Built by operators: Why we believe ERP had to change
NEWS

From Short Shorts to SaaS: Building the ERP-Alternative We Wish Existed at Chubbies

Kyle Hency
Article by
Kyle Hency

Former CEO & Co-founder of Chubbies. Co-founder & Board Member of Loop Returns.

Updated
January 15, 2026
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The SaaS world is waking up to something brand operators have known for years: legacy ERP systems are broken.

They’re expensive, slow to implement, and just don’t fit how modern businesses actually work. We experienced this first hand at Chubbies. We were moving faster than the software we could find. The existing systems weren’t built for dynamic, inventory-based retail brands like us. 

Why we’re here

At GoodDay, we believe now is the time for the next generation of ERP. 

In recent months, companies like Rillet, Campfire, and DualEntry have raised major rounds of capital to reimagine ERP for the AI era. They’re focused on financial operations for software and services businesses; rethinking the general ledger, automating workflows, and helping CFOs run smarter. These are incredibly interesting innovators that we look to for inspiration. 

Similarly, GoodDay is taking an AI-native approach to disrupting legacy ERP providers, but in contrast, we’re laser-focused on solving inventory-related operational problems for Shopify brands. It’s an absolute hornet's nest of inter-related operational problems with interdependencies across many systems (i.e., commerce platforms, WMS, RMA, EDI, data/analytics, planning, tools, accounting systems, etc.).  

Inventory-based businesses face challenges traditional horizontal ERP systems were never built to handle. Managing complex datasets across multiple distribution channels like DTC ecommerce, wholesale, marketplaces, and retail stores can quickly overwhelm your operations.

At Chubbies, we learned that the hard way. We avoided wholesale for years, not because we didn’t want to grow, but because our systems couldn’t handle the added complexity. Without a clear source of truth for inventory, small gaps in operations turned into big financial headaches.

Running a fast-growing brand on software built for manufacturers and accountants was exhausting. Our spreadsheets broke, our team was burned out, and the legacy ERP we tried only added more friction (and a ton of overhead & 💸).

That experience is what led us to build GoodDay—something designed for the way modern Shopify brands actually operate.

GoodDayOS™ is:

  • AI-native and vertical by design, a retail ERP alternative to manage your inventory better, not a broad horizontal ERP
  • Purpose-built for brands managing inventory and supply chain complexity across multiple distribution channels 
  • Embedded directly in Shopify for a simple, unified experience
  • Ecosystem-first, ready to integrate from day one with core systems like WMS, EDI, selling platforms, data/analytics and planning tools

Why being built by operators matters 

AI is making parts of ERP that once felt impossible, such as data ingestion, data cleansing, and custom workflows, far more approachable. But without real-world operational experience guiding the application of new AI tools, it has the potential to underwhelm or be explicitly incorrect.

Our core belief: For AI to deliver truly effective results for brands, it needs to be built and fine-tuned by people who have actually built and run successful brands.

That is the team we’ve built at GoodDay. Teeming with former brand operators & entrepreneurs. 

Every workflow in GoodDayOS™, from purchase order management to automated FIFO landed cost reporting to pre-sales automation, comes directly from lived operational experiences and pain points. We learned this in our experience co-founding Loop Returns. If you attack the root problem with a genuine operational point-of-view, you meaningfully increase your chance of having early product-market fit. We have that GoodDay as well. 

Over the last 2 years, we have been developing a sophisticated system of record because accurate, reliable, and accessible data is the foundation of everything that follows. With that foundation in place, we can offer a true system of work with GoodAI Agentic Workflows and Agents in 2026. These products will not just analyze your data; they will help you do the operational work.

"GoodDay is ushering ERP into the agentic era. Shopify merchants, who've endured nearly two decades of legacy ERP pain, finally have an AI-powered OS that streamlines inventory flows and doesn't take months to implement. Kyle and Dave, our old friends from Chubbies and Loop Returns, know how to relieve the agony of brand operators better than anyone. We're thrilled to once again support their mission to reimagine ERP."  – Alex Rosen, Ridge Ventures

The proof so far

This isn’t just theory, it’s already happening. 

