collecting AR for all of the hard work they just put in.
For engagements, we take the same approach to minimizing disruption. We reduce the workload by building much of the letter content for the team, setting recurring meetings at a cadence the firm is comfortable with, and making sure those meetings are productive and a good use of their time. We focus on doing the heavy lifting behind the scenes with our project team so that firms are prepared for the next phase without feeling overwhelmed, whether that’s letters, training staff, or rolling out new workflows.
Q: You work closely with firm leaders to align technology with their executive priorities. What does that actually look like in practice? How do you translate business objectives into an implementation plan?
A: We start by having honest conversations about what’s working, what isn’t, and where the real pain points are. That helps us understand what matters most to leadership and shape our plan around their priorities. It also allows us to learn from what they’ve already tried, so we’re not repeating approaches that didn’t work and can build an implementation plan that’s realistic and effective.
Q: There’s a moment in every implementation where the firm has to shift from “this is new” to “this is how we work now.” How do you help teams make that transition, especially when some people are naturally more resistant to change?
A:Change is uncomfortable and often hard, especially when it involves asking other people to change too. I completely understand that.
When I say I loved the Aiwyn products enough to join the team, I clearly mean it. I’ve used these tools myself and practiced what I now preach, and that experience goes a long way in helping break down barriers with teams that are more skeptical. It builds trust and helps teams get comfortable with the change and integrate the product into how they already operate.
Q: When you think about firms that have truly transformed their operations with Aiwyn – not just installed new software, but fundamentally changed how they work – what do they have in common? What makes transformation stick?
A: What those firms have in common is empowered teams and leaders who are genuinely open to change. They don’t just adopt new software, they take ownership of new ways of working, which is what makes the transformation stick.
Making implementation succeed
Successful implementations don’t happen by accident. They happen when firms have partners who understand their world, respect their constraints, and are willing to do the heavy lifting to make change stick. That’s what Megan brings to every engagement – and it’s why Aiwyn’s implementations don’t just go live. They succeed.
To learn more about the Aiwyn product suite, our implementation approach, and professional services, schedule a demo today.
