---
title: "Fall in Love With the Buyer, Not the Product"
episode: 146
podcast: "The LeanScale Podcast"
publisher: "LeanScale"
guest: "Zach Rego"
guest_title: "Chief Revenue Officer, Triple Whale"
date_published: 2026-10-27
date_modified: 2026-11-09
duration: 00:50:00
word_count: 9786
topics: ["sales-leadership", "pricing-packaging", "ai-in-gtm", "outbound-sales", "sales-enablement", "gtm-strategy"]
canonical_url: https://www.leanscale.team/knowledge/podcast/zach-rego-triple-whale-fall-in-love-with-the-buyer/
source: "LeanScale Knowledge Hub — https://www.leanscale.team/knowledge"
license: "Free to quote and cite with attribution to The LeanScale Podcast."
---

# Fall in Love With the Buyer, Not the Product — Full Transcript

> Episode 146 of The LeanScale Podcast, with Zach Rego.
> Published October 27, 2026 · 00:50:00 · 9786 words.
> Machine-transcribed and **not diarized** — speaker attribution is inferred, so verify
> attribution against the audio before quoting a specific person.
> Structured breakdown: https://www.leanscale.team/knowledge/podcast/zach-rego-triple-whale-fall-in-love-with-the-buyer/

## 00:00 — Cold open + intro

**[0:00]** But the lazy, hey first name LinkedIn and emails like, that is, you might as well not

**[0:09]** send them.

**[0:10]** I think that might kill your brand.

**[0:11]** So if you're going to do something, then you got to really take it to that next level.

**[0:15]** My guest today is Zach Rigo, Chief Revenue Officer at Triple Whale, the AI operating

**[0:20]** system for commerce used by more than 60,000 brands.

**[0:24]** So it was very scrappy, how do we collect as many dollars as we can?

**[0:29]** We'll figure out the rest later, motion.

**[0:31]** I think if you're making that decision, you need to go and try to sell it because the

**[0:36]** feedback loop is going to be so much faster for you to iterate.

**[0:39]** But I think in-person has become so mission critical and personalization is going to need

**[0:43]** to go to like the craziest degree to work.

**[0:48]** You said fall in love with the buyer, not the product.

**[0:55]** What did you mean by that?

**[0:56]** If I'm going to spend 9-10 hours a day talking to someone about their business, I would want

**[1:02]** to just sit down and have a beer with and have that discussion.

## 01:12 — Day one: an Airtable of 2,000 names and one rep

**[1:12]** Four and a half years ago, somebody handed you an air table with 2,000 names in it.

**[1:17]** No enrichment, no data, said go attack it.

**[1:20]** Walk me through that first week.

**[1:22]** What did you actually do on day one?

**[1:24]** Yeah, so our founders were incredibly scrappy and our CMO at the time was just amazing at

**[1:31]** generating demand.

**[1:33]** We had actually launched a wait list for a product that was just coming to fruition as

**[1:37]** I started, which is our attribution product today.

**[1:40]** It's kind of the core backbone of our data infrastructure.

**[1:44]** I brought one sales rep with me, so when I left Unstack, I had just hired a sales rep

**[1:47]** there.

**[1:48]** It happens to be one of my best friend's little brothers.

**[1:50]** I didn't want to leave him because basically me and him were the only folks on the sales

**[1:54]** team at the time and asked the CEO at Unstack if I could bring it with me.

**[1:58]** He was like, "Yeah, sure."

**[1:59]** I asked the CEO at Triple Well if I could bring it with me.

**[2:02]** He was like, "Yes, of course.

**[2:03]** We need someone."

**[2:05]** We just attacked the list.

**[2:06]** We had emails and first name and a couple data points from the form.

**[2:11]** It was just how can we reach out to as many folks as fast as we possibly can to get demos

**[2:16]** booked as well as manage the inbound pipeline.

**[2:20]** We started to stand up HubSpot because I had implemented that at Unstack to try to organize

**[2:24]** that, create tasks, and start to create some semblance of data collection where we could

**[2:28]** potentially build a lead score.

**[2:32]** Between Brantley, the first sales rep and I, I think he did 140 demos.

**[2:35]** He was doing six or eight demos a day.

**[2:39]** It was crazy.

**[2:41]** I think I did 109.

**[2:43]** Then we quickly started to see who's our ICP, where should we start to focus things, and

**[2:49]** who should we maybe not go after anymore on this list.

**[2:54]** Very quickly stood up HubSpot, built a lead score, and had to hire salespeople.

**[2:58]** We put a job posting up instantly.

**[3:01]** Sales were really coming in at that time between our two co-founders doing demos and our chat

**[3:06]** support team just sending people links to pay and sign up.

**[3:10]** We didn't even have a self-serve sign-up flow at the time.

**[3:12]** It was a very scrappy, "How do we collect as many dollars as we can?"

**[3:16]** We'll figure out the rest later motion.

**[3:20]** I think some people, they try to play business early in that stage and get too much process

**[3:25]** in place and too many things when, "Hey, it's kind of Wild West gunslinging stage right

**[3:30]** now.

**[3:31]** We just got to get out there and get it done."

**[3:34]** What are some of the things that you did during that time that you think, "Hey, this was the

**[3:42]** right fit of process," but made sure we weren't acting bigger than we were at the

**[3:47]** time?

**[3:48]** Yeah.

**[3:49]** I think a couple really quick changes was, "What data do we want to collect on the form?"

**[3:54]** As we quickly learned, what was a good brand for us to talk to in those first 25, 50 calls,

**[4:00]** it was like, "Okay, we've got to change our form strategy here on what data we're collecting."

**[4:04]** Actually, the changes we made then are pretty similar to the same form questions we asked

**[4:08]** today for booking a demo or a guide download or a webinar.

**[4:13]** We very quickly refined that process on what do we want to collect because it was just

**[4:17]** going to become, how do we want to route these leads to different sales teams over the course

**[4:22]** of time?

**[4:23]** That was one.

**[4:24]** It's like, you should be thoughtful about how you want the team to look in the future.

**[4:28]** When I interviewed for the job here, I actually white-boarded out, I would say, roughly where

**[4:32]** we are at today from a sales org structure with a couple small changes.

**[4:36]** I always had the vision of, what does 12 months from now look like when I hire people?

**[4:41]** What data do we need to collect today so that one day I can route SMB leads to our SMB rep

**[4:46]** or mid-market to our mid-market team, et cetera.

**[4:50]** That was a big part.

**[4:51]** Then the other one was enrichment.

**[4:52]** What tools are available to us that we can start to, if we have email and we have website,

**[4:57]** get some of the other data points because I knew I needed to refine a lead score.

**[5:01]** We were getting so much inbound demand at the time with so few people to fulfill it,

**[5:08]** that getting data enrichment was very, very important to us.

**[5:11]** Interestingly enough, there was a tool that's specific to the e-commerce space that had

**[5:15]** started spinning up around that time that was perfect for us.

**[5:18]** It was called Store Leads.

**[5:19]** We still use it today.

**[5:20]** Almost every e-commerce SaaS company uses it.

**[5:23]** Just to collect additional data points, we didn't really do anything with it to start,

**[5:26]** but it was more just like, how do we start to get our ducks in a row so when the time

**[5:29]** is right and I do start hiring, I can at least forecast, I need three reps in this segment

**[5:34]** and six reps in this segment because it was not going to be sustainable for Brantley to

**[5:37]** do 110 demos a month for very long.

