How to Run a Successful Launch Week

[00:00:00] Zack Katz: What if your product launch wasn't a single moment, but a full week of momentum? Most teams pour everything into one big release day, and then watch the inbox go quiet afterward. What happens when you flip that? Five releases, five emails, five days of attention instead of one. Today, on WP Product Talk, we are breaking down how to run a launch week that drives attention and keeps it.

[00:00:28] This is WP Product Talk.

[00:00:32] Matt Cromwell: This is WP Product Talk, the place where every week, we bring you insights, product marketing, business management and growth, customer experience, product development, and more. It's your go-to podcast for WordPress product owners by WordPress product owners. And now, enjoy the show.

[00:01:01] Zack Katz: Hello, hello. I'm Zack Katz with Gravity Kit.

[00:01:04] Katie Keith: And I'm Katie Keith from Barn2.

[00:01:07] Zack Katz: And before we get started, uh, if you benefit at all from WP Product Talk, we'd love your support. The easiest way to show your support for the show is to hit subscribe right now in YouTube. It only takes a second and makes a big difference to the show.

[00:01:19] Thank you so much.

[00:01:21] Katie Keith: And huge thanks to Freemius for being our exclusive growth partner. Freemius helps software makers to grow, monetize, and succeed. They are a merchant of record platform, which basically means that they handle everything around selling software, from checkout, payment, subscriptions, to licensing and updates, and even global tax compliance, so you can focus on building amazing products.

[00:01:46] Zack Katz: All right. So let's jump into today's topic, launch weeks. Uh, so I was watching my inbox last week, and I saw every day an email coming in from DocsBot talking about a really cool new feature, and it was r- impressive to see. Every day I was thinking about DocsBot. Every day I was impressed. Every day I was like, "Oh, I think they've got stuff going on over at DocsBot."

[00:02:11] And it made me feel like there was so much momentum. And behind those emails is Josh Dailey. Josh, welcome to the show. Uh Oh, one more.

[00:02:25] Katie Keith: Briefly.

[00:02:28] Zack Katz: Josh, hi. Thanks for joining us. Hey. Please tell us, uh, tell us about yourself.

[00:02:32] Joshua Dailey: Thank you, Zack and Katie, both just absolute legends. I'm so excited to be on here with you today.

[00:02:39] But yeah, I'm, um, the chief growth officer for DocsBot, where I'm leading the go-to-market strategy. Uh, before this timeframe, I helped launch and grow a variety of WordPress products, including Infinite Uploads, that's since been acquired. Um, we grew, uh, Smush, uh, to over a million active users. I was involved with that product, um, when they originally had acquired and launched that, or relaunched that.

[00:03:10] And then, um, my last role was at WP Engine. I was, uh, over the, um, e-commerce solution, helping to grow and scale that product. It became the fastest growing segment of the business. And then today, obviously, I'm focused on applying the same growth systems and marketing str- uh, processes, strategies to agentic workflows with a much smaller team now.

[00:03:38] So it's been a really fun and exciting kind of time, uh, in marketing.

[00:03:46] Zack Katz: Very cool, uh, story, and you've worked on, uh, some great products. Um, for-

[00:03:52] Joshua Dailey: Thanks ...

[00:03:53] Zack Katz: for those of you who are, uh, watching live on YouTube, we encourage you to leave your comments or questions or feedback in the comments section. We'll highlight them as the show goes on, and we'll discuss your questions on the show.

[00:04:05] Um, so Josh, I'd love to dive into what you just accomplished with DocsBot with your launch week, um, what your thought process was like. Uh, I'd love to learn more about the history of launch weeks at DocsBot. Is this a new thing? Is this something you did before? Like, uh, pl- you know, can you g- set the scene for what, what, what you were thinking, uh, over the launch week?

[00:04:29] Joshua Dailey: Yeah. You guys have had Aaron on here before. He's our founder, um, and he was a solo founder for a long time and was, uh, you know, having to kind of do all these things on his own and spent a couple years actually doing that. And in 2025, he did the first DocsBot week, so that was a- about a year ago now that he did his first DocsBot week.

[00:04:55] And it was really, at that time, a forcing function for him to complete some tasks that were at, like, 90% of the way there, you know? And when you're trying to roll out things alone as a, a solopreneur, a lot of times it's really hard to know, do I jump on this support ticket? Do I take this sales call? Do I, um, build this f- this feature, or how do I market it and make sure?

[00:05:20] So all of these things kind of compound. Um, and so he was like: "I'm gonna just take a step back for a second. I'm gonna keep doing the r- run the business efforts on the side here, but I'm gonna put a bunch of effort for a month or two into, um, creating a strategy and plan and then rolling out everything at once."

[00:05:41] One, it gets compounding interest from the customers and, and as you had mentioned, it kind of helps, uh, keep you in people's face day after day after day for a little bit, which we all know, like, you send that one email and you're like, "This is gonna be the greatest thing ever," and then crickets, you know?

[00:06:00] It's very, very frustrating when you're kind of working on that stuff. So DocsBot week was kind of an idea inspired by some stuff he had seen around Cloudflare. They had, like, even recently, they did another, uh, week of launches around AI features. And so for us, that's kind of the, the idea behind it was this forcing function.

[00:06:24] For us this year, though, why I wanted to kind of continue that legacy forward was because in marketing, there's been an experience where things have been flipped on their head that we don't really understand how to approach right now. Where development used to be the bottleneck, marketing is the new bottleneck, um, because things are being developed so quickly, features are being launched so fast that, um, trying to communicate the message and why you're doing what you're doing, the strategy, why you're doing what you're doing, the narrative, keeping that, um, up to date and in front of even just your customers, forget trying to get in new customers, but just trying to keep all the stuff that you're, you're delivering and the value that it can add, and people are still stuck on, let's say for DocsBot, it's like- AI that gives answers and creates a checklist that now, um, you still are having to function to, to go do, to these agents that can actually perform tasks for your users at the end of the day.

[00:07:32] Like, that's a, a huge pivot in market. And so how do you make sure that your customers are getting the full value out of what you're, you're, um, working on and delivering? So that's kind of a little bit of the, the story about, um, where that came from.

[00:07:50] Zack Katz: Yeah. Like, I was... Josh and I, when we were talking yesterday in preparation for today, uh, I was saying that one of the only times that I have emails coming into my inbox from e-commerce is, like, the outside world.

