The Transaction

TT - 051 - Ana Leyva
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Ana Leyva: [00:00:00] I am sick of personalized emails.

I know it's a hot take because everybody says you gotta personalize, you gotta personalize.

Ana Leyva: I'm all about the insight driven outreach rather than personalization, so I wouldn't even call it personalization.

We're living through this really exciting time where new playbooks are being written.

What's most exciting to me about my job is just that, feeling of we're building the future. I always tell our founders, you're not selling for the initial close.

You're selling for the renewal.

Craig Rosenberg: by the way, you guys, two, two quick fun facts before we go. There's a new crochet in the office and she was really sweet.

Did I show you this? She made me this pineapple. Um, and it's really well done. I mean, look at that. It looks pro.

Matt Amundson: Mm-hmm.

Craig Rosenberg: I, and I went back to her and said, look, I squeeze the pineapple all the time. And so she's gonna go to a new product and put a stress ball in the crocheted, and I get to choose a new animal, and I'm choosing a penguin.

So I will be getting a yes, A penguin one I can squeeze.

​[00:01:00]

Craig Rosenberg: The other thing is for my hat today, you guys, I just gotta show you. I, I got, uh, this.

Matt Amundson: Oh, we love it.

Craig Rosenberg: One of the only times in my life where my team that I root for actually won. And it was amazing you 95 UCLA Bruins. Yep. I watched it from a bar in se severe Spain on the farthest end of town at three in the morning.

It was amazing and I was going nuts and these guys just wanted to drink their cruise campo and, and smoke cigarettes. And I was just going nuts, man. It was. It was fun. I even, I didn't know what to do. There was no cell phones back then. I got on a payphone and Colette called my mom to tell her. I, I just, I had nobody to talk to.

Matt Amundson: The [00:02:00] international collect call, I love it.

Craig Rosenberg: I didn't know where I was in town. I mean, it was like, I mean, I don't know, but those were the memories we won last night. So I'm very pleased,

Matt Amundson: Easily hand handedly.

Ana Leyva: Who they beat in 1995 for the championship.

Craig Rosenberg: they beat the Arkansas Razorbacks.

Ana Leyva: Wow.

Matt Amundson: you remember who Arkansas's, uh, like sort of, uh, marquee player was in that, in that tournament that year?

I. Corless Williamson Yeah.

Craig Rosenberg: and Bill, bill Clinton was in a suite at for, because he was a huge, huge Hawks fan. So yes, so yes, I do remember. Uh, vividly. It was amazing. Then I went to the final four when we made it What with Kevin Love and those guys. We lost about like 50. We lost about like 50 to, to Memphis.

That, that hurt. Yeah.

Matt Amundson: yeah. We, and then we lost to Florida and the semis, and then in the championship.

Craig Rosenberg: we like to do that. We like to get people really excited. Then let 'em down. All right. No sports [00:03:00] talk. That's it. I apologize. I

Ana Leyva: March Madness is my favorite time of the year. Did you know that? That's a fun

Craig Rosenberg: Oh. We did not know that about you. It's not listed on your LinkedIn. I wasn't gonna include that in the intro, so,

Ana Leyva: I'm a big that's good.

basketball fan,

Matt Amundson: How's your bracket?

Ana Leyva: doing pretty well, um, so far, so I have a bracket going for men and women because the women's games are amazing too.

Matt Amundson: Yeah,

Craig Rosenberg: By the way, I actually have, that is a, the women's games are incredible, especially now that we know the players.

Ana Leyva: They're incredible.

Craig Rosenberg: I hate that she goes to USC, but I love Juju Watkins. I just

want to,

I have a huge like. Competency crush on Paige Becker's. You know, like she's just awesome to watch, you know, like, so, but the Bruins are good in that too, so we're hoping that, you know, both of them go down.

Um, and the Bruins win. That, that would be cool too. So, um, all right, so [00:04:00] we just got that fun fact. So we, today's guest. a person I just met and I've talked to you now 25 times since I met her like three weeks ago and got her on the pod 'cause she's yeah. Amazing energy. Amazing energy. So Ana.

His background, she did box and then ServiceTitan, which is a now famous success story in SaaS and then founded her own company. So she did sales, sales leadership and then founded her own company. So that's her amazing, well-rounded background, and now is running go to market at Pear vc, which is one of the, uh, best pre-seed seed funds out there.

And so today's guest, which is a new one for Matt, I believe you're, meeting Ana for the first time. So is Ana Leyva

pronounced

Ana Leyva: Hi

Craig Rosenberg: Hi guys. [00:05:00] Yeah. Oh, awesome.

Ana Leyva: the way it's Spelled. and they think.

Craig Rosenberg: Oh, that's awesome. Well, it's so glad we're so glad to have you on. And, um, the other thing that everyone should know is Ana and I are Ana's partnering on the go to market summit, Matt, so we're doing it together and it's we're, it's been really fun so far. And we just literally got started and she got to go to an AJ Gandhi dinner.

Matt Amundson: Whoa, OMA.

Craig Rosenberg: Oh yes. Omaze.

Yeah, we were at the same table. They're famous now, but you know, he's moving off Omaze. That's the word on the street he's going with. Yeah. New, new chefs going forward, which will be cool. I mean, we'll try some. What's that? Yeah, so I think he's doing, he's doing a Taiwanese Omaze. Uh, that, that should be really interesting.

And then I think on the [00:06:00] last one he did something more barbecue ish. Right? I'd have to see. Yeah. So yeah, so we'll, we'll we'll see. AJ Gandhi's a friend of the show. He is been on as well, so I. Now, and now Ana will be at all the different ones as, um, uh, following along as well. So, all right. So Ana, here's, we have two questions that guide the show.