**[5:41]** Although he did make a ton of money in those first few months and we tried to write commission

**[5:45]** plans and get really scrappy on some of that stuff as well, which was a fun and challenging

**[5:49]** time.

**[5:50]** Those are good problems to have.

**[5:53]** Those are champagne problems.

**[5:54]** Yeah, 100%.

## 05:56 — Why the CRO still takes demos

**[5:56]** One of the things I find really interesting is that you still, to this day, even after

**[6:00]** you've grown, scaled, you have the team in place, you're still doing quite a few demos.

**[6:06]** What's the logic behind that?

**[6:08]** We launch a lot of new products, which is awesome.

**[6:13]** I've worked for companies that are very strategic about how they want to build and their release

**[6:16]** schedule is once a quarter and we launch new things daily, it feels like now.

**[6:21]** When we have these kind of flagship launches, I still like to see how the market's going

**[6:26]** to react to it.

**[6:27]** We're figuring out pricing.

**[6:28]** We're figuring out packaging.

**[6:30]** I lead marketing, so we're figuring out how we want to position it.

**[6:33]** What kind of case studies do we need and customer stories do we need?

**[6:37]** We typically always start by launching new features to existing customers and giving

**[6:41]** them some sort of exclusivity to either preferred pricing or whatever, but I'm going to demo

**[6:47]** you the product or me and the product manager are going to demo you the product and take

**[6:51]** you through it.

**[6:52]** Then I'm going to test some pricing on you and see what I can get.

**[6:56]** We do that as recently as this week, we've launched a new product that our expansion

**[7:00]** sales team, which does all upsells into our base, is going to market with.

**[7:06]** This morning, I was literally working on refining the demo process with the sales leader and

**[7:10]** now I'm getting on demo starting in the next few days and we'll start to hone that craft

**[7:15]** and adjust pricing, which is a hypothesis right now.

**[7:19]** This will work and that's just me and a few other people banging our heads and saying,

**[7:23]** "Hey, we're going to try this."

**[7:24]** I think especially with AI, we're on our third iteration of AI pricing.

**[7:28]** This will actually be our fourth.

**[7:30]** This is an AI product we're bringing to market.

**[7:32]** We're trying a different variable for pricing here, a different value metric.

**[7:35]** When you're doing that, I think if you're making that decision, you need to go and try

**[7:38]** to sell it because the feedback loop is going to be so much faster for you to iterate and

**[7:44]** you'll know where the friction points are.

**[7:46]** You'll know what assets you'll need to arm the team with and then when you do roll it

**[7:48]** out to the broader sales org, most of those questions are answered.

**[7:52]** There's still ... Sales reps love to ask questions about things that are changing or different.

**[7:56]** There will still be things unanswered, but I think I can have some confidence on why

**[7:59]** we made the decisions we did and explain them from a boots on the ground perspective as

**[8:03]** opposed to a few executives sat around a room and said, "This is what's best for us and

**[8:08]** we think it's going to work with customers," and sales reps go figure it out.

**[8:11]** I think that's just a really hard way to collect feedback and make change quick.

**[8:17]** I'm going to want to get into pricing and packaging because that's a really big topic

**[8:20]** right now, so I want to table that for a second.

**[8:23]** I do want to get back to ... How big is the team right now?

**[8:28]** How many reps roughly are on the team?

**[8:31]** Yeah, so total sales-specific reps is between international and US-based, it's roughly 40

**[8:41]** with managers, a few managers across those various segments.

**[8:45]** We also have partnerships, which works through our agency network, which reports up to me.

**[8:49]** That's a big part of our business is driven by either agencies leveraging our platform

**[8:54]** internally or referring us customers, and then we have a solid-size SDR team between

**[9:00]** all of our markets that's roughly 11 or 12 SDRs as well.

**[9:06]** Practically speaking, with a team of that size and scale, how do you actually get in

**[9:12]** and do some of the demos?

**[9:13]** Are you getting some of the inbound?

**[9:15]** Are you targeting a few of the ones?

**[9:17]** Are you writing shotgun with a few reps?

**[9:19]** I think it's ... I'm always interested in the balance of being in the weeds and then

**[9:26]** letting the team run, not stepping on toes, but not losing touch.

**[9:32]** How are you managing that right now?

**[9:34]** Yeah, so again, we start with existing customers when we're trying to launch a new product.

**[9:41]** Something is somewhat ironed out.

**[9:43]** I'll do a shotgun ride along with most of the expansion sales team.

**[9:49]** Typically I'll start with one or two reps.

**[9:51]** We have five on that team, so start with two and let them kind of get in with the executive

**[9:54]** team on what we want to roll out, what it's going to look like, pick some target lists

**[9:58]** with them, do some outreach from myself specifically to them with the AEC seed, and book the calls.

**[10:06]** Then, more recently, if we set up an inbound router, which is a pop-up in our app of, "Hey,

**[10:11]** we've got ... You've been picked to kind of check in beta this feature, which I'd like

**[10:15]** to book a call," I just get added to those as we go.

**[10:18]** Listen, my goal is to get, in this case, the more recent one, which is our automated media

**[10:23]** buying product, I'm trying to get five in the next week, so not a massive amount.

**[10:27]** The team's also doing five and I'm analyzing those calls, but part of it is like, "Can

**[10:33]** I go in and test the messaging or refine the messaging or come up with new talk tracks

**[10:37]** or positioning for the pricing," while the team's also going to market with it and getting

**[10:40]** more data points.

**[10:41]** Then, in aggregate, we look at everything and see how can we refine what discovery looks

**[10:46]** like, how we should position pricing, what features we should lean in on, which customer

**[10:50]** stories are resonating the most.

**[10:52]** That's kind of where we're at and hope to be at by the end of next week.

**[10:55]** It's like a two-week process of us kind of really going deep on that.

**[11:02]** In parallel right now, we're training the new sales team on the product itself, what

**[11:06]** the features do.

**[11:07]** Then, next week, we're starting to roll out.

**[11:10]** Here's the discovery process.

**[11:12]** Here's the demo process.

**[11:13]** Here's how we pitch pricing.

**[11:14]** That'll be last because that's the one that I think we're farthest behind on right now

**[11:18]** in getting reps and real buy-in from brands.

**[11:22]** Yeah, I'm just making sure it's like, "Oh, Zach's not flying in slam dunking deals on

**[11:27]** his own and then building out a territory for himself," because I feel like I've seen

**[11:33]** that version of a CRO flying in and trying to do that.

**[11:38]** It's like, "Hey, I could have done that on my own."

**[11:40]** I feel like that's a really good, healthy way of, compared to you don't want an Ivory

**[11:46]** Tower CRO either, who's coming up with messaging that they think sounds good to themselves,

**[11:53]** pushing it to the team, but it's not really resonating with the market.

**[11:57]** Just think finding that balance is super challenging and it feels like you've kind of cracked the

**[12:02]** code on that.