[00:08:05] Uh, outside of WordPress, uh, I, my favorite socks are Bombas, and I go to bombas.com and I buy some socks. And then every single day after that, I get an email from Bombas, daily email about socks, about the other things that they sell. Uh, every week there's, like, a new sale on a sock bundle that hadn't existed before.

[00:08:26] I- until you unsubscribe, you get unlimited number of emails about socks. And yet we have hundreds or thousands of features that our customers don't know about that we have- I'm sorry,

[00:08:37] Katie Keith: how many socks do you have?

[00:08:39] Zack Katz: Do you have

[00:08:41] Katie Keith: more socks or domain names?

[00:08:43] Zack Katz: Ooh, more socks.

[00:08:45] Katie Keith: Ooh. At least they're cheap.

[00:08:47] Zack Katz: That's a good question, though.

[00:08:50] Um, and- Bombas are

[00:08:52] Joshua Dailey: premium socks, though. I mean, you should get sponsored- Okay ... by Bombas.

[00:08:56] Zack Katz: We should get sponsored by Bombas. Yeah. And Aaron, uh, from DocsBot says, "Love Bombas." Yep, I agree. So Bombas, if you're, if you're, if you're listening, uh, Freemius does global tax compliance, and Bombas covers your feet.

[00:09:12] Joshua Dailey: Yeah.

[00:09:13] Katie Keith: Um- Our exclusive sock partner.

[00:09:16] Joshua Dailey: Absolutely. Yeah.

[00:09:18] Zack Katz: So-

[00:09:18] Joshua Dailey: I- ... the,

[00:09:19] Zack Katz: the, the lack, the, the reticence that we feel as, uh, e-commerce providers is, I think, unwarranted. I think we could send way more emails. I think people like to know about the features that they, uh, that they're missing. And having a launch week is a great way, uh, to consolidate, like, all the things that you may have already launched.

[00:09:41] Josh, uh, did you include anything that you might have already launched in launch week?

[00:09:47] Katie Keith: Ooh.

[00:09:48] Joshua Dailey: Yeah, for sure. So, um, one of the things that was interesting is we had kind of already rolled out some things that were, uh, action-based. And since our campaign was all around AI that acts was, was the narrative and the message we were, we were going out with.

[00:10:06] And, uh- Lead capture was one of those tools that we were saying, "Hey, this is really the first iteration of what it looks like for us." It's this pre-sales kind of function where the, the bot can, uh, understand when the user is, um, is warm and ready to, to, uh, kind of talk- take that next step with your team, get on a sales call, that kind of thing.

[00:10:35] And so we had this lead capture function that we had released earlier in the quarter, and we rolled that forward to day one. Um, partly because the event, the way that we had structured it was to stack on top of itself. So we had different features, but these features, like lead capture, were just to communicate a bigger story around skills and, and actions.

[00:11:01] Um, and we can get more into that. But yeah, so, so I don't think it's ... It's funny because, uh, y- like you were just talking about in terms of emails and, and how we don't do enough of them, it's like we are the loudest voice in our own heads all the time. There's so many other things going on. We've sponsored Web Agency Summit same week as DocsBot Week.

[00:11:25] And, and a bunch of, of people that, that we know and love and support are a part of that. And so we don't even think that DocsBot Week probably, uh, was overshadowed by some of these other events at different, at different points, and more power to it. But really this is a compounding, like, um, uh, content engine for us to say, "Here's a whole bunch of stuff that we put together," blog posts, video content, um, social content that will be cut up, re-shared, reused in different ways, and a lot of messaging that still has to go forward for us.

[00:12:09] And so our biggest, uh, KPI in this or, you know, key performance indicator for us was more about the content that we created and how much of that we could produce rather than how many sales we left the week with, because we know that there's still a lot of education to take place around actions and getting people involved, and we have some ideas rolling forward that were a part of our, our, uh, board to get that done.

[00:12:40] Katie Keith: Yeah. Now, what do you think are the benefits of doing it in a concentrated way like that rather than drip-feeding new features over a longer period, like every month, for example?

[00:12:53] Joshua Dailey: Mm-hmm. Well, hopefully we continue dripping content, you know, o- over the months as well, and that stays a part of the rhythm of what we're doing.

[00:13:03] But, um, one of the big benefits from a, um- In, in AI, I think there's a, a, uh, a tension that we're all experiencing is the education piece. I think we get in our heads an old paradigm, which is that, uh, that things work a certain way based off of the internet that we knew. For DocsBot in particular, there's this whole other world of, of development and things taking place that require a ton of education and getting people to think outside of the box of what they're, they've been confined to.

[00:13:46] And sitting with you guys might be actually like this is an unfair room where we feel like we're behind, but we're actually probably way at the front of-- forefront of all of the, of this conversation, and you're sitting with people who know what they're doing technically and are experimenting and exploring this stuff.

[00:14:07] But the majority of small businesses and other products like are still just dabbling probably in the LLM side of things and, and like your ChatGPTs and, and just getting some help writing a blog post maybe or that kind of, that kind of use case. But that leap to actions, we said the reason this is gonna be critical for us is because trying to understand on day four we released, um, skills and a skill builder, uh, that codes a-actions into your agent, uh, like bespoke and you just tell it what to build and it builds that, right?

[00:14:50] That kind of thought in the SaaS world is just insane. Like, we were always confined to the opinionated choices of the business that we were doing business with. Like you-- if you give me a Stripe integration for my billing, then I use the Stripe integration, and if I wanna use something else, I either have to ask you to develop that and wait for that to be developed or I, uh, move to a different provider that's chosen PayPal or, or what are these other ones.

[00:15:24] For us to release lead capture, Stripe Calendly, TidyCal, like these different actions were more to, as a education piece of saying, "This is actually what's possible. This is not what you're confined and constrained to." So now you can go build any skill that you want to, but these are good examples of what skills would look like if you were to go out and to do that.

[00:15:49] And so for us this year, it was more a part of the necessity of the narrative and building up the, the storyline to get to why actions matter, why skill building matters, why these things are a paradigm shift for us, and how do we get people thinking out of the old way of thinking about, about your SaaS and into a new way of saying, "I can pretty much have whatever I need in order to integrate with and, and I don't have to wait for you to do that."