Uh, the first one? Yeah. Two. Two. And I will land this plane.

Matt Amundson: I, I've, I'm confident in that. The question is, is will you turn the ringer off on your phone?

Craig Rosenberg: Oh yeah. You know what? That's a good point. Yeah. Hold on one sec, everyone you know. Yeah. Brandon Redinger asked me to be on his webinar and he is like, and by the way, no texting. Turn off the Notif. I can't believe Matt lets you do this. And I'm like this, what do you mean by this? Anyway, um, so the first [00:07:00] question is, we love to lead with a story and it's, 'cause stories are the, have been the best pickup on the show and Matt was like, Hey, just literally start the, start the show with the story.

So we call it the Matt Amundson. Uh, feature enhancement 2.1 a and it is like, tell us a story, a go-to-market story. It could be anything heroic, sad, funny, whatever that might be. Um, and, um, just we're gonna hand you the mic and let's start there and let's, let's hear your story.

Ana Leyva: Story that is so broad. I'm like, I'm wondering what to share., tell me some of the most memorable stories you've heard so far. Actually, maybe we'll get my juices flow.

Like, oh, I have a similar one. Or

Matt Amundson: Yeah, so I would say maggots falling on people's head out of a, out of an airplane. I think that was probably most memorable

Craig Rosenberg: we, we didn't know what we were gonna get from Brent Adamson, and he is like. Uh, Craig probably already knows this. It's the maggots on a plane story. I'm like, no. And basically, yeah, he, he was flying [00:08:00] back from somewhere and someone on the plane starts freaking out and they just look up and maggots are falling from the, the overhead and there's video of it that was on the news with Brent in the back having to evacuate the plane because of all the maggots.

So we didn't. We didn't really, frankly, we didn't really expect that. Um, and,

okay, I have an airplane.

Ana Leyva: I.

Matt Amundson: all right. Here we go. Airplane story.

Ana Leyva: early days of ServiceTitan, uh, a lot of our deal flow was generated at conferences and so we were flying all over the country, um, doing conferences. It felt like every month, multiple times a month. And I was a new mom and you guys know women in sales, underrepresented. I was the only woman on the team, first pregnancy, first everything at ServiceTitan.

Um, and the team was incredibly accommodating. They let me travel with my baby, with my infant, like 1-year-old son because I was nursing him. [00:09:00] And nursing had been this big battle for me, so I wasn't ready to give that up. And it was before like, and all these cool, um, services now that allow you to like.

Ship your milk and all the things. So, um, I did, I wAna say like, I don't know, 20 plus trade shows and conferences with my baby in tow. And my mom, who was my traveling nanny would come and like, hang out at the hotel room. Yes, absolutely. Like mom, baby me and just crushing it on at all the conferences, all the trade shows.

So. Um, that was a big part of my kids. Then I had, my daughter did the sim, similar thing, but, um, they're early, you know, always talk about that, their zero to one journey involved, like being on the sales, grinding with their mommy, which, um, is always fun. So

Craig Rosenberg: That's a great and heartwarming story.

I love that.

Matt Amundson: Yeah, I love that

too.

Craig Rosenberg: so, okay, so the big question we like to ask, just to give you a little context, the, the show [00:10:00] started 'cause Matt was actually an EIR at scale. Like three years ago, and we were sitting there, these old school dudes, I'm like 20, 30 years older than Matt, but like it's still, we're both old school and you know, Matt, you know, Matt was like, no, dude.

Like things have changed. We have to find the new playbook. Right? And so we really, we started talking to people, et cetera, but we're having so much fun with it and the banter, and we're like, let's put it in a podcast. So there's two goals. Like one is like we, you know, we, we like broadcasting and showcasing people like yourself, but two is like, can we use this podcast to find the new things that are working and not working?

I. Um, and hear it from people that see it every day. And so the question we ask that is literally the last one, except for other things that sort of come as part of your answer, is what's [00:11:00] something that the market thinks they're doing right today? Um, it could be anything. Approach, methodology, strategy.

And they're actually wrong and they should be thinking about it differently. And what is that and, and what should they do about it? Ready? I'm gonna turn off my phone. I guess I did not. Um, and you go,

Ana Leyva: I loved it. It felt like a special time that was

Matt Amundson: Yeah, I was like, do we get a soundboard?

Sam Guertin: Surprise.

Ana Leyva: I love this question and I think there's, uh, yeah, there's so many things that come up. So in my day-to-day work, I am in the trenches with founders. I'm early stage, so I'm paired as pre-seed and seed. So really like figuring out product market fit as well as what I, I love the term. Um, go to market fit and figuring out like what motion's right for me and for my, um.

Business and, um, lots of pet peeves come from that. Um, and, you know, trying to teach, most of our founders are technical, have never done sales before, so I'm basically doing like [00:12:00] getting them up to speed with, um, sales fundamentals, marketing fundamentals, grow everything, um, and often and feel like I'm reeducating off of things that they see out there.

Like, oh, I read for example that personalization is what I have to do in my emails, and so here's my. Personalized email that I'm planning on sending out and I am like sick of personalized emails. I'll share more. I think absolutely you have to customize and, um, make your outreach individual and targeted.

But I think this, um, blanket idea of personalization has gone wrong, like taken a bad turn into, this is a random fact I found about you on your LinkedIn page, and I'm dropping it in casually in the front in the first line, and then. By the way, here's a pitch and the, it's the whole like pitch approach that um, I think really rubs buyers the wrong way.

And so, um, what I talk a lot about our. Focusing on [00:13:00] personalizing, which absolutely you wAna do as like, you know, an underlying aspect of the outreach. I think the most important thing you wAna actually do is drive value. Like can you share an insight? Can you share something that will draw this individual to you and say like, that was actually a really smart, interesting way of thinking about it.