**[12:03]** Yeah, I've tried to.

**[12:04]** I mean, listen, no doubt I've pissed people off or lost a deal because I didn't manage

**[12:08]** it appropriately and I didn't loop in an AE.

**[12:11]** It's humbling, right?

**[12:12]** It's good to go back to that of like, "Oh, I can do this.

**[12:15]** It's easy."

**[12:16]** Then my follow-up's horrible or I get sidetracked because I got other things going on.

**[12:21]** I'm like, "If I had just looped in an AE, that deal closes because they'll handle the

**[12:24]** follow-up.

**[12:25]** They'll handle the next steps."

**[12:28]** It took me a lot of failed experiences to find that out and we've gotten to a really

**[12:33]** good spot.

**[12:34]** Even like our COO and my boss, Max, is one of our co-founders.

**[12:38]** He was the first salesperson when we were building this thing.

**[12:42]** He's starting to get back into it now, which has been fun, but he even sees it now where

**[12:45]** he doesn't loop in a sales rep and that deal starts to drag on for four weeks longer than

**[12:50]** it should.

**[12:51]** I'm like, "Did you follow up with them?"

**[12:52]** I'm starting to do the micromanaging that you have to do as a sales manager to him and

**[12:56]** he's like, "I should have looped in a sales rep."

**[12:58]** I think we all know at this point we're going to drop the ball here, so it's best to do

**[13:03]** it, in my opinion, alongside the salesperson and even let them own some parts of the process.

**[13:11]** Just like if you brought in a brand new sales rep, I almost always let them own Discovery

**[13:15]** because you can somewhat script a Discovery flow for them and it feels a little robotic

**[13:20]** but it allows them to find their voice, but I'm going to do the demo and I'm going to

**[13:24]** do the close and then the next time you're going to do the demo of this feature and this

**[13:27]** feature.

**[13:28]** We do a lot of that as well.

**[13:29]** We're like, "I'll let the expansion sales rep do the Discovery."

**[13:32]** I might add a couple things in there, but I want to do the presentation and the pricing

**[13:35]** because I feel like that's where we're going to hit the most friction and need to uncover

**[13:39]** the value for the prospect.

**[13:41]** I love it.

**[13:42]** I love it.

## 13:43 — How to price AI when the economics have changed

**[13:43]** One question going into pricing and packaging.

**[13:48]** I think this is the biggest go-to-market challenge CRO, CMOs, founders, CFOs are having in B2B

**[13:58]** SaaS and AI today is how do we price and package this stuff when the economics have completely

**[14:05]** changed.

**[14:06]** A couple of weeks ago, I was at a CFO summit with Radian Capital, so I was in New York,

**[14:12]** full room of CFOs, we were presenting on getting your data model ready for AI, but probably

**[14:19]** the biggest topic for the rest of the event was talking about how to price AI features,

**[14:25]** full AI solutions.

**[14:27]** I was wondering if you could maybe walk through.

**[14:30]** I know there's not a silver bullet.

**[14:31]** I know there's not a one size fits all.

**[14:33]** I know there's not one answer, but I would love to just hear the thought process.

**[14:38]** What did you ask, what did you test, and what were some of the hypotheses that you had that

**[14:47]** led you through the process to how you ultimately ended up pricing and packaging?

**[14:51]** Yeah.

**[14:52]** Listen, we look for inspiration to a lot of folks that had tried and changed and iterated.

**[14:58]** At the time, we had launched a product that was similar to a gum loop, but very specific

**[15:02]** to our industry, so a workflow builder for AI tasks.

**[15:09]** They charged off of credits, so we tried to charge off of credits.

**[15:12]** It worked okay, but it actually inhibited usage.

**[15:17]** People were fearful of hitting the limits.

**[15:21]** That put an interesting discussion at play of where do we want to be in this?

**[15:25]** Do we want just incredible usage and let the usage metrics, which is the approach that

**[15:29]** Anthropic and everyone else has taken, like Anthropic's losing $80 billion.

**[15:33]** They don't care.

**[15:34]** They just want as much usage as possible, and they'll figure out how to bring down the cost

**[15:37]** per token over time.

**[15:39]** We were like, "Okay, we don't want to inhibit usage, so what do we do next?"

**[15:42]** Then we started adjusting credit value to where like, "Hey, let's whatever.

**[15:47]** We don't need to worry about margin on this.

**[15:48]** Let's just get usage and value to customers."

**[15:52]** Then we found that the sales process is just too convoluted.

**[15:54]** I'm trying to sell this base package, and you can add on this AI attachment that you

**[15:58]** can build off of.

**[16:00]** We didn't want it to be an afterthought.

**[16:01]** We wanted it to be integrated in all plans and really become more AI forward.

**[16:06]** Listen, we're on our third version of an AI product.

**[16:10]** We had a chatbot in 2024 that was unique to us and our data set and our customers.

**[16:14]** We were very early to that space and credit to our CEO, AJ, for pushing that very early.

**[16:20]** We redid our entire data infrastructure to support AI and normalized all of our data

**[16:26]** across billions of rows of different data points across every ad channel, every SKU,

**[16:31]** everything that you would need to know as an operator way before anyone else in our

**[16:36]** space did.

**[16:37]** We knew we could get usage.

**[16:38]** We knew if we priced appropriately, we'd get a lot of usage.

**[16:41]** We knew we wanted to be kind of AI forward and more learned from the AI kind of labs

**[16:46]** and leaders of like, "Let's get as much usage as we possibly can and make this just

**[16:51]** critical infrastructure to our customers, and the rest of it will take care of itself."

**[16:56]** We decided more recently to kind of do a good, better, best pricing model, which is like

**[17:01]** we started there and then we somehow ended up back there after a bunch of different stops

**[17:04]** in the middle where AI is included in all packages, but you unlock different versions

**[17:09]** of features and different, I would say, like rate cards around what a cost per token roughly

**[17:16]** would be, but we're not really trying to take much margin on tokens.

**[17:20]** In our foundation package, which is our base plan, you get AI usage, but it's more chatbot.

**[17:25]** You can ask our chats questions.

**[17:26]** You could build maybe a dashboard or a report out of it, but you're going to be limited

**[17:30]** in the models you can use, and you're going to be limited in the volume of tokens you

**[17:35]** have included in your package.

**[17:36]** You can always add one-time top ups or recurring top ups.

**[17:41]** Our next package, you get a more preferred rate on tokens.

**[17:45]** You're going to get more usage as a percentage of what you pay us.

**[17:48]** You pay us one fee, a percentage of that is allocated for us paying for tokens, and you

**[17:54]** get access to all of the models.

**[17:56]** There's a benefit and a downside to that, in that customers are blowing themselves up

**[18:00]** when they're like, Opus 5.5 max, and then ask a question, like, "How many sales did

**[18:07]** I have today?"

**[18:08]** It's like, "Please don't do that."

**[18:11]** Routing is important, and thinking about what your task you're trying to accomplish there

**[18:14]** is really important, but that's the approach we've taken.