[00:16:24] Zack Katz: That's, uh, you know, one of the things about having a campaign, a daily campaign. Y- steering a, a boat of how people think about your company is an interesting way of thinking about, uh, a launch week. It's like you're not launching a product so much as you're laun- relaunching how people are s- are seeing your company, and that's a, that's a really, uh...

[00:16:48] Like shifting that thought does take concerted effort and c- and a, a dedicated campaign. So you- Think,

[00:16:56] Joshua Dailey: think about this, Zack, like this piece of it for you. I know we've said, you know, we, we were kind of talking about this. We said, "Hey, we haven't, you know, we don't have experience in, in this." But think about it as creating an onboarding flow for new features.

[00:17:13] Like you've both created great onboarding flows, I'm sure, that have a trigger of emails every day or every couple days that kind of compound into telling a narrative and helping somebody go from point A to point B to make sure that adoption is good and churn doesn't happen and all of those things.

[00:17:32] And that really is what a week is, is just a, a condensed kind of like onboarding flow, and that's why it takes so much effort and work ahead because we all think very strategically about that onboarding flow. I don't... I, I think ours took three months to create, um, when we were working on it and going back and forth about what needs to be in the onboarding flow, how much, you know, of a case study, and how much of, you know, um, the actual features and value do we show and all these things, and you kind of go back and forth on these things.

[00:18:07] That's a really good like image of what the way that I was thinking about kind of the DocsBot week idea.

[00:18:15] Zack Katz: Mm-hmm.

[00:18:16] Katie Keith: Yeah. So you mentioned, like, skills a minute ago. Is everything you released during that week part of your product? The reason I ask is that when I announced this episode on Twitter yesterday, somebody responded with a really good comment, which is that DocsBot is a SaaS, and so whenever you release something, the user doesn't necessarily need to do something.

[00:18:41] Whereas with a WordPress plugin, it would actually be quite annoying for your users if you did a release every day for five days. That's not best practice. So I suppose we could do it in a more of a marketing sense, like we may do one big release and then drip feed the news about what's in that release potentially.

[00:19:01] That would fit with what you were just saying about the onboarding angle. But I'm curious to know about the technical stuff. Did you actually release a new feature in the plugin, or was it something else like you mentioned when we met at PressConf that you do a lot of free tools that aren't part of DocsBot, they're just useful things?

[00:19:20] Joshua Dailey: Yeah. Actually, this... So last year there were a lot of free tools that were a part of DocsBot week in 2025. This year, um, all of the features were released ahead, so they were all in the, the, um, dashboard by the time that we were pushing the emails out. Right. And they may have been out a month or two weeks or a week ahead when the launch actually took place.

[00:19:49] And so the, they've been sitting in the dashboard. We just may not have done the same kind of like notifications or release schedule that we normally do, um, around that. But because these all fit together so well, it wasn't as, as difficult for us, uh, to, um... 'Cause they were all things that you have to activate and choose to action on, uh, which would be different than what you're talking about.

[00:20:18] If something in a, in a SaaS software, it was a force function for, for the, the user where it's like, now you have this and it's running already. That would be scary. But these are, are more around like we can't predict what if you're gonna use a Stripe integration to help with billing or a calendar integration.

[00:20:39] And I, I feel like I'm kind of talking way up here for a second, um, uh, because we haven't really got into what we covered too much. Um, but they were... These actions are like if a customer comes in and says, "I wanna see my invoicing Uh, the invoice can populate right inside the chat window. It doesn't make you click away or look at something else.

[00:21:05] There's these beautiful cards. Or it says, "I wanna cancel my account," you could actually trigger a retention play beforehand and then allow the bot, if they meet all the criteria and policies, to go perform the cancellation. Um, and so these kinds of things are things that if we just, um, um, make them available, they're not just gonna be running by default for the user.

[00:21:33] Zack Katz: Well, and even if you do make them available and people log into DocsBot, they might not be looking for them. Uh, Aaron has a comment that says, "Good point, but it's amazing how slow adoption of new features is with current customers." And-

[00:21:46] Joshua Dailey: Yeah ...

[00:21:46] Zack Katz: you know, the overlap of launch week with onboarding is a really interesting one, uh, where, um...

[00:21:52] And I also think, like, the hype engine of a launch week is an interesting concept as well. Uh, Gravity Kit, uh, we're about to release Gravity View 3.0, uh, we've been working on it a while. Um, it's largely a refactor, uh, behind the scenes, but there are some new features. Every week we launch new functionality to, uh, our products, and every week they're kind of in- included in our newsletter, and people might see them in the change logs.

[00:22:20] We put a lot of effort into those things. We have a, a, a blog roundup every week saying when... What we've done that's new. But we don't email people, uh, regularly saying, "Hey, check out this specific new feature that you're gonna love," even though there are many new features that people might be wanting to have an email about and learn about and highlight and say, "Hey, here's what's coming.

[00:22:43] Get excited. And then once you launch, here's what's out. Here's how to enable it." Like, the hype and then the onboarding are kind of two parts of the same spectrum of just, like, getting people informed about what you are offering and then, um, or excited about what you're offering. L- let them, like, have them thinking about it and then having them actually implement them with your tools.

[00:23:05] So I, I love the idea of just, like, reframing how we... Well, how I- I, I'm a software developer. I think about, like, building new features and then I just, like, hand it off to marketing and, and assume that everything's gonna work. But, like, reframing the whole concept of what we're doing as it doesn't matter what we launch if people don't know about it and people don't activate it.

[00:23:29] Joshua Dailey: Yeah. Yeah. And w- we've felt that, I think, on the marketing side of that, to your point. As development's picked up pace-

[00:23:38] Zack Katz: Mm-hmm ...

[00:23:38] Joshua Dailey: we've felt like, man, our... We care about the whole life cycle, and adoption's really important for people not to churn and, and for them to find value in the product. And we're struggling to, um, spend enough time on one thing before the next thing comes out in order to get Get that kind of acknowledgement And it's hard

[00:23:58] Zack Katz: not to move on, 'cause you, so you release a new produ- a, a new feature, and it's a really cool feature and customers love it, but you have another feature coming up.

[00:24:06] Well, guess what? You've gotta keep on promoting the other features as well. Yeah. They might not know about that in a week from now if you don't tell them about it again and again. And that's where, like, the, I think it's Jeff Bezos, it's, uh, talks about, like, day one and, like, every day is launch day. And so you, you, you...

