Jordan Wilson

This is the Everyday AI show, the everyday podcast where we simplify AI and bring its power to your fingertips. Listen daily for practical advice to boost your career, business and everyday life.

I think the pre 2026ai story was single player whether you were an individual, small business owner or part of a large enterprise. I think the 2022-2025 strategy for AI was unfortunately a lot of copying and pasting and working in silos. But that's changed, right? We are in 2026 where everything is agentic first and headless and also multiplayer. So that's what we're going to be tackling on today's show. Not just that shift of AI going multiplayer, but specifically how everyone's favorite communication tool, Slack, is actually bringing that all together. So I'm excited for today's conversation. Hope you are too. Welcome to Everyday AI. My name is Jordan Wilson. If you're new here, we do this every day. This is your unedited, unscripted live stream podcast and free business free newsletter helping everyday business leaders like you and me not just keep up with what's happening in AI because it does stop. But I tell you what matters, what doesn't. You take that information to grow your company and your career. So if that's what you're trying to do, starts here. But make sure you go to our website at your everyday AI dot com. We're going to be recapping the highlights from today's podcast and it's going to be a good one. We have a great guest and all the other AI news that you need to know to stay ahead and be the smartest person in AI in your company. Sounds like a good deal, right? All right, but we have a treat for everyone today. It's not just going to be me yapping. We get to steal some of the secrets from someone building the tool tools we all get to use. All right, so I'm excited to bring on to today's show live stream audience, if you could help me. Welcome to the show. Let's bring them on there. Ryan Gaffin, the Chief Marketing Officer at Slack. Ryan, thank you so much for joining the Everyday AI Show.

Ryan Gaffin

Jordan, thanks so much for having me. It's great to be here.

Jordan Wilson

All right, so tell everyone a little bit. What is your role at Slack? Right? Everyone knows Slack, everyone knows cmo. But like, what does that actually look like? Because you guys are shipping so many things, especially on the AI and agentic side.

Ryan Gaffin

Yeah, I appreciate it. I like to describe myself as middle management overhead. That's really what I am. But I do get the privilege of looking after the Slack business and the marketing side. I also get to look after small medium business here at Salesforce as well as like something we call a digital growth systems team. But you know, at Slack it's really about how do we take and transform organizations and kind of get them ready for this moment. Um, it sounds cliche, but everyone is racing as hard as they can and many are struggling with what's going on with just the pace of change, the innovation, you know, the, the AI and agent buzzword drinking game continues and like everyone's trying to figure out how they navigate it and, and Slack's become an incredibly important tool for many organizations to do just that. So that's where I'm spending a lot of my time these days.

Jordan Wilson

Yeah, walk us through. You know, I kind of previewed it, but it seems like, you know, so much of AI's strategy, you know, especially in the earlier years of the online chatbot, was really just about how individuals can bring, you know, their best together and then somehow you have to duct tape it all together. You know, first of all, tell us like what the heck is Slackbot for those of our, you know, audience who haven't used it or maybe they haven't heard. And then what's Slackbot doing to try to turn the player from a single player game into a multiplayer agentic collaboration?

