A Sneak Peek at Pressable’s Plans for 2026  ## Document Notes ## Highlights - **Marketing Connects Product To Right Users** - Kevin MacGillivray views Pressable marketing as connecting the right product to the right user with clarity and focus. - He emphasizes positioning for agencies, Woo stores, and scaling businesses to show specific value. Transcript: Kevin MacGillivray Yeah. So first of all, hi, everybody. It's great to be here I'm Kevin, of course. I've been at Pressable for about six months. I joined the team in July as the chief marketing officer. So what does that mean in this context? It really means coming in and helping Pressable scale and keep pace with the growth that we're seeing from what is a great product and help make that story clearer, sharper, more consistent In the market and add some maturity to how we position our product out there for the users that need it most. ([Time 0:01:33](https://share.snipd.com/snip/2e561576-9d10-4374-852a-1ede37c95587)) - **Flexibility Is Strength And A Marketing Challenge** - WordPress and Shopify share a philosophy of enabling people, but WordPress offers far more flexibility. - That flexibility requires marketers to craft clearer, use-case driven narratives. Transcript: Kevin MacGillivray Think in some ways it is actually very much or there are a lot of similarities. It's very much the same. And in some ways it's not. So a couple of ways that it's the same is both WordPress and we'll use Shopify as an example. They're both building things and they're building tools that help get more things in the hands of more people to be able to achieve and succeed doing what they're doing. Giving people tools they may not otherwise have access to in more of a closed ecosystem. But like, they're doing that to help people start businesses, make a livelihood, you know, all really good endeavors. In a lot of ways, WordPress is the same thing. It gives people the building blocks to do, you know, arguably way more than commerce, when you're thinking about WordPress as a whole, but be able to build and have the pieces and tools To do things themselves, they might not normally be able to do. So in that sense um almost philosophically they're very similar um and that's one of the things why i love working at shopify and i've loved my time so far in wordpress is that's a really Cool thing to get behind um like it's it's about access right it's giving access to more people to more things, how are they different? Shopify is a little bit more of a, I'll use the word closed ecosystem, even though that's not like entirely, entirely true. But they are building a product roadmap for what they believe is the best path for building and selling and operating in a commerce world. And with that comes focus. It comes a lot of really interesting innovation that they're building in that space. But on the flip side, what we have on our side in WordPress and WooCommerce now is like you get that extra flexibility of you can really like build your own path in many ways. And that could be a curated one. It could be one where, you know, we suggest something and you build it. And it could just be that kind of barrel of Lego. You build whatever you want with. And that's part of the joy of working in WordPress. ([Time 0:03:24](https://share.snipd.com/snip/c662a513-70bc-4ca0-8252-42d32a669139)) - **Specificity Beats Vagueness In Marketing** - Vague messaging loses in today's market; specificity wins attention and trust. - Target clear user profiles and workflows instead of saying "WordPress can do anything." Transcript: Kevin MacGillivray Think it can be the kiss of death. So I know one of the things that you would want to chat a bit about was like well, marketing is shifting in general. The question you just asked is a great example of that where what I'm finding and what I think a lot of marketers are seeing is vagueness is starting to be a path to losing. Like you you don't win business, you don't win followers, you don't win advocates and evangelists by being vague. So when you're talking about how do you actually, you know, rubber hits the road and actually get a message across about what WordPress is and the value, there is benefiting focus and Specificity. So like, how do you how do you actually get real problems, real scenarios, real workflows in front of people who are actually building them and make it tangible and make it specific to Their use case. And that doesn't mean, you know, all WordPress users everywhere, like this one thing, it's like WordPress user ABC, who has this particular thing, that this particular workflow, This particular business, how do we talk to them and then find people like them? ([Time 0:06:28](https://share.snipd.com/snip/015c574e-548c-4c88-ade8-554ad0767873)) - **Use AI To Amplify, Not Replace, Trust** - Use AI to amplify marketing productivity, letting teams do more with less time. - Prioritize authenticity and human connection as AI proliferates to maintain trust. Transcript: Kevin MacGillivray There's two angles to this. One is how AI and the acceleration of that technology has actually helped me in my craft as a marketer. And that's just accelerating at an incredible rate. So what that means is all the marketers on my team and the people I work with have suddenly in the last six months gained an exponential amount of leverage to be able to do more things, build More things, like do some coding themselves, just do way more with less. So I think that's 100% true. I think the step further from that is AI is changing how people interact with products and evaluate products and look at products. So that's changing at a macro level and also in terms of what they're expecting products to do for them um and i think maybe one of the side effects of this as well before maybe we talk a little Bit more on the product side but one of the side effects is the need for authenticity is probably bigger than it's ever been before a world of AI proliferation. And this is, you know, video, it's things like community. And like, this is where WordPress actually has a huge advantage, I think, around the human component and the community component, people learning from each other, people, you know, Having a higher trust with other folks and agencies and partners and builders that they've worked with before or know as part of the community, that is what's going to add a lot of value And leverage at sort of that umbrella level going forward as more and more is just like swap. And it's hard to figure out what's real online. ([Time 0:12:05](https://share.snipd.com/snip/013ffe68-41a9-40fb-91d6-067f0cdd6aba)) - **Startup Energy Inside Automatic** - Kevin joined Pressable six months prior and felt attracted to its startup-like agility within Automatic. - He values short feedback loops and scrappy experimentation enabled by that culture. Transcript: Kevin MacGillivray 100%. 