[00:24:26] it's a mindset that says, like, "Okay, we gotta keep on promoting what we've got. We gotta keep on building as if, like..." There's a whole thing with day one. I don't know if this is the a- actual reference that I'm meaning to give, but always promoting, always acting as if you're, you're launching your product today, uh, is a good way to do it.

[00:24:45] Um- Right ... Ian, our co-host, says, "Still thinking about Bombas socks, to be honest."

[00:24:50] Katie Keith: You've just distracted everything now.

[00:24:53] Zack Katz: His feet are cold and clammy. He needs, you know, you know, some performance fabric.

[00:24:58] Joshua Dailey: That's right. We all need some performance fabric today. Can't say

[00:25:02] Katie Keith: I've studied Ian's feet.

[00:25:05] Zack Katz: No. No. He probably wears sandals.

[00:25:08] He's a relaxed guy.

[00:25:11] Joshua Dailey: Uh,

[00:25:12] Zack Katz: and Aaron also s- This

[00:25:13] Joshua Dailey: is, this is the outtake I want you to publish.

[00:25:17] Zack Katz: Aaron says, "Building is easier than marketing now with AI." That is so true, and one of the things that we're working on is integrating marketing more with AI, and h- trying to figure it out in a way that doesn't feel artificial and doesn't feel AI generated and still feels human.

[00:25:34] But, like, AI kinda queues up onboarding flows for specific people. Ideally, for example, if we know that this customer uses a Stripe integration, Josh, like, if we know that a customer already uses Stripe, then we push that a little harder if we have a Stripe feature. Yeah. That type of segmentation becomes more important when we are trying to focus the attention that our customers are, uh, being emailed about.

[00:25:58] Katie Keith: Well, how do you know that they're using a Stripe integration on a product without SAS elements?

[00:26:04] Zack Katz: Well, that's-

[00:26:05] Katie Keith: Most of us aren't putting that sort of tracking in our plugins yet.

[00:26:08] Zack Katz: That's where the telemetry comes in. Mm. Um, we're, we, we have a thing, uh, we have a initiative at Gravity Kit, we haven't implemented it yet, but one of the things we have as WordPress product owners is we have tons of blind spots for how people are actually using our products, and we're about to integrate PostHog with all of our products, uh, so that we understand the settings people have, we understand if there are rage clicks, is a thing, where, like, people click expecting something to happen and it doesn't happen.

[00:26:36] Like, understanding the product better is important for segmentation, but then it also has a privacy thing as well.

[00:26:44] Joshua Dailey: I, um- So it's

[00:26:45] Zack Katz: gotta be opted in.

[00:26:46] Joshua Dailey: Yeah, I, I was thinking about, um, you may or may not remember- There's still, like, the guerrilla marketing tactics, but you may not remember that early this year we sent out a survey for DocsBot, and the features that we created from that, uh, for this week were directly correlated to the, to the answers that we got in our survey.

[00:27:09] So, um, we, you know, a lot of our customers are using Stripe or we're actually looking at, uh, developing next a EDD integration because a lot of our users, um, use that, you know. And so there's, there's different approaches we could take and go like, "Well, you know, Shopify might be better or WooCommerce might have a bigger, broader base."

[00:27:33] But for us right now, for our users, it's a lot of, uh, easy digital download stuff. So we're, we're looking at an integration, uh, skill for, for that.

[00:27:45] Zack Katz: Yeah. I guess part of launch week is figuring out what you wanna build and then what you wanna launch.

[00:27:50] Joshua Dailey: Yeah.

[00:27:51] Zack Katz: Yep. Uh, Josh, you were very gracious in being willing to show us kind of what it means to actually run a launch week campaign.

[00:28:00] Uh, c- uh, you ready to, to give us a little tour?

[00:28:04] Joshua Dailey: Yes. So this is gonna be... I, I had already cleared the board and so I tried my best to rebuild what, uh, what we had created, but I'm gonna give you the most, um, vulnerable insights that I can from this, this sheet and how we got to where we got to in our Asana board.

[00:28:25] And, um, that's kind of the nice part of working with Aaron, uh, is in build in public, there's a lot more freedom for me to share some of this stuff than, than if we were trying to keep a bunch of stuff behind gar- walled gardens-

[00:28:41] Zack Katz: Yeah,

[00:28:41] Joshua Dailey: that's great ... as they say. But yeah, so this here, what we're looking at is our Asana board for DocsBot week, and we have, you know, other, um, thing...

[00:28:52] Let me get here, see if I can find my mouse. Here we go. So we got, um, you know, this DocsBot week board that we created, and what I started out by doing was saying, "All right, we need a, a brief about the context and everything else that we're gonna do." So inside of this, we have a description of the campaign, the narrative, and, um, a little bit about the goals of what we're trying to communicate and to who based off of our ICPs.

[00:29:25] This right here seems like a small thing to do, um, but who would've thought that if, for all my corporate homies out there who've, who've been in the corporate world before, when you had to create brief after brief after brief for leadership and to provide these up to the CEOs, that really that's the work that AI can't do for you The thought work is the work that we still have to own.

[00:29:55] Mm-hmm. And so one of the things that Aaron and I did at the beginning of the year, uh, was we had an on-site, and we created kind of, um, a overview of what we're trying to accomplish and all these things. Like, we looked at every employee, which is basically us and a, and a couple of freelance people. We looked at, um, our marketing, who's the market we have, you know, how many people across each feature and what they're using and those things.

[00:30:27] But then coming down here, you could see, all right, we have channels. We've got, um, our SEO and GPT referrals. We've got free tools. We've got social and paid ads and, um, affiliate marketing, and these are all the things that, that matter to us. So in creating DocsBot week, I was able to take everything from our marketing strategy for the year and to plug that back through and say, "I want my, my, um, brief context to match our ICP and what you know about our business."

[00:31:05] So those, those things were paired together. But that-- coming up with that strategy is not something where you just say, "Give me a business plan, GPT," and it, and it's, it's kind of like the most frustrating part of, of, uh, talking to people about AI right now is because most people are still using it like a slot machine and don't give good enough prompts, and they're frustrated with why and then just say it doesn't work, kind of an idea.

[00:31:32] And both of you as DocsBot users know how important the, um, the instructions are. I mean, y- it gets you about 70%. If you wanna push that extra 10% of the way there, you have to really work on your instructions and do that. From a marketing perspective, exact s- same thing applies. Um, we have to know our businesses and to, um, be able to plug that information back into our brief and then, uh, be able to develop some of our, our, uh, metrics that we want us to drive off of and those things, those all have to come from us.

