Day.ai raises $20M from Sequoia to build an AI-native CRM that thinks like Claude, not a spreadsheet

Bill Bill Argo.

That's right. uh Bill Bill Wong's uh infamous hedge fund.

Well, we have Christopher O'Donnell from Day AI in the rear room waiting room. We'll bring him into the TVP Ultra Dome. Christopher, how are you doing?

Wow. Unique.

Uh very well. Yeah. How are you guys? Thanks. Beautiful. Beautiful setup here that no one's ever done before. [laughter]

I feel like I'm watching Honestly, I feel like I'm watching an OpenAI launch video. Uh but it is fantastic. It looks fantastic. Uh, we can get a little OCD, I guess. And we were pumped for this. And so we like teaching ourselves how to use lights and stuff like that. You know what I mean? Like ordering this [ __ ] on Amazon and like trying.

I'm pumped for this. I've had my favorite experience ever when I when I check X in the morning, I see a cool startup launching

and I'm like I'm like thinking like I got to get this I got to get these guys on. And then you're you were already on. So it's great.

Uh, first time on the show. Please introduce yourself, the company, tell us what you're building.

Yeah, so Christopher O'Donnell, uh, longtime listener, first- time caller. Um, I led product, uh, led product at HubSpot for about 10 years and am now, uh, lucky enough to be with a group of a dozen or so of my, uh, closest friends doing

a similar but also very different thing from scratch in the age of AI. you know, it's sort of, you know, what if we were to start from the very beginning and do everything in this, as you guys are constantly discussing, wildly evolving and radically different, uh, world. Yeah.

So, that's that's the short story.

So, early product, uh, market, how are you segmenting things? What's the key value prop? Um, I mean, I'm sure there's AI, but, uh, take me a cut deeper. Yeah, I mean I think looking at CRM there's a funny thing which is I feel like in everybody's head

everybody's expectations are wildly different for everything. Um and you guys talk about this and you know every vertical you know our lives are changing so rapidly

and yet nobody's really expecting that to happen with CRM. Everybody's kind of like, but Salesforce isn't going anywhere. And it's like, hold on.

There's a layer of it that is, well, we could eliminate the manual data entry and we could maybe better integrate with some other systems. And what we're seeing is there is a wildly different level of what's possible. That really was the original promise of CRM. Like, hey, I'm a CEO. I have concerns about my business. I have existential questions. I want to know if this whole new cohort of sales reps that we hired two months ago is going to make it. You know, I want to know what I can do, what deals I should be involved in. I want to know if I'm spending my time the right way. And you can actually get instant answers to that if you had the entire record of everything that had been said or done at the company instantly indexed

and readable by, you know, an AI agent. Yeah. uh that's the heart of what we're doing is ingesting everything and storing it

in a way that is LLM optimized. So, you know, easy for it to explore this whole network of relationships.

Um but also in natural language and with explanations about why everything is what it appears to be.

Uh you know, we're seeing it's just a completely different set of use cases. Uh so that's really interesting to navigate with customers, but everybody's starting to kind of go from wait what uh to of course this is exactly the thing that we should have.

What is like the killer feature or experience that you're optimizing for? Obvious you're you're trying to somebody signs up, they you know sort of integrate whatever tools they need and then like what's the first moment like that you're trying to get people to kind of see the future? Yeah, I think the most obvious thing is a better version of the meeting recorders that we've come to kind of rely on. You know, here's this thing, it's watching, it's taking notes, and I don't have to do that on the call because it's all being captured and recorded.

Uh, and then from that, you know, I can ask questions about it. I can, you know, automatically have my deals moving based on what happened on the call. That's really great. if I want to write follow-up emails, they're incredibly good and the UI is just snapping and moving around as I go through this whole workflow. That's kind of the entrylevel uh magic trick that people see when they come in.

Then there is this much deeper realization that oh wait a second, I can actually ask and understand anything that is happening in the business.

Um and and and that you know people get to that pretty quickly, you know, within a week usually. talk about bottom up adoption versus top down. Do you want to go for the big enterprise have them rip out some massive system or uh I remember using a product called Streak that just plugged into Gmail. You know, you could I I I've also built a CRM with Visual Basic in Excel. Like you you can start a CRM project just in a spreadsheet. Um how are you thinking about uh where where you want to plug in and start getting traction?

