From Sidelines to the Parade: Why I Joined Datadog
I can honestly say that aside from myself, Datadog is the best employer I’ve ever had.
I’ve got an update. I’ve been meaning to write about it but something was holding me back.
So I’m just gonna say it now.
Last August, I started at Datadog. I just hit the 6-month mark.
I am group product manager for observability data platforms. I work with the teams that ingest, index, store, and query all of the observability data that Datadog clients and engineers rely on every day.
For those unfamiliar with the observability space: Datadog is like the dashboard of a car—it tells you what’s going on inside the complex machine. But instead of being a dashboard for a car, Datadog is the dashboard for software programs.
And I can honestly say that aside from myself, Datadog is the best employer I’ve ever had.
What Was Holding Me Back
For eight years, I ran Product Science Group. I built it from nothing to $880K in revenue by 2024, with 117% year-over-year growth. I worked with Fortune 500 companies like Pfizer and Novartis. I coached product leaders at growth-stage startups like GTreasury and FalconX. My podcast hit nearly 100,000 listens. I taught at NYU Stern.
I was proud of what I’d built. I loved the work—helping product leaders develop evidence-based strategies, watching teams I’d coached ship products that users loved, seeing the Product Science Method take root in organizations.
Then 2025 hit.
The first quarter was brutal. The economy was in disarray due to the threats and reversals of tariff plans, as well as the impact of AI on corporate leaders' spending decisions. Corporate budgets froze. Or more accurately, they redirected—everything went to AI, and only AI.
My consulting pipeline dried up. And I had to face the reality that this wasn’t a temporary blip—the market had fundamentally shifted. The only two things selling in tech consulting were: (1) AI-specific expertise, or (2) helping laid-off product managers find jobs.
The Decision I Didn’t Want to Make
I considered both pivots, but neither felt right to me.
I love the craft of product management. I didn’t want to move further away from it by focusing on coaching job-seekers. And I didn’t feel like I knew enough to sell myself as an expert on AI—so I wanted to go in-house to get closer to it.
That’s when I realized: No matter what I think about AI, that parade is marching on. I’d rather help guide the parade than stand on the sidelines.
But to guide it, I needed to be in it.
On April 1, 2025, I started looking for a product leadership job.
Why Datadog
I wanted to get closer to AI—the close you can only get when you work in it day in and day out. But I didn’t want to work at Anthropic or OpenAI. Those seem like hypercompetitive, intense jobs.
I feel like I got as close to that as I can without actually working at one of those companies.
Datadog serves many AI-native companies, both frontier labs and startups building AI products. We deal with big data—my team manages the data pipelines that process trillions of data points daily across hundreds of terabytes. The company has a frontier model, Toto, for time series data. We’ve got AI platform teams to help the company adopt and use and build AI. We’re innovating with AI solutions in our product.
And it’s a great NYC-born public tech company. As a veteran of NYC startups and scale-ups, it felt like a natural next step.
On top of that, the work-life balance is amazing for a company so intense and successful. I can still be present as a single mom. The income and stability that I have, at least for now, is great.
Six Months In
I’m having fun. I’m learning. I got exactly what I wanted, in spades.
The technical scope is exhilarating. It’s the kind of systems thinking I love, but at a scale that pushes my understanding daily.
I get to see how the company processes all that data and how it makes decisions about what practices to follow. I’m leading the PM team for 500 engineers who work on data platforms that power Datadog’s core products. The discipline of evidence-based strategy isn’t theoretical here—it’s essential.
And I am loving it at Datadog. In many ways, I got exactly what I wanted—engaging and interesting challenges, top-notch teams, a flexible culture where I feel supported and happy to be a part of.
Full Circle
Here’s what makes this story feel complete: Product Science Group isn’t gone. It’s evolving.
What I’m learning at Datadog—about AI, about data platforms at scale, about product leadership in the age of LLMs—is already informing what comes next for PSG. My team at PSG is still with me, and we’re developing AI and product management training. We’re getting ready to kick that off in 2026 as one of our offerings.
The expertise I’m building in-house will make me a better teacher when I share it. Sometimes you need to step into the parade to understand how to help others join it.
This wasn’t the path I expected when I started Product Science Group eight years ago. But it’s exactly where I need to be right now—both building product at massive scale AND helping others get here too.
The craft of product management continues. It just looks different than I expected.
And I’m excited about both versions of it.
Let’s march in this parade, together.
Best,
Holly