[00:32:09] So that's where I'd say you gotta start thinking like an owner, especially if you're a young marketer out there- That's the best advice I could give to you right now is like, don't just think like an employee with a task and a checklist. Start thinking like an owner and, and, uh, a manager, because we're to the point where we're managing bots, and they're like employees and they're doing tasks for you, but they're only gonna be as good as a junior level employee, um, if you don't give it the right instructions.

[00:32:38] So-

[00:32:39] Zack Katz: I love that- That's- I love this Josh, because intentionality is so important. When you can do anything pretty much immediately, within a day you can build out a plugin that does X, Y, Z. But if you don't know why you're building that plugin, for whom you're building the plugin, and how you will market it, and why you're gonna market it that way, the AI is just gonna do a generic thing that may or may not be appropriate for your business.

[00:33:03] So I love that you're, you- first step, think about what you want the outcomes to be.

[00:33:08] Joshua Dailey: Totally. Yeah. We're gonna be bloat software down the road if we're not careful. Like, especially if SaaS stays a, a thing, which we, we already know that everything's become token cost. But like, as opinionated software stays kind of important because you have the, um, these other external teams owning the security and the privacy and, like, the important parts of that, and able to kind of do the maintenance side.

[00:33:39] Um, I think we're gonna be in SaaS land for a while. Um, but the, the, uh... Uh, if, if they don't, um... I lost the train of thought there, sorry. Um, what was, what was I rambling on there?

[00:34:00] Zack Katz: So you've got, you've got your, uh, content brief that's before. So then what's the next step of, uh, of putting together the DocsBot week?

[00:34:07] Joshua Dailey: Yeah. So we go into, um, I had some bonus features because there were things like you had mentioned that you said, "Are there things that, uh, don't fit the story?" So we tried to release those as, as just bonus features or sub features if we were gonna do that. Um, then I went

[00:34:26] Zack Katz: in- Josh, you just made me f- re- sorry to interrupt, but I just realized Apple has started doing launch weeks where instead- Oh, yeah

[00:34:32] of having launch days, they used to do launch days on Tuesdays, and now it's every week, uh, or every day in a, on their launch week they're releasing something else, and they kind of end with a bang. And, uh- Oh,

[00:34:43] Joshua Dailey: wow.

[00:34:44] Zack Katz: Yeah. So that's-

[00:34:45] Joshua Dailey: I didn't see their last, uh, presentation. That's interesting.

[00:34:49] Zack Katz: Well, that's the thing- 'Cause I've only- Like the-

[00:34:50] remember- Before WWDC, their developer conference where they launched some new stuff, and before their iPhone event where they launched some new stuff, they now, th- they've been dropping things that they don't feel fit into that narrative In the week be- before the launch of the, like, of what they actually wanna talk about.

[00:35:07] So they, so they announced some other smaller stuff, and then they talk about the big things that they wanna talk about, and they've r- been starting to do the launch week process of releasing, like, uh, per day.

[00:35:16] Joshua Dailey: Yeah.

[00:35:17] Zack Katz: Yeah.

[00:35:17] Joshua Dailey: Yeah, yeah. That's great.

[00:35:19] Katie Keith: Well, it's definitely- That's- ... becoming more of a thing. Like, I think...

[00:35:22] Is it the whole of Automattic? I think it's all of Automattic are doing Radical Speed Month at the moment. So it's a bit different to launch week, but the overall theme of it is getting stuff done faster and really committing to shipping things. So I think particularly for an o- a large organization like Automattic that maybe hasn't moved as fast as it might have done in the past, I think that's really positive and, and interested to see what they do launch after Radical Speed Month.

[00:35:50] Zack Katz: It's gonna be radical.

[00:35:52] Katie Keith: Oh, yeah. Yeah.

[00:35:52] Joshua Dailey: It will.

[00:35:53] Katie Keith: It sounds like a drug, doesn't

[00:35:54] Zack Katz: it? Radical speed.

[00:35:56] Katie Keith: Yeah. Yeah.

[00:35:56] Joshua Dailey: I've been a big fan of, of the approach that they've taken on a lot of the, um, ways they're approaching AI. And even down to developing a team to be in New York, and they all have to be on site. Like, to move at that pace, um, it, it shows a commitment to that.

[00:36:17] And you... I've, I've said this for a while, um, after being in, in bigger teams, is like the only way to really stay up with the pace of AI was to almost create a team that wasn't beholden to all of the legal stuff and the, the, you know, the normal corporate way of doing things and letting them just run wild behind the scenes, and then only release the best things out of that, but give them the space to be creative and to use all the tools and do the stuff that, that, uh, uh, that, that they can.

[00:36:52] I mean, that's- Yeah ... I, and I think, um, Matt's done that well with, with, um, Automattic in giving that team kind of just freedom to go and autonomy to go at that, moving pretty quickly.

[00:37:04] Zack Katz: But- So you, you focused on the story you wanted to tell with DocsBot week, launch week? Yep.

[00:37:11] Joshua Dailey: And then we did, um, just basically put together a c- a s- schedule going, "All right.

[00:37:18] Here's all the pre-launch tasks we have to do. Here's the kickoff week," which was 23rd and 24th, that we needed to get information out. And then I just put at the top of every day what we were covering. So we had lead capture, Stripe skill- Calendar actions on day three. The skill builder was the big reveal, that one we just kind of teased at and hinted at, and then MCP everywhere.

[00:37:44] And then I also still have wrap-up things that I have to do that you can see are not checked off, so post-launch things that I'm gonna do. But inside of each of these underneath, if you remember in my on-site, like, marketing strategy, then I took every channel that we have available to us and plugged it into a card and said, "All right, for social we wanna do..."

[00:38:07] This was around lead capture. For social, we hadn't talked much about how you do web hooks or a Zapier integration for, um, connecting your leads that you collect into Salesforce, let's say. So being able to create that. So we created a, a social around that. We created a video around that. We created a blog post announcement.

[00:38:30] Um, and then we also did, like, a countdown to the, the webinar to continue to grow how many people had subscribed. And we had set a pretty modest goal for, for sub- subscriptions to the webinar of 100. We wanted 100 people to sign up to say they were going, and we were able to break that, which was, was really cool.

