Bryan Friedman

The Evolving Technologist: Adventures of a Recovering Software Generalist

Between Two Summits: One Year In

One year ago today, I started at Moderne. It was the week just following the inaugural Code Remix Summit.

One week ago today, I gave a talk at the second Code Remix Summit. It was my first conference talk since 2019.

So last year I missed Code Remix by one week. But this year I was on the schedule.

When I joined Moderne, it was pretty clear that it was the right move for me, and I shared my reasons why. All of that is still true, but what I didn't share at the time is my own list of personal goals I was bringing with me and the areas of growth I wanted to work on. Now, one year in, feels like a good moment to share some of that list and check in on where I've landed.

# Speaking and showing up more

One of the things I hoped to do more of this year was speaking and being more visible in the community. I had definitely let that muscle atrophy a bit in my last few roles, and I missed it. My Code Remix talk was the culmination of a year of slowly turning that dial back up, along with more LinkedIn writing, more demos in front of bigger audiences, and more willingness to put myself out there. I've been really happy with the engagement I've gotten on LinkedIn and fortunate for all the opportunities I've been given to appear and participate in presentations, webinars, and our weekly livestream.

In fact, we've got a little internal leaderboard going for most Code Remix Weekly appearances. I'm at four, chasing someone who's been at the company at least 4 times as long as me, and he's only ahead by one. Feels pretty good for someone in their first year on the team!

I'd love to do more talks, podcasts, and livestreams, because the only way to get better at it is to keep doing it, and I've got plenty of room for improvement. The funny thing is, every single time, my anxiety builds up so much leading up to it that I wonder why I chose to do it. And then the moment it's over, I'm always glad I did it and already looking for the next one. Apparently this is what wanting it looks like for me.

# Demos and narrative

I came into this job thinking I knew how to build demos in my sleep. A year of doing it at Moderne has reset that for me. The product moves fast enough that staying up-to-date with it is half the work, and you can't tell a story about something you don't understand yet. It's been challenging and fun to follow all the Slack threads, pull requests, and ADRs enough to keep up.

The other half is figuring out the narrative. The demos I'm proudest of this year are the ones where I crafted the most compelling story: the Java 25 modernization walkthrough, the Prethink launch video, and the internal, full product demos we created for analysts. I've always considered tech marketing to be a storytelling role, but storytelling for smart, technical audiences is its own discipline. These are people who can spot a hand-wave from a mile away, and who'll ask thoughtful, challenging questions that you can't fake your way to answering. Plus, getting that audience to lean in instead of lean back is the part of the job I've spent the most time trying to get better at, and the part I find the most rewarding.

# Contributing code

Getting closer to code was one of the things I most wanted out of this role, and Moderne has delivered on that in a few different ways. I've gotten to contribute a little code here and there: training modules and recipes, minor commits to the CLI, and especially documentation, where I'm most comfortable anyway.

But I also spend real time reading through code to understand it, whether it's product code or even the code the product operates on. From picking up more Java to revisiting other languages like Python, JavaScript, and .NET, it's been fun tapping into my engineering core while still staying in my marketing lane.

# Working more closely with product

When I was job hunting last year, I was mostly looking for product roles. Technical marketing wasn't the plan, but it was the path that opened up for me and it turned out to be the right one. Even so, I kept the option of moving back into product open in my head, figuring maybe somewhere down the line I'd eye a product role inside Moderne if the right one came up. But so far, the mix of skills that my technical marketing role has required seems to fit better for me anyway.

So I'm not really chasing a product role right now, but I'm leaning hard into product partnership. We've recently brought on a new outbound product manager, and I'm excited about what that opens up. Another technical storyteller to bounce ideas off of and collaborate with will make my work better. And an outbound PM gives technical marketing something that can sometimes be tough to get enough of: a sharper window into actual customer conversations. That's the part I'm most looking forward to.