I never thought about it that way. Or something that will make them wAna spend more time with you. That will make them wAna give you the time of day.

Craig Rosenberg: Want

Ana Leyva: I think people get that wrong so often they just like personalize and think like, oh, I did it. I checked the box personalization, and they're just doing it the wrong way.

So that would be one of my, um, I, I would say most commonly, uh, discuss pet peeves with our founders at least.

Craig Rosenberg: So, but you're differentiating personalization, which is the, I think the examples you gave for like personal, so that's like, you know, like for example, the people that write, Craig, you went to UCLA.

You know, um, whatever, or [00:14:00] they, you know. Yeah. But with, but the insight that you deliver, that's based on what you know about the company, is that Right?

So you are still personalizing, you're just not,

uh,

Ana Leyva: Exactly.

Craig Rosenberg: Okay.

Ana Leyva: It's. Been twisted almost to like, I think the, Hey, you went to UCLA and if it's put in the email there in a forced way, you can tell it's forced and it's kind of makes you wAna throw up in your mouth a little bit, right? Like, I don't know when the last time you received an email like that, but I receive emails like this. and I, I think it's beyond like an insight. I, you know, I, I know about a little bit about the business. I think it's more that founders have a unique perspective given all the customer conversations that they're having. There are insights if they're not getting to a point of like having. You know, some unique perspective.

Then I think like, oh, maybe should you be building this? Like you need to really be pursuing sort of that thought leadership expertise. And if you can't get to that point, and if you [00:15:00] don't have anything to share to your market, that would be the most concerning piece. I'm like, focus, let's focus on that.

Let's get you to some unique insights, synthesizing all the things that you're learning from these customer conversations. And then in the outbound, offer a perspective, right? Like I had a conversation with so and so. You know, you can, again, as a founder be writing this, and this came

up

probably relevant for you too, and this is why you should spend more time with me.

That, you know, I'm not saying like that's the right structure for an outbound, but something that again gets to, gets beyond I, what everybody can do, by the way. And now with ai, it's getting easier to do like a blanket search of an individual. Tell me what they might be interested in, that's just not gonna stand out anymore.

And, and. Um, frankly, I think is the wrong thing to be like reaching out to people in what feels like a really dehumanized way when personalization was supposed to get us to a more human approach. So, um, yeah. I'm all about the insight driven outreach rather than personalization, so I wouldn't even call it personalization.

I think it's [00:16:00] like, that's the wrong blank statement. Hot take. I know it's a hot take because everybody says you gotta personalize, you gotta personalize.

Craig Rosenberg: Yeah, by the way, sorry, there was a delay and I believe it might have been Matt. It could have been Sam did a heavy breathe. Was that you, Matt? Were you exhaling?

Matt Amundson: No, I was just thinking, I was just thinking of my thoughts here because I think, uh, I, I totally agree with what you're saying, Ana. I think the, the, probably the place to go just slightly deeper here is how do you, how do you sort of pull that out, right? Like there's, there's a couple of different ways to demonstrate that you have unique insight on the bi on the space that maybe they don't have.

And, you know, we've had like Chris Orlob on, on the show and his, his sort of take is like, uh, you know, if you're selling to a CRO, you're like, Hey, you know, I talk to, you know, 20 plus CROs a week. And one thing that I consistently hear is like. You know, three years ago they were having no trouble getting their AEs to quota.

Uh, you know, they were hitting their, their quarterly goals on a pretty regular basis. [00:17:00] Um, you know, and now things have changed and they're, they're not really able to get there. And I, you're experiencing this, I'd love to, you know, give you a, a sort of my take on how to solve for it.

Uh, if you're not, then congratulations. You're sort of, you're, you're on to either raising the next round or, taking your company public. Um, is it, is it something to that effect or is it more like, Hey, you know, the one thing that you know. Company X, y, z has, has, has, has discovered is that 99% of companies are suffering from this.

And the big, the fastest way to solve it is by doing this. And let me explain to you why, if you have 15 minutes, like how, how, how do you sort of take that idea, which I think is correct and start to put it into actual practice.

Ana Leyva: Yeah, I love it and I, I think it's, I, I honestly feel like this is the work of a founder. The work of a founder is. Taking the time to sort of step back and synthesize, right, and create the map of what no individual, no customer's gonna be able to tell you and articulate. [00:18:00] Um, it perfectly, right? But you're having all of these, again, touch points and you're deep in the industry and connecting with all these people.

And I think the, the work of the founders to step back and synthesize. And so, um, it can look so different, right? Depending on, um. Who, even the persona that you're reaching out to, but I think ultimately some reframe of like, this is again, a challenge that you've had. Here's how you're thinking about it the wrong way.

And you of course wouldn't say that in an email, but you wAna offer a reframe. And actually, Jen Allen Knuth, who was amazing, um, I had recently had her on our, um, webinar series, winning Wednesdays. She, um, articulates this so perfectly. Like you think that not having an umbrella is costing you this amount, but actually you're thinking about it the wrong way.

And this is the big, you know, again, in the insight of like, you are leaving so much on the table with this. If you agree, let's chat. So it's, it's more like a reframe, I'd say. Like, you know, an offering, a perspective [00:19:00] and, and a hot take even. You know, like we're, we're talking about hot takes right now, but a sense of like a challenge, um, a challenge to how they've been thinking about it.

Um, so I, I don't, again, I, I don't have like a perfect email for formula of like, this is what you should

spirit of challenging and saying. I'm somebody who you should talk to. I'm somebody worth your time, or, or my company Is, is worth your attention and time because we have this unique new way of, um, solving a pain that you're really, you know, viscerally dealing with today.