Over 40 Shopify brands including, Lola Blankets, Halfdays, Poncho Outdoors, American Tall, Kenny Flowers, The Normal Brand, Hill House Home, Still Here, and Margaux are already running their operations on GoodDayOS™.

Legacy ERP systems are prohibitively expensive and take months to deploy. GoodDay brands are launching in weeks and they don’t need to hire outside consultants. The total cost of ownership of GoodDay is 70% less than the cost of a legacy ERP. The old paradigm of value in this category is dead. What we are building isn’t incrementally better, it is changing the game entirely.  

“GoodDay has been a game-changer for us. We finally have an ERP that actually fits the way modern brands operate — simple, flexible, and built for Shopify. It’s rare to find a partner who really gets both the brand and the business side, but Kyle and his team nailed it."- Jimmy Sansone, The Normal Brand (Hear their story

Today’s announcement

I’m thrilled to share that GoodDay Software has raised an additional $7M from existing investors Ridge Ventures, FirstMark Capital, Flex Capital as well as new investors Long Journey Ventures, Seguin Ventures and Adverb Ventures as well as many brand operators from Shopify and GoodDay’s ecosystem. This brings our total capital raised to $13.5M. 

This funding will help us:

  • Launch GoodAI Agentic Workflows and Agents to help operators make smarter decisions and get real work done faster
  • Rapidly expand GoodDayOS™ into finance and accounting operations 
  • Invest deeply in our partner ecosystem to expand the number of out-of-the box integrations
  • Continue hiring the most ambitious team in ecommerce infrastructure
“AI is transforming how brands manage operations, and GoodDay is leading that change for Shopify merchants. Their focus on inventory — the most complex and mission-critical part of a retail business — sets them apart from other next-gen ERP players. This is an AI-native system built by operators who’ve lived these challenges firsthand.” — Amish Jani, FirstMark Capital

This is the GoodDay movement

GoodDay was born from the idea that modern retail brands shouldn’t have to fight their own systems to grow. 

We believe brand operators deserve better.The era of bloated ERP projects, endless consultants, and painful implementations is over. The future belongs to tools that are fast to set up, intuitive to use, and built for the real people running brands every day.

Our community includes some of the most innovative, high-growth brands in commerce. They share a common belief that operational excellence should be within reach for every ambitious team, not just enterprise giants with unlimited resources. 

We are helping level the playing field for challenger brands on Shopify.

GoodDay is building the foundation for a new era of retail operations, where technology works as hard as the people behind the brand. Where data flows freely, decisions happen faster, and teams can focus on getting customers the products they love.

Today is a GoodDay. And it’s only the beginning.

Join us!

The GoodDay Software team kicking off the year with an offsite in Austin.
Article by
Kyle Hency

Former CEO & Co-founder of Chubbies. Co-founder & Board Member of Loop Returns.

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Our speakers:

Panelists:

Jimmy Sansone
One of the brothers, The Normal Brand
Max Ottenlips
CFO, The Normal Brand
Kyle Hency
CEO, GoodDay Software

Our speakers:

Panelists:

Kyle Hency
CEO, GoodDay Software
Emily Brauer Gill
Chief Revenue Officer, Margaux NY
Steven Feczko
Head of Operations, Lola Blankets

Our speakers:

Panelists:

Dipti Desai
CEO & Co-Founder, Crstl
Kyle Hency
CEO, GoodDay Software
Christian Castellani
Director of Wholesale Sales, PAKA

Our speakers:

Panelists:

Kyle Hency
CEO, GoodDay Software
Kevin Harwood
CEO, GoodDay Software
Scott Dulany
COO, Mugsy

Our speakers:

Panelists:

Kevin Lavelle
Harbor Sleep, Mizzen+Main
John Merris
Solo Brands, Flooret
Isaac Mertens
Flux Footwear

In this webinar, you'll discover:

Here’s what we’re talking about: