SaaStr 845: How SaaStr Built a $5 million Pipeline Machine with 1.5 Humans and 20 AI Agents with SaaStr's Chief AI Officer and Momentum from Salesforce's VP of GTM

0:01Jonathan Kvarfordt:Welcome to the official Sastra podcast where you can hear some of the best Sastra speakers. This is where the cloud meets. Up today on the Sastra podcast.

0:11Amelia LeRutte:But it's interesting, like I'll go through the chat. I used to like when we first deployed this, I was like, I'm going to read all the chats as I can in real time. And I was like, okay, I'm not learning like a ton. So then I was like, okay, I'm just going to like at the end of the day, see like what are the like the highlighted chats. And like, it's interesting to see how people interact with Amelia AI, like especially when the video component is on or even just in like a chat format. But like sometimes people ask like, hey, I have a question for like real Amelia. And so like it'll help answer them, which I think is really cool.

0:43Amelia LeRutte:Like it's funny. It had this effect where like census was live for a couple of months before a London event. And I, you know, I'm always running around our sass for events. People would come up to me during London and be like, hey, I talked to your AI. Or they'd be like, oh, you're real Amelia. Like I talked to Amelia AI. And I was like, yeah, that's me. And it's really funny because the conversations would be like, you know, totally like socially awkward. And I'm like, I feel like you had a better conversation that wasn't as awkward with my agent. But I was like, yeah, that's, you know, that's me.

1:16Amelia LeRutte:And I'm glad you used it because that's what it's there for.

1:23Amelia LeRutte:Hey, Sasser, imagine having agents for every support tab. one that triages tickets, another that catches duplicates, one that spots churn risk. That'd be pretty amazing, right? HappyFox just made it real with Autopilot. These pre-built AI agents deploy in about 60 seconds and run for as low as two cents per successful action. All of it sits inside the HappyFox Omni Channel AI First support stack. Chatbot, Copilot, and Autopilot working as one. Check them out at happyfox.com slash saster.

1:55Jonathan Kvarfordt:Hey, everybody. SaaSter Annual will be back May, 2026. The world's largest SaaS and AI gathering for executives. Just as last May, we hosted 10 ,000 attendees with 68 VP level and above attendees, 36 % CEOs and founders, and 25 % were AI first professionals. It's the very best of S-tier attendees and decision makers that come to SaaSter Annual and AI Summit each and every year. But here's the reality, folks. The longer you wait, the higher ticket prices get. They're cheap now. They're cheap, so just get them. Early lock in your spot today. Use my code Jason100 for exclusive savings. Get your tickets at podcast.sasteranual.com or just use code Jason100 when you check out.

2:36Jonathan Kvarfordt:See you there. Saster Annual and AI Summit 2026. It will rock. I am thrilled, pleased, privileged, excited, and ecstatic. I try to do five. This particular episode because I have my dear friend, Amelia LaRoute, who is a Saster chief AI officer, which I'm geeking to talk to you all week. We've talked many times before because we're Momentum's a sponsor, so we've talked. But this episode, I've been so excited for because I love what Saster's doing. Jason has said many times that you're the AI agent whisperer, and so now I get to have you to talk to. I'm so excited. So first off, how are you? And thank you for coming.

3:14Amelia LeRutte:Wow, thank you. I feel like you've nailed the Jason Kelsey type intro of podcasting. I love it.

3:20Jonathan Kvarfordt:Well, that's very nice. So a little bit about you. You have a social media background. I was just going through your stuff before the show. You came from social media and then it's old school. And then you came to SaaS versus demand gen social media. And you've kind of gone up the ranks where last year you were the, you were the general senior vice president. And then in August is what you put down. You shifted to chief AI officer. So I'm curious, like, tell me a little more of your journey and how did this come about to be? You're the agent whisperer, as Jason says. How's that coming about?

3:47Amelia LeRutte:It's been an interesting journey. So when I first started, I was like, you know, OK, I had been a sponsor of Sastra. Actually, I worked at this company called EverString, which is now not around. But the founder is doing, JJ's doing Vulture. And I was like, oh, I know Sastra because we were a sponsor from EverString. And I know they do these events and I don't know too much else. Like I was there for like a day when we sponsored and I did boot duty. So I didn't really do a whole lot. So it was just interesting of like I had done events that scaled previously more in my B2C background. so I had worked at a bunch of like beauty companies and they did like you know 100 ,000 person events and so when I got to Sastr I was like okay I got hired to do like marketing and social so I'm just going to do that so I was just like working on annual you know getting people to come and then that was the first year because that was 2017 I joined and then 2018 was the first year that Jason wanted to do a London edition because it had only been an SF and so in that I was like oh I was like I see things being made like I see some poor decisions being made in like events planning event production and i couldn't help myself i was like oh you know what about this okay okay oh you like okay what about this and then it like quickly grew from there into like i i did the the first ropa with some help and then like the next events after that i was like okay you gotta let me just rock because i can i can rock this uh so for a while like my svp gm role was like okay i i led a bit of you know like the now we have like an events agency too but like i helped run like the events coordination and then market i still do like a lot of the marketing myself sent all the emails right got people to come and i started helping the sales team along the way by that time i was like pretty ingrained with the sales team because i was like here's what you can i can't sell some event because they weren't as you know they came from like traditional sass they didn't know the boundaries as much then we did the 2021 saster annual was the only major event in the bay area and it was because we figured it out like between me and Jason mostly just you know pushing the rock up the Maui and we're like we're gonna make this happen right right so that was that and then after that yeah I fell into more of like okay I'm managing you know sales marketing just everything like everything going to market everything events all the stuff all the stuff and then I remember last year we were like okay we have so many AI speakers already but I felt like I didn't know it as much then I was like oh you know I use Claude whatever and i use chat gpt definitely not the level of agents i have now and so it was just like this journey where jason started it when he cloned himself on delphi because you know he wanted to be able to give people more advice on like saster and but then from there that was like we kind of saw in delphi like we famously saw people started asking questions about like saster annual about the events about saster like getting involved and it because it was built to be a jason clone and like give advice like sass advice to people it wasn't as good at that and so after sass for annual last year which was in may that's when i went deep i was like okay i'm gonna look at every agent and go to market i'm gonna figure out which ones we need and then we like i basically locked myself in a room for like three months until we started working on our london event and i was like i'm just gonna work on agents like don't talk to me like i'm gonna figure this out and i'm just gonna figure out how to make it work right not only figure it out but like figure it out so that is successful.

7:03Right.

7:03Jonathan Kvarfordt:I don't think people understand, like, it does take some time to do it, but the fact that you, I always call it the slingshot effect of AI, because when you start to focus, you feel like you're slowing down because you have to learn it. But as soon as you get there, you're like, you have to fly. Yes. A hundred percent. Yeah. It's crazy. So now you're here, you guys, you talked about, you have 20 agents now. So you start obviously with Delphi and Jason and mimicking him and for his advice. And I think I heard Jason say the increase of amounts you guys are getting with a smaller team is greater now than it was before.

7:30Jonathan Kvarfordt:Something like that it was so an interesting sound that he had do you know that yeah so like i know he's talked about it online so i'll just touch on it briefly like the pre-annual last year we had more than three humans and a dog and like we had one agent and you know because of how saster is again it's

7:47Amelia LeRutte:not a traditional sas company sometimes we i mean i'll just be honest we don't have like pads to like promotion on our sales side because we had a few we had like a couple of aes going into annual last year and like a couple sdrs and like some of the sdrs were like oh well like can i become an ae i was like yes but like let's put you on a path to doing that not just like okay sester annuals over and you automatically become an ae which i think is what they kind of wanted and i was like that's just not i get like this major event is happening for us but like you're

8:18Jonathan Kvarfordt:not there yet like you're not ready yeah and so for a lot of reasons like folks left on more so

