S2E7: "Be the Olympist of Your Field" | Guillaume Cabane

Welcome back to the GTM Engineers School Podcast, Season 2, From Hype to Operating System. Because now that GTM here is here to stay, we want to know where it's heading. And today's episode is a masterclass in what happens when a CEO lives through both sides of the GTM transformation of the last 10 years. Last years, the old and the new way, and comes out the other side with a fundamentally different playbook, which we all wanna hear about. So Chris Rudyrap is the co-founder and CEO of Sendoso, the sending platform that lets revenue teams trigger physical gifts, direct mail, and branded swag right from their CRM, and even enrichment tools now. So we wanna hear about that in a bit. Think of it as the physical channel in your GTM stack. Made programmable. Before founding Sendoso in 2016, Chris was an SDR and AE at companies like Talkdesk, which is where the aha moment for Sendoso came from. He was actually hand-packaging gifts, going to the post office during lunch breaks, and manually tracking who got that. So he saw the gap between the CRM data and physical sending, and the rest is history. So here's what makes Chris's perspective essential for the GTM engineering audience. He scaled the old way first. During the ZIRP era, Sendozo raised over $150 million, including a $100 million Series C from SoftBank, grew up to 500+ employees, and ran a 50-person SDR floor. Then the market corrected and Chris had to rebuild from scratch. So today Sendozo runs with a fraction of the team, an agency model for outbound, and AI agents handling what used to take dozens of people. The GTM engineering team reports directly to him. We'll definitely hear more about that too. And just this month, Sendoso's Klaviyo integration went live, meaning GTM engineers can now trigger personalized physical sends as a Klaviyo action right inside their Klaviyo tables. So today we're covering the full transformation arc from headcount-driven to capability-driven GTM, why physical mail might still be the most underrated channel in an AI-saturated world. And what Chris has learned about building AI agents inside a revenue org. Chris, we're fired up to have you on the show.

Thanks for having me. Really excited to be here and a lot of hot topics to cover today.

Yeah, great, great to have you on, Chris. Chris, I want to get into it, but I want to start from the beginning. Sendoso launched back in, what was it, 2016?

Yeah, exactly. Okay. So what?

I'm very interested. What did the first version look like? Who was your initial customer? And then, uh, like how did you realize that you really had something special here?

Yeah, so the first version and the first customer was me, for me. I built this because I was, you know, prospecting, outbound, trying to book meetings, close deals, and I found that email was becoming more saturated. Ironically, that was a decade ago. And so I was testing out, sending out handwritten notes. I'd go to our marketing swag closet and pack up swag boxes. I'd even hear like a dog. On a, a call bark, and I'd send over a dog toy from Amazon. And it worked really well. It was just super manual. And so I said, hey, let me build a solution to solve for this. Now, my first V1 was kind of a nights and weekends, kind of a hackathon project called Coffee Sender, actually. And this is where I would actually just send out Starbucks gift cards as another way to, uh, break through that digital email-only noise that I was doing. And that worked really, really well. Um, in fact, so well that my co-founder, quit his job to start full-time at Coffee Center even before I did. And then kind of the, we quickly realized that there was more to that and people were asking, hey, I love sending gift cards, like what else can I send? And you know, that was kind of, uh, an aha moment combining my pain of sending physical gifts, packing boxes, Coffee Center starting to work, and then, uh, seeing that this was gonna be more than just a tactic. This was gonna be a strategic kind of channel going forward. So, uh, Sendoso was born and then we quickly built out all of our warehousing infrastructure, built out all, uh, full-blown, you know, SaaS software suite, data layer. It was quite a bit. And, uh, luckily we had a lot of early customers and, but being customer one, I think gave, gave me a unique advantage to figure out how to build the product, sell the product very early.

Yeah, that's That's key. That's awesome. Now fast forward a decade later, lots of organizations, they are redesigning, they're reimagining what their teams look like, what their stack looks like, which channels to invest in. And you know, they're doing this with go-to-market engineering, with, with now with AI agents, Claude Code, maybe OpenClaw, who knows? So what's remained the same in terms of your customers and their needs? Or your own go-to-market and, and, and what's, what's been the biggest change for the, for the better?