Craig Rosenberg: So you would do, if you combine Matt and yours and we were taking your, you know, basically, uh, the, your, the lead of the show is a reframe. And you would say, you know, dear, Hey Matt, you know, as you, you know, as you go through your pipeline efforts and try to figure out what's working, what's not working.

I'm sure you've heard from the market that they think personalization works, [00:20:00] but actually, you know what we've found in working with thousands of different. Uh, prospecting machine, you know, organizations that actually personalization doesn't work. And what we've found is that, uh, you know, delivering the, you know, a, you know, uh, organizational insights, relevant organizational insights to a prospect actually is better, right?

And we'll achieve higher conversion. We'd love to talk to you about what we're seeing would be the right email there. What do you think of that? That was pretty good.

Matt Amundson: bad.

Craig Rosenberg: Yeah. Thank. Thank you Ana. Ana, thank you for being on the show. Matt just sat there. I was so hurt. Sometimes he nods and it makes me feel better.

Wait, you didn't nod? I think that's great actually. So

wait, is he frozen?

Sam Guertin: His indignation, uh, froze his internet connection.

Craig Rosenberg: when he was indignant? It froze. Alright, go ahead [00:21:00] Ana. Sorry. Sorry.

Ana Leyva: when you said would love to, um, I always give my founders a hard time on the, would love to because of course you would. It's not, but it's not about you. So just working on that last, um, last piece of the, the ask on the call to action, um, there, you know, to something that again, more, Uh, maybe even a question, like, do you think it'd be valuable to spend

Matt Amundson: Mm-hmm.

Ana Leyva: on on a call? You know, like, just put it back in there. Yeah. Just all about the, that end user and, um, and I think even to the point of what you said earlier, um. This idea of founders wanting a playbook, like just coming to Playbook or there is like we're, we are, we're living through this really exciting time where new playbooks are being written.

And truly the approach that we take at pair is every founder is rewriting a playbook, right? You're figuring things out. Things are always changing in markets and so it's, it is a dynamic. You take frameworks and best practices and yet. I can't tell a founder, go do this, and that's gonna work. Right? It's this iterative, [00:22:00] experimental, um, process.

And if a founder doesn't have that approach of like, okay, I'm pioneering, I am again, need to figure out my insights, need to figure out what I uniquely can add to this market, if they don't have that bandage. I, I think that's, they're already, you know, behind. So you really need to have first that mindset of like, I'm pioneering, I'm building, I'm figuring, I'm figuring out, I'm leaning in.

And that's, you know, that's my favorite type of founder to work with. down.

Craig Rosenberg: yeah. I love that actually. So I do have a comment to make on that, and I'm not sure to bring it up now.

Matt Amundson: Bring it up now.

Craig Rosenberg: Bring it up

now. Okay. All right. All right, thanks. That delay was to receive encouragement. I have a, I'm gonna go back to follow up on. But, you know, uh, most in tech, I'm gonna say all this is my hot take in tech.

All revolutionary go to [00:23:00] market strategies and tactics. Start with. Small, the small VC-backed companies, the Seed Series A folks, here's why. One, they got nothing. Like they don't, they, they can't lean on brand, so they gotta go figure out how to go do this without that. Number two, they're more likely to be tech forward, so they're gonna try the tech stuff first, right?

And um, those two things combine often lead to these. So like, if you take. By the way, CRM, if you got, you know, if you're old like me, and saw Salesforce was just racking up wins in the SMB and it was all San Francisco. I remember the first segment cut someone was telling me about at Salesforce, they cut up the city blocks in San Francisco.

Right? Because that's where the, that's where the game was played. Uh, sales engagement platforms, that was SMB, mid-market, Marketo [00:24:00] mid-market.

Matt Amundson: Mm-hmm.

Craig Rosenberg: Um, you know, and the, the vast majority of really creative marketing stuff from that came from the mid-market. I would even argue. S-E-M-S-E-O was from gr like early growth hacking less so big folks, and now we're hearing all the stories on what works from outbound perspective are not coming from the veterans.

They're coming from like Ana's crew of founders who are like, dude, I gotta get meetings. Like I'm reading all your crap, but here's what I'm doing. Is that,

yeah. No, a hundred percent Craig, and honestly, it's probably what's most exciting to me about my job is just that, that feeling of like. We're building the future, right? Um, in many ways, more than one way. Um, I don't know if you saw Jason Lumpkin's recent post that Stevie case also commented on or shared, um, about SMB.

Ana Leyva: Selling in the SMB segment is underrated because people, you know, wAna like it's [00:25:00] last year to sell enterprise in mid-market. But if you're in the SMB world, you're getting so many more at bats. That you just have that many more opportunities to test, like you said, to get better. You're getting all these reps in, right?

And so if you're in the SMB world or doing these, um, quick deals on the ground, certainly, uh, you are just getting better at a faster clip than these long enterprise cycles that take forever. And you're like, oh, in six months I'll know if I did something wrong. But like right now, I'm not sure. Um, I thought that was so insightful and that I think it was this week that they're talking about that.

So you're right on the money, Craig. I couldn't agree more.

Craig Rosenberg: Oh, that's, it's good to be right on the money once in a while.

Um,

Matt Amundson: broken clocks, right twice a day.

Craig Rosenberg: I need. Yeah, I, I, the clock thing is a sore subject with me and Matt. He, when I was late to a, a recording and we were talking about like Christmas gifts, I believe, and he offered to buy me a [00:26:00] clock for Christmas. Um, so yeah, that was,

Matt Amundson: cause he got me such a good Christmas gift and I, I, you know what, I still, maybe Easter. Here we go.

