Onboarding Orah: What's Changed, What We Built, and Why It Matters

For those of you I haven't had the privilege of meeting yet, I'm Grant. I joined Orah as Head of Customer Success in September 2025, and I've been meaning to write something like this for a while. Onboarding is a word I think about a lot. It's the lens through which every new school first experiences Orah, and it was the lens through which I experienced this company too. With the 2026/27 onboarding season on the horizon, it felt like the right moment to reflect on where we've been and share where we're going. This is an honest conversation about who I am, what I found when I arrived, and what we've been building since.

From Startup to Scale-Up: Round 2

I spent nearly twenty years building Beanfield, a scrappy telecom startup, where I joined when there was just a handful of us. There were no playbooks, no formal departments, no clear job descriptions. You just did what needed doing. I wore more hats than I can count across customer experience, sales operations, people and culture, process design, and eventually leadership. Over time, that handful of people became hundreds, and Beanfield grew into a major national telecom.

That kind of journey stays with you. You develop a deep instinct for what breaks when a company grows faster than its systems can keep up, and how much that cost is felt by the people on the other end of the experience. I came away from those years with a firm belief: customer experience isn't a department. It's a reflection of how much a company actually cares.

When I came across Orah, something clicked. Schools come to Orah to answer one critical question: "where are our students?" Emergency rollcalls, leave management, attendance, family communication, in real time, when it counts. That's not routine software usage. That's a team of people trusting a platform to help them look after kids. I wanted to be part of building something worthy of that trust.

I joined during a heavy season: significant growth, real pressure, and some honest friction that needed to be addressed rather than explained away.

Re-Engineering Our Onboarding Process

I'm not going to walk you through a list of things that were already fine. What I will tell you is what we've changed, because some schools had rough experiences getting started with Orah, and ignoring that would be dishonest.

The patterns I found when I arrived were consistent: onboarding plans that were too generic, training that focused on the software rather than the school's actual workflow, and post-launch support that waited for schools to raise their hand instead of proactively checking in. Those are solvable problems. Here's what we've built:

ONBOARDING RESOURCES BUILT AROUND YOUR WORKFLOW

We built purpose-built onboarding documentation from the ground up. Not a general help library, but structured getting-started paths designed around how your school actually operates. Those are live now, and they're genuinely good.

Each guide walks you through setup, configuration, go-live preparation, and first-week best practices in the right order, for your specific use case. They include both written step-by-step articles and video walkthroughs, so whether your team learns by reading or by watching, there's a format that works. If you're setting up boarding operations, the boarding guide reflects that workflow. If you're implementing class attendance with a Blackbaud, FACTS or Veracross integration, there's a dedicated path for that too.

TRAINING BUILT AROUND YOUR WORKFLOW, NOT OUR PRODUCT

We overhauled how we run training sessions. The old approach leaned too heavily on feature walkthroughs. The new approach starts with the school's workflow: who does what, in what sequence, under what conditions. We map Orah onto that. Role-specific sessions. Real scenarios. What happens when a student doesn't return on time. How leave requests flow. Who gets notified and when.

The goal is confidence, not just familiarity. Your staff need to be able to act in Orah without second-guessing themselves. That only comes from training that mirrors how your school actually runs.

POST-LAUNCH SUPPORT THAT DOESN'T WAIT FOR YOU TO RAISE YOUR HAND

Launch day is a milestone, not a finish line. Real adoption, the kind that becomes second nature across every role and shift, happens in the weeks that follow. We've built structured check-ins into that window, and we use early signals to get ahead of any gaps before they compound. If something isn't landing, we want to know in week two, not week eight.

AI Support That's Actually Good: Meet Fin

Fin is Orah's brain on demand.

Fin is our AI support agent, and it's genuinely useful. You can ask it anything: setup questions, workflow questions, integration questions, "why is this happening" questions. In most cases it will give you a clear, accurate answer immediately.

• Instant answers, 24/7. Fin draws on the entire Orah knowledge base. Most questions get resolved on the spot, without waiting for a human to respond.
• When Fin can't solve it, a real person can. If your question falls outside what Fin can handle, it routes directly to our support team. No dead ends.
• It gets smarter every week. Every conversation Fin can't fully resolve gets reviewed by our support team. We use those gaps to build out Fin's intelligence further, so the more schools use it, the more capable it becomes.

Fin is available directly through the help icon on any page in Orah, or at success.orah.com.

What's Coming: 2026 Onboarding and the Future

We're building something meaningful here, and we're doing a lot of it in real time. The work isn't finished. It won't be for a while. The direction is clear. Here's what I'm focused on:

Staying close to what's actually happening in your schools. The best intelligence we have doesn't come from dashboards. It comes from conversations. We're investing more in proactive outreach, listening loops, and making sure that when something isn't working for a school, we hear about it early enough to actually do something about it.

Getting in the room with you. Within weeks of joining Orah, I packed my bags and did a tour across the United States with our team, east coast to west coast, hosting workshops, meeting our schools face to face, and listening. Not pitching. Listening. And what we heard shaped a lot of what we've built since.

The value of being in the room, having real conversations, understanding the pressures your teams are actually operating under, is something you can't replicate on a Google meeting. That's the direction we're heading as a company: getting our designers, engineers, and customer success team directly in front of you. We have workshops planned across the US for the new school year — Q3/Q4 2026 — and we'll be sharing dates and locations soon. More of that is coming.

We're Here, Any Time

Our support team is available to you at all hours. If something isn't working, if you're mid-implementation and hit a wall, if you have a question before a big go-live day: reach out. That's what we're here for.

Start with Fin at success.orah.com. It resolves most things instantly. If it doesn't, you'll be talking to a human being on our team within the hour during business hours, and we monitor critical issues around the clock.

And if you want to talk to me directly about your experience, good or bad, I mean that genuinely. I'm always available on my email grant[@]orah.com