# Learning marketing-y stuff

I'll always be technical first. No doubt about that. But one of the things I didn't really expect to come out of this role at first is my growth into the marketing part of technical marketing. Product marketing, demand gen, SEO and the digital side, even social media marketing (like I mentioned about LinkedIn earlier) are all areas I've gotten more fluent in over the past year. I've been part of positioning and messaging conversations before, but sometimes I felt like I only half understood, or had to sort of wing it. (I still feel like that at times.) Even my competitive intelligence work, an area I actually had some experience with, has grown through the challenges of a complex and ever-changing market.

Through it all, I have a supportive and experienced team to learn from, and I definitely feel like a more proficient marketer than I was a year ago.

# The AI of it all

When I started, AI was certainly popping up everywhere. It was in job descriptions, market consciousness, and just the general culture. I used AI in my day-to-day, mostly copy-pasting things into and out of ChatGPT to help with writing. Now that workflow looks so primitive. Engineers on our team (and everywhere) started using agents for serious coding work, and I followed suit for docs and demo construction. Now across our marketing team, we're constantly finding new places where agents can help: demand gen, competitive intel, content production, research, anything else we can think of. I don't have it all figured out, and I'm pretty sure nobody does yet. But leaning in, trying new tools, and adapting to new workflows, has been one of the more interesting parts of this last year (but really only 6 months probably).

Not coincidentally, this story is mirrored in our product narrative itself. The conversation around what Moderne does has credibly shifted to include agents alongside humans, because the same thing that makes our platform useful to a developer turns out to be very useful for agents too. Maybe even moreso. The underlying engine hasn't really changed, but the framing has, and so has the work.

# The people

Reflecting on everything I've mentioned so far, I realize that nearly everything I've made progress on this year has a person attached to it. Someone on the team who knew a thing I didn't and was generous enough to bring me along.

I've learned about social engagement and what actually makes content land. I've gotten a real demand gen education and a better appreciation for how leads drive the business. I've had a manager who's pushed me on personal growth and thinking like a marketer in equal measure. I've gotten sharper on narrative and outbound storytelling from working closely with product and product marketing. I've started to [kind of] understand some SEO stuff and the digital side of marketing in ways I certainly never have before. And then there's all the deeply technical stuff I've learned from engineering and leadership. The list goes on.

But it isn't just learning from colleagues. So much of the most rewarding work this year has been very collaborative: writing and reviewing drafts back and forth with product marketing, building video content with our multimedia manager, pairing with engineers and sales engineers on demos and training, and tightening narratives with product. The work is better for it, and the process is more fun.

This is one of the gifts of joining a small, sharp team. I came in ready to contribute, which I am, but the real benefit is how much I've picked up from the people around me, and how much I can still learn from them. I love this team!

# Gratitude, and the next year

A year in, I'm realizing how lucky I am to have landed somewhere that fits so well at this particular moment. The team is amazing, the product is compelling, and the market keeps handing the company new and bigger reasons to exist. Even better, the work itself lets me bring more of myself to the job than most roles would.

I don't know exactly what this next year looks like, but if this last year is any guide, nobody does. Still, I know what I want to keep working on, and I know I'm in the right place to do it.

See you at next year's Code Remix!


So... What Exactly Is Technical Marketing?

I've found there to be plenty of variance in the industry around job titles, so I usually don't put a ton of weight on them. I've had titles that weren't very descriptive of my actual role. I've had titles that seem to imply something that isn't even true about what I do. I've seen junior-sounding titles for people who seemed pretty senior, and senior-sounding titles for people who acted more junior.

Regardless of the names and levels, I've worked in technology for long enough to have collected several job titles that are difficult to explain at dinner parties or to family members. That's why, when I transitioned from enterprise IT into product management ten years ago, I wrote a post to help answer that dreaded question: “So... what do you do?”

Fast-forward a decade, a few roles, and a handful of technology fads later, and I’ve once again found myself in a job that even people inside tech sometimes struggle to define: technical marketing.

Despite being an important function, particularly for developer-facing products, the role of technical marketing can sometimes be confused with engineering, product, or traditional marketing. That's actually fair, though, because tech marketing does borrow elements from all three.