Yeah. Yeah. part of our crew built a bunch of streak in addition to uh to

HubSpot. Wow.

Yeah. Um

it's a cool company. I I I I enjoyed it at the time. It was like very like lightweight. You know, you could just bolt it on basically.

Totally. Totally.

Yeah.

The adoption story, it's a great question. You know, we saw over I've been working in CRM for I don't even know what 10 15 years.

Let's go.

And thanks for your service.

[laughter]

the the march of history always seemed to be from the CEO toward the buyer with, you know, a big swing through rep productivity and these bottoms up tools. And when I kind of moved from the rewrite of the HubSpot marketing product to do a startup, then a startup and the sales tools that became uh HubSpot sales and CRM, that was the thesis, like we're going to go bottoms up. We're going to do what these other sales acceleration tools are doing. and that worked really well. Um, and then you know marching toward the buyer being able to drive as much of the sales process as possible. I think that still exists and I think that solving for frontline people is absolutely huge and giving them things they can come in get started on day zero. Absolutely. No big top down roll out.

We're also seeing a little bit of a return to the CEO. And I spend a lot of my time actually I I mean I spend most of my time just demoing at this point other CEOs and showing them how I use it.

That's the clo because you can't really say it in I mean we try in our marketing messaging and everything like look at all these examples and everything but if you see me use it you go oh wait okay I got it. This is like this chief of staff that's watching everything and coaching me and giving me the data and you know we're having it up at a board meeting. Pat Grady um who I know you guys had on recently that was a great great segment there.

He had a tweet today about our last board meeting.

Yeah.

And we just had the assistant up on the big screen. There was no deck.

It's like I sent a big memo and I I send a a memo and a context file so the board can ask questions and get instant answers.

But we just had the assistant up on the screen the whole time and there's no like, "Oh, that's a great question. Let me, you know, get my ops people to circle back or it's like which changes things and it's going to be interesting.

That's amazing.

What uh there's so many large software companies that are working to become AI native. The first step is obviously to say that you're AI native, put it on the website, but what are some of what done what what are what are kind of the challenges having worked in in big CRM uh of of kind of evolving? Yeah, I mean if you think about it from the perspective of the AI agent and you really, you know, you switch from putting yourself in the user's perspective and you put yourself in the perspective of Claude or one of these clients that is asking questions and calling tools and trying to solve problems for you, you actually want something pretty different. Um, we had a customer connect their Claude to both HubSpot and Dayai and said, you know, what do you think? And Claude says, "Are you asking me which I prefer?" And she's like, "Yeah, yeah, I'm asking which of these do you like more?" Uh, and Claude says, "Well, look, you know, how do I how do I explain this? This old CRM is like a spreadsheet, and this day thing is everything that I need to answer any question you have. I can find the answer like let's go what do you want to know

that's a very different approach that gets all the way down to disk

like literally all the way down to how you are capturing and storing the data having worked on these systems and many versions of these over the years it it's a problem that starts at the very lowest parts of the stack to be able to give the agents uh you know this kind of information I mean we all know that opus 45 with the right context window can do magical things. I mean, it's godlike. So, the question is, how do you give it exactly the right piece?

That's amazing.

I don't think it's God. I don't think [laughter] it's God. It's like

it's like

Yeah. It's like a precursor to like we're definitely living in a simulation. Five is like about to become the thing we think of as our creator. I think that's like fair to say.

That's pretty wild. Uh, you raised some money. I want to talk about the deal. I want to kick off the lambda lightning round. I want to bring down the mallet from the heavens so I can ring the gong for you. How much did you raise?

Uh we raised 20 million.

Whoa.

From uh Sequoia and who else?

Seoia uh Permanent Capital Conviction

Sound Ventures and Green Oaks.

Fantastic bunch of nobodyies.

Quite quite [laughter] the group.

That's a fantastic crew. Congratulations and I'm sure you'll be back on the show soon. We'll talk to you later.

I hope so. We have a lot coming.

Can't wait for it.

Great to meet you, Christopher. Congratulations team.

Goodbye.

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