Workforce Operations, Sales Onboarding, and the Data HR Has Been Missing
The E1B2 CollectiveMay 8, 202638m7,104 words
Arielle Kilroy, CEO and co‑founder of Datto, explains how stitching HR systems to business tools creates measurable workforce operations—starting with sales onboarding and preboarding in high‑compliance roles.
Summary
Arielle Kilroy traces a path from music and direct‑to‑fan experiments to building Datto, an employee experience management platform that automates people processes across existing tools. She argues HR lacks the behavioral data to show impact and says Datto connects HRIS, Atlassian/JIRA, learning tools and revenue systems so teams can measure where onboarding breaks. The episode focuses on sales onboarding as a high‑leverage use case—faster ramp, earlier signal on poor hires—and touches on preboarding in healthcare and the practical benefits Arielle found living in Berlin ("going to the doctor and having no bills").
Key takeaways
- — Datto is an "employee experience management platform" that automates complex people processes across the tools companies already use.
- — Arielle Kilroy is Datto's CEO and co‑founder; she previously worked in entertainment (digital strategy/design) on campaigns for Michael Jackson, J Lo, Okay Go and Amanda Palmer and helped pioneer direct‑to‑fan monetation
- — Companies typically outgrow all‑in‑one HRIS between ~150 and 250 employees, then accumulate point solutions and business tools that create noise and lack measurement
- — Datto integrates HR tools with business tooling (examples named: Atlassian/JIRA, Trello, learning tools and revenue systems) to track tasks and statuses automatically across platforms
- — Quote: "We're not that different from like a Salesforce, but for an internal audience," — framing Datto as a CRM for employee journeys
- — Measurable outcomes matter: moving a new rep to close their first deal five days faster or identifying poor hires within 90 days yields substantial financial upside and lower churn
- — Research point: organizations measure customer behavioral data but typically lack equivalent quantitative measurement for employee behavior and onboarding success metrics; that gap prevents funding and scaling people ops
Transcript
Speaker 1 · 0:00All right, Arielle. I truly appreciate you being on this podcast and having this conversation today. Now, you know, and I know this has been a long time coming. The audience is probably used to hearing this because this is probably the same theme for everything. My life is crazy.
Speaker 1 · 0:15My my schedule is insane. You actually just gave me some advice about that offline, but, but I am very excited to have you on this podcast today. Your, your product, the tool, frankly, the way that you just think about this space is very consistent with, my thoughts, my perspectives, my values. I'm honored, I'm blessed, and, I'm very appreciative. So please tell the audience who you are, little bit about the brand, where you come from, how you're thinking about the world today, anything you want to add.
Speaker 1 · 0:44Then we'll, we'll jump into the episode.
Speaker 2 · 0:46Yeah, absolutely. So I'm Arielle Kilroy. I'm the CEO and one of the co founders over here at Datto. We are an employee experience management platform. We allow you to automate every type of people process, no matter how complex across a diverse set of tools that you're already using.
Speaker 2 · 1:04And I am, my background is actually I'm a former chief product officer. So I come from that product perspective. And before I worked with HR tech, I actually worked pretty heavily in entertainment, working with rockstars. And then I kind of went traditional tech and came over, fell in love with like the HR space a lot. And it's always an interesting journey to have gone from rockstars to HR.
Speaker 2 · 1:27So I bring, I'll say new perspectives and fresh eyes to the problem space.
Speaker 1 · 1:33That's exactly what I felt when I first met you. I could tell that you were, looking at the world a little bit differently. I think we both have a little bit more of a, how do I want to describe this? Like an authentic, raw feel and take on this space. Actually, I shouldn't speak on your behalf, but I try not to be super polished.
Speaker 1 · 1:57I just want to be honest and raw and not true with my perspectives. I always felt that way when I spoke with you. So I guess let's start here. Take us back to your music days because everyone that knows me knows in some version of a world, at some point, I will get into scoring and creating films. And I always wanted to be like an A and R.
Speaker 1 · 2:16I've been obsessed with like the Dame Dashes and the Rockefellas. Like, I've just always loved the independent music, get it out the mud kind of mentality coupled with just music and design and like putting together the packaging of an artist. So I don't know. I'm obsessed. Tell me about that, that part of your life.
Speaker 2 · 2:36Yeah. So, you know, when I was younger, I really felt like, and I still think there are spaces for it, that music changes the world. And so I really wanted to be part of, helping, helping bring around my generation's change and I thought that music would be one of the best working music would be one of the best ways to do that. I do, you know, enjoy playing music. I'm not very good at it.
Speaker 2 · 3:02I've never been very good at it and that's totally fine. I'm also a bad dancer and I still dance.
Speaker 1 · 3:08I love it.
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