He. I. Oh, I wore it on a couple episodes. You got me this really nice, uh, uh, hooded sweater. It's like a sweater, but it was hooded. It's so nice. I wear it whenever I wAna relax.

Craig Rosenberg: whenever I wAna remember. Yeah, it was, I got it. Like, so the, yeah, my wife's, uh, hairdresser's son, like, does, you know, spider essentials, like all the cool gear. Uh, he works at a store, but he'll go grab stuff out of the back. Not illegally, anybody. He could

Matt Amundson: Mm.

Craig Rosenberg: back, but he brings it to our. Who brings it to our house, and the kids look at it, and I saw this essentials, sweater.

Hoodie. I'm like, dude, Matt, this is right at Matt's alley. And so I'm like, you know, I'll take it with the very minuscule discount he gave me. And then Wendy, my wife's like, well, you need one. So I, I bought [00:27:00] one. I just, thankfully we haven't worn it at the same time.

Matt Amundson: I didn't know where matching.

Ana Leyva: You just subtly drop that you have like a popup store in your house. What What was that?

Craig Rosenberg: Oh man, that's a good point. That's a really good point. I just kind of dropped that. Alright, so going back to this idea, I love this, this insight driven prospecting. So you like, uh, and I'm just thinking, so I, you know, we're. Um, I would, what I would want to do, let's just all brainstorm here, is pull the insights out of the founder founder's head. Put it into the hands of sales and SDRs in order to execute what you're doing. And there's two reasons for that, right? One is, with all due respect to my friends in sales and [00:28:00] SDRs, you're, the insights you decide to use are often terrible. I just, it's true, right? But the founder who's living, breathing and eating this stuff and out there having these conversations, is finding true insights like.

Uh, so what we want to be able to do is take things outta the founder's head. Now, I'll give you an example of what we did at Topo. They would meet with me and they would, they created just a spreadsheet of insights, and what they would do is they'd say, like, it, I forget what it looked like. We'd have to ask Scott for that.

And it was like, scenario. And then I'd be like, they'd be like, give us a hard insight. And then it was like. Is this data, is this quantitative qual because we were a research company, um, and they sort of built this library of insights or snippets, I, I forget what they called it. That was an example of something I've seen.

But like, you know what, what, like, what are your guys' thoughts on that? 'cause we want to be able to, [00:29:00] as we scale even a little bit outside of just founder-led selling, we want to be able to pull it out of their heads and, and, and get into the hands of the people that are prospecting. What are your thoughts on that guys?

Matt Amundson: I will let the guests go first. Go ahead, Ana.

Ana Leyva: Yeah, I, I have a thought. I think. Um, I love that example, Craig, and I think one way that I can, I've been helping founders crystallize those insights because again, they're living in their head and it's hard to organize. But one question that I've asked is, look, if you were to go out and start the business in the market, that a business in the market that you're selling, so whatever it is, like whoever their buyer is, if you're gonna go in and be that person or start a business and that, how would you win?

What have you learned? From speaking to all of these people that would help you stand out? Like what unique perspective right, have you gleaned that could help you win in their seat? And when thinking about it that way, when sort of like taking off their founder hat, like, oh, I'm building this tool. It's really cool and sexy [00:30:00] to, oh, now I'm in the, I'm my user.

What would I do to win whatever it is, get a promotion, like it be good in that role of my, the buyer that can help, has helped. I, I've seen, helped our founders be like, ah, here's what it is. Like my, currently my users are thinking this way and this is what I would do differently. Or this is, this would be my unique approach based on what I've seen.

Um, so I, I don't know how they got all the insights out of you, Craig, but that's been for, for me and for our founders, one of the cool ways of like. Helping them come to terms with all the things that they've, they're seeing um, really saying like, tomorrow you wake up, you're in that role. What are you doing differently?

Matt Amundson: That's really smart. That is a really, really smart way of thinking about it. You know, one of the things, uh, about the company that I work for currently is we sell to a lot of seed stage and a round companies. And, you know, they typically, you know, they, they don't always stand out from like a category perspective.

I think we have a, we're, we're probably, uh, our install base is heavily. [00:31:00] Oriented towards AI startups, obviously, just because there are so many right now. Uh, but thinking through like, oh, if I was to start an AI company and I was gonna use the product that we create. How would that help me? You know? And, and, and then I think synthesizing that down into core benefits is something that is, that's just a really smart way of thinking about how do we, how do we actually talk about the product?

And obviously, you know, you could, you, you may change that depending upon the category that somebody is in. But, um, but that I think is, man, that was really insightful.

Craig Rosenberg: Uh, how do you, how do you guys figure out insights right now though?

Matt Amundson: Yeah, I mean, I think it depends upon where you are in, in your, in your growth stage. Because I think one of the things that's challenging for like, um, the early go to market team to work with the CEO on is like that CEO E is like just incredibly busy, right? Like he or she is dealing with a board trying to raise capital, worried about finance, worried about operations [00:32:00] overhead, a million things.

And so they're always. They will always tell you, yeah, I'm here for you. Like, let's schedule some time. And you, we all know inevitably that that time like pushes and pushes and pushes and pushes. I, I, I know this isn't like su something super amazing, but I think, you know, if you still have a CEO who's heavily involved in the selling process, you know, sort of mining out.

Uh, if you have like gong or some other call recordings, uh, uh, um, uh, platform, just going in and listening to the way that person sells. Uh, because oftentimes, like if you sort of pinpoint them into a corner, or if you, you pin them down in a corner and you're like, Hey, what are the things that are most beneficial to you?

They, they sort of struggle, right? Because they're like, yeah, I'm really good on my feet. And I think the thing that they don't often realize is they end up saying the same thing over and over and over again. But like in these like weird hypothetical situations, it's hard to extract that value from their brain.