**[18:18]** It eats into our margin, and again, we believe that is fine, and we want to grow with our

**[18:25]** customers around using our product in the right ways to scale their business and provide

**[18:30]** them as much value as we can, and we'll figure out the rest from there.

**[18:34]** Without revealing any real numbers, did you and the finance team think about having a

**[18:40]** floor of what the margin needed to be and working backwards from that, and then just

**[18:44]** having like, "Hey, this is an acceptable range as long as we can model, most of the

**[18:48]** customers will fall within here?"

**[18:50]** Yeah, roughly, and I think you got to look at it as like, if you look at all of your

**[18:55]** customers that buy these packages, whatever, 20% are going to use all of their tokens.

**[19:04]** Yeah, those ones, they're going to be maxed out on the floor of the margin, but then you're

**[19:09]** going to have this middle of the pack that's going to make margins slightly better, and

**[19:12]** then you're going to have this other like bottom, the people that just aren't using

**[19:15]** nearly as much, and blended, the margin will look quite good.

**[19:19]** If you only looked at the top users, your margin is going to look pretty bad as like

**[19:22]** a "SAS" company, right?

## 19:24 — Why they hired a head of pricing and packaging

**[19:24]** So I think it is a bit of a model there, and listen, one of the best hires we've made is

**[19:30]** an internal pricing and packaging leader, you know, he's our head of pricing and packaging.

**[19:35]** We had hired consulting firms before, we had done external surveys before, we've iterated

**[19:40]** on pricing a bunch internally, we've created internal task force.

**[19:44]** Finally, we were like, this is like going to be critical infrastructure, it will be

**[19:48]** a leg up to us.

**[19:50]** And we just hired someone from a great background, awesome resource.

**[19:53]** He's actually out right now for his wedding and honeymoon, and I'm like, just can't believe

**[19:59]** how much we rely on him just six months later of him starting, where it's like, that is

**[20:03]** a super important hire right now, in my opinion.

**[20:07]** You can't have our guy, but I would be looking for someone in that realm, because it's going

**[20:12]** to keep you nimble, and it's going to allow it to not be a distraction, but always be

**[20:15]** top of mind for you.

**[20:17]** Where?

**[20:18]** I actually haven't had a CRO have that particular role on their team.

**[20:22]** Maybe I've seen it in really, really scaled out companies, like near public sized companies.

**[20:32]** What type of background are you looking for?

**[20:34]** Did he have pricing and packaging experience before, or did you have a transferable skill?

**[20:40]** Yeah, he's not on my team.

**[20:43]** Obviously, I spend a ton of time with him and we're bouncing ideas off of each other.

**[20:47]** He reports into the COO and kind of the more like biz ops teams.

**[20:53]** Yeah, he actually had, he came from like more of a consulting background.

**[20:58]** And there's a bunch of firms out there, you know, most SaaS companies have hired one at

**[21:01]** some point in their time, you know, I would say Series A, you're kind of like, I got some

**[21:07]** money to go scale.

**[21:08]** You got to start to refine that, figure out how you get some NDR.

**[21:11]** You know, when you get to that point, I'd put a job wreck out, like at this point in

**[21:18]** the game, you know, being able to iterate on pricing every six months, or you're going

**[21:22]** to be launching features faster than you ever have before with AI, you know, in the engineering

**[21:27]** and product world, you don't want to be slowed down by figuring out pricing, like you want

**[21:32]** someone who is thinking about that, you know, before you know, skate to where the puck is

**[21:37]** kind of thing, like you got to know where you want to be, and have someone that's always

**[21:43]** like living and breathing what that looks like for every product you're launching.

**[21:47]** Makes a ton of sense.

**[21:48]** And I do think the difference now, like you mentioned, it's the cycle time where the velocity

**[21:55]** of new features, new products, new things that will be a forcing function to adjusting

**[22:00]** your pricing and packaging.

**[22:02]** Also release of new models, new AI capabilities that you can leverage.

**[22:07]** It may change the economics.

**[22:08]** You may adjust pricing that can give you a bigger advantage.

**[22:11]** I agree.

**[22:12]** I think you're going to need to be tweaking this so much more often than you did in the

**[22:17]** legacy SaaS world.

**[22:20]** And I think it's a good investment.

**[22:23]** And if you can get your pricing and packaging nailed down, right, the return on that is

**[22:27]** immense.

**[22:28]** Insane.

**[22:29]** Insane.

**[22:30]** There's such great value can be attributed to that.

## 22:35 — Fall in love with the buyer, not the product

**[22:35]** One of the things you talked about during our prep session that I thought was really,

**[22:38]** really interesting, because it is a little contrarian to how a lot of people navigate

**[22:44]** their careers.

**[22:46]** You said fall in love with the buyer, not the product.

**[22:52]** What did you mean by that?

**[22:54]** Yeah, listen, I, you know, I started my career in IT consulting services where I was basically

**[23:02]** calling IT directors and CIOs of Fortune 500 companies all day and getting hung up on often.

**[23:10]** And when I connected, you know, the only objective that the person on the other end of the phone

**[23:14]** had was to make me look like a dumb sales guy, which they did quite often.

**[23:18]** Like, I was successful at that job, but I never enjoyed the conferences.

**[23:25]** You know, I never enjoyed when I was taking, you know, the IT director from XYZ company

**[23:31]** out to dinner, like, it was fine.

**[23:33]** But it was like, I kind of always wanted to love who I was selling to and talking to them.

**[23:39]** Like, if I'm going to spend nine, 10 hours a day talking to someone about their business,

**[23:45]** their goals, what, how they want to grow personally, professionally in their business.

**[23:50]** I want it to be someone that like, I would want to just sit down and have a beer with

**[23:53]** and have that discussion with at all times.

**[23:56]** And when I joined word stream, it was like, I loved calling our customers or our prospects,

**[24:04]** right?

**[24:05]** Like, it was like, I enjoyed the conversations.

**[24:06]** I enjoyed the demos, you know, we were selling a Google ads management platform at the time

**[24:12]** to mostly SMBs and mid markets, but a lot of entrepreneurs and there were businesses

**[24:16]** I would like get on off the phone with and I'd be like, that's insane.

**[24:20]** Like that felt like an episode of Shark Tank, like this guy is brilliant or, you know, she

**[24:23]** built this amazing business that you would never think about.

**[24:26]** I remember one where it was like, they sold, you know, crib sheets.

**[24:30]** The margins on crib sheets are insane.

**[24:33]** A crib is only, you know, this big and like, it's always the same size.

**[24:37]** And I was just like blown away.

**[24:39]** I was like the whole business around crib sheets is just crazy.

**[24:42]** And like, I was so inspired after every demo and I was always like, I will never work for

**[24:47]** a company where I'm not selling to somebody that when I hang up the phone, I'm like, that

**[24:52]** was awesome.

**[24:53]** Like I am so excited.

**[24:54]** And I think, you know, Unstack, I was selling to mostly startup founders and operators and

**[24:59]** it was awesome.

