Going Enterprise

For the past two years, I've been working with a client , an enterprise software company (built with Ruby on Rails, of course), particularly in the niche of software used by enterprises of all sizes + MSPs and IT administrators for real businesses like law firms, municipalities, architects, hospitals, manufacturers, financial institutions, and government agencies.

Working with an enterprise software company has revealed a whole new world of B2B software companies and managed service providers (MSPs) that I had no idea existed before. I guess most people building typical SaaS startups and Rails apps don’t know much about it either. Personally, I’ve had to revisit many of my priors about how a software business works.

So many things work differently in the enterprise world: how the software is developed, how it is marketed and sold, how it is licensed, how it is deployed, and how customers are supported (support is a huge, non-negotiable part of enterprise software, something I learned after handling a ton of support requests lately).

Take authentication, for example. Beyond email and password, there’s SAML, SSO, identity providers, and multi-factor authentication. Then there are the related concerns of SCIM provisioning and role-based access control, along with all the complexity of making these work with an enterprise’s existing systems.

And authentication is just one part of it. Audit logs, backwards compatibility, documentation, support, data retention, and encryption all demand your attention when building for enterprises. So do service-level agreements, disaster recovery, observability, compliance, configuration and customization. Then there’s the work of deploying on-premises, navigating security reviews and vendor assessments, and dealing with licensing and procurement processes.

These products are also not sold directly to the end users of the software. They involve IT administrators, security teams, procurement departments, legal teams, compliance officers, 3rd party software vendors, company executives, and a bunch of other roles you wouldn't come across in B2C or consumer software.

I seriously wish the mainstream software development discourse included these topics as much as growth, raising funding, product-led growth, freemium, going viral, building in public, becoming an indie hacker, or whatever the current SaaS trend happens to be. I also wish universities, colleges, and programming curriculum taught about this side of the industry.

Anyways, the more I work on the enterprise software, the more I'm enjoying working on it. It’s not as visible or fashionable as the typical SaaS apps, but that’s part of what makes it interesting and fun for me. There is a ton I don’t know, which also means there is plenty to explore, learn, and write about.

I also think this industry is very much immune from AI disruption, as the customers (which are real businesses and not developers) are just not interested in building, maintaining, hosting, securing, and debugging their own solution with AI. Here's a tweet from Jack that perfectly summarizes this, except the fact that enterprise customers are not paying $15/month, they're often paying hundreds, thousands, or even hundreds of thousands of dollars and perfectly fine with it.

On the other hand, with all the power of AI agents we now have, I think there’s a lot of room to speed up all areas surrounding enterprise businesses. Plenty of businesses have software they want to improve and a long list of things they’ve learned to live with. They could use someone who can understand their business, help decide what’s worth fixing, and follow through.

That’s the work I want to do more of.

Everything can be better, quickly

A few days ago, Jason Fried tweeted:

"Building new stuff and improving existing stuff has never been more fun! EVERYTHING can be better quickly, but it's still a secret, plenty have no idea, and even those who do need a lot of help and direction to see what needs to be improved."

"I love to fix. I love to make stuff easier on people. I love to show people a better way. I love to blow away the fog. I love to untangle."

That describes exactly how I feel about enterprise software right now.

Enterprise software is where you find the most tangles. Products have been running for ten, twenty, sometimes thirty-plus years. The software works and real businesses depend on it every day, but it's often slow to change, hard to work on, and painful for the people using it. That's also where the opportunity is biggest. With modern tools (and yes, I mean AI agents), we can now improve existing software faster than ever.

Going forward, I want to go deep on the topics surrounding enterprise software: MSPs, SSO/SAML authentication, licensing, support, deployment, and the technologies and business models behind enterprise products. In short, anything and everything that touches the enterprise. The goal is to understand this largely invisible world deeply, and then use that understanding to make enterprise software better, using the powerful AI agents we have at our disposal.

In a way, this feels like coming home to me, as I started my career in a 35-year old enterprise software company (CityView) running on .NET that built and sold municipal software to local municipalities all over North America. I don’t think I fully appreciated that world at the time.

So enough about writing Ruby on Rails tutorials on the Write Software, Well blog. The agents are perfectly capable to explain all your programming questions. Enterprise software technology + business is what I will be learning and talking about going forward.

If you’re building, buying, selling, or supporting software in this world of enterprise software or managed services, I would love to connect with you.

Stay tuned!