In this vlog, Matt Ragland walks through ConvertKit’s “brute force onboarding” system – a highly manual, personalized approach to welcoming new users. Each morning he pulls a list of all new sign‑ups from the previous day, classifies them by perceived quality (high, medium, unknown), and uses a custom BuiltWith script (created by manager Matt Newbill) to auto‑populate each account’s tech stack (e.g., WordPress, MailChimp). With this data he records a short, individualized video using Bonjoro, embedding the user’s name and specific migration instructions (e.g., how to move from MailChimp to ConvertKit). He sends the video via email, creating a human connection that many new customers describe as the best onboarding experience they’ve ever had. The process is time‑intensive – roughly 2‑3 hours per day for up to 90 new sign‑ups – but the automation saves about two hours daily compared to manual research. Matt discusses the emotional payoff (positive customer emails, personal satisfaction), the logistical challenges of scaling, and his participation in a ConvertKit product stand‑up to align onboarding insights with upcoming feature development. Personal anecdotes (dropping his child at daycare, walking 4 miles) provide context but the core focus remains on the workflow, tools, outcomes, and future considerations.
Chapters
Today I'm trying something we're calling brute force onboarding. So that might sound a little intense, and it is, and it's very— it's a manual, very time-consuming process. So what is it? What are we doing? What's going to be happening is that I pull a list in the morning— already done this— of every single new account that signed up to ConvertKit. Yesterday. And then I quickly sort through each account and make an estimation on which ones are high quality, which ones are kind of medium quality, and which we're not really sure how much information we have about them. What I do with that is now I have some really high quality data to customize their onboarding. And so I can send them an email that says, hey, I noticed that you were using WordPress and MailChimp. Here's how you would make that transition to ConvertKit. Late start to the morning for little man here. Get up and out to daycare. We haven't been feeling too great this week. Been a lot of this, which honestly I don't really mind. Just dropped Kanan off at daycare. Headed to Wired Coffee Bar. In Goodall, Tennessee, which is just the next kind of town over, and got a lot, a lot of good work to do today. Gonna stay in with this brute force onboarding, and I'll give you a little bit closer look at what that entails, but for now, seat belts. As you saw, I just had a great call with a customer, and I really enjoy doing those, like the vast majority, because I get a lot of excitement just seeing like the light bulb go off for people. And so that was a lot of fun. To be able to chat with her. Now, going to be spending— I have a meeting in 30 minutes with Newbill, our customer success manager, and I'm going to be going— we're going to be going through onboarding, and then really that's the rest of the day. So I'm going to be showing you a little bit more about that, just the brute force onboarding. Excited about that and already paying off dividends. It's just figuring out how, how to best scale that process going forward. It's really interesting because I'm out here, I'm at the outer garden of the Chattanooga Choo Choo Hotel. It's right there behind me. Really fantastic to directly connect with people through video when they sign up for something. In a world that, like it or not, it's becoming more and more digitized and more and more automated, breaking through that to deliver something really specific— there's no way to automate right now saying someone's name. I can put in merge fields so that I can type your name in, but we haven't automated saying someone's name. And that's, that's what we get to do. That's what I get to do every single day. Morning. So a little bit of a kind of a record scratch on what I was talking about at the beginning of the video. Very talented manager Matt Newbill wrote a program with BuiltWith, that extension that you saw in the top right of the browser, so that it pulls the majority of the data for me. So whereas I was spending a couple hours a day going through the different websites, I'm still going through a lot of them, but the majority of the data is already there. It saves me like 2 hours a day., which is awesome, especially on a day like yesterday where we had 90, 89 new signups. Saves a ton of time. Also getting ready to hop on our first or second ever ConvertKit product standup. Mostly just gonna be there to listen and to learn and get more experience and understanding of just our product, the road mapping process, how Nathan and Dylan are gonna be talking through some of the new features that we're rolling out and put all those things together cuz it's all stuff that I want to know more about, not just from a ConvertKit standpoint, but from a bigger picture of like, what do we do with the product and how do we continue to develop it over time? Okay, so after I have all of that data kind of mapped out, I know what platform they were using, I know which email provider they were using before ConvertKit, I'm able to grab it. So what do I do next? I do a video. All right, so I use a tool called Bonjoro, and I'll link to it in the description below if you want to try it out. But what I'm able to do with Bonjoro is send them a video in their email and connect with them personally, individually, and I can say, hey, my name is Matt, welcome to ConvertKit, really glad that you're here. And I also get to say, I noticed that you're using MailChimp, I noticed that you were using WordPress before, so let me tell you how to make that change. And just being able to give them that specific feedback The comments that I've gotten from people are just like, this is the best thing that I've ever seen in terms of signing up for a new product. So 100% worth the time. Okay, so what are we talking about in terms of time? Because you may be thinking to yourself, this sounds like it takes a lot of time. It does. It's the biggest chunk of my day right now. Armed with this information, this really valuable, helpful information for them, I use their name and say, hey, my name is Matt. Really happy that you've signed up for ConvertKit. I noticed that you were using WordPress and MailChimp, so be on the lookout for an email from me that is gonna show you how to make that transition a lot smoother and show you how to move all your subscribers, all your lists from MailChimp over to ConvertKit. As you can imagine, paying attention to this level of detail and giving new customers this type of information specifically tailored to their account is a really great thing. I've gotten some of the best, most encouraging, most celebratory emails I've ever gotten. This is the best experience I've ever had signing up for a new service. And when you can deliver that, you can deliver that, making that connection— you know, people are wired to connect with other people. This is really what we're driving at, what we're trying to build into the early process of ConvertKit, is making that connection person to person. A little bit more context on the videos. Just finished up about 50 of them. Took me a couple hours and I walked 4 miles, so that's pretty standard. A little bit of fit. It's a beautiful day. Probably have a little red on my neck, which, you know, I'm in Tennessee, fit right in. That's— it's been a good long day. Lots of videos. Lots of emails, but a lot of good work. Really like what we're doing, and it feels really good to be taking this specific of an action. Looking forward to sharing more of this with you, and if you have any questions about this or anything that you're curious about, please make sure that you subscribe to this channel. It's where I'm putting most of my work this year. If you have any specific questions, go ahead and drop them into the comments. Looking forward to chatting with you. Take care, see you next week. Bye.