So how is technical marketing different?

# How Technical Marketing Fits In

Admittedly, the first time I joined a marketing team, I was a bit trepidatious about it, at least initially. Isn't marketing too far removed from the technology itself? Would I ever get to talk to an engineer or even write code again?

I quickly learned that actually, technical marketing isn't so far from product management, or any of the roles I've had in my career really. When I first got a job as a product manager, I described it as a role "in the middle", like the connective tissue between customers, engineering, and the business. Technical marketing lives in that same neighborhood, just a few doors down. While product management decides what to build and why, technical marketing focuses more on why what we built matters, and more importantly, how to show it.

I guess that might sort of sound like marketing more generally. Traditional marketing, or more specifically, product marketing, is indeed (at least partially) about telling the story of why something matters — the value proposition, perhaps you've heard it called. But it's that last piece I mentioned before, the "how to show it" part, that I think is the key distinction. A technical marketer can't just say something, they have to prove how it works and build understanding. If marketing inspires people to want to learn more, technical marketing helps them actually get there.

It's sort of analogous to the sales associate and sales engineer. When a salesperson pitches something in a room full of executives, talking about what it does might be enough. But invite some architects or developers into the room, and you better have a sales engineer there to field the tougher technical questions and show them how it works.

# What About Developer Relations?

Another area I’ve worked in and around is Developer Relations, which I’d describe as at least adjacent to technical marketing. Both disciplines are about building trust with a technical audience, so there’s definitely overlap.

In my experience, Developer Relations is primarily about cultivating a community of practitioners, sparking curiosity, earning credibility, and helping people succeed whether or not they ever become customers. It’s about awareness, trust, and engagement. Technical Marketing, on the other hand, focuses more on enablement and adoption, showing how the product delivers value, differentiates, and solves real problems for customers and partners. It's not a perfect delineation (like I said, there's overlap), but I guess you could say DevRel makes fans and Technical Marketing builds believers.

Truthfully, all of these areas — PM, DevRel, and Tech Marketing — sit along the same bridge between technology, communication, and empathy. But each one might put a little more emphasis on a different area: Product Management on strategy, Developer Relations on community, Technical Marketing on proof and enablement. I’ve been fortunate to work in all three, and each helped sharpen different skills from strategic clarity, to technical depth, and creative communication.

It's why I love these types of roles so much. They let me bring all sides of myself to work: the analytical and the imaginative, the engineer and the storyteller, the tech enthusiast and the theatre kid. It’s where my left brain and right brain finally get equal billing.

# So...What Do You Do?

There are probably several different views on what technical marketing is and how to define it. For me, when I explain my role, I find it’s helpful to break things into two categories (the same ones I used a decade ago when I wrote about product management): what we need to know, and what we actually do.

# What Technical Marketers Need to Know

Unsurprisingly the three key knowledge areas are pretty much the same as I listed for PMs.

To do this job well, we have to know the product as more than just a list of features. We learn it by using it. We dig under the hood to understand how things work, explore the user workflows, and every now and then work through a rough spot to figure out what’s really going on.

We try to stay close to the market too. That means understanding not just who competes with us, but what existing customers and potential users are actually struggling with, what’s changing in their world, and where things are headed next. Context matters as much as capability.

The best technical marketers also pay attention to when something isn’t clicking for customers (and prospects). Whether it shows up during a demo, in a training session, or in the questions we hear out in the market, those moments usually reveal a gap in how we explain the product. That insight shapes what we build next, from clearer docs to new demos and enablement. Which leads nicely into...

# What Technical Marketers Do

To me, the most fun (and challenging) part of technical marketing is crafting a narrative. I'm not talking about inventing spin, though, because credibility is key with a technical audience. I mean we distill the heart of the value and figure out the most compelling way to reveal it. We make technical concepts feel relevant and even exciting.

