August 6, 2025

Why Waiting for Desktop Tools to Go Cloud-Native Is a Losing Bet

Why Waiting for Desktop Tools to Go Cloud-Native Is a Losing Bet

Dustin DeVan
CEO & Co-Founder

A future of estimators working from the cloud is not a matter of if, but when.

Cloud-based estimating is faster. It’s safer, more collaborative — and, if we’re honest — inevitable.

But, too many companies are selling cloud dreams they can’t deliver, offering bloated timelines, empty promises, and (rather doomed) “big bang” launches.

Cloud migrations aren’t technical upgrades; they are full-scale rebuilds and there really are no short cuts.

If you want to modernize your estimating process with a jump to the cloud, it’s important to understand what it takes to migrate and operate a cloud-based system, and what to look for — so you don’t get stuck with a vendor who can’t follow through.

The struggle of moving desktop software to the cloud

Everyone talks about moving to the cloud, but few talk about how tough it really is.

Research on desktop to cloud software migrations highlight the underlying concerns that shackle stakeholders in the process: cost and time resources, data security issues, and performance flashbacks for the end user.

But, the most cited concern is the technical challenge — the act of actually making it happen at all.

“A major apprehension [of cloud migrations] is the compatibility of original legacy software,” one study reports, “There’s concern that software needs extensive adjustments or customisations to run in the cloud.”

The concerns are founded.

  1. Only 25% of surveyed organizations complete their cloud migrations on project deadlines
  2. And 33% of all migration projects simply fail

“ Building web-based software is a dynamic beast,” explains Ryan Miller, software engineer at Ediphi, “Anyone could ‘vibe code’ to a web app, but just “shipping to the cloud”? It doesn’t work.”

It’s easy to assume desktop and web-based apps are the same thing in different packages — that you can write some code, host it on AWS, and call it cloud — but web-based systems demand a different kind of investment across infrastructure, performance, and user experience.

The 3 pillars of a cloud-based system

Cloud-based estimating tools have three foundational capabilities that aren’t in a desktop tool’s DNA — and can’t be “coded in”.

1. Operational rigor

Desktop-based estimating tools (Destini, WinEst, and Sage come to mind) employ a business model that harkens back to Microsoft in the late 90s; when you’d package up software, ship it out on a disc, and leave it to users to babysit the updates and installs.

But web-based software is always-on — with 24/7 service, live updates, fresh rollouts, and real customer support built in.

At Ediphi, we’ve learned (through a lot of trial and error) how to effectively resource an engineering team that supports cloud-based users. We have a dual “on-call” strategy — one for features, one for backend — to ensure reliable coverage and zero downtime.

" You need to make sure at any moment you have coverage across your entire infrastructure."— Ryan Miller, Software Engineer at Ediphi

And the resources required to create that internal process and expertise? They are substantial.


2. Data integrity

Database collaboration is a beast that desktop software was never built to battle.

“You’re  going from a world where your data is on one machine to one where you've got multiple individuals all working on the same dataset,” Ryan says, “And how do you ensure data integrity right in the midst of that?”

Each estimate can include thousands of interconnected data points, from line items and user permissions to intricate, nested formulas.

And all of that needs to account for:

  1. Who’s touching the data and when
  2. How it’s changing
  3. How to keep it all compliant
  4. And how to restore and repair it if it’s lost

“Cloud-based applications have to support thousands of concurrent users without compromising performance,” says Grant Joy, another one of Ediphi’s engineers, “Achieving this requires carefully engineered systems.”

You can’t carefully engineer those systems overnight.

3. User experience

The third, final, and arguably most important pillar of cloud-based software is user experience. Not just how it looks, but how it works under pressure.

Unlike desktop tools, cloud-based systems have to serve multiple users, across multiple devices, in real time without crashing, lagging, or corrupting data. 

And, for companies moving to the cloud, that workload is now doubled — running the old desktop product and building the new cloud version in parallel.

As one VP shares, “I've been at companies transitioning from desktop to cloud. You're running two separate businesses…”

If they are fully committed to building a quality cloud product, they are no longer investing in their current solution. For you, the user, the days of improvement are over.


Why the “big bang” launch is destined to fail

Launching one big cloud migration sounds like a dream.

But given the new muscles desktop-based tech companies need to develop to move to the cloud, skipping the crucial “trial and error” phase is a gamble you really can’t win.

  • Unexpected bugs cause crashes, slow load times, and lost work
  • The risk of exposing sensitive data is increased
  • Sudden changes negatively impact familiar workflows
  • And, without gradual rollout, customer support becomes flooded

Despite the challenges (and all of my concerned musings), cloud migration is possible

But only if it’s done incrementally, carefully, and with realistic timelines that don’t negatively impact the end user.


Choose cloud-built tools from cloud-first companies

What makes working in the cloud feel so light — instant sync, seamless access, shared data — is exactly what makes migrating to it so heavy.

You can’t “switch” to the cloud with a big-bang launch. You can’t shortcut your way there by throwing engineers at the problem. And you definitely can’t retrofit desktop software into something it was never designed to be.

Ediphi was built as a web application from the first line of code. And 7 years of careful cloud development, incremental testing, and intentional feature adds have made it the kind of enterprise-product endorsed by some of the biggest names in construction.

"Ediphi is the next generation of estimating platforms."
— Kyle Bonde, Senior Estimator at Hensel Phelps

When you’re evaluating software, don’t buy the vision. Take it for what it is today. 

Because everything else is just noise.