Burn it Down and Start Over: When is it Time to Rewrite?

If you’re scaling a SaaS business or building a software startup, this episode explores rewrites, UX, and product strategy.

Software rewrites are rarely the right solution. But when necessary, they require clear vision, strong business justification, and careful execution to succeed. In this episode of SaaS That App: Building B2B Web Applications, Daniel Cannon, Chief Innovation Officer at Delta Systems, and Nolan Alimonti, Senior Architect and Team Lead at Delta Systems, join host Justin Edwards to discuss when software rewrites make sense, how to avoid them, and real-world experiences with successful and challenging rewrites.
What You’ll Learn:

• How to determine if a rewrite is truly necessary versus addressing technical debt incrementally
• Why finding product-market fit should happen before significant software development
• How to execute a successful rewrite when supporting existing users and revenue streams
• Why scalability alone is rarely a valid reason for a complete software rewrite
• The three critical signs that indicate a rewrite might be necessary
• How to maintain code quality and avoid technical debt through regular maintenance budgets

Nolan Alimonti is a Senior Architect and Team Lead at Delta Systems, where he tackles complex client projects by uniting front-end speed with backend clarity. With deep experience in React and Ruby on Rails, he’s known for simplifying messy codebases, improving scalability, and steering apps toward cleaner, maintainable architecture. A hands-on specialist in modern Rails development, Nolan has led significant refactors, helping teams migrate from TurboLinks-era code to sleek, serviceable Turbo and Stimulus builds. His goal is to make apps snappier and smoother, while keeping the stack lean and intentional.

Daniel Cannon is the Founder of Strive DB and Chief Innovation Officer at Delta Systems, where he drives the adoption of emerging technologies and modern development practices across the organization. A senior developer with a history of tackling thorny technical challenges, Daniel has a knack for questioning assumptions, stress-testing ideas, and finding pragmatic ways to turn cutting-edge tools into everyday solutions. His perspective on Turbo, Stimulus, and Rails comes from hands-on experience shaping how these tools are used in real-world applications and mentoring teams through the learning curve.

This podcast is brought to you by Delta Systems, your one-stop shop for front-end, back-end, and full-stack software development. At Delta, Justin and Aaron share the same philosophy when it comes to clients: they treat people like colleagues, not just customers. Maybe that’s why Delta typically spends years working with the same companies: how many software engineering firms can you say that about? So, if you’ve got a big SaaS project in mind but have no idea where to start, come and get a free scope and estimate from Delta Systems on their website.


Highlights:

• [00:00] Introduction
• [01:43] When a Rewrite Actually Makes Sense
• [03:54] Scalability Is a Nice Problem to Have
• [07:09] Code That Scares Off Developers
• [11:30] Are You Rewriting or Reimagining?
• [16:03] Transitional APIs
• [17:10] How to Avoid Ever Needing a Rewrite
• [21:35] Real-World Rewrites
• [28:09] Final Advice

Episode Resources:

• Daniel Cannon on LinkedIn
• Aaron Marchbanks on LinkedIn
• Justin Edwards on LinkedIn
• Delta Systems Website

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