Yeah, well, I think, uh, our customers still need to grab the attention of their prospects. They still need to build pipeline. They still need to retain and engage customers and, and ultimately still need to build relationships too. And so I think that, uh, will never change regardless of how AI is and the, the AI tooling and the, the go-to-market engineering stacks evolve. I think people need to buy from people. People need to, you know, build pipelines. So I think that has stayed true this whole time. But the way we sell into organizations, the way companies use us, the way customers want to deploy Sendoso is starting to evolve fast, especially for our early adopters and how they think about kind of more programmatic direct mail and gifting from like click a button direct mail and gifting. So that's been interesting to see. And then from our side, Similarly, we've changed with the times too, and, you know, go-to-market engineering, AIOps, and agent building, all of that, which I think is something that both we want to be ahead of the curve on because we want to be able to educate and share our wins and our stories of how our go-to-market engineering team is evolving with all of our customers who see us as a forefront innovative partner. But also it's fun. I think it's really a fun time to be in go-to-market because you know, it's not just a rinse and repeat playbook from last year. It's like you're reinventing not only the playbook, but also kind of the team and the strategy behind that playbook.

Yeah. That's great.

Yeah. Great segue. Like I want to definitely dig deeper into this and let's try to separate hype from reality here. You know, we've been on both sides. You scaled headcount heavy models during Xerpa and now you been rebuilding for a leaner and AI-first era, right? So where do you think, you know, like having been on both sides, GTM engineering is actually feeling more of like a step change versus, you know, like a bit overhyped by everything we're seeing on LinkedIn?

Yeah, well, for us, about 3 years ago, we invested heavy into kind of redesigning our SDR and our outbound strategy. We went heavy into Clay. User Gems, a handful of other tools that really allowed us to take our old model, which was let's continue to hire rapidly, you know, and each person can set a number of meetings and then it's just like a math function. They ramp, they, you know, a bunch of them, you know, end up leaving, we rehire, and it was just this like, this cogwheel of people. Instead, we really looked back at, hey, what does the day-to-day look like? What are the parts of this that can be, uh, orchestrated through automations, through Clay, through what kind of, what are some of the steps that take a lot of time and effort that AI could get better at, like data orchestration, like writing segments of emails. And so all of that really allowed us to kind of take one step back to take like 10 steps forward because, you know, the plane's in flight, so you can't, you know, just like stop your outbound team. So we had to like, really strategically say, hey, we're going to do this. And there was about a quarter, 3 months-ish time where we were really doing both of these motions at the same time, just so that we could kind of transition. But in the end, I think it was critical and we were probably still a little earlier than most companies saw the light to this, but it was also because we had a sizable team and we are also focused on, you know, transitioning out of that ZIRP era into transitioning into this more, thinking of the unit economics and thinking of, uh, more of a cash flow strategy.

And what have been those main challenges in going from, you know, like a 50-people sales floor and this people cogwheel, as you mentioned, you know, like into a more like AI-driven or orchestration-first setup?

Yeah, so I think some of the challenges were how do we educate the company on this change? How do we think about enablement differently? How do we think about hiring and headcount? Because we, you know, the SDR team was really all the same, and now our SDR team became this hybrid of kind of these like super SDRs mixed with GTM engineers. And so that structure needed to change. There's also kind of an agency component to bring in to make our shift to Clay that much faster. So that was a critical new component before because we were not ever using an agency when we were in kind of the old model of just headcount-driven SDR outbound. So all those things changed. And then there was following that, you know, forecasting changed a bit. As we previously, it was very easy for us to look at, you know, the output, uh, or the capacity of a single SDR and then do the, the math in a spreadsheet. In this newer model, it was harder to forecast, hey, how many clay tables, how many contacts, how many, plays are gonna generate how much meetings and pipeline. And it was less tied to the headcount and more tied to the activity and, you know, the different types of tables and plays we were running too. So forecasting became more unique as well.

Very interesting. You know, like, and how is that so? Like, you know, like, just can you share a little bit more? You know, like, cause if anything, like, it sounds to me like it is also like expectations from investors maybe, or like from the market. Do you think like had like a big step change that influenced your forecasting process or like with this whole narrative that, you know, like AI is a big forcing function for productivity and so on and so forth, or does it have to do anything with also like the, this change in forecasting or yeah, like for planning for volumes and stuff?

Yeah, so I think part of this was driven by our board and our strategic change from kind of the ZIRP era to like, how do we rethink our business where there's not infinite cash and you're not fundraising infinitely every year? So that was a directive and, and AI was one way for us to see, uh, an opportunity to impact our, our bottom line. But on the forecasting side too, we had to reevaluate our forecasts and reevaluate both from the, the top-down and the bottoms-up model on, you know, all aspects of the forecast and then within each one. Because I think entering a new world, you know, for, call it like 6, 7 years, we had this predictable revenue model that most SaaS companies did that was kind of the same playbooks. You know, we brought in new hires, they all knew the same playbook. It was all very headcount driven. The spreadsheets were already built. People could reuse it when they came over to their, from their last company, their new company. And then all that changed, like for us, you know, 3-ish years ago. Where we had to now kind of like reinvent some of the, uh, headcount models, reinvent some of the go-to-market engineering strategies, reinvent some of the forecasting. So that's been fun and it's been getting better and better. And, you know, I think the— a lot of folks are on the same path. And so now there's more data, more examples, more, uh, opportunity to, to trade notes too.