8:25Amelia LeRutte:of the sales side and like because our events team is typically part-time anyway like they're not year-round right like it's like we spool them up we need them for events it was almost the same like in marketing we just couldn't find any good help to be honest and so we we developed this agent thing and yeah the lift that jason always talks about is because like because now we have all these agents like i i hearken back to it a little differently of like this time last year I had oh yeah we probably had like 10 humans around this time last year no agents right like maybe one like one we had the Delphi going barely and like the amount of time I would spend just talking to people or like talking through the drama or oh I want to do this or oh I want to do that but like we gotta go like it's January the event's in May yeah I'm like we don't have time to like debate this stuff that we've done for you know 12 years now like some of this just has to get done so that's where we get a lot of the lift out the agents so like that's where we started doubling down on the agents because we're like okay we can get we're not that many people but we can get a lot of scale out of them when we do them right so these ones obviously the left-hand

9:33Jonathan Kvarfordt:side is the repli ones you guys have made for whatever reason so those ones yeah you guys used internally it was ones you send the people and say hey go talk to this agent or how do you handle

9:41Amelia LeRutte:those yeah we more so send them to people so the ai mentor actually goes to delphi so that one goes So there are the other five, the four slash in the middle. So there's like a VC pitch check one, evaluation calculator, the startup benchmarking. Like those three were ones that Jason had been wanting to put out as Aster for a long time and just could never get like a developer to do it. And so finally, he was like, you know what? I already have the specs of what I want because I've been sitting on this. He's been sitting on it for years. Waiting for everything. Yeah. And then, you know, through the magic of Vibe Coding, could launch those products.

10:13Amelia LeRutte:And I think it's a lot. I think the pitch deck or the valuation calculator combined has been used almost like a million times or something crazy like that. Like, it's just helpful for our community, right? Like, it's so helpful for the startups, the founders to be like, okay, this is actually giving me pretty good feedback. It's reading the other decks and giving me feedback. It's honest in the valuation calculator. And so I feel like it's just giving people a lot of, like, honest advice via a tool. So he was kind of sitting on those. the deal flow one is one that we've been wanting to make for saster specifically because we're like okay we always have like these vc programs that are events right that are somewhat hard to automate and it's a lot of like manual like looking at spreadsheets and like literally matching people so that's why we built that one the content review one also interestingly we replaced how we were doing content because we had a human agency that was like hey we had a few good years of saster and we just don't want to do this anymore and i was like that'd be fine if you told me like any other time of year but it was literally last january when they told me right before may and i was like okay okay so so yeah so then you know we we talked about through may and then post may we're like okay the first thing we're gonna do is build this ai content review agent so people can submit a speaking session for saster it gives them real-time feedback it tells them like the chances that will you know accept it or not and for us we're like we just need this time back like we have no more agency doing this because but the ai's maybe i don't want to say it's better at it it's about as good as like the human agency was because i'm like we put in the same context right we're like hey here's all the good sessions from sas reanels here's all the bad ones here's what to look for here's what we don't you know want and also we're limited on how many slots we have and so because the ai is like less biased sometimes it is like the grades it gives is like a little bit more fair then sometimes you know humans would be like oh this was my client or this was my friend like can i get them on stage like the ai agent just not care i love it so these the right side i'm

12:13Jonathan Kvarfordt:curious like when you think about do you think in the terms of jobs be done or because like some of these could have some overlap so how do you they do overlap yeah how do you think like you narrow them down to silos or they overlap in certain ways that's strategic for saster how do you make sure

12:27Amelia LeRutte:all these work together and in yeah we we do events we have sponsors like momentum and we have other sponsors like a sales force where like we do try and use the apps that are you know our partners have and that our sponsors have and that's why we have so many like some of them do have direct overlap but honestly even though some of them have direct overlap right like agent forces is an AISDR, Artisan's an AISDR. We use both of them. But actually, it's fine for my perspective, like, other than the cost of paying for two platforms, which most people don't want to do, right? Costs aside, I would say because my brain can split how I'm putting leads to each of those different agents, to me, it makes sense to say, okay, I'm going to use AgentForce for people I want to follow up with that are already in Salesforce, because duh, they're already in Salesforce.