**[25:00]** I got to see like some really cool companies were customers of ours early and I grew to

**[25:04]** become like pretty awesome businesses.

**[25:06]** And at triple whale, similarly, like we're selling to e-commerce brands that I'm a customer

**[25:11]** of a lot of them, you know, or every one of our prospects I've, I can go and buy from,

**[25:16]** for myself or my wife or my kids or whatever.

**[25:19]** And that gets me really excited and I love it.

**[25:22]** Obviously you want the product to be good, but if you're in sales or CS or any go to

**[25:26]** market function, even marketing, whoever you are trying to get in front of, or you have

**[25:31]** to talk to for eight to 10 hours a day, you want to be able to sit down and have a beer

**[25:35]** with them or play around to golf with them in my case, right?

**[25:38]** Those are the things I like to do in my spare time of preferably a beer and golf at the

**[25:42]** same time.

**[25:43]** Usually hand in hand.

**[25:44]** Yeah, yeah, yeah, exactly.

**[25:46]** But I want that, right?

**[25:47]** Like I want my prospects, I want to be excited to invite them to an event and that's a rings

**[25:51]** true here for sure.

**[25:52]** And it's been a big part of our successes.

**[25:54]** I think everyone on our sales team kind of loves and is excited about who they're reaching

**[25:58]** out to.

**[25:59]** No, I think that's really, really insightful and my personal experience, I've worked in

**[26:09]** companies that have sold to a number of industries, but this is my favorite one.

**[26:13]** And I don't know if I recognized that it's because I get to talk to CROs, CMOs, heads

**[26:19]** of RevOps, founders of companies I'm really excited about every single day, multiple times

**[26:24]** a day.

**[26:26]** And I think there's a lot of compounding that happens during that time too.

**[26:32]** So if you build a bigger network with people that are similarly connected or have similar

**[26:38]** problems and you continue to grow to be more and more valuable over time as well in that

**[26:45]** particular industry or function, I think a lot of people miss out on that.

## 26:51 — Chasing the hot product vs. staying in one pond

**[26:51]** And I think they're just chasing what's the sexiest product on the market right now, who

**[26:57]** got funded the most, especially in sales roles, like really, really chasing that when, hey,

**[27:03]** you could actually build a pretty fruitful, substantial career if you kind of hang in

**[27:09]** a pond for a while.

**[27:11]** Yeah.

**[27:12]** 100%.

**[27:13]** Listen, there's nothing wrong with going from Mongo to Snowflake to Databricks to whatever

**[27:20]** the next up and coming data warehouse company is because you're going to make a ton of money.

**[27:25]** And I know a lot of those guys and they've had amazing careers and have made a ton of

**[27:31]** money.

**[27:32]** I don't want to sell to that person.

**[27:35]** I want to enjoy my day to day.

**[27:36]** I do all right.

**[27:37]** I'm happy with where I'm at.

**[27:38]** But like, I think it's just, you know, people are, people are motivated by different things.

**[27:42]** And I love entrepreneurship.

**[27:43]** You know, both of my parents were entrepreneurs, like they scared me out of it, which is why

**[27:47]** I've always done like the, the next riskiest thing, which is work for very early stage

**[27:52]** startups without starting anything on my own outside of a little mobile golf simulator

**[27:56]** business.

**[27:57]** And it's just, I love talking to entrepreneurs all day.

**[27:58]** I'm super inspired by them.

**[28:00]** And I think that's, you know, every podcast I listen to is talking to entrepreneurs for

**[28:04]** the most part.

**[28:05]** And I get that, that gets me expired up and doing demos feels like I'm doing a podcast

**[28:10]** episode or an episode of shark tank and I'm one of the sharks asking them, what's your

**[28:14]** CPA?

**[28:15]** How did this business get here?

**[28:16]** You know, where are the flaws?

**[28:17]** How can we help?

**[28:18]** You know, I think that's really fun and interesting.

**[28:20]** So I don't think it's too far off being, being in the early stage, you might as well

**[28:27]** be the entrepreneur, especially when everything changes so much, you have to reinvent, go

**[28:32]** to market differently, come up with a new product.

**[28:35]** I mean, if you're right there in a series, a company, it's almost, you might as well

**[28:38]** been there from the beginning.

**[28:41]** So it is an exciting time.

**[28:42]** I think there's a lot of energy around it and it attracts really, really smart and interesting

**[28:49]** people to come into that.

**[28:52]** And then you can really feel the impact every day too.

**[28:55]** So you know, and I'm sure you're feeling this in the sales process too, when you're working

**[29:00]** with somebody like that, you could be helping them fully change how they're running their

**[29:05]** business.

**[29:06]** A hundred percent.

**[29:07]** Those are the best.

**[29:08]** We have, we have clients that have gone from a few million dollars in revenue to a hundred

**[29:12]** million plus.

**[29:13]** And it's like over three or four years, one, I'm always like, what the heck am I doing?

**[29:18]** They just built a supplement company in three years to a hundred million.

**[29:21]** But you know, it is, it is amazing to watch and you just see these folks and then they

**[29:25]** spin up another business.

**[29:26]** Like they have, they've cashed out, right?

**[29:28]** They're done, but they're starting from zero again.

**[29:31]** They got a new idea they're going to run with.

**[29:33]** And it always just blows my mind.

**[29:34]** I'm like, I am not sprinting fast enough and like that's, there's a, there's a guy Zach

**[29:39]** who really inspiring started an agency, started this brand, started that brand, started another

**[29:45]** brand.

**[29:46]** Just won't stop.

**[29:47]** It's like, he's just loves doing it.

**[29:50]** It's like, that's really, really inspiring.

**[29:52]** Yeah.

**[29:53]** I heard a quote that was some people play to not lose.

**[29:58]** Some people play to win.

**[30:00]** Some people play for fun.

**[30:01]** They're not even in it for the money or whatever, like, yeah, they're nice trophies and accolades,

**[30:06]** but they just have fun building new things, birthing something into existence and seeing

**[30:12]** it through.

**[30:13]** And I think it's really exciting to watch when people do that.

**[30:17]** Yeah.

**[30:18]** It's amazing.

## 30:19 — Hiring: why the first reps came from his network

**[30:19]** I would love to get into one of the areas that I think is one of the most difficult

**[30:26]** things to do as a CRO and that is building your team and hiring sales reps.

**[30:34]** Where I found it to be so difficult is one, people who are in sales interview very, very

**[30:42]** well.

**[30:43]** Uh, they're good.

**[30:44]** They're good at selling at least themselves.

**[30:47]** And I found it hard to know if they're going to be successful in their role for the long

**[30:51]** run.

**[30:52]** What is your approach to hiring, ramping and retaining your best reps?

**[30:59]** Yeah.

**[31:00]** Listen, hiring, we were very fortunate early on that we, we brought in a bunch of people

**[31:07]** we knew for the most part, you know, I brought our first sales rep with me.

**[31:10]** It was one of my best friends, little brothers, he, my best friend is now the director of

**[31:14]** our measurement product, which is our, one of our most important products.

**[31:17]** Um, so he's on our product team.