Awesome. And in this like massive change, like, uh, how is the narrative for Sendoso still valuable? You know, like you've, uh, clearly like, you know, we're all being overflowed by, uh, um, cold outbound and, uh, emails has reached higher and higher levels of saturation. So how is like direct mail, you know, like the silver lining or like the differentiator in all of this?

Yeah, I mean, it's kind of ironic that about a decade ago I started Sendoso because I thought email was saturated and spammy, and I think that was definitely not peak spam yet, not even close. So I think by luck or just by like being early, I, you know, we are in a perfect spot. I think there's a ton of tailwinds now where, you know, email as a channel is becoming harder. Now I'd say I am not anti-email, but I'm anti-email only. And I think for a while, for maybe the past couple decades, companies could rely on an email-only strategy and still win. But I think now it's more of an omnichannel strategy that wins. And so again, I don't think it's a direct mail only strategy is gonna win. I say that's not a good strategy either, but it's how do you think about this buyer's journey and how do you think about email and social and ads and direct mail and phone calls and field events and, and these different channels to grab the buyer's attention because it's harder than ever. And so I think, uh, you know, there's no longer an opportunity just to be an email-only, you know, go-to-market strategy.

Chris, at the peak, let's— when, when you had 500 employees, 50 SDRs, what was that mix?

Uh, you know, when—

what did, what did the perfect go-to-market motion actually look like for you? How, you know, where did you go from sending out emails to sending out gifts? And, uh, how did, you know, how did you think about in, in investing in, well, I don't know if events were much going on in, in that particular year, but, uh, you know, something was working then and then you realized that things had to change. Um, what was that moment when, when you realized things had to change?

Yeah, I mean, so for us, we've always been very omnichannel, uh, because of the fact that direct mail has always been in our blood. So we were always running that playbook of emails, events, I mean, even virtual events when COVID hit and direct mail and phone calls. We've always been big on cold calling, et cetera, et cetera. So like this transition from, you know, yesteryear into this new phase, the channels haven't been a big impact to us. It's been some more of like the people and the, kind of go-to-market engineering, AI-first mindset has shifted. But in terms of that old era, you know, it was kind of that model of, you know, you pick an annual plan, you pick your, your growth number. Do you want to double the company? Do you want to triple the company's ARR? And then what are the heads that need to be filled in fast to support all that growth? And I think that, uh, shifted because we, and a lot of companies, moved away from this like growth at all cost model to this like more sustainable growth, uh, from '22, 2022, 2023, 2024. And so that really, we had to reevaluate headcount planning, you know, the aggressive growth strategy wasn't, uh, effective anymore because a lot of people maybe either knew this or didn't realize this, but the, that like doubling and tripling the business really is like hiring ahead of schedule and hiring a bunch of people before you, uh, have the need for them in, in essence. And so you have to like basically overperform early to hit your numbers. Um, and so that strategy just kind of like fell by the wayside a bit for a lot of VCs directing their boards to say, hey, you know, you can't go raise another infinite dollars next year. And so we had to rethink that. Um, and it, it's been a, a fun path, uh, both from rethinking, uh, our go-to-market strategy, rethinking our headcount strategy, thinking our agent and automation strategy, our M&A strategy. All those things evolved from like having to think differently.

And now this is something a lot of leaders are going through, but you've been, you know, more candid than most on the human cost of downsizing. So like what, What in these transitions was, was like the hardest decision you made? And, and, and what would you tell a founder who was, you know, sitting now where you were a couple years ago, uh, knowing that they need to, to cut and, you know, not, not get paralyzed by it?

Yeah. You know, I think, uh, I mean, the hardest part is the people and the, the friendships that we had to part ways with. You know, the Seneso family that wasn't, you know, critical for that next phase of, of life for Sendozo. Now, that being said, we were able to retransition a lot of people, um, and a lot of folks moved in different roles, different departments. You know, like, uh, one of our best SDRs became one of our best partner development reps, and we, we were able to shift a lot of smart people around. One of our best SDRs ended up becoming like a community evangelist and went on to becoming a VP and And like, so there was a lot of smart people that we just like repurposed because they were not fit for this like SDR of, of yesterday's world of just like repeat, you know, copy paste, click, click, click. It's like, hey, you're, we, you are way more valuable. So let's move you into another part of the business. And so that was fun. But I think in the end of the day, you know, some advice is to just think about how do you educate the rest of the company on what's going on? Uh, and try to remove any skepticism and any rumors and really reset the expectations. And, and it's almost like a, an Education 101 class on like what you were doing before, what that strategy was, why that strategy changed, what's the new strategy, you know? And I think a lot of that we did well. And so a lot of employees were just like, cool, I get it. It makes sense. And thank you for giving us the details behind the why instead of just like, doing it.

