Rewrite Your SaaS Codebase Only When This Is True

Most SaaS founders who say “we need a rewrite” are really saying something else: we can’t reliably create customer value fast enough anymore. That’s a business problem, not a code problem.

In the SMB Content Marketing United States series, we usually talk about content, channels, and compounding distribution. But here’s the less glamorous truth: your content marketing can’t outgrow your product’s ability to deliver. If your codebase blocks onboarding fixes, pricing tests, integrations, or a template library your market needs, your “marketing problem” becomes a “product throughput problem.”

This post is inspired by Startups For The Rest Of Us (Episode 516) where Rob Walling interviewed Matt Wensing (Summit) right after Matt spent about 70 days rewriting his SaaS. The interesting part isn’t the tech. It’s why a rewrite made sense for a VC-free, sustainable-growth startup—and when it doesn’t.

The only good reason to rewrite: you built the wrong product

A rewrite is justified when your current codebase can’t support the product your customers are clearly asking for—and “clearly” is doing a lot of work in that sentence.

In the episode, Matt described his first version as a “vending machine” forecast: enter a handful of numbers, press a button, get a forecast. It worked for a narrow use case—very early founders with nothing but an idea. But his retention and paid conversion didn’t hold. Users tried it, appreciated it, then left.

His breakthrough wasn’t “our framework is old.” It was this:

Customers weren’t buying a forecast. They were buying flexibility.

They were comparing him to the real competitor: Excel.

Spreadsheets are painful, but they’re endlessly adaptable. When a SaaS product replaces a spreadsheet, it’s not enough to be “simpler.” It has to be flexible in the exact ways your buyer’s business is flexible.

For bootstrapped founders, this matters because you don’t have infinite shots on goal. If your product is structurally wrong, you’ll waste months shipping “small improvements” that don’t change the outcome.

Rewrite trigger #1: feature requests don’t converge

Matt noticed that requests from serious users didn’t line up into a neat roadmap. The requests seemed scattered—until he saw the pattern: they were all asking for different customizations because the underlying system was too rigid.

When requests don’t converge, you typically have one of two problems:

• You’re serving multiple personas with different jobs-to-be-done.
• You’re serving one persona, but your product is missing a platform capability (like customization, rules, templates, permissions, integrations).

A rewrite can be the right move in the second case, because you’re not adding “Feature #38.” You’re installing a new foundation.

A VC-free lens: rewrites are risky, but “slow death” is riskier

The internet loves to quote Joel Spolsky’s old advice: “never rewrite your codebase.” Rob Walling pushed on this in the episode too—he’s seen plenty of startups use “rewrite” as a procrastination strategy.

I agree with the skepticism. Rewrites destroy momentum if you do them for developer taste.

But a bootstrapped (or mostly bootstrapped) SaaS has a different constraint than a venture-backed one:

• VC-backed companies can brute-force mistakes with hiring and spend.
• VC-free companies win by being disciplined and fast at learning.

If your codebase makes learning slow—slow experiments, slow onboarding fixes, slow integration work—you don’t just ship slower. You market slower too.

The episode highlights a nuance most founders miss: Matt didn’t rewrite because he was bored. He rewrote because he wanted demos that closed.

A rewrite is a go-to-market decision when it materially changes your ability to sell.

Rewrite trigger #2: your “sales hat” says the product can’t win

Matt framed it well: he wasn’t wearing his developer hat; he was wearing his CEO/sales hat.

Here’s a simple test you can run this week:

• List the top 5 reasons deals stall (or trials don’t convert).
• Circle the ones that are structural (not copy, not pricing, not a missing FAQ).
• Ask: “Can we fix these within 4–6 weeks without turning the codebase into a junkyard?”

If the honest answer is “no,” you’re in rewrite territory.

The practical decision framework: rewrite vs. refactor vs. template

You don’t have two options (rewrite or do nothing). You have at least four.

1) Keep shipping (no rewrite)

Choose this when the product is fundamentally right and you mostly need distribution: content marketing, partnerships, outbound, SEO, demos.

Signal: retention is decent, your best customers are happy, and requests are additive—not existential.

2) Refactor behind the scenes

Refactor when the product direction is correct, but the code is slowing you down.

Signal: “We know what to build next, but it takes 3x longer than it should.”

Rule: refactor in slices tied to customer-facing outcomes. “Two weeks of cleanup” with no shipped value is a morale killer in a small team.

