A key question in the "future of software" debate entails understanding how durable enterprise business processes will be in the future. In the old world, companies could go so far as to assume their inventory management processes, for example, would be static for a decade and then implement SAP and not materially upgrade it. Today, I'd imagine most CEOs have less confidence that their businesses will be static a decade from now than they did before. Many likely have a more short term-oriented approach - "solve my problem today." SaaS was definitely a step in this direction, cutting deployment times and improving agility. Yet, many actual enterprise SaaS implementations represent the customer's business as it was a few years ago. This is often the root of the "my CRM is broken" issue. In a world of increasing short term-ism, the question then becomes what approach is faster and more agile: 1. Buying purpose-built SaaS with AI and configuring it and hoping the vendor keeps evolving to their needs 2. Vibe coding a custom solution and then investing to keep it relevant When I look at this tradeoff, I don't see things being as obvious as others do. I could talk myself into either alternative. But what is pretty clear to me is that the world will need increasing speed and agility - perhaps forever. Whichever approach delivers that will win.
One big problem with traditional software is it depends on the customer being great at their job. By definition most customers aren't above average in their work. A positive side effect of agents is they decouple software success from client...
Fired up* to work w/ @rfradin @jlarrison @aktwits @arampell @a16z on the Board of @Larridin. We used Larridin at Gainsight to measure the ROI of our AI investments & this is a problem every company will need to tackle. *Russ promised to...
"I have this superpower now that has blown my mind" Just caught up with a former Gainster who is in a mid level role at a big company. He likes his job but has gotten vibe coding-pilled. He uses @Lovable non-stop and...
Ppl often ask me for advice about "category creation" from my time at Gainsight. My first instinct is "don't!" It's expensive and Sisyphean 🤦🏽♂️. But after my warnings, I share that the biggest needle-mover for us was having an evangelist that came...
Is AI constrained by software TAMs? When people think about the TAM for AI B2B software, a common refrain is "it's so much bigger because AI will automate services and labor." I think this will happen long-term, but it requires a...
Banger by @emollick. His Jagged Intelligence concept really has become one of the most important ideas in AI. In B2B AI, you could argue that it reveals a framework for disruptor versus incumbent success: * Jagged Intelligence area => advantage to incumbents,...
There are few pieces of advice that I feel strongly about - one is near the top of the list: be careful about swap deals. In B2B, there is a temptation early on to do the old "I'll buy your product...
One of the biggest decisions for a B2B startup is picking the right early clients. There is path dependency from those customers as you build your company for them. Selling to anyone who wants to buy can be dangerous.
One of the worst pieces of advice in startups is telling people that the best product always wins. There is a graveyard of companies that followed that advice. "Great products" are necessary but not sufficient.
The AI gold rush is covering up a painful truth: most point solutions won’t be retained. In 2026, as “buy all the AI tools” mandates disappear, churn will become the toughest Bitter Lesson.
A big question I ask myself if someone is thinking of raising a lot of venture money: "Can this idea eventually become a (legal) monopoly?" People don't like to talk about it because it sounds bad, but the truth is the...