**[31:20]** The first five or six of the first six sales reps we hired, I think four of them came from

**[31:25]** my network and then we hired a manager and the next four came from previous experience

**[31:31]** working with him.

**[31:32]** So I think when you're in that very early stage, you kind of need people who will not

**[31:37]** let failure be an option because they want to succeed for you.

**[31:41]** Like there is a relationship there that is strong enough that they're like, we're going

**[31:45]** to figure this shit out together.

**[31:46]** Right.

**[31:47]** And that's really, I think important in those early days and almost, I think all of those

**[31:51]** guys are still with us for four years later, four and a half years later.

**[31:54]** So that's one, I think in the early days, it's like, who can you rely on from your network

**[31:58]** that you trust and that trust you as you're hiring and you having to add managers.

**[32:03]** I actually think that's where it gets really hard in kind of building a team is like, who's

**[32:08]** the first manager you want to bring in to either take over some of these, you know, existing

**[32:13]** reps and build that, that function out, um, or to attack a new market.

**[32:18]** How do you want to build that infrastructure out?

**[32:20]** So you know, one thing that we did in our early days is when we were going to build

**[32:25]** like an outbound motion and we had, we relied on inbound for, I would say like a year only.

**[32:33]** And then we started to build out our partnerships ecosystems and then we were like, okay, we,

**[32:37]** we've got enough brand awareness.

**[32:38]** We should start going outbound.

**[32:39]** Uh, we hired a manager.

**[32:41]** We had actually poached a few of his reps, was an early hiring cohort.

**[32:45]** He was kind of left standing at the other company going, all my best reps just left

**[32:48]** for this, called us up and was like, Hey, I'm interested in joining.

**[32:52]** I was like, Hey, we're, we need to build out an outbound motion.

**[32:55]** If you want to join as a manager, I will hire you as a manager, but you're going to start

**[32:59]** by doing outbound on your own and figuring out the infrastructure we need to get this

**[33:03]** right and he came in in October, I believe, and you know, basically from October through

**[33:11]** the end of January, just did outbound as if he was an SDR to figure it out with very little

**[33:18]** success.

**[33:19]** February, he had a lot of demos hit and by March, he had a team of, uh, you know, four

**[33:25]** of our most senior reps and had hired four SDRs to go to market.

**[33:29]** And now it's our biggest team in the company and he leads, you know, our SMB mid market

**[33:35]** and kind of upper mid market commercial is what we call it teams.

**[33:38]** But he came in like from a manager, managed a team of eight to I'm going to be an SDR.

**[33:42]** He had never really done outbound figured it out and has built an amazing organ and

**[33:48]** process and hired, you know, great managers underneath him.

**[33:50]** And I think to answer your question on like, how do you figure that stuff out?

**[33:54]** I think one find people you trust to refer as best you can, which I think everyone knows

**[33:58]** that works well, but find ways of testing out and putting them into building the infrastructure

**[34:04]** that needs to scale as quickly as you can.

**[34:07]** In the case of Jordan, like, you know, we brought him in to do the job.

**[34:09]** We wanted to prove out and built around him.

**[34:13]** You know, when we interview now, I try to scare people out of the job as best as I can

**[34:17]** from a sales rep perspective, because this is not an easy place to work.

**[34:20]** We have incredibly high quotas.

**[34:22]** We have, you know, aggressive growth targets as a company.

**[34:27]** It's an ever moving and evolving product.

**[34:30]** And I don't want anyone that's not ready for that because it is going to be hard.

**[34:35]** But when you succeed, you'll win in a big way.

**[34:38]** And a lot of our reps have and, you know, there's a lot of places that validate that

**[34:43]** and that people are very happy here and do, do really great work.

## 34:48 — Interview red flags: job hops, no progression, severance asks

**[34:48]** Do you have any interview judo moves that can help you suss out assuming you get to

**[34:54]** the point, I mean, with 40 reps, I don't, some people have had to come in that weren't

**[35:00]** necessarily referred any advice for a CRO or VP of sales that's trying to build out

**[35:07]** a team and interviewing people that might not be connected to the company.

**[35:12]** Yeah.

**[35:13]** You know, things that I look for a lot is a lot of it's on, I think, on paper, like

**[35:19]** the resume itself, you know, you see so many resumes now where people have jumped around

**[35:24]** in 11 months, 12 months, you know, I'm very loyal.

**[35:26]** My resume is like three companies over 15 years.

**[35:32]** And I like to see progression within a company.

**[35:35]** I want to see someone that was an SDR and got promoted to an AE of the company and maybe

**[35:39]** moved into a new segment has dealt with change within the same company.

**[35:43]** So I spend a lot of time when I look at a resume that does not have that.

**[35:46]** That's usually what I pick out a lot is why did these moves happen?

**[35:50]** What were the reasons for it?

**[35:51]** What was your success, you know, at the companies in 11 months when you decided to leave?

**[35:56]** You know, some of that is out of reps control, but I think especially over the last six years

**[36:00]** and COVID and layoffs and all of this that's happened, you're seeing people bounce around

**[36:04]** a lot.

**[36:05]** I think both on their own accord and then things that, you know, happened at the company, but

**[36:08]** it's important to really dig there.

**[36:10]** So I look a lot for progression within one company, like did they figure stuff out to

**[36:16]** move to the next spot?

**[36:17]** Did they deal with change, you know, where they were an enterprise sales rep and moved

**[36:21]** into new markets or something else?

**[36:22]** Like, I like to see that because that's what's going to happen here.

**[36:26]** And if you're not willing to fight through that, you know, you're in nine months from

**[36:31]** down the road from here, you're probably going to be looking because we're making some change

**[36:35]** that has to happen.

**[36:37]** Yeah.

**[36:38]** And I think I'm looking for something similar.

**[36:40]** It's like COVID did create some weird nuances, I think everybody working remote, it became

**[36:48]** a little bit easier to move around to, but I am looking for like, did you have one, three

**[36:54]** to four year run somewhere?

**[36:56]** Just one.

**[36:57]** You didn't have to be at every one.

**[36:58]** You bounced around a couple of times here, but was there a place where you could just

**[37:02]** like sink your teeth into it, really go through a ride with the company?

**[37:08]** I'm usually looking for something like that too.

**[37:09]** And I think it's really telling.

**[37:10]** I think the people who, cause you don't want to hire someone who's just going to be around

**[37:14]** for eight to 12 months.

**[37:16]** I mean, by the time you get them ramped and trained and somewhat productive, they're on

**[37:21]** their way out.

**[37:22]** It's, it's not a good formula.

**[37:24]** A hundred percent, a hundred percent.

**[37:26]** The other red flag I try to look for, which I think has become really common and I see

**[37:30]** a lot of the like sales gurus putting this out there is the, they're like negotiating

**[37:36]** severance before they've started or they're negotiating some sort of like ramp quota bonus

**[37:41]** from the jump.