How much did the structure of the actual structure of the company change? Were there certain departments, certain functions that you just eliminated completely and others that, that you created out of nothing? Or was it like, you know, all the departments kind of just transformed, but basically the same structure?

I mean, the biggest transformation was just thinking about our kind of go-to-market engineering and thinking about how do we really think about operations and automations more. And so I think for probably last year and the year before, uh, before I'd say agents were such a hot topic, um, that's really something that over the last year has been critical for us. But kind of 2 to 3 years ago, it was more of like automations was the, the keyword for us and automations and operations. And so we figured out what are the different, uh, leads in the different departments that had subject matter expertise and could help understand business processes and, and operating processes that we could look to automate through N8N and through other tools. And that was kind of the biggest aha moment for us was how do we create productivity gains in a world where you can't infinitely add more humans? And so how do you make your, uh, humans, uh, more effective?

You know, they say in, with, with change management, it's always best to find some early wins that can kind of inspire the team and show them that it's possible. Were there some that you think about as kind of early wins here?

Yeah, so I mean, outside of the early win with the SDR org, which was a great signal to the company that AI was an effective way to evolve the business and still see, you know, effective progress., then, uh, some other early wins were, um, what, so we were pretty early on in building this kind of what I would call like GTM engineering/AI ops team. And one of the early wins from, from the account management side was this agent, kind of think of it as like an, so our first agents were really around like more analysts, Biz Ops type of agents, which were really processes or workflows that were usually internal that were more like helping employees work better. We have a newer strategy now, but for let's say last year and the year before, that was really our mindset. And one of 'em was we found that a lot of our, over the last decade, we had contracts that were hidden in like PDF links in Salesforce. And this was painful for the account managers that went in to do renewals where they would spend like 30 minutes remapping what that old contract was, what were the custom parts of that old contract. Pulling that out, copying those into the new contract for the renewal. And so just the contract effort was like an hour-long busywork. And some of these, some of these account managers were doing, you know, dozens and dozens of these renewals a week. And so we were quickly able to build this like date contract analyst that basically went in, parsed all these documents, threw them into Salesforce fields, and then use those Salesforce fields and then pre-populate the next contract. Again, it sounds kind of basic now, like, duh, that's easy. But like, I don't know, 2 years ago that was, you know, a unique opportunity for us. And that was something that was a big win because all the account managers were like, this is amazing. Now I don't have to like copy paste busywork. The other one that comes to mind too, from, you know, a year plus ago was how we looked at our like win-loss analysis, uh, which again historically was someone in Biz Ops, an analyst would go and to the board, to the GTM leadership team every quarter, would pull in a bunch of Salesforce fields based on what the, the reps, uh, either the AEs or the AMs would mark as closed lost and then do some pivot tables and say, hey, here's a spreadsheet. Instead, we built this, you know, analyst, win-loss analyst that pulled in all of our, uh, Gong calls and all of the transcripts, all of the emails, all of the, uh, Salesforce data, all external data, and then put together using AI, a real story, a win-loss analysis. What's also built instead of a spreadsheet was like a webpage you could click into and you could go deeper on and you could listen to parts of the transcript that mentioned things. And, and so that was a big transformation too, because that was now instantly available real time. So instead of being a quarter behind, we were, you know, real time seeing this weekly. Um, and then also instead of it being, you know, what the sales rep picked in the dropdown, which not always is what the real answer is, it was more of a data-driven from all this GTM information. So those were probably our early wins in terms of like agents that we built to make ourselves more productive and smarter.

Do you have like a whole backlog of agents you want to build and the prioritization methodology?

So basically what we did is, uh, we, some of the low-hanging fruit, built a lot of workflows last year, dozens if not hundreds of these. Most of these are, you know, productivity gains, prep for meetings, post automation for meetings, things that reps would take time on. Um, we realized too that, uh, now the tech, you know, with Claude Code, with these other coding agents, um, the, the infrastructure is ripe for building full-blown agents for us now. And so we're shifting from more of a, a workflow mindset or an automation mindset to a kind of a digital colleague coworker mindset from a, uh, and, and even customer, more customer-facing, purely automated, uh, agents as well that multitask porting into a human. And so we have spent like the last couple months thinking about that framework, thinking about that strategy, rebuilding some of the agent infrastructure. So previously kind of our go-to-market engineering org was a bit more hacky, you know, going out and finding tech solutions that they could work through. And instead now we're like rebuilding some of the foundation from our engineering and product team, refocusing on kind of that base infrastructure layer, the data pipelines, et cetera, so that we can set up ourselves for success to then rapidly roll out probably 20 or 30 agents. Some of these are like, you know, field marketing agents, content marketing agents, customer success at scale agents, some finance agents, you know, it spans more than just go-to-market, but I would say if we did this podcast in a year, we'd be looking at probably 30 to 40 agents that have dozens and dozens of tasks that each of them do.

