Fall in Love With the Buyer, Not the Product

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.

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%.

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 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 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 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 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 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 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 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 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 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.