But like if they're a seller, they're talking about it all the time on the, on the phone, and they, they think that they're often reading and reacting to what the prospect is [00:33:00] saying, but so often the prospect is saying the same things over and over again. So I think there's, there's this interesting sort of illusion in the early stage of business that like, oh, we sell to all different types of companies with all different kinds of problems.

You probably don't, right? There's subtle nuance that that exists there. You know, maybe they have a different infrastructure, they're on a different cloud provider or like whatever. But the reality is, is like they're all trying to solve for the same problem. And so, you know, pulling that out of, uh, out of gong is always really easy, right?

Because the search functions work really, really well there. Um, that was always my big hack when I had gong. I'm at a company that doesn't have gong. And the Gong Sellers know it. Um, hence all the emails about going to UCLA. But, um, uh, yeah, that, that is a very, very powerful tool. And it's a real, like, just get to the places where your CEO is speaking and, and, and it's been recorded.

Don't try to, I mean, it's great to get time on their calendar, but like, don't overwhelm them. They've got a million things that they're worried about, like, and they're leaving a digital trail for you to [00:34:00] pick up. Just pick it up and run with it.

Ana Leyva: And I, I mean, when we help founders all the way from like a founder in the seat of sales and growth. Through expansion. We have a really great talent team that will help them hire and find their, their first, um, salespeople. And even in that process, you know, we always advise, look for somebody who is.

rep that's gonna be able to extract from you, not just like follow the playbook that you've written, but also like build on it, right? Like see, notice something about your process founder that you yourself haven't even noticed, right? They can bring kind of their sales expertise and background and say, oh, I know you.

This is what you're doing. Like, you, you always mention this, or this is, this is how you handle that objection. And yeah, there's this. Founders don't even know what they're doing often, right. And so that's why they need a team around them to say, uh, this is, this is part of what is helping and moving the deal forward.

And, um, so yeah, I couldn't agree more, Matt.

Matt Amundson: I think the other thing too is like if you want to be a, a, a great employee to your CEO, like show up [00:35:00] with. Hey, I, you know, this is what I think it should be. And the reason why is, you know, I listen to your calls, or I, I talk to, you know, 50% of our customers, or, you know, I've been working really closely with the customer success team.

Show up with a hypothesis and let them tell you if it's correct or incorrect. That just goes such a long way, right? Especially, you know, if you're, if you're a new hire, if you're new to a business, like, don't just try to only extract value from them. Like, Hey, tell me all the answers, right? Because. You know, that's, that's exhausting.

We know that on a daily basis, whether it's with our own teams or if you're a parent, like, you know, you got people asking you for the answers all the time, right? And you just get to this point where, where you get fatigued by it. But if you can show up and say, Hey, you know what, um, the last 10 deals that we closed, I heard this was mentioned on the call, and it seems like, you know, it's something that.

Could be a really compelling, uh, talk track for us to start incorporating into our broader messaging, into our sales cycles, into, you know, our BDR approach into our, you know, ads, [00:36:00] whatever, you know. Tell me if you think I'm correct.

Ana Leyva: Yeah. I love that. That's an A player, right? When you're bringing, when you're building an A team, you're build, you're bringing in people like that, not people that are just like, um, you know, be able to do what you tell them, but really be able to help co-create. That's what founders yeah. Absolutely.

Matt Amundson: I, uh, Craig, if you wouldn't mind, I have some questions just about, you know, her day to day, if that's okay. Thank you.

Sam Guertin: Roger, Roger.

Matt Amundson: Yeah. Over hunger. Um, so, you know, when, when you're working with your portfolio companies, um, obviously they're, they sort of range into lots of different categories, but as you're thinking about like building out the first go-to market strategies, I'm curious to. To get your opinion on like what is the foundation from what you start to grow everything off of?

It's varied from, from uh, uh, you know, I think things go in and out of the zeitgeist, but like, you know, is our focus on SEO is our focus on great messaging, is our focus [00:37:00] on, you know, uh, being customer centric. Like, how are you starting to put together the, the puzzle pieces and like, what's the, I guess what's the corner that you start with?

Ana Leyva: Yeah, so good. That's such a good question.

Matt Amundson: Thank you.

Ana Leyva: I think one of the corners, one of the corners that I love starting with that is unique is, um, I talked a lot, um, with my founders about discipline, and I'll explain what I mean. Um, I. Tell our founders that they're writing this epic story. They are gonna come into a market and transform how things are done today and make the their buyer the heroes of their orgs.

And they're writing this epic narrative and it's their job to figure out who the protagonists are gonna be. And so when I, when they are, you know, figuring out like, who are my buyers and what's my ICP and what's the right motion? I, um, want our founders to think of themselves in a very active role of choosing who their protagonists are gonna [00:38:00] be.

So literally saying, you're not finding your first users, you're choosing them. And so what that means, and why I go back to discipline is discipline is being able to tell the wrong fit, the wrong people. Someone who is not gonna get value from your tool. It's your willingness to say, no, thank you for taking the call with me.

I don't think this is gonna drive value for you, so let's. You know, like, let's not have a next step. But I think founders, you get a step of like, you're, this, you can get in this place of desperation where you're just like, I just need users. And so you wAna say yes to everyone and that's a really, that's the wrong way to build.

And so I'd say one of the most important cornerstones is the discipline to say no to the wrong, to people who won't be. Absolutely obsessed with what you're gonna be delivering to them, because especially early on what you want, I always tell our founders, you're selling for the renewal. You're not selling for the initial close.