Ryan Gaffin

Yeah, so there's a bunch there that's important to unpack. So I think, you know, first and foremost I'll kind of let me touch on the multiplayer piece and then I'll kind of, I'll get into Slackbot a little bit. You know, there's this interesting thing that's been happening that we've all experienced like this explosion of intelligence tools that are now at our fingertips. All of us have had our ChatGPT moments, had our cloud coworker and Claude code moments and just like been blown away what these things can go do. And you know, organizations and enterprises are sprinting, in some cases spending unbelievable amounts of money to deploy these tools. But what's not happening is we're not seeing this throughput to employee productivity and the return of that investment in terms of the outputs of the business. You know, customer success, better revenue, you know, improved margins like those, those in those impacts of like employee productivity aren't translating through the system. So there's like this like dissonance right now of like unbelievable great intelligence, but yet it's not showing up on one of the company's most important resources. Which is their people and the productivity of their people. And the reason for that is because work has always been a multiplayer sport. Like work happens in the conversation. You know, a good idea is not nearly good enough in terms of tills. It gets matured and maturated and debated and, and then built and built and, and built in the open, in the collaboration, those ideas don't come to fruition. And so work has always been in the conversation. And so what needs to happen is all this unbelievable intelligence needs to come to the humans and it needs to come where the humans are working and collaborating. And it needs to come in a way that feels unbelievably accessible. And so what Slack is really having this incredible moment right now is, you know, it's always been for many companies this beloved collaboration tool, but it's rapidly turning into this critical component to companies AI stack. You know, we like to say it's, it's the 2% of your AI spend that unlocks the value from the other 98% because it's bringing AI into your humans and it's allowing your teams to work and collaborate together. And then, you know, to do that really successfully, you're going to have all these incredible applications inside of Slack, whether it be from Salesforce or from third parties like Box or Atlassian or Anthropic, OpenAI, perplexity, linear, the list goes on and on. It's an open platform, but you know, how does an employee navigate all that? You know, how does an employee go through and get the value from all these enterprise systems, get the value from all that conversation, get the value for all these agents? You know, in, in the fullness of time, which may be like six months, who knows? Most companies are going to have more agents than they're going to have employees. But the problem is how do employees know what all those agents do? Like, how do they know what their skills, how do they know where to find them? And like in some cases we're making the same problem that we've had in the past worse by just spreading all this stuff to, you know, another system, another tab, another place to go to another agent to go learn another skill to go develop. And there's some poor employees just sitting in the middle of this thing. Like, I don't know, I've got all this intelligence, I don't know how to use all this stuff. So this is where Slackbot comes in. So Slackbot is this unbelievably powerful tool inside of Salesforce that we built at Slack. It is the fastest growing feature in Salesforce history by far. And it's because it's an AI personal assistant for me that knows me, it knows my team, it knows my context, it has access to the permissions that I have inside of Slack and it has. And it's connected to all my enterprise systems so it's trusted from day one and I don't have to learn a thing. I just ask Slack and Slackbot can go and query all those systems, whether it be an inbox, whether it be 15 different agents, whether it be my CRM. And it can not only read those things, it can write to those things and I can just have a conversation and I can get work done across two dozen systems without ever knowing those systems exist in the back end. It's unbelievably transformative for how we work. It's unbelievably transformative for employees because now all this intelligence is actually accessible because we gave this simple, delightful personal assistant called Slackbot that allows you to get access to it. That was a bit of a long

Jordan Wilson

winded answer, but no, a lot to unpack there. But I think Ryan brought up like a really important point, right, when you talked about, you know, not only does it bring in all of these enterprise systems, right, which your standard AI, you know, chatbots, they do that as well. But you said something important there that I want to unpack. You said it knows me and it knows my team, right? And I think that our longtime listeners here will know I have this, this weird thing when, you know, I talk about the models themselves going from, you know, these, these transformer next token predictors to models that can reason and go over logic. And I talk about this thing called first party reasoning data, right? Because everyone can, you know, hook up your, your Salesforce and your email and all these other things, but it's how your team works, it's how they make decisions. And you know, come to think of it, it's like, wait, so much of that just literally lives and it breathes inside of Slack. So walk me through kind of the reasoning or the rationale and how those Slack conversations that sometimes people think are just, you know, noise that actually might be the goal that's hiding beneath the surface.

