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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 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.
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.
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.
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.
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 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.
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.
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.
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.
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Akshay retweeted
Omarchy is forever free. There's no monetization scheme coming. I'm already rich and the Omacom Foundation is a well-founded nonprofit.
The only ulterior motive here is to make Linux win on the desktop and create the perfect, malleable computer for all to enjoy!
The only ulterior motive here is to make Linux win on the desktop and create the perfect, malleable computer for all to enjoy!
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Learning about AI using AI is so underrated. I have no AI/ML background and despite a big user of coding agents, have pretty much ignored the underlying tech so far. But recently started going deeper by having long conversations with Claude to learn anything and everything around how it all works, asking it to dumb it down for a typical web dev like me. Learning is so much fun with AI.
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Reading Omarchy 4.5 changelog, and shaking my head at those still calling it a collection of dotfiles.
Huge respect to the Omarchy team and @dhh for this awesome OS.
Huge respect to the Omarchy team and @dhh for this awesome OS.
Omarchy 4.5 is finally here! Traditional desktop mode, M1/M2/M3/Neo compatibility, 50 languages, 7-second installs, and a million other features, fixes, and improvements. omarchy.org/news/2026/11/o…
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Akshay retweeted
Hey, Rails peeps. Security updates have been released, this is a big ol' batch of fixes including another Critical in image processing.
I strongly recommend you upgrade as soon as possible.
rubyonrails.org/2026/11/4/Rail…
I strongly recommend you upgrade as soon as possible.
rubyonrails.org/2026/11/4/Rail…
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Akshay retweeted
In the year 2000, Joel Spolsky (founder of Stack Overflow) wrote a famous article titled “Things You Should Never Do, Part I.” In it, he talks about how rewriting your code from scratch is the single worst strategic mistake any software company can make. However, times have riting software is dropping exponentially and that has changed the math entirely on if it is worth rewriting your codebase. For instance, this year Anthropic’s Jarred Sumner ( @jarredsumner ) rewrote Bun in Rust in 11 days leading to many performance and correctness benefits.
Likewise, Stephen Toub (Distinguished Engineer at Microsoft, @stephentoub ) rewrote the GitHub Copilot runtime (400,000-line codebase) in Rust by himself. I thought it’d be interesting to lay out everything he learned in the process. So I interviewed him about how and why he did it.
In this episode:
• Why he choose Rust of all languages
• Rollout strategies (incremental vs all at once)
• How he prevented regressions
• Steering agents and which models he used
• Career lessons and engineering advice
Where to watch:
• YouTube - youtube.com/watch?v=PLMOVl…
• Spotify - open.spotify.com/episode/4zthBK…
• Apple Podcasts - podcasts.apple.com/us/podcast/the…
• Transcript - developing.dev/p/e073-stephen…
Thank you to the sponsor of this episode for supporting my work:
• WorkOS: makes your app Enterprise Ready with easy to use APIs to add SSO, SCIM, RBAC, and more in just a few lines of code, check them out at workos.com
Chapters:
00:00 Intro
01:06 Why the Copilot runtime needed a Rust port
05:38 Why he chose Rust
11:28 Discussing rollout strategies
21:57 How he caught regressions
32:08 Guiding the agents
42:11 Catching regressions before prod
45:16 Which models he used
50:03 The end benefit and costs
01:03:24 When to do a full rewrite
01:06:40 Career learnings on the way to Distinguished
01:16:00 Top technical book recommendation
01:17:49 Advice for young engineers
01:21:00 Outro
Likewise, Stephen Toub (Distinguished Engineer at Microsoft, @stephentoub ) rewrote the GitHub Copilot runtime (400,000-line codebase) in Rust by himself. I thought it’d be interesting to lay out everything he learned in the process. So I interviewed him about how and why he did it.
In this episode:
• Why he choose Rust of all languages
• Rollout strategies (incremental vs all at once)
• How he prevented regressions
• Steering agents and which models he used
• Career lessons and engineering advice
Where to watch:
• YouTube - youtube.com/watch?v=PLMOVl…
• Spotify - open.spotify.com/episode/4zthBK…
• Apple Podcasts - podcasts.apple.com/us/podcast/the…
• Transcript - developing.dev/p/e073-stephen…
Thank you to the sponsor of this episode for supporting my work:
• WorkOS: makes your app Enterprise Ready with easy to use APIs to add SSO, SCIM, RBAC, and more in just a few lines of code, check them out at workos.com
Chapters:
00:00 Intro
01:06 Why the Copilot runtime needed a Rust port
05:38 Why he chose Rust
11:28 Discussing rollout strategies
21:57 How he caught regressions
32:08 Guiding the agents
42:11 Catching regressions before prod
45:16 Which models he used
50:03 The end benefit and costs
01:03:24 When to do a full rewrite
01:06:40 Career learnings on the way to Distinguished
01:16:00 Top technical book recommendation
01:17:49 Advice for young engineers
01:21:00 Outro
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Akshay retweeted
The age of agents is going to be amazing for most programmers, but it'll be hard times for the cantankerous ones.
Specialized knowledge and rare skills will no longer offer immunity for those who are a pain to work with.
Best learn some basic people skills.
Specialized knowledge and rare skills will no longer offer immunity for those who are a pain to work with.
Best learn some basic people skills.
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Treating book chapters like blog posts is the biggest change that increased and improved my reading recently. Must try if you're struggling with reading.
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Again, an excellent time to read this classic 2006 essay by Joel Spolsky.
joelonsoftware.com/2006/04/11/the…
joelonsoftware.com/2006/04/11/the…
vibe coders will be in shambles when they discover that every popular piece of software already had an open-source alternative long before ai
soon they will discover what the second s in saas stands for
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Akshay retweeted
@TaliaRinger You're already an exceptional researcher. When the kids are young, there is the tension you highlight, but it gets easier when they get a bit older. In the meantime, enjoy them at their current age, because they grow up fast!
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Does anyone know the original source of this poem / essay?
Incredibly emotional watching this because I’m painfully aware that “the good old days” are right now.
At 42 I have a perfectly imperfect life with a wonderful wife and two great kids. I don’t long for my younger years. I want to freeze time right now.
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Learning marketing and sales by reading Jesse's tweets (especially replies) on X 💪
@gregmberry PostShiba can send emails on your behalf and receive emails. When you receive emails it sends a webhook to your app which you can parse and do whatever with. It also retains it's own inbox which an agent can fetch emails from if you would like.
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