I've said for a long time that the first-line manager is the most important and most underinvested person in any organization.
We promote people into the role and then basically leave them to their own devices. There's no real training. No ongoing support. You figure it out as you go, and hope you don't do too much damage along the way.
That's been true for decades. And honestly, we've all just accepted it.
What's changing now is AI. And I mean genuinely changing it — not in a buzzword way. In a real, practical, this-is-going-to-look-different-in-three-years kind of way.
How Rypple came along
A woman who sits on both our HR advisory council and Rypple's introduced me to Ian, one of Rypple's founders. He was looking for some marketplace advice. We started talking, and I got interested fast.
What he built is an AI-native coaching application — built from the ground up with AI at the core, not bolted on afterward. It connects to a manager's calendar, their Slack, their day-to-day work. And then it nudges them in real time. Things like: one of your direct reports hasn't updated a goal in a couple weeks — maybe check in. Or: there were a few things in your last one-on-one that should probably be on the agenda for next time. Want me to add them?
For new managers especially, Rypple lets you actually role-play difficult conversations before you have them. A performance conversation. A PIP. Situations where most managers just wing it, because no one taught them how. Rypple coaches you through it. It tells you what language to use, what to remove, how to approach it.
That's not a training course. That's a manager getting better in the actual flow of their work.
I went from giving advice to thinking, wait — this belongs inside Betterworks.
Why this moment matters
There's a lot of talk right now about the so-called SaaS apocalypse. The idea that traditional SaaS companies are in trouble because AI is going to replace what they do.
I don't fully buy that framing. But I do believe AI is transforming the processes around performance and talent management. And companies that don't move with that are going to struggle.
We're in one of those rare transformation moments — like the early internet. You can't fully predict where it ends up. But you know you can't sit on the sideline.
Betterworks is already well-positioned. Our next-gen platform isn't 25 years old like some of the legacy players we compete with. We can move. And now, with Rypple, we can move even faster — and in a direction that I think is going to matter a lot.
What Betterworks + Rypple makes possible
Betterworks helps HR leaders run effective performance programs across the organization. That's not changing.
But performance doesn't only happen in review cycles. It happens every day, in how managers coach people, give feedback, have hard conversations, and show up for their teams. Rypple helps with exactly that.
Together, we can do two things at once: keep improving the formal processes HR runs, and give managers real support in the day-to-day moments that actually drive performance.
Over time, I want to bring Rypple's capabilities directly into the Betterworks platform — what we're calling Rypple for Business. Voice interactions. Real-time coaching. AI that actually knows what's going on with your team because you've given it access to the right data.
More data, given to AI thoughtfully and securely, means better coaching. Better outcomes. Less bias in the process. I know the data access piece will be a journey — a lot of companies will say no at first, just like they said no to SaaS twenty years ago. But the outcomes are compelling enough that eventually, the yes will come.
Our goal at Betterworks
I want managers to love what we build. Not tolerate it. Love it.
I want a CFO to go to their HR team and say, why do we still pay for this? And I want the managers to put their hands up and say, don't take this away from me. It makes me better at my job and I can't get this anywhere else.
That's what we're building toward.
Rypple is a big step in that direction. I'm genuinely excited — and I think the managers we're building for are going to feel that when they use it.
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