Selling Transformation
Why enterprise software won't implode overnight
Rate of change
I remember my time at Citi. The junior team members spent hours manually extracting data from tables. Inputting numbers from PDFs, one by one, for financial analysis. For some reason, we didn’t have reliable OCR or extraction tools internally. This was in 2019!
I got so frustrated I wanted to build my own micro-service: email out an extract, process it with a Lambda using the latest document extraction tech, and email it back to myself. Unfortunately, that would have been a massive security breach. Easier than trying to navigate internally to buy Adobe Pro though…
There were other instances of this kind of remarkable lag behind true tech capabilities. I automated our weekly newsletter mail-out using VBA—recreating a live document linked to Factset, publishing to PDF, and drafting emails, all within Excel. We could have used Mailchimp.
Once I discovered VBA’s connectivity to Outlook, I found it quite amusing to flood my colleagues calendars with hundreds of 5 minute long meetings 😂
Jokes aside - it was the first time I felt a marked difference in rate of change between the world of work and my personal life. No one in the org could buy or change practices that quickly. Although, reflecting now, I wonder if people would have easily concluded the juice was worth the squeeze.
Back then there were far fewer software vendors than today. Now we have hundreds of vendors across every vertical vying for attention. The technology to replace and improve business has always been available. The challenge is navigating the fog and driving change. That’s why enterprise software isn’t going to implode overnight.
Customers want to buy clarity
The opportunity I see coming down the turnpike: helping companies transform and adopt AI.
Customers want to buy clarity (and change management).
Right now, the large software vendors are selling AI features and agents by bundling. “Notion + AI chat.” We’re using this internally already. The Notion environment probably has everything I need to adapt the EVP business and drive productivity improvement. But I’m still running AI workflows outside of Notion on Claude Code. No one has driven the change management yet to lock us in.
Imagine where the issues sit in other industries. A transformation approach to selling might be a strong differentiator. Use your software as a centrepoint to build AND transform the business’ workflows. Use your organisation’s domain expertise to select what matters and offer a breadth of tools/integrations.
What impacts rate of change within a company?
Complexity of the organisation. Size, number of departments, and scale of the tech stack all slow things down. How quickly can you move a 10,000-person org versus a 100-person org?
Scope of service. Entirely digital service businesses, such as marketing or design agencies, may have a fast rate of change. White-collar versus blue-collar versus mixed matters. Offline businesses like service providers, farmers, and construction may have a slower rate of change.
Level of digitisation. This one I’m torn on. Companies that haven’t already adopted tech are more of a blank slate for AI workflows. At the same time, they don’t have the same familiarity and foundations to build from—data repositories, for instance.
It’s war-time again in product
This diagram shown to me by Glen Kruger at Raymond James articulates very neatly a feeling I’ve had about the new war-time in the product world.
New AI-native software competitors are offering completely new experiences (characterised by the agency Y axis) which emerged in the form of things like legal drafting in 2024, high fidelity transcription/note-taking in 2025, to agentic systems in 2026. They’re all competing to be more that just the above. That more is a fully fledged system that contains, put simply, a lot of data and a lot of automations.
The incumbents are coming at it from the other direction. How do we incorporate these game changing new use cases into our platforms.
What an exciting time.
war time baby!!!!