And is the, you mentioned N8N and then, and then, and then Cloud Code. Are you using, like, what does your stack look like? Are you using other off-the-shelf agent building tools?

Yeah, so we, you know, I think N8N was a really awesome fit for us a year and a half ago and we built some really cool automations. The, there's a couple things that spawned from that. One is Some of those workflows were harder to update and were also very invisible to the company because we had so many single workflows running that it, for some employees, didn't feel like they were getting any help from their bandwidth. It was like some of, some people just couldn't see what you couldn't see. So conceptually switching to this agent model actually makes it a little bit easier for people to be like, oh, there's a content marketing agent that's writing a bunch of content and they're doing all this stuff. Like I conceptually get that. Or, oh, there's this. Tech touch account manager agent that's helping engage with customers. That's interesting. I can, uh, comprehend that. So the, that shift has helped us kind of from an employee awareness perspective, think about these like digital colleagues, like, hey, who else should we hire/build? And that mindset has been interesting to shift. Um, and with that shift came us, uh, focusing less on NNN and rebuilding a lot of those through cloud code. Uh, a lot of it's still built on Databricks, LangChain, AWS Bedrock. There's a magnitude of new tools now that are helping us with agent infrastructure, observability, governance, evals, orchestration, runtime, workforce planning. It's a whole new tech stack that evolved and it's exciting times because a lot of new companies are building, you know, dev tools. To support this new era of agent building. But I think Claude Code is the obvious winner here, and there's so much you can do with Claude Code.

And how are your employees accessing the agents? Is that through— they're interacting through Slack or?

Yeah, for the most part, it's a Slack interaction. We think that's kind of the easiest way to interact with these agents from the, like, non-builder teams. Obviously, the builders are on in all these tools, but we're trying to, uh, build out Slack as an easy way for, for interaction with these agents and, and awareness. And, uh, um, yeah, so I think that Slack's a great way for that.

Amazing.

Do you feel like you're really at the very tip, the, the cutting edge here, or you feel like what you're doing, your, your, your peers, other CEOs, you guys are all talking about the same thing, all doing the same thing?

Um, I think we are cutting edge. I think we are ahead of the curve in terms of our, you know, learning curve from 3 years ago, building out our Clay automations from last year, building out dozens or hundreds of end-to-end to now building agents and how we think about that from a strategy, from a workforce planning. You know, I think there's probably folks that would say, hey, we've got way more agents running than you, but I don't think that that's necessarily like the You know, the definition of success, it's like, how does this work with your business? How are you scaling, growing, retaining customers? How is this integrated into your overall business strategy? Because I think it's easier to have these rogue agents and say, hey, I just built an agent last night. But having that definitive strategy that your entire exec team and employee base is on board with, um, I think is a big win. And rethinking our framework so that we can, you know, scale our agents is big. So I think there's a lot of things that we're doing that's cutting edge.

Is there a tension sometimes between employees coming up with ideas, you know, sharing ideas around, hey, you know, I'm 20% of my work right now is this thing. Hey, can we go build an agent for this? But then the fear that their work is going to be AI'd away. Is there that tension at all?

You know, I thought I would— yeah, AI'd away. I know there's like, we need new vocabulary now for all these new things. I sometimes call it like AI-ify and I'm like, that's probably not a real word, but it's probably some like, I don't know, tech company name now. AI-ify sounds like—

there's an Apple-fi, so that's—

yeah, it's true. So I think there was a lot of kind of hype that, you know, employees would be scared of their jobs as it relates to, to this new AI agent era. But I think there's a lot of, we're seeing a lot of employees are embracing it and And it's a fun new way to, to learn, to expand what they know, to adapt to this changing world. And I don't think for the most part, uh, employee, a lot of employees are, you know, worried about their jobs. They're just worried about how do they get better at, you know, understanding this new world. Because I don't think this is a world where like agents are just gonna come and go. I think this is like a new way of work. And so people are excited to figure out how do they work with this new way of work and how do they, see their ideas turn into actions. And so I think it's an exciting time for all employees across the company. And we're seeing some of the employees like raise their hand to want to join, you know, this new like AI center of excellence we built because it's so exciting and they want to learn these new skills. So I think there's just a lot of media hype that is maybe scary for people, but then once you talk to them, there's real excitement.