[00:38:53] Zack Katz: Nice.

[00:38:53] Joshua Dailey: Um, so yeah, this is, this is, like, the dirty underbelly of practical and, and it would be nice if it was magic, but it's literally just get organized, take this, the information. Like, the ways that I was using AI to augment this would've been our bot has access to Asana, so after the, the whole week was mapped out in a Google Doc, I said, "Take this doc and create all of the tasks for me," and it was able to go generate all the tasks and spread them across the days that they needed to be in and that kind of stuff.

[00:39:28] So that was a nice help, but it was still our strategy and thought and narrative that had to be developed inside of that.

[00:39:37] Katie Keith: It looks kind of like a Black Friday campaign to me. Yeah. It most reminds me of that. So it's almost like doing a mini Black Friday week at a different time- Yeah ... of year, and creating that buzz that wouldn't happen otherwise.

[00:39:49] Joshua Dailey: Yeah. Yeah,

[00:39:50] Zack Katz: exactly. And are you gonna be taking this strategy forward and using it... Like, are you gonna be doing launch weeks many times a, a year? Like, are you gonna do launch months like, uh, Automattic does? Like, what's... Because it seems to help organize marketing, like, is this something you're gonna use more often?

[00:40:11] Joshua Dailey: I think right now, um, we'll have to, like, debrief on that to figure out if that's the approach we wanna wanna take. Yeah, it's

[00:40:18] Zack Katz: a lot of work. Yeah,

[00:40:19] Joshua Dailey: yeah. Uh, but with that said, I think, um- The approach, like you said, Katie, of, of it looks like other things you've done. On the i- internally, it's like, yeah, you could take this, apply it to a quarter, you could take this and apply it to a, a holiday week that's like a classic for...

[00:40:43] We just don't see a lot of success around holiday weeks, to be honest, for, because of the, the, um, persona that we go after. The, the-

[00:40:51] Katie Keith: People aren't working as well. Yeah. Yeah. As much then. They're

[00:40:54] Zack Katz: taking their

[00:40:54] Joshua Dailey: holiday weeks. Yeah, yeah. So like we've find a, a much better appeal a little bit earlier in the year and, and that kind of thing.

[00:41:04] Katie Keith: Yeah. But also it's just, you know- Oh, sorry Josh, you've been overridden by the boss. He says- Yeah ... two times a year for sure. Sorry, Josh.

[00:41:12] Joshua Dailey: We haven't had a chance to talk about it yet.

[00:41:14] Katie Keith: Yeah, outranked there.

[00:41:15] Joshua Dailey: Aaron's gonna have to get me some Bomba socks if I'm gonna be doing another- Yeah ... another one.

[00:41:21] Zack Katz: And, oh, I'm sorry, we have something else coming in from, oh, Zack Katz.

[00:41:26] Five times for sure.

[00:41:30] Joshua Dailey: Five times for sure.

[00:41:35] Man, my life. I like what Katie sa- I saw your post on X that said, "Is anybody actually working half as less now that AI's out?" And I was like, "I don't know anybody working less. I know a lot of people working more right now, but I don't know anybody-"

[00:41:49] Katie Keith: We're just achieving more. We're more efficient. We're not sat on the beach.

[00:41:53] Joshua Dailey: Right. Exactly. Maybe that's our problem.

[00:41:56] Zack Katz: In terms of, like, what you found was, uh, successful during launch week, I'd love to hear more about that because, like, I know different channels have very different responses to things. Uh, can you, can you talk about what you feel, feel like worked?

[00:42:10] Joshua Dailey: Yeah, what do I think worked?

[00:42:12] Um, I find... So for us right now, because our growth has been largely organic, we, we still are shy on ads. We have not done that. Um, like, we've done a few ads, but we have not really done any ads. Uh, that's a next wave for us and something we've already been talking about doing is, like, paid, paid ads. Um, but because of that, the, the founder-led kind of positioning, we get more traffic from sharing across both our LinkedIns and, and X and that kind of stuff than we do any other way.

[00:42:54] The other thing I'm really excited about that I can't validate as, like, we've, um, seen success from it yet, we do have historic precedence on this though, is because we're launching a skill builder, there's a really cool, um, um, semantic SEO play that we get to kind of go after a whole bunch of keywords now that we couldn't before.

[00:43:22] And so, um, we- Added some really cool new pages to our website, and we're able to, like, put brand names in because we can build skills for all of those brand names now, and every one of those are getting a page, and we're spinning all of those pages out. Um, right now this week has been kind of a, a big effort on that, and so that's kind of a, a fun thing.

[00:43:46] And then just having what I would call a content blitz gives me a lot of stuff to share without having to think about what to create. So over the, the next several months, um, video, video, video, video, video. You know, like, it's all there. We... I don't have to, like, go back and create some, but I also do have video topics now that I can, can, uh, create.

[00:44:10] So those are kind of the things that I would say have been most helpful. I don't know if success is the, the right word, but for me that, as a measures of success, the amount of content that we ha- we were trying to produce, we were able to check off every one of our, our categories. We have another, uh, um, marketing person on our team that, um, helped with some of the video.

[00:44:36] You might have seen Justice in there, and he did some video work that is really helpful. He did some of the writing and that kind of stuff, and so having all of those pieces together to be able to share out is gonna be really helpful for the rest of this year.

[00:44:50] Zack Katz: Yeah. We do a monthly call at Gravity Kit, and part of why we do the, do it, of course, is to get in touch with our customers and have them be able to ask questions and stuff, and it's forcing ourselves to do video content.

[00:45:02] It's forcing ourselves- Oh, yeah ... to come up and prepare maybe a demonstration of a feature that has documentation that's written and it has screenshots, but it doesn't have video. And then we say, "Okay, like, let's focus around this for this call so that we can break it down into pieces and reuse it in our docs, reuse it in our marketing."

[00:45:20] So it's a great content event. It's a great

[00:45:21] Joshua Dailey: idea. Yeah.

[00:45:22] Zack Katz: Katie, you do a bunch of stuff. Wha- what- I do,

[00:45:25] Katie Keith: but it never work. Like- ... we're doing walkthroughs and stuff of new features, but it never works in the context of putting it in our knowledge base, for example, because when you take something out of a live stream, I suppose you'd have to maybe plan a lot better.