You're selling for the renewal. And if you don't feel conviction that this person's gonna be so obsessed with your product that [00:39:00] they're gonna wAna absolutely renew in a year, or tell everybody they know about you, then it's not the right protagonist. Let's move on. Say no and let's find another. So. Um, I, yeah, I spend so much time with.

Matt Amundson: I love that. I love that there is always this, uh, obviously there's the urge to try to close everything that comes to you, right? And try to build this compelling case sometimes out of thin air. I think there's also like that discipline probably go extends even further out, right? Like. Don't go multi-product too early.

Don't try to sell to multiple ICPs too early. Right? Like I, I, you know, the number of early stage companies that I've talked to who are like, yeah, we're building this for sales and marketing, and I'm just like, no, no. Like that's the two people you definitely don't want to build this for.

Ana Leyva: Oh, you're building. Okay.

Matt Amundson: Yeah, exactly.

Exactly. Yeah. Don't, don't do the PERT Plus, do [00:40:00] a shampoo and conditioner.

Craig Rosenberg: Oh, geez. it. What just happened?

Ana Leyva: I think it's really hard for founders 'cause they want so much to get to scale and they, you know, I, I feel like I hear this all the time from our product too. It's like, I'm doing this, but I don't think it'll scale. It's like you're not, in especially early stage, we're not super like, focused on scale.

We're, we're focused on customer obsession. Like, you need to really find that first. And then once you have that boom, like I, I always tell them, I'm like, eventually you'll sell to whoever else. That's like chapter 10 though. We're on chapter one

Choose this protagonist right now. Be disciplined of like remembering.

I'm in chapter one and then chapter 10, it'll come, you know, and you'll be ready for it. And, but you need to get chapter one, right? If you wAna ever write a chapter 10,

Matt Amundson: Love that.

Craig Rosenberg: Matt, do you have more? You said you had questions.

Matt Amundson: Yeah, I think I rattled off like three-ish there, but,

Craig Rosenberg: Oh, did you? Oh, I didn't, I wa yeah, I,

Matt Amundson: Yeah, you kind of zoned

Craig Rosenberg: the, no, I was more focused on the guess [00:41:00] insightful answers than I was on your question abilities.

Um, yeah. You know, I do these things, so, um, but, but I, I just want to go back to, to two things. 'cause I was going to ask you about, you said targeting when you talked about.

Uh, you know, the anecdote to just ridiculous personalization and then you and Matt just had this conversation. Now this is like, um, uh, in my opinion, it is one of it. People are surprised 'cause their first instinct to do better at prospecting is to send more to more people. But actually the more that you.

Isolate who you go after, you see better results. Like we had Scott Burker on, he is like, yeah, you know, if I really needed leads, I would actually go to people and say, you have a hundred target accounts, now you have four. And he is like, and they would get the, you know, the meetings. [00:42:00] Uh, I What's your experience in helping people?

I know you just kind of talked about it. Well, actually you did talk about it, but I wAna double down here because this is. A point that I think we need to to make here. And I just wAna say one other thing before you answer because you know, I wrote so much stuff on a BM and Matt spoke on a BM, I don't want you to call it anything anymore, guys.

Let's just, it's better to target. It just is and, um, and it, for a lot of reasons, by the way, the customer obsession. Which is at the tail end of what Ana said. It's very hard to do if you have 6,000 different use cases. Actually,

you, there's no such thing. So anyway, Ana, uh, back to you. Please respond.

Ana Leyva: I'm getting lost in that. Uh, the question that you're asking is, I

Craig Rosenberg: didn't ask, I I I was, I was setting a scenario up in getting your guy. Did I ask a question?

Matt Amundson: I am not sure.

Ana Leyva: I dunno if I caught it. I'm sorry.

Craig Rosenberg: no,[00:43:00]

Ana Leyva: I, yes,

Craig Rosenberg: I kept talking. That's, you know what you guys, that is an example of selling past the close.

Matt Amundson: Yeah.

Craig Rosenberg: I, I am like one, I, you know, I, I always give sales, you know, when I listen to calls, I always give salespeople that feedback and then I am the biggest culprit.

I mean, it is nuts. Okay. What do you do to help people get over the, get into the targeting mindset versus the, um, everyone concept?

Ana Leyva: it's hard. It's literally like talking our founders off the ledge. 'cause they come and they're like, I heard I have to send 6,000 or like, I've heard conversions or email cold emails are gonna be like 1%. And they're terrified. They're like, okay, so if I wAna get this many leads then I need to send 10,000 this week.

Can you help me? I'm like, uh, you know, let's revisit. And, um, you know, often in having the conversation of you gotta go narrow, focus small. [00:44:00] In order to win. It's not this, you're not doing a spray and pray. We don't, it's not gonna work. And um, how do I get them to do it? I honestly, it's like. Asking them, let's just try it for a week.

Right? Let's, let's focus on, again, you have a hundred, let's go to four. Let's try and working side by side with them and, um, figuring out, tailoring that outreach message. Um, so literally, um, this week working on with founders on multi many different sequences of like, okay, this is the right message. And me providing them, again, bringing the insight, me providing sort of best practices and frameworks on like.

Is, is this email, for example, 50 to 75 words, like all the best practices that we know, but helping the founder insert the insights that, again, uniquely they're positioned to, to bring to the fore. So it's a lot of just trust me and then it works and then they're bought in, you know? But it's a lot of talking people off the ledge, Craig.

'cause I think it, it is like. They feel like this is the way to do outbound. And it's like, well, no, and a [00:45:00] lot of people are doing it that way. It's not working.

Craig Rosenberg: Yeah.

Ana Leyva: Lets.

Craig Rosenberg: Hundred percent. What I'm gonna throw this to you guys. Uh, the phone. We're hearing a lot of good feedback on calling. Are you Ana or no?