**[37:42]** Like that's a great, like I just, I want to be asking for upside.

**[37:47]** I want to be figuring out how I get more upside.

**[37:50]** I don't ever want to present that I'm looking to protect the downside so much.

**[37:56]** Those things are like, I understand it from a business perspective, but always seem like

**[38:00]** I would much prefer someone be asking me about how do I get into accelerators?

**[38:04]** What are your accelerators look like, right, as opposed to, you know, what's the severance

**[38:08]** before you've started?

**[38:09]** It's like, ah, you've had two stops and you're asking about what severance looks like.

**[38:13]** It's like, okay, let's maybe not progress here.

**[38:16]** It's kind of like the business prenup like, yeah, sure.

**[38:21]** Maybe it makes sense.

**[38:22]** And I don't know, maybe for a few couples, you have reasons why you need to do that.

**[38:26]** But as a rule of thumb, yeah, are you, why are you going in with the exit package already

**[38:32]** ready to go?

**[38:33]** 100%.

**[38:34]** 100%.

**[38:35]** One of the things you mentioned too, because I'm curious once you make the hire, then what

**[38:40]** is, what does the first 90 days look like?

**[38:44]** And how do you suss out if there's someone who should stay on the team or not?

**[38:49]** And the way you phrased it, I thought it was interesting.

**[38:51]** Hire people who will bang their head against the wall for 90 days.

**[38:55]** What did you mean by that?

**[38:57]** How do you assess that period of time?

**[38:59]** Yeah.

**[39:00]** So I think like Jordan was a great example of that, where we hired a manager and made

**[39:03]** him an SDR and then allowed him to build out an SDR in our mid market team, which is like,

**[39:06]** Hey, do the job.

**[39:07]** You're going to have to figure out how to scale.

**[39:09]** You know, from an IC perspective, uh, we put people on the phone very quickly, like within

**[39:14]** two weeks, we're trying to get them, uh, prospecting into our database.

**[39:19]** So we have, um, a kind of a free product that has a ton of data.

**[39:24]** We've got, you know, thousands of them at this point that are sitting and have not had

**[39:28]** a demo or have had a demo of it didn't close and are closed loss now.

**[39:31]** We assign those to, you know, the eighties very early and allow them to start test messaging,

**[39:36]** record loom, start to understand where to look within the product and put them on the

**[39:40]** phone within two weeks.

**[39:41]** Um, and we have reps that have like hit their full quota in, in four weeks, um, for the

**[39:48]** month and we work out monthly quotas, but you know, you'll be blown away by some, how

**[39:51]** quickly some reps can take action, you know, on the database and really find value that

**[39:56]** was untapped before.

**[39:58]** And then, you know, within 90 days, our, our ramp schedule depends on the team.

**[40:01]** So we've got an SMB, a mid market and enterprise team.

**[40:04]** All of them have slightly different ramp schedules.

**[40:05]** You know, our SMB sales cycle is 45 days.

**[40:08]** So like if you're on a ramped rotator by day 60, theoretically by day 90, you should be

**[40:13]** starting to hit full quota.

**[40:15]** And so we give them some runway, but we throw them into demos as fast as we possibly can

**[40:20]** and get game tape.

**[40:21]** And then, you know, managers are responsible for really refining that.

**[40:25]** I usually will spend some time with newer reps kind of between day 60 and 90 doing a

**[40:29]** demo review, um, and some coaching and refinement just to dip my toes and get to know them a

**[40:35]** little bit more, understand their process.

**[40:37]** And then I think the other one that we spend a lot of time on is peer to peer coaching.

**[40:40]** I think like some of my best learnings always came from listening to people who were really

**[40:46]** strong in areas that I'm weak.

**[40:48]** You know, one of those people we hired as a sales manager here, uh, you know, he was

**[40:51]** a rep that worked alongside me at word stream and he was just like, could sell anything

**[40:55]** to anybody.

**[40:56]** You know, one of the guys that could just talk to a wall and like convince them that

**[41:00]** they needed something.

**[41:01]** And I'm not that person.

**[41:03]** Like I was very much always selling on, I would say like you can sell on logic or emotion.

**[41:07]** The best salespeople kind of can do a bit of both where they can build the ROI model,

**[41:11]** but they're also just so emotionally in tune with what, um, people are looking for or what

**[41:17]** makes them excited and they're exciting people to listen to.

**[41:21]** You know, Gleb was one of those people.

**[41:23]** So we do a lot of peer to peer coaching where I'll match, you know, Anthony's not strong

**[41:26]** at this portion pricing, you know, I'm going to match him with a person who does the best

**[41:30]** pricing pitch in the entire company and have them work together on that.

**[41:33]** Um, and we have some reps that have been with us for a really long time where we know where

**[41:37]** they're very strong and allow them to do some peer to peer coaching, which is great for

**[41:41]** them because you learn a lot when you tell someone how to best do their job.

**[41:46]** I feel like when I was first sales manager, I was like, you know, I keep telling the reps

**[41:49]** to do this, but I didn't really do this.

**[41:50]** I just know it's the right thing to do.

**[41:52]** Um, and I think it helps sales reps a lot when they start coaching people one-on-one

**[41:56]** on certain processes.

**[41:59]** I think anytime you can get the team managing the team, you're going to see really, really

**[42:04]** good things happen.

**[42:05]** Of course, like top down vision, but if you can get the team helping each other or holding

**[42:10]** each other accountable, uh, that's when I've seen the best results.

**[42:14]** Um, and you don't have to intervene as much.

**[42:16]** Yeah.

**[42:17]** Yeah, it's, it's great.

**[42:18]** And if you have senior people, you can rely on for that, like treat them well and make

**[42:22]** sure that they know that that is, uh, you know, you're very thankful for their work in

**[42:27]** those areas that take away from their day to day, but are, are additive and helpful

**[42:31]** and a lot to the organization.

**[42:34]** Absolutely.

## 42:36 — AI in GTM: top-down or bottoms-up?

**[42:36]** One last topic.

**[42:37]** I was hoping to pick your brain on, this has been an interesting year, 2026 really seems

**[42:42]** when AI has become ubiquitous across go to market teams.

**[42:47]** I would love to hear maybe two things, two things, because I think it's impacted these

**[42:54]** two areas the most one, how people are generating pipeline.

**[42:59]** A lot of the outbound plays have needed to be shifted, changed in order to remain effective

**[43:05]** over time.

**[43:07]** And a lot of companies are struggling with building pipeline and getting in front of

**[43:12]** their prospects in a meaningful way that makes them want to engage and get them to a demo.

**[43:17]** And then the other is how are you leveraging AI as a go to market team?

**[43:23]** And are you leaning on rev ops to help you implement AI workflows systems, manage the

**[43:30]** data?

**[43:31]** And what does that look like?

**[43:33]** It's a great question.

**[43:35]** We use, I think we're, we're relatively advanced from like an AI usage perspective.

**[43:40]** We've looked at a bunch of external tools, we've tested a few.