[00:45:40] It feels random. Like, it doesn't have a good beginning, middle, and an end in the same way that a self-contained video was, would do. So we haven't done a great job at repurposing live stream content. It remains on YouTube forever, but I have no idea if people come back and watch it later.

[00:45:57] Zack Katz: Well, that's where I got less precious and decided, well, A, I, I freeze up whenever I give an online demonstration of software.

[00:46:05] Like, it... I just, like, have a existential dread moment and I can't handle it. Our growth person, Casey, doesn't have that problem, so he does the live demo, he talks it through, and I ask him questions So just identifying that that's not my strength and handing that off to somebody else means that Casey can talk through a, a, a flow that he's prepared in advance for how, like that he has a thought that this will be reused by our docs so that when he demonstrates it, it's more comprehensive in a way that can be broken up.

[00:46:36] So yeah, like- Mm-hmm ... one additional thought around like how will this video be reused, uh, unlocks that for us.

[00:46:43] Katie Keith: Yeah. Like one thing for me was if only one person speaks, then there's a weird floating head who's not involved, so- I

[00:46:50] Zack Katz: turn my head off. Yeah.

[00:46:52] Katie Keith: Yeah. And

[00:46:52] Zack Katz: then I come back on, I pop back in and I ask a question, then I turn my head off again.

[00:46:56] Katie Keith: Yeah, that works better 'cause it's things like that that- Yeah ... in, in isolation, it's like, well, why is that other person there if they're not speaking in this snippet?

[00:47:03] Zack Katz: No, it's really awkward, yeah, if, if I don't do that. Mm-hmm.

[00:47:07] Joshua Dailey: Have you tried, uh, Riverside?

[00:47:11] Zack Katz: We have tried... Well, I've seen Riverside. I haven't tried it.

[00:47:13] Um, do you recommend it?

[00:47:16] Joshua Dailey: I mean, I, I'm not sure the interf- back end of, of Restream, but from an editing perspective, it gives you all the video and screen sharing and all of that stuff, um, as separate files so that when you go back to edit, you can remove people or add people in that weren't up on the screen, um- Oh, that's cool

[00:47:36] and just show the screens that you need to do. So the editing functionality of it is, is pretty nice. We just had the subscription for, uh, DocsBot Week, and so I'm familiarizing myself with it. But, uh, yeah, I'm, I'm not sure how it compares to something like Restream or, or, um, other softwares, but I enjoyed the experience with it.

[00:47:58] Zack Katz: Yeah, Restream's gotten a lot better and I think, uh, we use StreamYard. Uh, they've both... The AI clip generation has gotten a lot better, where it was pretty-

[00:48:07] Joshua Dailey: Yeah ...

[00:48:07] Zack Katz: horrible before, and now it's actually usable for sharing on things like social media.

[00:48:13] Joshua Dailey: Yeah. Yeah. The other, the one other thing I'd add to that is we didn't use a lot of, uh, streaming stuff.

[00:48:22] Um, I did... We have a software that is very basic for recording, um, for recording, uh, video, like screen sharing stuff, and that sandbox has really helped me a ton because I get way too edity. Like I go back in and I'm like- Oh, gosh ... trying to fix things and like having explosions and- It's so... Video is just like a

[00:48:48] Zack Katz: perfectionist-

[00:48:49] Joshua Dailey: Yeah

[00:48:49] like

[00:48:49] Zack Katz: favorite

[00:48:50] Joshua Dailey: worst thing.

[00:48:50] Zack Katz: Yeah, yeah. Yeah. Yeah. So for-

[00:48:51] Joshua Dailey: And

[00:48:51] Katie Keith: it's so scary 'cause you can't edit it later if it's on YouTube. You, it, it doesn't... It's not a feature. Right.

[00:48:58] Joshua Dailey: Yeah. So we just did... I, I recorded all of our dem- overview videos except for the webinar pre-recorded, and then had small edits that I was able to make ahead of time

[00:49:10] Zack Katz: And that is one thing that we did, uh, Casey and I, for, uh, when we launched something recently.

[00:49:15] I forget what it was e- exactly, but we had pre-recorded our webinar, and then we were there live chatting with our customers and, and h- like talking about it with our customers in the live chat while we were playing the pre-recorded webinar. That's not something we had done before, but it allowed us to have a more professional presentation while also making it so we were more interactive.

[00:49:35] And I... We got really good engagement on that 'cause we promoted it.

[00:49:38] Joshua Dailey: Yeah. Did you see, did you see our nightmare experience on the live stream?

[00:49:43] Zack Katz: Uh, no. Did

[00:49:43] Joshua Dailey: you guys see

[00:49:43] Zack Katz: that? I didn't. No. What, what happened?

[00:49:45] Joshua Dailey: If, if you're doing a live demo, it's, it's prone to have some fail, you know? Yeah. And so we were doing the skill builder live.

[00:49:53] First one worked great. Second one looked like the skill kept failing, but the API keys for, uh, OpenAI were down.

[00:50:06] Zack Katz: Oh, no.

[00:50:06] Joshua Dailey: So we're trying to- Yeah ... generate an image, and it just kept giving a 429 error- Oh, I did see that. Yeah ... over. We're like, "Well, I guess we're not gonna be able to demo this," and then something with work- And it looks like a problem with your software It looks like a problem with the product.

[00:50:19] So- Mm ... I w- I went back and edited that, so the edited version's up now. But I do have a, a failed one on our YouTube you can see failed. So it's

[00:50:29] Zack Katz: good

[00:50:29] Joshua Dailey: to see that- And

[00:50:30] Zack Katz: that, that, you know, that could be its own clip, uh- Yeah ... that would get... that could go viral, is with the, you know, "Damn it, OpenAI."

[00:50:37] Joshua Dailey: Exactly.

[00:50:38] Everything, everything started working instantly as we turned off the live stream. That's cool. And then we were- went back live and it started working, so we were able to capture kind of a, an ending that made sense. But yeah.

[00:50:50] Zack Katz: One of the things we have to do as businesses is appear human. Yeah. Uh, in the world of AI, I think we have to, like...

[00:50:57] Our, our customers, you know, people love, uh, on Saturday Night Live, when people break during a skit and start laughing. Uh- Oh, yeah ... 'cause, you know, the comedy is one thing, but seeing actual people performing it is another. So seeing a demo fail, I think, is a, a thrill that your customers probably will remember for the rest of their lives.