Ana Leyva: I, um, I've sort of, I, my, I've had a hard time getting founders. I'm gonna be honest. I'm just gonna be getting founders to do a lot of cold calling. I think they're not used to it. You know, they've never done the SDR thing. Um, it feels awkward and, um, and yet I, I think cold calling can still works. I think it still works.

Um, is it. It's not the first thing that we go to though. I'll, I'll be, I'll be a hundred percent transparent. We're mainly doing outreach on email, um, and LinkedIn, uh, is what I'm seeing from my founders. But I have, you know, advised founders. I never force them, but I've advised them. I [00:46:00] say, Hey, if you are seeing that people are opening your email and they're not, um, responding, and you wAna follow up, like try a call.

Right? Like Apollo, Apollo gives you email and phone number for a reason. Like, try a call, um. I still think it's, it, it, I'm still a believer, but I don't know. What are

Craig Rosenberg: Yeah, probably not for founders. That's a

Matt Amundson: I, yeah.

Craig Rosenberg: but but for SDRs. But for SDRs in certain markets, you know, like I talked to a guy who does, you know, uh, IT infrastructure and I asked him what's working. He is like nothing except calling because email is absolutely dead in this market like you have.

And so, yeah, I don't know. Matt, are you guys calling

Matt Amundson: Yeah. Yeah. Most of, most of the meetings that we book are over the phone.

Craig Rosenberg: look at that?

I actually asked a question that yielded results.

Matt Amundson: Yeah.

Yeah.

Craig Rosenberg: I

mean, and

Ana Leyva: Yeah, I just, I just have to, just for my, for my founders, I'm wondering, because you guys are like, probably not gonna work for founders, why is it just, 'cause you know, it [00:47:00] takes a certain amount of reps or like, why? I am curious to get your take on. If this is something somewhere where I should really like double down with our founders or just

Craig Rosenberg: I, I, I

Ana Leyva: it work.

Matt Amundson: Yeah, I don't, I don't, I don't think you should. I don't

think you should.

Ana Leyva: Say more, say more. I'm

Craig Rosenberg: really to

Matt Amundson: I would say at this stage of the business that you work with founders. One of the things that's most important is that they have confidence and there is nothing that will blow your confidence apart than somebody telling you to, you know, go jump in a lake after a phone call.

Right? Like, it, it is really easy to ignore emails and InMails and like, and also give people like really like, oh, I think that's great, but now's not the right time, right? Like. W calling is time consuming and calling is fraught with like really negative answers that are, aren't actually indicative of the product as a whole.

It's more just like you're meeting somebody where they don't wAna be met and they're gonna be in a lot of cases, like overly harsh for no real [00:48:00] reason. And I think like you want a founder to believe that they are building the next billion dollar organization, uh, and dealing with negative feedback that frequently I don't think is healthy for a founder.

They have enough on their plate as it is, and going to that place is, is sure, you know, in one, in every, you know, a hundred connects or maybe one in every 25 connects, you're gonna turn it into a meeting and that, that, that might make them feel really good. But it's the 24 where like you don't even get to get through your pitch.

It's just, somebody's just mad that you're calling them. Like, yeah, I don't think they need that level of stress.

Ana Leyva: I

Craig Rosenberg: and the smartest guy in the room doesn't win in the cold call. There's too much technique upfront. That requires training, beat downs, et cetera. So that, but I will, fun fact, one of the biggest founder cold callers was Matt's old boss, Phil Fernandez. And I have a funny anecdote on that, so nothing will surprise anybody on this call.

But at Tip [00:49:00] it, we were like employee, uh, customer number four or something of Marketo. And I moved desks, so I had to handle it. I moved desks and I left my phone. We didn't have it, so like, I forgot, I had a phone at Tippi. We got, we got bought and our acquirers like, you know, doing their thing in the integration like, Hey, does Craig Rosenberg want to check his messages?

I'm like, what messages? They're like, his phone has been full for four years and there was, you know, whatever amount of messages there were. 25% were from Phil. 25% it. He, the guy went after it. He called, he was doing all the techniques he was calling me before work, during, after. I mean, it was incredible. So, anyway, fun, fun fact there.

He's, he may deny it if this goes on LinkedIn, but, but he did because he was, by the way, that guy was one of the better sales [00:50:00] founders of all time. Um, but yeah, I mean, he was ama he wasn't gonna back down to anybody, but no, look, guys like the, the, here's the thing. You know, one is the, the great thing for prospectors is that with AI role play and AI phone. The fact that buyers are responding to phone, you're in better shape than you've ever been in the history of B ding s ding. Without a doubt that's not appropriate for founders. It's like if they say F you, here's what you say, we need the 23-year-old kid doing that. Um, and so is it the right thing if your market, uh, is, you know, responds to it?

For sure. It's just not, I don't think it's for founders. Um, that was a great. What a great redirect on, on a, on my question. I I love that. Ana, you. Yeah. Thank you. She's just making it happen. Clearly. A sales leader for a long time in her life. Yeah. Uh,

Ana Leyva: Asked me to be co-host to this and

Matt Amundson: [00:51:00] I am retiring. I'm

Craig Rosenberg: We wAna get, we've been trying, Sam and I have been trying to get rid of Matt for a while. So Ana, thank you for that generous offer. We've just been looking for the right candidate. Um, all right, well this was a great show. We had a lot of fun. Um, and we were able to talk to, you know, Matt and I are like, we're deep into tactics that worked.

So it was really fun to get in the weeds here with you and to have you on the show. And, um, yeah, let's do it again sometime.

Ana Leyva: Thanks for having me guys. This has been fun. Thanks for, thanks for joining us. It was a blast to have you on. [00:52:00]