Awesome. All right, let's switch gears for a minute. Talking about, you know, direct mail as a programmable channel, you know, your, your core business here sort of foreshadowed all of what we're talking about today, but 10 years ago, and that's kind of what you did early on. But most, uh, still most go-to-market engineers probably purely think in digital channels and, you know, they're thinking email sequences, they're thinking LinkedIn sequences. Make the case for folks, why should they be sending physical products, gifts to people? Why should that be part of their stack? Who's definitely gotta be thinking about it and who, you know, for whom is it really, you know, likely below the line for good reason? Like, you know, where do you, where do you draw that distinction? And then after that, I wanna get into scoring for, for a minute, 'cause it becomes so much more important when you're, when you're sending a $50 gift.

So I, I mean, call me biased, but I think every single company, every single go-to-market team should be sending out gifts and direct mail. There's no excuses anymore. I think pre-Sendoso era, sure, there's bandwidth constraints. Oh, I don't want to pack boxes for 50 hours. Oh, I don't want to become a supply chain company and order all these items and kit things like, but that's not the problem anymore. And it's also not the problem that you have to worry about. Spreadsheets and clicking buttons. We've created, you know, automations and APIs and easy ways to, you know, programmatically do direct mail and gifting. Even the costs shouldn't be a concern. Even if you're a very SMB ICP, you can find gifts that are, you know, $5. You can even get creative with it. You could, you know, we've seen people get creative with like sending an empty pizza box with like a little mailer inside or sending like a, a golden ticket trying to drive people to an event. So I don't think cost has to be the reason. I don't think effort has to be the excuse. I don't think what to send is no longer an excuse. Where to send is no longer an excuse because we've even rolled out AI tools on top of our programmatic infrastructure and AI agents for our customers that will suggest what's the right gift to send based on the person's interests and everything we know about them. Where should we send it to based on the address data we know? What should the note be that goes with it? When should you send it? All that stuff now is available through our platform. So yeah, I mean, I think the, any listeners or any folks that haven't done it yet probably were either scared of the operational efforts and/or just didn't know we exist. But once we, you kind of know we exist, it's, uh, you know, uh, kind of a no-brainer to try to automate us into your workflows.

When can you actually send to addresses that come out of, you know, some enrichment tool? 'Cause people are working at home, they're working at the office, who knows, right? Or when do you, you know, when do you really have to send them an email and say, hey, we'd like to send you a gift, click here and put in your address?

So we rolled out a smart delivery agent probably 6 months ago that will optimize for if the person's at their home or their office. Based on, you know, a lot of different data sources. And so we actually through that have like a 95% plus confidence in just sending it to where they are. So I think that there's less of an excuse there. Now there is a reason why maybe opting someone into it and giving them the email heads up, pick the gift or to exchange the gift could be a strategy. But I think the data now is good enough where you can send it without having any hesitation.

Really? So like 9 out of 10 times your clients are just using the algorithm to determine where the person is and where the gift ought to go.

And yeah, we have that option for them. Now there's still a lot of people that want to, uh, provide that, uh, digital first ask, especially in scenarios where they want to give them optionality because recipient choice is a thing. And sometimes people want to say, do you want this or this or that? But for direct mail, you know, postcards, other things like that, there's no reason not just to send it. Yeah. Yeah. Yeah.

For direct mail. Yeah. And then scoring, you know, once companies are thinking we, okay, we're gonna do this and yeah, whatever, they're gonna get a speaker or, you know, whatever, uh, Thermos, you get into scoring real quick. So do you help them with that or do you have advice? How do you?

We have some playbooks and advice, um, and we are gonna be rolling out a new, like, feature that allows for us to pull in some of these signals and scoring and, and give help if they're not using any tools already. But I would say like for the more savvy listeners on this podcast that are more like GTM engineering mindset, they've probably been able to use, you know, intent scoring signals and a lot of different data to score their own, uh, leads or contacts. And then ultimately we suggest segmenting that and then gifting dollar amounts or the gift campaign based on the different segments and where you are either in the funnel or where you are with your lead score, depending on what you get. Okay. Now it's not necessarily means that if you are very, have a huge score where your likelihood to want to become a customer means that you should send them a $2,000, you know, cool bottle of Whiskey, like maybe the better thing is like some, like, you know, $15 gummy worms because they like were bragging about that on social media, or you had an SDR call and we picked up on the transcript that they were, you know, a golfer and we fed that into our algorithm and we suggested you send them a sleeve of golf balls. So it's not always segmenting to try to find the most expensive gift. Um, that doesn't always win. It's more of the personalization piece, but I think it, it's never bad to score and figure out where you want to spend more money on first if you have a very limited budget.