13:18Amelia LeRutte:And then like Artisan, I'm going to use more so for like warm follow-ups so like this is my this is like across my agent so this is like my outbound AISDR funnel and this is just for outbound this is not including inbound but I like to show this to people because I'm like some of these people are in Salesforce yes some aren't so like if they are in Salesforce I'll use Agent Force for it because it's just easier like that data is already there I don't have to move it if they're not though then like a website visitor not necessarily is in Salesforce then I'll use something like an artisan agent and do an AISDR there because I'm like they are on the website and that is cool because obviously they're taking an action but I want the agent to maybe like not talk about all the historic stuff that they did with us in you know our Salesforce account records like maybe that's TMI because they're just on the website like they're just you know very top of funnel and so I go through like these are all the things too and it's funny too and like in building this list and like trying to mentally map and model like okay which agents should be doing which like go to market things i was like dude there's just so many things you could do with agents because they can do it at scale and when you do it right they do it pretty good that we have an almost like endless supply of people to go out to and i think that's true of anyone like somebody sometimes people challenge me i'll be like well i'm a startup i don't have like an endless like pipeline or i don't have the brand of saster i'm like do you have customers do you have like free trial users do you have competitors of customers do you have website visitors do you have people on your website do you have people who turn yet like like there's so many people you could start to reach out to before you ever get to like a truly cold lead that i'm like that's how i thought about splitting it up between the agents because i'm like as you start to use different tools you'll see that they're kind of like the specialized ones are kind of good at like one thing or another right like the sales force like agent force is like really good at following up with with stuff that's in salesforce because it's already there like artisan's really good at doing clinical cold outbound even though even if the outbound's kind of warm it's just better at that because it can look at their linkedin and like see what they're talking about and like tie it back to them so each of them has like strengths and weaknesses that

15:21Jonathan Kvarfordt:we've kind of like now played to that's awesome so how how do you um how do you personally see you have all this other stuff how do you because obviously what you're doing is not necessarily like you said you don't recommend people have 20 different agents but so how do you think about it is it doing a silo saying okay like like you just said salesforce um aist are used for this one and for non-salesforce they use this one you kind of have to segment it like that for whatever we do

15:46Amelia LeRutte:yeah so and that honestly there's no like magic way to do that that's just a lot of exporting and importing and like google sheets like it really just is for now and then your main connection

15:57Jonathan Kvarfordt:piece you're not using a maker in the end using zapier most of the time correct yeah there's some flexibility with it but i mean i tell people all the time if you go to zapier you can do a lot of dangerous things and it's a very simple interface to use you know what i mean yeah i think it's

16:09Amelia LeRutte:pretty cool for sure like this like what i'm showing now is like how you know we do have these multiple agents and so mentally how do i keep track of everything like one i most of these tools even if they're third party do push back into salesforce like either natively or through Zapier and so that's where you know we get a lot of I will say like we we've always used Zapier since I've been here but like in the last year like along with all the agents I was like wow I have a lot more zaps now and a lot more stuff like running through right every you know every day it'll be like you did whatever 800 actions today on Zapier and mine used to be like a couple hundred and now it's like over a thousand like every day I'm like that's just because I'm having it like well I'm having it push context from like one agent to another right so it like needs to be able to do that but it can do that which I think is cool so that's kind of what I'm showing here is like it's cool because of some of the stuff we have internally that's either external facing or just super like internal facing is like vibe coded a lot of times you're going to need to like do webhooks just like everywhere like webhooks webhooks like everything needs a webhook but it's fine because that's how you know data gets from one place to another and so yeah i've kind like now and managing all these like this is one flow out of you know many but like it's like okay

17:27Jonathan Kvarfordt:so it's telling you this one what's the purpose of this this flow of all these tools but what's