Ryan Gaffin

It's massively the gold in the AI world. Unstructured data is the, is the context that fuels relevance for any AI system. And the most valuable unstructured data by far is the richness of years and years and years of organizations organizational context. And one of the reasons why Slack is such a powerful tool is because it's open architecture, it allows for these public channels, these private channels where people are working and building in the open. They're not locked behind an inbox, they're not locked behind a, you know, a simple chat message. You have organizational context in the open that's living and breathing. That honestly has always been valuable. But you know, once it kind of happened, it's largely been inaccessible because, you know, are you really going to go back in time to a message or a thread from three years ago, but now it is accessible and now it's there and so, you know, I'll just give you an example of, you know, I have hundreds and hundreds and hundreds of channels that I, I'm included inside. Do I read all of them? Heck no. Do I monitor all of them? Heck no. But what I can do is I can have a Slackbot skill that I have run every morning and it says, you know, Slackbot, go through and look at all the areas that my team are working on right now. I want you to give me a prioritized list for areas they may be struggling or need my help or maybe stuck. I want you to give me an update of where you see my team making great progress on our stated goals. And then please help me understand what are the areas that I should probably have as my top focus areas for today and for this week based on what you're seeing now. Simple prompt. But imagine like what would be required to get those answers, like pre Slack bot. I'd have to go, maybe call a staff meeting. I might have to make, you know, a dozen different Slack messages or heaven forbid, an email. Dear Lord, hope not. You know, I might have to call a meeting and get everyone in a room and kind of, all right, what's you working on? Whatever. But the reality is Slack is looking at all these channels that I'm not looking at. It's looking at all these conversations today, tomorrow, in the past, etc. And it's able to know when I say my team, it doesn't say, who's your team? It knows my team because it knows me. It knows the people I'm working with. It knows what I'm talking about when I say my goals, it doesn't say, okay, great, tell me your goals. It knows my goals because there's a published in a document that I put in Slack that it's accessible via Google Drive and it can read those and interaction over those. And when I say look at all the full actions, it can look into the systems of like my calendar, it can look into the systems of record like Salesforce, and then it can pull all that. And so I get one simple prompt, I get this unbelievably rich answer back that gives me insights of like, hey, your team has been over here debating this topic. They could really use your help. And you have no clue that's even going on. This thing's coming up and you really need to spend some time on it. And here are the five areas that your team's made some incredible progress on. Your goals. And it's like, boom, in like two minutes. I'm like the best equipped manager I've ever been. All because I've got Slackbot that's working on my half across all these systems, all in a conversational prompt. It's crazy. And it, it, that's like a, a very simple use case of, of how these things show up and why the, the power of conversation and connecting, you know, the structured data and unstructured data becomes unbelievably powerful in this.

Jordan Wilson

Yeah, you kind of gave that example, right, of, of having these hundreds of channels and even channels that you like, one human cannot go in and monitor hundreds of channels. Right. So I think that that's a great use case. But maybe. Can you walk me back a little bit? You know, maybe when you were, you know, testing out Slackbot internally, before it was released to the public, did you have like one of those aha moments where you were like, wait, this is going to change how we do multiplayer work? And if so, you know, what can our listeners learn from? Maybe that example of, you know, dog fooding is internally.

Ryan Gaffin

Sure, yeah. I mean, one of the things we talk about a lot and we see it and do it inside of Slack, but it's also a pattern that plays out at all native AI companies right now. And I think very quickly every leading company is going to want to follow suit, which is what I call building in the open. If you look at the origin stories of ChatGPT, if you look at the origin stories of Computer from Perplexity, Anthropic, Claude, and the unit announcement from a couple weeks ago with Tag and Claude, all those in Slack bots, all those are byproducts of building in the open. You're in Slack, you're working on this project, you're iterating with a group of people who are writing code, developing, building new pull requests they're going through, they're saying, this is working, this isn't working, I'm trying this, et cetera. And you iterate, you iterate, you iterate and you go through and you collectively go and build this thing at unbelievable speed. That's how we built Slackbot. You know, Slackbot started as a small team that was working on something. There's a channel, everyone's in there, we're testing it out, etc. We have a thing called Slackbot Unbaked, which is like the, you know, where the team's like, hey, I just built this feature. Everyone go try it out and we all bang on it and see this is working. This is great. This is amazing. This totally didn't work. And it's unbelievable, the collaborative power when you build in the open and the speed that happens. There's. And something super powerful is happening right now, which is. It used to be that building was the domain of product and engineering, but now builders are. Everybody in your company and everybody at your company now needs a platform to build in the open. If you're in marketing, you need to build in the open. If you're in finance, if you're in hr, everyone's a builder. And you have these incredibly powerful tools, not just Slackbot, but tools from Vercell, tools from anthropic, tools from OpenAI Linear. All these tools are deployed in Slack because that's where the humans are working, that's where the collaboration is coming together. And then you can use these tools to go and build and create incredible stuff. And so that, that kind of moment for us, when I saw the pace and the power of building in the open, how quickly we could iterate by doing that, and then I, you know, we're seeing that play out through all of these unbelievable AI companies out there. You know, it dawned on me is like, this is how everyone's going to be working in the future. We're just a little bit ahead of the curve. But everyone's a builder and everyone needs a building platform.