Now your, your Clio integration, uh, when did, when did that go live?

That went live a month or two ago.

And, and, and are you seeing an uptick from it? How's that going?

We are. Yes. Uh, that was, uh, very well adopted and asked about many a times. Previously, you were able to do some HTTP API calling, but it's always better to have a native integration inside of Klai. It makes it so much easier. And the integration is great because we bring in the ability to trigger off GIFs as well as our trigger off SmartSend as well, which is like our kind of agent that goes out and finds people's interests. And so you can use that in your emails as well. So you can personalize an email before you send the GIF. Mentioning the gift that's coming, um, and then trigger off the gift itself. And again, it's perfect for folks that are running like us. They're, uh, a lot of their outbound through Clay.

So I've got a, I've got a list of prospects, use the integration and it's going to say, hey, here's where you should send it to. Here's what you should send. Um, you know, you put in your, your budget cap and that's it. The whole thing works.

Uh, the budget cap, not necessarily like that. There is some—

so I might send them that $2,000 bottle of whiskey.

Uh, well, you can set up an approval queue. I would say that's the better way to think about it, but it's not going to, uh, and, and, and you can also connect it to like a campaign in Sendoso that already has preset budget limits. And so you're just triggering off of things that you would be sending in a campaign. So it's like same concept, just like, not like you're entering in like, hey, I only want to spend this. It's, but Same, same where you have some controls over what you're sending, who you're sending to, and then you're just triggering it off through the Clay UI.

All right. You, we touched upon also your GTM org restructure, right? And you also told me that GTM engineering reports directly to you. So how's that? And you mentioned also about the AI, the agency component. Can you tell us a bit more about how the overall GTM org is structured in this post-zero payroll at Sendoso?

Yeah, so I would say we brought in, we bring in agencies to help offset from a technical or just headcount perspective where we need it. Bringing in a Clay agency was an obvious choice for us early on because we could augment what we didn't know with super smart agencies. I'm a big pro-agency fan wherever you can find them. I think we're leveraging some agencies for kind of the AEO, GEO right now. So there's, we're open always to exploring like the smartest people that are in the agency world that we can augment our talent with. Our GTM org, the GTM engineering and AI ops team's evolving to, you know, a place where it's so critical that I want to be a part of that conversation. Now, uh, there's still kind of more like some dotted lines there because of just the structure of the org and how that sat in marketing and how that evolved from like RevOps. So I mean, the long story was it was like SalesOps to RevOps to GTM engineer to AOP, AI Ops. And so there's been evolutions of that team and their needs, um, but they still kind of sit very close into marketing for that purpose, being, uh, directive by marketing. But I'm helping shepherd this new kind agent era, because I think when you rethink about this agent strategy, it really encompasses your entire company. There's workforce planning, there's budget strat, there's, you know, more of a global footprint that we're impacting across our entire company. So it's critical that I can help come in and, and see that from, from my seat at the top. But from a go-to-market perspective, you know, I think the bigger thing that we're doing is just continuing to think about agents in the org and what different teams would wanna hire somebody right now. And I think that's a unique way that we've rethought about yesteryear automations and, and gone to employees and said, hey, what automation should we build? To, hey, if you could hire somebody today, what, what would they do? And that's unlocked a lot of ahas for us because they're like, ooh, I'd hire another field marketing associate for the 50 field events. We need to like send out emails and we wish that we could send out hyperlocal emails and enrich our database up to date with their LinkedIn locations. And we're like, boom, we could build a field marketing agent that does all that for you and reports into you. And that's a win-win. And so that's been a big unlock. And, you know, over the next few quarters, we'll see many more of these agents pop up in our GTM org across sales and marketing. But also when I think about GTM, I also think post-sales too, and our account management team. Has a lot of opportunity to add agents to that team as well. Love it.

And you also like touched upon capability count as opposed to headcount, right? Can you unpack that a little bit for our audience? How do you actually—

Yeah, well, as well. Yeah, yeah. I think, you know, the old world math was always headcount driven. That is you can rethink that now because the unlocks that agents and automations and AI are bringing. And so you really need to think about like, what is the capabilities and the capacity of these agents, but also the employees that are kind of running them or reporting into them and really trying to do the math there around, you know, uh, what's that, what do those ratios look like? What kind of capabilities do you need? And thinking about like more like task-based than just like, uh, headcount-based. So I think it's just that you gotta kind of rethink a lot and almost unlearn what you learned before to take advantage of all of the kind of opportunities this new world is giving us.