17:31Amelia LeRutte:going on here like this is a sample agent flow and like zapier flow of like i'm sending information from one agent to another and also like i'm i'm telling it what to do with it so like this one is for example i think this one i picked because it's a webhook was something like you know on to astrayanial.com there's like a bunch of forms you can fill so if somebody fills a form and they don't and they don't book a meeting via a different agent then this then this hook is catched and then i'm i'm type a so i just push everything to google sheets and it really has as a backup and then it's pushing to salesforce to make a contact it can add that contact to a campaign so i highlighted that one because the campaign this one is adding to is like when people download of our perspectives it will add them to a campaign that will automatically trigger the agent force workflow that's separately in salesforce and then they'll get added to the agent and then they'll get like that those emails it'll find their record basically what i wanted to do then is like okay add this contact find the records tell me about them so like you know what's in the record attachments that's what the clay one is supposed to do it's like it's supposed to look them up in clay and like get you know some of their social stuff and just see what else they're doing and like enrich it and then send it to slack so that i know what it's doing and it knows what it's doing and then if we want it to it can make a gamma so that it can make them in this instance right since they're filling out a form on the website to potentially throw down money for sas re-annual it can make them a gamma kind of on everything it's just learned in the last couple seconds between the agent sales force and the website and say okay i'm going to make a gamma on why this person should be at sas reangel and it can be as simple as like you know we gave it a template that is like you know put their logo here use whatever their colors are like you've got like a hybrid of colors like a gradient in your background it'll be like okay i saw you know that's jonathan's logo i'm gonna put jonathan's logo in the gamma i'm gonna choose gradient colors so it matches his vibe and his theme and then i'm gonna send a gmail draft to whoever's the rep is right so either me or David or whoever.

19:31Amelia LeRutte:And then if they want to, they can send it automatically, but they don't have to. Like they can, like the human can still pick what they want to do from there. But I feel like this one is a pretty cool flow because I showed this the other day and they were like, oh, there's some, I was like, there's some agent on agent action going here. Cause like the,

19:46Jonathan Kvarfordt:yeah,

19:47Amelia LeRutte:there's like a lot of layers of agenting.

19:50Jonathan Kvarfordt:Do you feel like, so tell me about the results because one thing I love to talk about on the podcast is like the impact. So I love the workflows. What does this do for you for the business? Does this, does you feel like it has more opportunities, more pipeline? What's the end result? Yeah.

20:02Amelia LeRutte:I'll give you a little context, too. So we started deploying go-to-market agents, let's say, June of last year, because that's when we got serious about it. We did not deploy 20. Yeah, yeah. So in eight months. Yeah. And that's layering in a couple agents at a time. So yeah, we're now at 4.8 in additional pipeline. And so this is something we learned to track distinctively. And that's across our agents. And then we've closed 2.4 of that, which half is like actually a better rate than our old inbound rate. And I can tell you why. But then beyond that, like our deal volume doubled, which maybe makes sense because, you know, the agents do work 24-7.

20:42Amelia LeRutte:Like they're constantly working. You can always book a meeting with one of our agents to talk to a human. You can pretty much always get a response from one of our agents. And if it doesn't know, it will escalate to a human. And then you have to wait. But, you know, you've got some initial answers first. And then our win rate doubled. And that's, again, I credit that to like, because the agents are doing so much in the background with the person, like with the prospect, with different people in the deal cycle, like it just, it makes them feel better, but it also makes us feel better. Like now when we get an inbound lead, for example, like I can show you, like, like we use inbound for our, or we just qualified for our inbound meetings booker.

21:17Amelia LeRutte:And like, it will say like the exact conversation that the agent had with that person as they were booking. so then like i'll pull that up with david on our sales team and we'll read the conversation we'll read the conversation we'll be like oh okay they already told the agent they were interested in xyz so then we get on the call we're like hey you told our agent you were interested in xyz we think that could be a good fit here's why or here's why not and like here's the price so like we have much better like more fruitful conversations too because i'm like we kind of know what they want we're not just like hey how's the weather i love it so and this is what when we first got into this

21:51Jonathan Kvarfordt:you're talking about the AISD or AIBDR STR. This is the result of that flow. Obviously the way you just showed.

21:57Amelia LeRutte:This is the result of that flow. Yeah.

21:58Jonathan Kvarfordt:Yeah. That's, that's pretty rad. I love it. Do you feel like you have, is there like a Jason ask, like demo bot on the website as well? So it's not like the consulting side, but the other one.

22:08Amelia LeRutte:Yeah. So if you,

22:10Jonathan Kvarfordt:and that's the qualified, that's a qualified tech.