100%. It's actually one of the things that attracted me to this role at Pressable is you have all of the benefits or most of them of being in a startup of moving agilely, you know, being scrappy, Lots of experimentation, lots of lots of testing things, lots of short feedback loops from customer feedback to things we build in the product. Those things are possible because we operate very much like a startup. But we're nestled within automatic, of course, which has benefits from being part of that broader ecosystem and infrastructure. ([Time 0:14:01](https://share.snipd.com/snip/46e4f904-33ca-4e68-a5dd-931a5eb562e5)) - **Differentiate By Outcome, Not Shared Features** - Shared tech like Jetpack spans Automatic brands, so marketers must sell outcomes not duplicate features. - Pressable differentiates by focusing on agency-specific value and support. Transcript: Kevin MacGillivray Yeah, I think using Jetpack is actually a great example of there are things that kind of transcend the different pieces or brands or products within Automatic. And as a marketer, you do have to get creative around how you position those products and features or whatever the instance is. Let's jetpack as an example um the differentiation there comes in how good you are at explaining the value and leverage those tools can provide to your customer or your audience for The problems they're trying to solve so even though there may be technology technology that transcends multiple products being able to articulate that well that's the challenge In those instances. And then there's absolutely things that we lean into across brands that are, that are, you know, different and, you know, pressable as an example, like we lean quite heavily into how Good our product is for agencies. And that that's a very pressable thing. And we build to solve for a lot of those problems. ([Time 0:15:55](https://share.snipd.com/snip/e802acb0-3b95-433c-8561-88baff7940e6)) - **Make Agencies Feel Secure** - Make agencies feel secure: prioritize support, smooth migrations, and on-demand access to tools. - Use human touch plus reliable tech to remove agency fear about client work. Transcript: Kevin MacGillivray I think the number one thing that stands out is actually like a feeling type thing, which is we strive to never have agency customers feel scared about what is going to happen to their Customers. So we work with the agencies, but we know that the agency's number one priority is delivering an excellent experience to the customers that they're working with. So that rolls up to things like support. It rolls up to things like smooth migrations. It rolls up to things like being able to access tools that you need when you need them, get questions answered. In the fall, we just went through this big agency storytelling exercise where I think we added nine, seven or eight or nine new case studies to our repertoire. And the common theme across all of them was, I don't have to worry anymore. ([Time 0:19:58](https://share.snipd.com/snip/b524a334-6230-4242-a86e-4dbda43d2d73)) - **Share Practical AI Wins In Community** - Facilitate community knowledge-sharing about practical AI uses and margin gains for agencies. - Host events and co-learning to help agencies adopt AI strategically, not superficially. Transcript: Kevin MacGillivray So number one, one of my goals heading into 2026 is to have Pressable play a much larger role in knowledge sharing. So that's not just like, here's what our product does and like, go use it. This is like, how are you using AI to plug into Pressable? Agency one, let's talk about it and share that resourcing with the rest of the community. How are you increasing your margins by doing this with AI? Great. Let's share that within the community. That's probably from a content standpoint the most valuable content that can go out there and this goes back to being specific it's not like oh god ai like use claude it's more like we Know that these are the five problems that agencies are going to be running into whether it's margin or efficiency or just tool integration let's talk about them and help facilitate The sharing of that knowledge. On the human front, we're actually hosting with one of our partners, Big Red Jelly, that's actually based in Utah. In February, we're doing a joint event with them that is all about how community can help you accelerate your business. And that human piece can actually help you accelerate with AI and tech. If you operate and learn from each other and, and, you know, stay tight knit and, and, and all that kind of stuff. So we're definitely leaning into helping facilitate and foster what you just described. ([Time 0:22:44](https://share.snipd.com/snip/ab213e5f-ffde-4194-81a7-c1233f6d506a)) - **Design Hosting For AI Agents** - AI will act as an agent; hosting products must support agentic workflows and recovery actions. - Design products so AI can explain, act, and recover rather than being a mere add-on. Transcript: Kevin MacGillivray You kind of have to think holistically about how you want AI to interact with your product. And, you know, hosting is an interesting example where, you know, AI in a lot of cases going forward is going to be the user or an agency wielding ai is going to be the user like how do you How do you build and and and shift the the um you know best practices to a world where you know the systems can uh you know explain things take action recover like if we hit this threshold Do this, and just have that agentic kind of component built into products as a user would be interacting with it rather than, you know, let's put this interesting magical feature here. Yeah, yeah, yeah. You know. Matt Medeiros Yeah, yeah. Like dashboards and reports don't need to look pretty anymore because literally no one's going to look at it. Their AI is going to consume the stats from the hosting yeah and then on their end just spit it out in a dashboard of their own you know usability that's a that's definitely an interesting Um you know thought uh on how on how people are going to be interacting