**[43:44]** We've built a lot of internal processes using our own kind of AI infrastructure.

**[43:49]** So all of the kind of our BI and analytics are actually on a triple will instance.

**[43:55]** So our own internal AI that our customers use, we actually use as often as we possibly

**[44:01]** can.

**[44:03]** And we do have a rev ops team, we do lean on them a lot.

**[44:07]** We did move someone into like a go to market engineering role within that team.

**[44:11]** So he is building workflows, you know, we have a morning account attack list that gets

**[44:16]** sent to every salesperson.

**[44:17]** We've got a handoff skill that basically allows us to review transcripts, create a handoff

**[44:22]** document for, you know, implementation.

**[44:25]** We've got one that scrapes podcast transcripts to try to find nuggets of information about

**[44:29]** the prospect to come up with gifting ideas.

**[44:32]** So we've tried to create a bunch of automations that work across the business.

**[44:37]** I think what is, what I've had a really hard time with, and I think is a really like big

**[44:43]** discussion and we've tried a little bit of both is, does this need to be top down or

**[44:47]** bottoms up?

**[44:49]** Meaning, like, am I the one coming up with the AI infrastructure?

**[44:52]** Like I'm the one that came up with the podcast thing, I was like, Hey, let's build this and

**[44:55]** like, let's scrape some podcast episodes and see what we can find out about prospects and

**[44:58]** do some really personalized gifting because personalized gifting has worked well for us

**[45:02]** from an outbound perspective.

**[45:04]** Someone sent me this car because they saw this car in my background.

**[45:08]** It's like, that was a nice gift.

**[45:09]** It was really thoughtful.

**[45:11]** It worked really well.

**[45:12]** We've done the same thing where like we look in the back of a podcast episode and we see

**[45:16]** a poster for a band on tour and we sent the very high value prospect, a signed record

**[45:22]** of that from that band.

**[45:24]** So that works really well.

**[45:25]** So like that's tops down.

**[45:26]** Right.

**[45:27]** And then we have bottoms up where I have a bunch of sales rep creating some AI slop outputs

**[45:31]** that I'm like, please don't ever create a deck like that again.

**[45:34]** And then I have some that are like incredible and building, you know, really hyper personalized

**[45:40]** handouts for events.

**[45:41]** I was at an event last week where there's a bunch of enterprise prospects there.

**[45:46]** The sales rep went through the attendee lists, found the 10 that were on his, you know, prospecting

**[45:51]** and target audience lists that were going to be in attendance, reviewed all of their

**[45:55]** quarterly earnings and created a personalized infographic using AI for each of them and walked

**[46:01]** around the event and handed him to the people and you could see the people that he was handing

**[46:04]** him to being like, can you believe what this guy just gave me?

## 46:07 — Personalization to the craziest degree

**[46:07]** So I think, you know, what's going to become really mission critical here is personalization

**[46:12]** and you know, being in person is really critical.

**[46:15]** Personalization has been, I think to us like the one thing that you need to lean on more

**[46:19]** and more and obviously that has always been the case, I think with email or phone calls,

**[46:22]** you want a little bit of prep and personalization, but like you've got to go so far now.

**[46:27]** So you know, we're sending cookies to the office that are branded as triple whale from

**[46:30]** one of our customers with a case study about that customer.

**[46:33]** And that's just like unprompted.

**[46:34]** We're just sending them to people's offices, working very well.

**[46:38]** Personalized gifting like the mention of like looking in the background or listening to the

**[46:41]** podcast episode.

**[46:42]** We're doing in-person events that like from a budget perspective, five years ago, I would

**[46:49]** have never approved, but now it's like, all right, we got to take this swing.

**[46:52]** Like we did an event at an amazing resort in the Berkshires and we took a bunch of prospects

**[46:58]** from New York, drove them out to this event in a big limo bus and it's 25 of them and

**[47:04]** spent two days at a very expensive resort going over their AI strategy and a bunch of

**[47:10]** different kind of workshops on AI.

**[47:12]** And then allowed them to have a bunch of time for events, time for the spa, whatever it

**[47:16]** was, just kind of unplug and it was expensive.

**[47:20]** The CFO was not, he's like, this isn't going to work.

**[47:24]** I need to say we closed our first deal from it just four weeks later today.

**[47:28]** That's what I'm talking about.

**[47:29]** Sent it right to the CFO.

**[47:30]** We got one down.

**[47:31]** We got legal in another.

**[47:32]** We got a couple more that I'm feeling really, you know, um, but I think in-person is going

**[47:37]** to become so mission critical and personalization is going to need to go to like the craziest

**[47:42]** degree to, uh, to work.

**[47:45]** And that's, that's what we've tried to lean in on as much as we possibly can.

**[47:49]** Yeah.

**[47:50]** And I think to your point, the bar has just been raised, so you still have to work just

**[47:56]** as hard.

**[47:57]** You still have to be as creative as you can be, but the lazy, Hey, first name LinkedIn

**[48:04]** and emails, like that is, you might as well not send them.

**[48:09]** I think that might kill your brand.

**[48:11]** So if you're going to do something, then you got to really take it to that next level.

**[48:14]** And I think only the companies that are doing that are really building pipeline in the space

**[48:19]** right now and leaning into, leaning in into AI in a meaningful way and in a way where

**[48:27]** you have taste like the person who was building this infographics, you have to have some taste

**[48:31]** and understanding of what good looks like so that it's actually helpful.

## 48:36 — Wrap

**[48:36]** Zach, thank you so much for sharing everything you did in the podcast.

**[48:40]** It just is really refreshing to hear tactical, practical blocking and tackling advice that

**[48:47]** you're that you're experiencing in the CRO position.

**[48:51]** And especially taking it to the beginning of, Hey, do the job that you're managing and

**[48:56]** don't lose touch.

**[48:58]** Find a way to get involved.

**[48:59]** Keep doing demos.

**[49:00]** Keep talking to customers.

**[49:01]** Keep talking to prospects.

**[49:03]** I love the way you do it without stepping on anyone's toes and you do it in a really

**[49:08]** helpful and productive way.

**[49:11]** And also when it comes to hiring, look for those people who can stand for the long haul.

**[49:16]** Okay.

**[49:17]** Did you have a stint?

**[49:18]** Have you gone through a few times where you've had some progression in your role?

**[49:23]** And I think all of your advice on how to use AI in 2026 for go to market is really, really

**[49:28]** strong.

**[49:29]** You have to step it up.

**[49:31]** You have to be creative.

**[49:32]** You have to take personalization to a level you didn't even know personalization could

**[49:36]** go to.

**[49:38]** And that is the recipe for success in 2026.

**[49:42]** Zach, thank you so much for being on the podcast, can't wait to see what you and Triple Whale

**[49:46]** do next.

**[49:47]** Awesome.

**[49:48]** Thank you, Anthony.

**[49:49]** Everyone please connect with me on LinkedIn or X at Zach Rego, excited to connect to everybody.