In my day-to-day, that might look like:

  • presenting a live or recorded demo
  • recording feature walkthroughs
  • building, facilitating, and maybe even delivering training courses
  • writing technical content
  • developing competitive materials to help sales and partners position the product
  • enabling field teams with deeper technical context
  • giving live product demos at tradeshows or events (I was doing this in only my second week on the job!)
  • taking questions, confusion, or objections and turning them into clearer messaging or new content

It's a lot of learning in public, which can sometimes mean pushing through impostor syndrome to ultimately show expertise and prove the narrative.

If you’re curious what this all looks like in practice, here are a few recent examples I had a hand in:

# Why I Love It

Across every role in my career — IT, product, developer relations, and now technical marketing — the theme has been consistent: translate technology into possibility and turn complexity into confidence.

What’s great is that I get to blend analytical precision with creative expression. The architecture diagrams matter, but so does the storytelling arc. The tech and the theatre kid get to show up every day. That combination is where I feel most at home.


Life Finds a Way with OpenRewrite Part 2: Code Evolution

When I last left off, I’d done the unthinkable. I resurrected my college senior project from 2003—the Help Desk Scheduler. It was running again as a Java 8 web app on Tomcat 4 with Struts 1.0 and MySQL. To continue my Jurassic Park metaphor, it was the software equivalent of a creature that shouldn’t exist anymore, but somehow came back to life.

And also because, now that I’m at Moderne, I spend my days thinking about automated code transformation with OpenRewrite. (I'm super fun at parties.) So of course I wanted to see if this ancient app could evolve enough to survive in 2025. I don't need to go full Jurassic World reboot yet, but what if we can tweak things just enough to get to The Lost World at least?

# From Batch Files to Build Tools

In college, my “build system” was literally a batch file that ran javac and copied the results into Tomcat's webapp folder. To modernize anything, I first needed a real foundation. It was time to pick: Gradle or Maven?

I chose Gradle, mainly because I was less familiar with it and wanted to learn, but also because it seems to be a common choice among devs I respect. So, to get things working, I had to:

  • Restructure the directories to use src/main/java and src/main/webapp
  • Set up a build.gradle.kts file (I went with Kotlin over Groovy because I'm a follower)
  • Declare dependencies for the old Servlet API and Struts 1.0 (which required a local JAR since the old version didn't seem to exist on any repository anywhere)
  • Specify Java 8 and configure the war plugin
  • Update my Docker Compose setup to build and deploy a WAR instead
  • Add the OpenRewrite Gradle plugin since there would be recipes in my future

For the first time in two decades, HDS had an actual build pipeline. Now OpenRewrite could start working its magic.

# Automation: Nature’s Next Step

With Gradle in place, I was ready to run some recipes. I wanted to take this from barely runnable on Java 8 to something that could at least sort of live in the modern Java world. I started with UpgradeToJava21, which handled compiler targets and cleaned up a few deprecated APIs.

Next came JakartaEE11, which migrated javax.*packages to jakarta.*. What could possibly go wrong at this point?

Everything. The changes were clean, but it turns out that Struts 1.0 simply wasn’t built for a Jakarta world, and the build logs made that abundantly clear. Huh. What to do?

# Finding a Path Forward

First, I'd need a newer version of Tomcat. I got that up and running manually and figured I could automate it later. (Which I did...see below.)

Then, I considered trying an upgrade to Struts 2, but that honestly looked almost as hard as a full-scale rewrite. Same for moving off of Tomcat altogether to a Spring application. I hope to get there eventually, but this first step was just about some incremental change. I wanted to run Java 21 without too much manual effort, if possible. Could I automate everything with OpenRewrite and make it all work?

Rather than give up, I went hunting for a compatible solution and I stumbled upon Struts1 Reloaded, a modernized fork that aims "to bring Struts 1 to a current technology." This looked like the best route, at least for now. The latest version (1.5.0-RC2) supports more recent Jakarta namespaces. Sweet!

Using OpenRewrite dependency recipes, I swapped out the old framework for the new libraries. That meant replacing the old Servlet API with the new ones, retiring the old com.sun.mail packages in favor of new ones from Eclipse, and replacing the local Struts JAR with all new references to the Struts1 Reloaded libraries.