Jordan Wilson

Yeah, Ryan, that's, that's a great point. And I think it was zapier, you know, last week, the CEO there who was talking about that exact same thing, right, Building in public and maybe doing less in dms, right, for the reason that you can share more of that decision making with your team and make AI more, you know, multiplayer. So, you know, I'm wondering, you know, with the advent of Slackbot and you shared, you know, some of those obvious wins, does it change how you communicate? Whether for the better or worse, you know, knowing that essentially what you're putting into Slack is probably going to help you and your teammates in three months or three years, how does that change even how you use Slack or how you communicate something.

Ryan Gaffin

Yeah, you know, just building on your opening point, you know, there's, I'm going to, I'm not going to get it perfectly right, but the, the Shopify CEO Toby, he made it, they built an incredible agent called river and they deployed it and they said it's only allowed to be deployed to channels in Slack and the reason why, and I'm not going to get his quote exactly right, but he basically said, hey, if you're not like using AI and building and learning in the open, like you're, you're fundamentally in this kind of closed loop system where like an individual is working and getting better, maybe they're getting productive, but the larger team, the larger group, the larger system, that learning is not compounding. And so like you have to be in the open. And that's why, you know, I think companies that still run out of the inbox are going to be in trouble in this, in this era because we do need to go to move at the speed that the market demands right now. Learning has to compound and has to compound quickly. And so that's why, you know, having, you know, a tool like Slack where like you are working in channels and you are doing that in the open, it's really simple things. Of course there's always a time and a place for an individual message or something that's more private and like, you know, of course we have all the affordances for that inside of Slack with private messages and private channels, etc. But the simple truth is when I have a question for an individual, there are nine times out of 10, there are eight other people on the team that are going to benefit from seeing that back and forth and learning from that. And when someone gives a piece of product feedback on a feature and there's a responsive eye, the whole team being able to see and understand that benefits. So this idea of learning and building in the open and allowing your AI to see and learn from that means the AI becomes exponentially more valuable. It becomes trusted because I know it knows me. And when it talks and it's giving data, I know it's coming from and it's, I can see the sources in Slack. So you know, that is why you know things like Slack bottom in like this incredibly fast adopt feature because it, it creates that trust where you're not coming into this with like, ooh, what do I share? What do I not share? Like, it's, this is my Slack and it's, it's in my permission base, it's in my trust, everything in there. And then I know that AI is permissioned against that. And so I can just operate as I would like. A trusted teammate. And that's how it feels. It feels like I have a trusted teammate who I trust just as much as I would any other team.

Jordan Wilson

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Yeah, and you know, we've been talking a lot so far working inside Slack, which I think is super valuable because so many teams, you know, run their day to day inside of Slack. But there's been a recent shift which you alluded to with you know, things like Claude Tag, right. Which integrates with Slack, you know, model context protocol, you know, recent Slack mcp and you know, the Slack's parent company, Salesforce has been a leader and one of the first big SaaS companies to say, hey, we're going to really focus on headless in the future. So can you explain kind of this shift from maybe, you know, quote unquote pushing people to go into Slack and use Slack versus should we be just using the data from Slack in these other platforms? How do you begin to unpack that in kind of this more recent shift toward just working headlessly?