3) Build a “v2 lane” inside the product

This is the middle path Matt implicitly took: Summit 2.0 became a flexible modeling system that could even recreate the old Summit 1.0.

Signal: you need a new foundation, but you can’t pause revenue.

Tactic: ship v2 capabilities gradually and migrate users with templates, education, and concierge onboarding.

4) Full rewrite

Rewrite when the old system can’t support the new product shape.

Signal: your business model depends on capabilities that are hard to bolt on (customization, rules engines, permissions, multi-tenant architecture changes, etc.).

Matt’s timeline is instructive: about 70 days of consistent coding, shipping daily commits. The discipline matters. The rewrite wasn’t a year-long science project.

Marketing lesson for SMB SaaS: product flexibility widens your content funnel

This is where the SMB Content Marketing United States angle shows up in a non-obvious way: a more flexible product gives you more marketable stories.

When Summit moved from “push button, get forecast” to “replace your financial spreadsheet,” the positioning expanded. It unlocked:

• More keywords (financial model templates, SaaS runway planning, headcount planning)
• More use cases for content (hiring plans, ad spend payback, sales-led vs. self-serve)
• More partnership angles (accelerators, fractional CFOs, bookkeeping firms)

In the episode, Summit’s product experience begins with templates (self-serve SaaS, early-stage SaaS, sales-driven SaaS) and even the option to upload your own model. That’s not just UX—it’s acquisition strategy.

A template library is content marketing in product form.

Rewrite trigger #3: your onboarding needs “starter kits,” not more copy

If new users hit a blank screen and don’t know what to do, no amount of blog content saves you. Your content gets them to sign up; onboarding gets them to stay.

When you can’t create “starter kits” (templates, blueprints, pre-built flows) because the product is too rigid, your activation rate becomes capped.

For SaaS businesses growing without VC, activation is everything because it reduces your need to buy traffic.

Common rewrite pitfalls (and how to avoid them)

A rewrite can still go wrong even when the motivation is correct. Here are the failure modes I see most often.

Pitfall: rewriting to a blank slate nobody can use

Power is great, but blank slates kill adoption. Matt heard this too: some users loved the old version and felt alienated by the power tool.

Fix:

• Add templates early (even if you hate them)
• Teach with short Loom-style videos
• Build a “recommended next step” inside onboarding

Pitfall: widening the funnel before retention is stable

Matt’s sparse homepage was a deliberate choice: keep signups high-intent while the product settles.

That’s smart. A large funnel with poor retention just creates more support load and noisier feedback.

Fix:

• Grow traffic after your best persona consistently converts
• Use content marketing to attract the specific ICP you can serve today

Pitfall: rewrites without a measurable business outcome

Rewrite goals like “better architecture” don’t keep you honest.

Fix: define rewrite success in business terms:

• Activation: “% of trials reaching the ‘aha’ moment within 24 hours”
• Time-to-ship: “new template shipped in 2 days, not 2 weeks”
• Sales: “demos close without ‘we don’t support that’ blockers”

A simple checklist: should you rewrite your SaaS codebase?

Use this as a quick gut-check before you commit your next 60–90 days.

1. Do we have a clear “wrong product shape” problem? (Not just messy code.)
2. Is our best customer asking for flexibility we can’t add cleanly?
3. Are requests scattered, but pointing to one missing capability?
4. Will the rewrite improve sales demos and onboarding conversion?
5. Can we timebox it and ship daily/weekly progress?
6. Do we have enough runway to absorb the opportunity cost?

If you can’t answer “yes” to at least 4 of these, don’t rewrite. Refactor and keep learning.

Where this lands for VC-free founders in 2026

January 2026 is a funny moment for bootstrapped SaaS. AI features are everywhere, buyer expectations are higher, and “just use a spreadsheet” is still the default in many SMB finance workflows. That combination pushes a lot of founders toward rewrites—either to add flexibility or to keep up with modern UX.

My stance: rewrites are justified when they increase customer value velocity. If you can ship faster, teach better, and convert more of your hard-earned traffic, a rewrite isn’t indulgence. It’s compounding.

If you’re growing through content marketing on a budget, your product has to meet your content halfway. Otherwise, you’re paying (in time or ad spend) to invite people into a house you can’t renovate.

What would have to be true for a rewrite to directly increase your trial-to-paid conversion in the next 90 days?