with this stuff and ([Time 0:25:21](https://share.snipd.com/snip/f707eb80-d1d4-4ef5-b4ff-2ae460fbff9d)) - **Leverage Partners For Side Quests** - Use partners for specialized "side quests" while the core product focuses on the main mission. - Proactively identify partner gaps and route customers to qualified agencies for complex needs. Transcript: Kevin MacGillivray Think it absolutely is and should continue to be. Analogies that I really like to think about is and this was true at Shopify so this is a this is a Shopify adage but I think it applies here where like Shopify or WordPress or automatic is Building in many ways for the main quest you are trying to make whatever you build as applicable to as many people as you possibly can that's what you normally do to try the product adoption Side quests are things that may be valuable and definitely are valuable to smaller groups along the way maybe particular use cases particular you know whatever functionality but It's not core to um e-commerce or uh you know web development or or site building um that is where partners come into play where like you can have the main company focus on a main quest and Have all of these partners that are building things or are well situated to have products that add heaps of value along the way for these side quests type environments where like we absolutely Need that built but would we ever build it ourselves probably not but that's where this like ecosystem comes into play um and in terms of your like lead sharing piece like i i'm i'm looking At you know opportunities even just now about how we can do more things like that um particularly as community becomes more important to drive growth for our business but also our agency Partner businesses And a lot of them offer a ton of really great value that works in a very compelling way adjacently to the pressable stack. Matt Medeiros I know it's probably it's that hard balance of being under the automatic umbrella with the dot com and the VIP and both of those divisions are trying to do best, the best they can for their Customer. But is there plumbing in place for somebody to go from.com to go, hey, look, they're really pushing the boundaries of what.com can do. They need their handheld to move over to something like Pressable. And at that moment, does the Pressable team go, I've got an agency that can help make this transition? Is that a common plumbing piece in this? It is. Kevin MacGillivray And I think even more so like the more complex you get as a business, the more of these you run into, where we honestly need to do this more about identifying agencies that can plug one of These gaps in a migration or move or transfer or setup or something like that, where that's exactly what their skill set is developed for. And we do have those all the time, by the way, where people move from a.com to a pressable or a pressable to a VIP, you know, and there is change management that has to happen. So the example you're describing is spot on. Matt Medeiros If an agency is knocking on your door going, hey, I want to be a partner, how can I get better situated with Pressable? How do you evaluate them? Heck of a better phrase, that says, here are our capabilities so that you can measure like, okay, this could be a fit for the pressable agency partnership program or just for you to recommend Them. Is there certain requirements you want to see? Kevin MacGillivray Yeah, I think on two levels. One, we have a broader program called Automatic for Agencies, which is sort of our existing framework for working with and managing agency partners across all of Automatic. Pressable is a huge piece of that because we have a lot of partners we work with within Pressable. But there's sort of that overarching framework of how to become a partner and how to work with and Pressable in that regard specifically though i think it's actually on on us on the technical Side and also as these partners kind of come up or crawl out of the woodwork to identify the most important opportunities where there are gaps today and both reactively and proactively Solve this so if we if we see something that is a gap in our product or experience in some way that a partner can fill we should be actively looking for you know partners that could potentially Play a role there rather than just reactively where oh this partner does something really cool how do we plug it into somewhere in our process i think making sure that the need is there Is also a really important part of that process. Because you're right, you don't want needless proliferation of complexity in how we operate either. ([Time 0:27:44](https://share.snipd.com/snip/c0a9ee16-50d2-4f24-ad51-cff10bce8302)) - **Invest In Brand, Community, And Coordination** - Hire dedicated brand and community leadership to coordinate co-marketing and events in 2026. - Focus marketing on coordinated storytelling with partners rather than random acts of marketing. Transcript: Kevin MacGillivray A bunch of things. So number one is we're in the process of hiring our first brand and community leader to be on the Pressable marketing team. And what they're going to spend a lot of time doing is leaning into A, the Pressable brand and making sure we continue to mushroom in terms of visibility. This is the role that's going to be building um uh co-marketing you know partner programs community building events we're going to work camp asia work camp europe for the first time Um in the spring uh we were increasing our presence at other events in ecosystem. We partnered with WooCommerce for our first partner event at an e-com expo in London back in September. There's a lot of like new spaces that we're going to be moving into. And then content is obviously one we already talked about, but actually building content that meets the needs we described about kind of co-sharing, co-learning through real experiences Of customers using our product agencies we partner with, and all that and getting that much more accessible than it is today. That's like only a small handful of all the things that I've got in my pocket that I want to go do. But the theme is really being coordinated and focused. So it's not just random acts of marketing either. It is a coordinated, like these are the messages we want to get across in these places with these partners and the stories we want to tell. So it feels very smooth. ([Time 0:33:00](https://share.snipd.com/snip/3ce0cd3a-9312-4425-bc69-b7d44028183f))