Is this era of AI innovation more like the mainframe revolution or the dot-com era? Stratechery's Ben Thompson made a case for the former on a recent podcast episode with Nat Friedman and Daniel Gross.

While both these have merit, I find the most relevant analog to the current AI apps explosion is the golden age of enterprise software that occurred from 1994-2000, driven by the transition to client-server computing. I was fortunate to participate in that wave, as the GTM leader at Trilogy Software where we grew revenues from $1M in 1994 to $300M in 2000. Massive companies created during that era include Siebel Systems ($40B market cap), i2 ($25B), Ariba ($40B) and BMC Software ($20B). And in a direct parallel with Nvidia’s insane appreciation, Dell (which sold the picks and shovels of the client-server revolution) saw their market cap increase a staggering 120,000 percent from 1990 to 2000.

In that era, enterprises rolled out PCs to information workers across their companies, and a new wave of apps unleashed “knowledge” and “expertise” that was previously in the heads of only a small number of people in the company. As a result of these new applications, millions of salespeople, marketers, supply chain execs, and finance professionals could now leverage powerful compute on the edge with new apps that unlocked business processes and intelligence.

AI similarly is a transformational new capability driven by breakthroughs in software, compute and semiconductors that is unleashing new capabilities for information workers. Knowledge and expertise, codified within foundation models, is now available at the fingertips of information workers who can utilize agents and copilots to automate tasks and streamline workflows.

What were the lessons from that era and how can they apply for leading AI Apps companies in 2025?

Top-Down Selling Matters Once Again

The 1990s world of software was all about top-down selling. Tom Siebel, founder of the wildly successful Salesforce precursor Siebel Systems, ran full-page ads in the Wall Street Journal featuring CEOs of the largest companies (Schwab, Starwood, etc.) who extolled the value of buying Siebel software for managing customers. Companies like Siebel, i2, and Trilogy had average deal values well north of $1M and many $10M+ deals per year. Trilogy famously closed a $100M TCV deal with a large automotive OEM.

The last 15 years of software has seen a movement away from big-deal selling to higher velocity and more repeatable forms of selling: inside sales, product-led growth, freemium sales, open source, etc. 

The new wave of AI apps is ushering in a renaissance of C-Suite selling. Every Fortune 500 company CEO has an AI counsel that is tasked with bringing in new technologies. These mainstream companies want a trusted advisor that can help guide them on the best way to adopt AI – this includes not just the technology but the process for adoption, change management and continuous learning.

The best AI apps companies understand this well: they have founders who can effectively pitch a vision to the C-Suite and they have business models that incorporate the type of high-touch handholding required during and after the sales cycle. The payoff is that these AI apps companies are regularly closing $1M annual contracts. The good times are back!

Sam Lessin in his latest blog post writes that the modern AI apps founder archetype requires “storytelling” and “expertise”. I generally agree with his emphasis on expertise and evangelism, but I disagree that this doesn’t play to the strengths of “kids.” Trilogy’s entire front line enterprise team was made up of 25-year-olds. A good friend and founder of BCV-backed Iodine, Mike Kadyan (while in his 20s) sold Williams Telecom for a $10M+ TCV deal. Joe Liemandt, the founder of Trilogy, was invited by Jack Welch to address all of the GE division CEOs at Crotonville when he was 27 years old.

Implementation is Key

The conventional wisdom around SaaS has been to reduce, mitigate or eliminate the need for professional services and implementation. The best SaaS companies required very simple onboarding that could be completed in weeks, not months – without the need for armies of professional services personnel.

In the age of AI, implementation matters – not just upfront, but over time. Whether these professionals are called PS (professional services) or FDEs (forward-deployed engineers), the function is the same: help customers with ingesting data, tuning the models and iterating on the efficacy of the solution. This effort not only occurs up front but will be required over time to ensure the solutions can adapt and still be performant with new changes to the business (new product lines, revenue streams and workflows).

In the 1990s, i2 built an entire Strategic Value function where they forced every prospect to sign up for a 60-90 day paid engagement that resulted in a custom-built working demo and an ROI case. i2 had an incredible 90 percent + conversion rate of these POCs or SVAs to signed contracts (most of which were worth north of $1M in annual contract value).

At Trilogy, we sold hundreds of millions of dollars of high-margin professional services to help companies like Boeing and HP ensure the “knowledge” of their best engineers was correctly codified and programmed into our expert system that their salesforces used daily. Every new product launch or product change required our help.

Similarly, the need for fine-tuning, training and adaptation will be ongoing as the core foundation models change and the business needs evolve. The ROI on these implementation dollars will be massive as each hour of an FDE’s time on-site can meaningfully drive improvements in the AI solution.

Sell High With A Strategic Call-to-Action

The best AI companies of this generation will not be selling LLMs or cool technology features but will be selling a strategic “call to action” to the largest companies in the world. C-Suite execs don’t want to buy features and functions. They want to buy strategic transformation.

Siebel Systems wasn’t selling a database to manage prospects and opportunities. They were selling an ethos of being customer-centric and a solution for managing customer relationships.

i2 wasn’t selling a software engine for supply chain network planning. They were helping companies “re-engineer’ their core business and turn their supply chains into real-time strategic assets.

Trilogy wasn’t selling a product configurator. We were selling the vision of mass customization.

Does the strategic call to action need to be credible? Sort of…. Did Siebel’s software really help companies manage their customers better? At some level, yes, since companies now had a record of each customer interaction. Did Trilogy help enable mass customization? Yes, in a sense. With our needs analysis interface, a salesperson could generate a customized product configuration more suited to that customer’s exact requirements.

In today’s market, every large company is grappling with how AI will unlock productivity inside their businesses and how AI might create existential threats for their company. The best AI apps startups will align their mission to helping these companies drive the required strategic transformation to survive and win in an AI era.

Every founder should ask themself: what is my strategic call to action for the corporate C-suite? Having a clear and elevated message will significantly increase deal sizes while massively accelerating sales cycles.

Winning with a Focus on Sustainably and Profitably

The winning founders will build a culture and DNA around C-suite selling. They will hire an army of forward-deployed engineers and will charge for ongoing implementation services so that they can be delivered sustainably and profitably. They will invest energy in crafting a message that drives a sense of urgency and opportunity for the C-suite of their ICP. They will be unafraid to ask for big dollars and will be maniacal about having their team deliver against that ROI. They will establish their company as the trusted partner to the CEO and her lieutenants as they embark on this strategic transformation.

For the founders that embrace this philosophy, the reward is a path to hundreds of millions in revenue at a speed and pace that will feel unprecedented. The big deals and big logos will establish market leadership. Being on the inside of these large companies will lead to endless new product opportunities and revenue expansion. The power of distribution, brand value and marquee references will be the ultimate moat in a world where the underlying technology is being commoditized so quickly.