Ryan Gaffin

Yeah, so it's a great question. The, you know, just start with Salesforce and the announcement that we made last week which was, you know, anything Salesforce can do, you can now do through Slackbot. It's the simplest. So we Slackbot's an MCP client. It connects to our Salesforce MCP servers and so Slackbot cannot Just read. But it can write and can take actions and go and work directly with your CRM, which is unbelievably powerful. And we'll start with kind of a just a simple frame. If you back up and you say, wow. Many companies use Salesforce sales service marketing. But the reality is even as successful as Salesforce event, only a small percentage of the employees actually ever see Salesforce. Right? The sellers see it, the service team may see it, maybe the managers see it. If you're in the marketing side and using marketing, you'll see it. But like the product engineering teams don't, you know, marketing teams don't see sales cloud. Like they don't, they don't use that system. It's, but it's an unbelievably important system. It's like the customer record. It's the source of truth. It's where you're seeing what's going on with your customer's service issues. Like this is unbelievably valuable data, but it's not really accessible to most employees. So what happens when you can take a tool like Slackbot and you can safely, in a permissioned way, have that connected up to the Salesforce data? Well, it turns out that data becomes infinitely more valuable. That resource, that system of record becomes infinitely, infinitely more usable. Because now whether in marketing, you may never have seen Salesforce, you may not even know what it looks like. But now I can ask a simple question of like, hey, I'm prepping for this IBM meeting. What's been going on with the IBM account? What's the latest issues? Are they having any service issues right now? Tell me about the last five meetings we've had with them. What went well, what didn't go well and what do you think are the things that they're going to be most excited to hear about from now? Slackbot can go talk to the service, you know, our agent Force service cloud, it can go talk to our agent Force sales cloud. It can go look into the IBM account channel again, that's in the open and go and see all the discourse of how the team's been working through it and bring me back this incredibly rich answer and insights. And not only that, I can then take action based on that. I can say, oh, that opportunity record, I actually just met with them. The opportunity is actually 250,000. It's not 200,000. Update that opportunity. And I can just do this by talking to Slackbot and you know, I'll just, I'll give you as reading a stat just Last week this kind of blew me away. There was 1.8 million slack bot messages that were sent inside of sales by Salesforce employees just last week, 750,000 of those were talking to and writing to Salesforce. So like think about that like in terms of, and these, these type out will tell you hey, it's querying Salesforce. But these people didn't have to say go talk to Salesforce or go talk to agent for Sales. They just said what's going on with this account? Or I want to go in this opportunity. So this headless strategy is like the exponential unlock for the value of your CRM data. And when you can bring it into the conversational interface of Slack, when you can bring it into where the humans are working and when you can make it super accessible with a tool like slackbot that, you know, to cite a design principle that we have aside, you know, we think we say all the time, like when we build software we don't want you to have to think like don't make me think it should just work. And when you can couple those things, it's a really, really powerful moment. And of course it extends to our entire ecosystem. So you were talking about anthropic. You know, Slack's an open platform. So whether you're Box Atlassian, whether you're Vercel or Linear, all these organizations are building their AI into Slack because that open ecosystem, we know the enterprise doesn't stop at just Salesforce. It's got Microsoft, it's got Google, you've got all these other enterprise systems, got your own custom applications, all those need to be working, connected in and the power of those systems becomes exponential when it's easy to access with this conversation.

Jordan Wilson

So you know, obviously as builders of the technology, you know, I, I assume that many within the Slack organization have been working with an agentic first mindset for quite a while. But for the rest of our audience, you know, for our maybe non technical business leaders who, you know, their organizations run inside of Slack, how should they be changing their mindset right now? Right. Like how does someone become an orchestrator of work, you know, versus just a doer of tasks and you know, how does that change with things like slackbot or the, you know, Slack mcp?