Still got a bunch of build errors, but far fewer. Getting closer.

# A Little Genetic Engineering

The errors were mostly type and method name changes from moving to Struts 1.5. Thankfully, those trusty old OpenRewrite standards ChangeType and ChangeMethodName came to the rescue for that. Action perform() is now Action execute()? No problem. Oh, ActionError is gone in favor of ActionMessage? Easy. But ActionMessages empty() needs to be ActionMessages isEmpty()? Done. Thanks OpenRewrite!

type: specs.openrewrite.org/v1beta/recipe
name: com.bryanfriedman.hds.MigrateStruts
displayName: Struts 1.1 to 1.5 API adjustments
description: ActionError→ActionMessage, perform→execute, messages.empty()→isEmpty
recipeList:
  - org.openrewrite.java.ChangeMethodName:
      methodPattern: org.apache.struts.action.Action perform(..)
      newMethodName: execute
      matchOverrides: true
  - org.openrewrite.java.ChangeType:
      oldFullyQualifiedTypeName: org.apache.struts.action.ActionError
      newFullyQualifiedTypeName: org.apache.struts.action.ActionMessage
  - org.openrewrite.java.ChangeMethodName:
      methodPattern: org.apache.struts.action.ActionMessages empty()
      newMethodName: isEmpty
      matchOverrides: true

But now, things got a little more complicated. There were two changes that I needed to make and I couldn't find any existing recipes to do the trick. But hey, I said I wanted to learn how to write some custom recipes. This was my chance. So I wrote two imperative recipes to handle these cases:

  1. DataSource access. The old Struts ActionServlet findDataSource() helper no longer worked. They needed to be converted to use standard JNDI lookups.
  2. Method signature. The new Action execute() method in Struts 1.5 added a throws Exception declaration, meaning any overriding methods needed to also.

I had a little bit of help from Claude Code to write these recipes. (I'd had some experience doing that at work.) But still, writing these custom solutions gave me such an appreciation for how elegant and extendable OpenRewrite really is when you need that level of precision. And the test framework is so easy to use, you can see exactly what needed changing in both cases.

One more little ChangeType tweak to broaden some exception handling, and the build finally worked. Too bad the run didn't...

# JSPs, XML, and Other Endangered Species

Now the app was failing to render, so I knew it was time to look to the JSPs. In fact, the Struts 1 Template tags had been retired in favor of Struts Tiles. That meant a whole host of changes to the JSP files would be required.

Although OpenRewrite doesn’t parse JSPs, I was still able to automate into my recipe by using the text-based FindAndReplace recipe to do some regex magic.

And finally, for the XML config files (web.xml, struts-config.xml, and Tomcat 11's server.xml), I used some XML recipes to make the necessary changes, and some Create*File recipes to drop in the new ones.

# It's Alive... Again

After all the dust settled, the project now:

  • Builds cleanly with Gradle
  • Includes a build step within Docker Compose
  • Runs on Java 21 / Tomcat 11
  • Uses Struts 1.5 (Reloaded)

Is it modern? Not really. But it does compile cleanly, deploy reproducibly, and doesn’t require completely ancient toolchains to run. I'm quite proud that (after manually setting up Gradle) I completely automated all of the changes using only OpenRewrite. It was all refactored through deterministic, repeatable automation. No frog DNA required.

# Evolution, Meet Ambition (and Chaos Theory)

There’s a point in every old-code resurrection where you remember Dr. Ian Malcolm again. Just because you can modernize something, doesn’t mean you should.

That said, though, I’m probably not done experimenting. Some next steps I’m considering:

  • Swap MySQL for Postgres. (Probably only config changes?)
  • Skip right over Struts 2 and try a Spring Boot migration, just to see how far automation can carry it.
  • Move off of JSPs to...something else?

Each attempt is both an exercise and a curiosity test: how much of this can be done through recipes rather than rewriting by hand?

Part 1 was the resurrection; this sequel is the evolution. Give it a few more transformations and I'll have my own cinematic universe.