The Three “Digital Transformations” (and how to bring them together)

Ben Sigelman
3 min readSep 20, 2021


Originally posted as this twitter thread.

0/ The more time I spend in this industry, the more I realize that, while “Digital Transformation” is real, there are actually three of them. :)

And that we need a new kind of observability to complete the transition.


1/ The first “Digital Transformation” is a transformation of Operations. This isn’t just SRE or ITOps, to be clear, it’s much broader — basically “all Opex,” or “everything that employees do.”

2/ First we digitized the filing cabinet via mainframe databases, then we added boxed software and LANs, and now we’ve gone further with SaaS tools that cover operational workflows across roles and functions: see ServiceNow, Microsoft, Salesforce, etc.

3/ Now, if any custom software gets developed as part of this “first digital transformation,” it is often quick, dirty, and/or outsourced: this custom software is not customer-facing, and typically small or at least small-ish.

4/ By contrast, the second “Digital Transformation” is a completely different category of software: it’s software as the product, as the way of engaging with the customer, and often as the way of generating revenue.

5/ For any large business, the choice is simple:

a) Use software to improve (or define) your customer experience, or

b) Be replaced by a competitor who does.

So naturally there’s an appetite to invest a great deal of capital and a great number of developers in the endeavor.

6/ Now, “lots of developers” begets “lots of teams” begets “lots of services,” and — before you can say “Kubernetes” — every enterprise finds themselves building planet-scale distributed SW systems.

And if you’ve ever tried to manage a planet-scale distributed system: “Yikes.”

7/ And that brings us to observability’s “scope” today: allowing enterprises to innovate quickly with these giant, revenue-generating, distributed software applications while maintaining high reliability and an excellent customer experience.

8/ Is that important? Definitely.

Is it enough? Not at all.

We’re only scratching the surface with observability today. What’s just around the corner is arguably much more important and much more exciting: observability will enable a third digital transformation.

9/ For digital products, these very large, strategic, first-party software applications have diverged from the ITOps tech stack, both in terms of tooling and in terms of the org chart; so while there’s software everywhere, it’s disconnected between product and operations.

10/ In this third digital transformation, we directly connect the (employee-facing) software of the first transformation directly to the (customer-facing) software of the second transformation — and we connect them with observability.

11/ Why?

Because observability can give any employee the clarity and confidence they need to design / develop / test / operate / market / sell / support / finance / secure (/ etc, etc, etc) these customer-facing software apps.

12/ Put simply, observability can connect customer behaviors with employee workflows.

We can get ahead of poor experiences before the customer notices; or explain a $10M+ AWS bill in terms of product features; or help marketers tell the right users about a new release; etc.

13/ There’s a lot of work and innovation left ahead of this third digital transformation, but we can all look forward to the day when the transformative benefits of application observability apply to every operational role — not just the technical ones.

For more threads like this one, please follow me here on Medium or as el_bhs on twitter!



Ben Sigelman

Co-founder and CEO at LightStep, Co-creator of @OpenTelemetry and @OpenTracing, built Dapper (Google’s tracing system).