So it's the shift towards more outcome-based and measurable outcomes, right? You know, and like actually owning that and unpack, like, or unlinking that compared to, like, from like a specific person or like a flat salary, basically.

Yeah, I think that's a good way to put it.

Very cool. And, um, yeah, I think where you moved also like from a large internal SDR team to an agency model, we talked about that a little bit. When do you think, in your opinion and your experience, like, uh, dealing with agencies, it makes sense for a company to actually, you know, lean on external experts and masterminds in their field versus internalizing it in-house?

Yeah, I think it's critical to do both. I think you want to lean on agencies who are, like you said, the masterminds in their field. They can, their ability to execute can be a step function above you trying to learn something. Um, and so I think we try to lean on agencies, um, as much as we can. Uh, with that though, we want our team to be proficient. So like we leaned on an Clay agency, but we also became proficient in Clay. So it wasn't like we were blind, but we just needed the experts to come in and continue to help, uh, augment our team and also augment our expertise. And I think that's a smart framework to think about entering this new era. Where you can bring in agencies or kind of fractional consultants, freelancers that might not wanna work for you full-time because they're having so much fun in their kind of agency freelance world, but you still wanna be able to, you know, leverage their expertise. And so it can be a win-win to bring 'em on and have 'em be a part of the team, especially in this new world where there's a lot of learnings and a big learning curve around building agents, building workflow automations that you might, uh, have kind of paralysis if you're a team just focused in-house only, and you might be too slow where you can rapidly run with an agency or consultant model or just augment your time. Like another thing we're doing is we're augmenting agent building with, you know, smart agent builders that we, uh, run across that, uh, we can say, hey, instead of us building 3 agents this month, you know, maybe we could build 5 by augmenting that. And ideally some of these people we would hire in the future if we could, but there's so many smart people that just don't want the corporate 9-to-5 grind and can make a boatload of money just being fractional expertise or agency owners. And so power to them and we'll work together with them.

Okay, I think we're coming close to the end of this episode, which I've enjoyed so much. Couple of final questions. If you were advising a VP of marketing or head of revenue today, and for whatever reason they've never invested in really deeply in the direct marketing or gifting channels before, what's the first step for them to kind of get off the starting line?

Yeah, I mean, I'd say the first step is to probably educate themselves a bit more on the channel if they're not familiar with it enough. We've got an awesome, like, certification and university where they can learn a ton. Talk to their peers too. We have got tens of thousands of people that have become, you know, gifting, you know, and direct mail experts. So I'd say collaborate with your peers. I think that's the, or find and learn and, you know, watch videos and, and that's a great way to learn. And then I'd say jump in. I mean, the other thing that I would say not to do though is not to think about this as this like one little A/B test where we're gonna send out like 10 gifts and if we get 10 meetings from that, then we're gonna continue. I think it's more of like, hey, this is a new channel that it's obvious you need to do. So let's build this into your annual plans and then just go incorporate it into your strategy instead of thinking about this as this, like, you know, do this little baby test.

Yeah. It's always tempting to, to think that we can take anything we want to do and run a very cheap, very quick test to prove yes or no, this works or doesn't work. That'd be nice. So I'm gonna synthesize kind of my takeaways here from talking to Chris. Sadoso's arc from, you know, gosh, $150 million raise and a 50-person SDR team now to a lean, definitely agent-first team. One of the clearest real-world proof points that the headcount-driven go-to-market model is, well, it has some cracks in it. That's just, just not efficient. And, and, and Chris's framing of, what'd you call it, capability count versus headcount, right? That, that really reframes how teams should, should think about capacity planning. And, and Chris's approach of asking employees, who would you hire if you could in order to surface agents, agent use cases, that, that, that's a, that's a repeatable framework that I think any go-to-market leader can probably steal. And then I guess probably the sharpest irony here is that the company that built the physical channel because email was too saturated a decade ago is now the most defensible channel in the stack precisely because everybody else has doubled, tripled down on digital. Fascinating. Chris, where can, uh, our audience kind of connect with you and anything you want our audience to know about what's coming up?

Yeah. Uh, find me on LinkedIn. Uh, you know, check out Sendoso.com. We've got a lot of interesting data studies, interesting examples. If you're curious about some more of the, the what and why behind, uh, gifting and direct mail, shoot me an email. I love networking with other smart people. Uh, it's Kris, Kris@sandoso.com. Always love networking and meeting new, uh, people, especially in the, the GTM world.

That's fantastic. All right. Thank you, Chris. This was great.

Yeah, thanks for having me on.

Okay.