Ryan Gaffin

Yeah, I mean there's a couple fundamental trends. Like one, you know, we do need to kind of recognize that this agent and agent capabilities are kind of reaching this like explosion inside the enterprise. And you have to empower your teams and your individuals to be able to manage that din. And I Say din. Not to diminish these tools or the value of them. They're incredible. But, you know, at the end of the day, there's still an employee who's trying to get their job done, and we're asking them to leverage and take advantage of these tools and technologies. But it's overwhelming in some cases, in some cases, entertaining. So the first thing you need to do is you realize you've got to have a platform that you can go through and have a deployment place for all this in technology and intelligence that your employees can use and understand and makes it accessible. So you need to have those agents connected into something like Slack. Slack, really the only platform right now that allows you to do this at scale and then allow your humans to be able to work with those agents. Why a simple interface like Slackbot? So to your point, we can get to the place where everyone can start to feel like a builder. So, you know, I have more agents available to me inside of Salesforce and Slack than I even know about. But when I, you know, think about getting a task done, I'm deploying probably four or five different agents at any given Slack bot query that I don't even know about. And that, that allows me to work without friction, and it allows me to tap a lot of these capabilities without, you know, under underlying kind of the, you know, patterns and practices of the sins of enterprise software, which has been, you know, we have a thousand enterprise applications inside of our enterprise. I'm switching between 10 to 12 of them every single day, and I'm wasting 40 to 50% of my day and like, the work of work. And I think that's the real thing. The, the piece that many people aren't talking about right now is, you know, go back to something I started with. Employee productivity. Like, sounds kind of like buzzword nonsense. And sometimes it's like, oh, yeah, what, what does it really mean? Like, most companies spend most of their money on their people. Like, 30 to 60% of companies spend that, you know, their capital on people. And if you can make your people, like 3 to 4x more productive and get the work of work off their plate, that's like 100% revenue growth. There's not a lot of 100% revenue growth ideas just floating around the boardroom. And so this is a moment where everyone kind of needs to reevaluate how your company works. And that's why I made the comment earlier about the inbox. The inbox is death for this. Like, if you, if your employees are spending a good percentage of their work time in the inbox. You're in trouble. You've got to, you've got to shift that because you will not be able to keep this.

Jordan Wilson

Yeah, that's, that's a great call out there. But you know, Ryan, we've talked about a lot on today's episode. You know, from what's new in Slackbot Headless Revolution to changing your mindset and the value of those back and forth conversations. But you know, what's the one most important thing business leaders can do today as they're grappling with maybe transitioning, you know, their AI strategy from being a collection of individual AI contributors to that true multiplayer agentic orchestration. What's the one most important move they can make?

Ryan Gaffin

Well, you know, I don't know if I can always sum it down to one, but if you're a company like Box, Box is saying, hey, our sales team out of their working time, their non selling time, they're going to spend 80% of it all in Slack. And those, the, Slack is going to be the connective tissue between all the enterprise systems that they have, including Salesforce. You know, if your engine who gets like 800,000 customer inquiries, they're saying the way we're going to manage the, the, the, the, the scale of our business and having one connected truth is by bringing it all into a connected system like Slack. So the, the, the one thing I would encourage is like you have to really take a cue from how, you know, a perplexity or an OpenAI or anthropic how they build. There's a reason why those companies say Slack is their work operating system. You know, Anthropic said Slack is our work operating system. There's a reason why they say that they run the company from this tool. And you know, the one thing I would encourage everyone to do is like this is the moment to reevaluate how your organization works and how you build and how you enable everyone to become a builder. And it's not about one tool or one AI. It's about all the tools and all the AI and be able to unleash those in a way that is sensible and manageable for your employees. And that's kind of why Slack and Slackbot are kind of having this incredible moment right now. It's almost a, it's a renaissance in many ways because we're seeing this explosion of AI coming into Slack. We're seeing explosion of AI utilization in Slack because of Slack bots making it simple and approachable. So it's time to rethink work is the short answer.

Jordan Wilson

I love that. And what a great way to end rethink work. It's what we're doing every single day. And hey, at least for today, Ryan, you helped us give us the good insights on how to do that. So thank you so much for taking time out of your day to join

Ryan Gaffin

the show, Ryan Jordan, I really appreciate you and I hope it was helpful. Look forward to chatting again soon.

Jordan Wilson

All right. And hey, if you missed anything, don't worry, we're going to be recapping all those golden nuggets Ryan just dropped in today's newsletter. So if you haven't already, please make sure you go to your everyday AI.com Sign up for the free D free daily newsletter. Thanks for tuning in. Hope to see you back tomorrow and every day for more Everyday AI. Thanks y'.

Ryan Gaffin

All.

Jordan Wilson

And that's a wrap for today's edition of Everyday AI. Thanks for joining us. If you enjoyed this episode, please subscribe and leave us a rating. It helps keep us going for a little more AI magic. Visit your everydayai.com and sign up to our daily newsletter so you don't get left behind. Go break some barriers and we'll see you next time.