[00:51:14] I hope

[00:51:15] Joshua Dailey: so, and I hope they don't remember it for the wrong

[00:51:17] Katie Keith: reason. I think I went to reassure him that no one remembers.

[00:51:20] Zack Katz: I mean, nobody will remember it, and it'll be fun, uh, for you to remember in retrospect. Yeah. Uh, Josh, we wrap up every show with a quick roundtable question, uh, which is, what is your best advice for anyone thinking about running their own launch week?

[00:51:36] Joshua Dailey: Yeah, I think we touched on it a little bit already. Um, but I would say build your plan and- That includes what success looks like for it. So not just kind of like, "Here's what I'm gonna do," but how the outcomes that we wanna see from this. And for us, like I said, that was content heavy, uh, more so than just signups, like w- how much pieces of content we wanted to get out and things that we could share.

[00:52:03] The second thing is be organized, and that sounds like cliche, especially if, if you're a, a business owner, you're like, "Yeah, what does be organized mean?" In, in my sense, this is the part where it's like it doesn't just make it easier for you to work with humans, it actually makes it easier for you to work agentically in, in, um, AI workflows.

[00:52:26] Because, uh, how many of us are going through the nightmare of saying, "I don't have enough structured content to make agents actually work well for me"? And so being organized even in this small way gives you the ability to use agents more effectively and efficiently, plus keeps your team happier. And then the last thing is ownership matters.

[00:52:49] So especially for small teams where I like to get my hands into a lot of stuff, being back on a small team has forced me to step back and go like, "Justice, I trust you with this. Aaron, I trust you with this, and I'm gonna do this, and we have to own this stuff, and it has to get done by this timeframe." And, and having that kind of ownership with smaller teams is really important, I think, to, to be able to deliver on something that has so many moving parts at the same time, or else you'll run yourself, you know, ragged.

[00:53:26] Zack Katz: Yeah. How about you, Kitty?

[00:53:28] Katie Keith: Um, my advice is to think about what type of product you sell and in what ways your audience might want to engage with this sort of thing. Docs Bot, Bot is an excellent example for a launch week because it forms a fundamental part of somebody's workflow, and it's also in a really rapidly changing area where people can constantly take advantage of improvements to, um, implement in their own docs bots.

[00:53:54] Whereas in contrast, let's say if you had an import plugin, people aren't importing stuff every day, and it would probably be- Right ... quite annoying to be getting an email every day. But it doesn't mean none of this is relevant, it's just maybe you don't communicate it every day. Maybe you do a daily thing behind the scenes t- like maybe Automattic are doing more of that with their, um, radical speed stuff.

[00:54:17] Um, you can still work quickly and follow the principles of getting stuff released really quickly, uh, but that may be different in terms of your marketing approach. So I say analyze your product and consider the best way to tailor what we've heard today to your audience.

[00:54:34] Zack Katz: That's good advice. And, uh, one of my best advices is to not be precious of what's worthy of an email Uh, emails Yeah Just we, like you were saying earlier, Josh, it's, uh, we, we put out so much focus and effort behind the perfect email.

[00:54:51] Well, sorry, uh, nobody like, you know, a large portion of your audience is not gonna open that email, less of they are gonna read it, fewer are gonna click that. So, um, don't worry about that. Uh, but also, I'm going to commit to thinking, shifting how I think about launch weeks and how I think about future releases.

[00:55:10] For my next feature release, uh, at GravityKit, why not tease it a little bit? Why not build up anticipation? Like, uh, we do so much cool stuff behind the scenes that our customers don't know about. Yeah. Build up anticipation 'cause everybody has more fun, and, uh, and including the team when you launch it if there's a build up to it.

[00:55:30] So I'm gonna do it for future releases, not just, uh, for marketing pushes as well. Like, so shifting the whole concept of what we're doing here.

[00:55:41] Joshua Dailey: That's amazing. Yeah.

[00:55:42] Zack Katz: Well, that's a wrap, Josh. Thank you so much for joining us and for, uh, taking the time and for, like, presenting. This is, this is really great. Uh, where can people find you online?

[00:55:53] Joshua Dailey: Yeah. So, uh, my handle's Josh Dailey on pretty much the two main platforms, uh, that I use, and Dailey is D-A-I-L-E-Y. Um, I know there's a lot of different ways to spell that. So on LinkedIn, Josh Dailey, on X, Josh Dailey. And then, uh, if you're looking to see DocsBot, it's on the web at DocsBot.ai. Um, and if you want to get in touch with our team, it's [email protected], and that we, um, have one kind of central drop, uh, box so that you can talk to myself or to Aaron.

[00:56:31] Um, makes it easy for us to both respond that way. So would love to, uh, be in touch and to, um, you know, to be able to continue helping businesses.

[00:56:46] Zack Katz: And, uh, can you spell DocsBot? Because I know that- Oh, yeah ... transcription, uh, loves- Yes ... to misspell it. Yeah.

[00:56:52] Joshua Dailey: Yes. You're right. It ends up being weird iterations all the time, or Docs Spot sometimes.

[00:56:59] There you go. No, it's D-O-C-S-B-O-T, DocsBot. Like documents- Awesome ... bots.

[00:57:09] Katie Keith: Yeah. And honestly, I think everyone should probably go to DocsBot.ai just to sign up to your newsletter because then we can see you releasing these things, um, in six months when you do it again, or as often as Aaron dictates. Um, so- And everybody should- Yeah

[00:57:23] Zack Katz: go out and buy some socks

[00:57:24] Katie Keith: Yeah, yeah

[00:57:25] Zack Katz: From the book from bombas.com.

[00:57:27] Joshua Dailey: I know.

[00:57:28] Katie Keith: Yep, our new exclusive growth partner. Um, so if you're enjoying these shows, please do us a favor and hit that subscribe button on YouTube. It's literally free, easy, and helps our work. And special thanks to Freemius again, and Bombas Socks, who didn't pay us a penny.

[00:57:48] Zack Katz: And we'll see you here next week, uh, on May 13th, for an episode, uh, focusing on the state of vibe coding a WordPress website. Ooh, what's that gonna be like? With Andy Peatling, hosted by Matt Cromwell and me. Uh, I can't wait to have this chat. Um, please make sure to follow us on YouTube and social media so you don't miss it.

[00:58:09] Uh, thanks again, Josh. Bye.

[00:58:11] Katie Keith: Bye.