Apero Advisors

Media/Apero Advisors Podcast/YouTube

How AI agents are changing GTM engineering

Apero Advisors Podcast/Jai Toor, Deepline/

Apero Advisors Podcast/Oct 26, 2026
Transcript

0:00 And you talk about like GTM is code, but

0:01 I always think like sales and marketing

0:03 really can't be reduced to code.

0:05 >> Can we abstract all that away? So it's

0:07 find a contact, add them to the CRM, and

0:10 send an email. It's just three lines of

0:11 code. That unblocks a lot of

0:13 non-technical users or less technical

0:15 users from accomplishing things that

0:17 used to take a team of like 10

0:18 engineers. What we've seen work well on

0:20 that end is human in the loop approvals

0:23 of basically just draft everything for

0:24 me. Then I go in provide feedback or

0:26 make the the final approval before

0:28 something gets done. I have a one of my

0:31 first 10 calls for initial product arrow

0:33 where it was the CRO of uh the company

0:36 Service Titan, but he was like, "Yeah, I

0:38 would not do what you're doing." And I

0:40 ignored that one sentence. He focused

0:42 too much on the product instead of the

0:44 person and the problem that person is

0:46 facing. So, I got to shout out our

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1:28 purchase up to 10,000 credits. Hi, how's

1:31 it going, man?

1:32 >> Pretty good, Ben. Thanks for having me.

1:36 >> Awesome. Um, well, thanks so much for

1:37 coming on. Uh, so your X bio says that

1:40 you're a Paddington 2 evangelist. Is

1:43 that accurate?

1:44 >> It is arguably the best movie ever made.

1:47 >> Why Why is it so good? it uh unique Brit

1:52 like it's the British humor. Uh it's

1:54 it's got the same Pixar thing where it

1:56 is both funny for children and adults. I

1:59 have not shown it to anyone who has not

2:01 said it's one of the best movies ever

2:03 made, but also you might cry at the end.

2:06 So, for it to be both humorous for

2:08 adults and children and also get like 50

2:11 60% of people to cry at the end, uh, it

2:14 takes a special amount of skill that I

2:16 don't think any other movie has ever

2:18 accomplished. And, uh, Hugh Grant is the

2:22 villain, and he is an extremely

2:23 effective cross-dressing

2:26 nun villain.

2:29 >> Have you seen it? No.

2:30 >> Have you seen Oh my god. I actually

2:33 heard about it. It's a a joke. in that

2:36 movie with Nicholas Cage, the unbearable

2:38 weight of massive talent. It was just

2:40 like a side joke and it's like, "Oh

2:42 yeah, petting two two was the best movie

2:43 ever made." And then I looked up the

2:45 ratings and it's 99% on Rotten Tomatoes.

2:48 You're like, "Oh, well that's pretty

2:49 impressive for both audience and uh

2:52 critic score." So you're like that

2:53 that's pretty rare. Uh and then I went

2:55 and I watched it. I'm like, damn, they

2:57 were 100% right on that bit. The entire

2:59 bit is accurate. Yeah.

3:01 >> Okay. Well, I might have to check it

3:02 out. The last movie that almost made me

3:04 cry was probably Nolan's Odyssey. So,

3:09 >> way outside the bounds of GTM

3:11 podcasting, but

3:12 >> there's there's a lot of similarities

3:13 between the two movies. That's all I'm

3:15 going to say.

3:16 >> Oh, okay. I mean, I feel like every

3:19 movie, you know, follows kind of like

3:21 some variation of the hero's journey or

3:22 whatever. So,

3:23 >> yeah, that's that's what we're gonna

3:25 see. And Paddington's in prison for half

3:27 of it.

3:28 >> Oh, okay. Does he have to fight anybody

3:31 for a top punk? He does.

3:34 >> Okay.

3:35 >> You will. I can't ruin anymore.

3:38 >> Yeah.

3:38 >> Okay. So, um, a lot of people uh may or

3:42 may not know what you do. I'm going to

3:44 give you a really bad overview of what

3:46 Jai does, but he's got this little SAS

3:51 that basically uh makes uh

3:56 your coding agent do stuff for your for

3:59 your GTM stuff. Is that accurate? You

4:02 want to give a little bit more of an

4:03 accurate description?

4:04 >> No, that that's basically it. That's

4:06 that's what we're doing. Just the the

4:08 elves in the machine that make you good

4:09 at go

4:11 in the machine.

4:13 >> Yeah. No. Uh the the problem that we're

4:15 solving is essentially uh historically

4:18 it's been very hard to express go to

4:21 market tasks in code. So uh like the

4:24 most fundamental level if you can

4:26 express it in code, coding agents are

4:28 very good at doing it. uh a lot of what

4:31 go to market tools uh do is they

4:33 abstract like sending an email or

4:35 reading state about a customer but

4:37 there's a hundred different CRM they're

4:39 all kind of unique so your options are

4:41 build hundreds of integrations uh buy

4:44 data from all these enrichment data

4:46 providers and then piece it all together

4:47 in a system that you spin up yourself uh

4:50 or can we abstract all that away so it's

4:53 uh find a contact add them to the CRM

4:55 and send an email it's just three lines

4:56 of code and then once we've abstracted

4:58 it to code. Uh now any set of steps that

5:02 you want to do, a coding agent can test

5:05 all the possible ways of solving that

5:07 problem and find the optimal one for

5:09 you. So by turning it into code, you've

5:10 now made it way easier for coding agents

5:12 to solve the problems. Uh and that

5:17 unblocks a lot of non-technical users or

5:20 less technical users from accomplishing

5:22 things that used to take a team of like

5:24 10 engineers at a company like RAMP uh

5:26 to to execute on. So, um I know you guys

5:30 had done something before this called

5:31 Arrow, right?

5:33 >> Yeah.

5:33 >> Yeah. And and I one of the things I

5:35 really wanted to talk to you about was

5:36 like finding product market fit. Um

5:39 because obviously you guys are a

5:40 venturebacked startup. I don't know how

5:41 much money you raised. It was like two

5:43 or three million or something like

5:44 something like that.

5:45 >> Um

5:47 >> uh

5:48 >> and I know from like my own experience

5:50 like working at a early stage, no you

5:52 guys are farther along than I was at my

5:55 the startup that I was at. um uh where

5:58 we were like pre-product market fit. Uh

6:00 we were basically pre-revenue for most

6:02 of the time that I was there.

6:04 >> Mhm.

6:04 >> Like how are you thinking about finding

6:07 product market fit? And I guess like if

6:09 uh another founder or maybe somebody

6:11 who's thinking about starting a SAS

6:12 company is out there, like what would

6:14 you tell them about how to find it? I

6:17 know if you knew how to find it, you'd

6:19 write a book on it and just go consult

6:22 uh for people to help them do that. So I

6:24 don't expect you to have all the

6:25 answers, but yeah,

6:26 >> you're operating in a very interesting

6:28 space for for talking about this.

6:30 >> No, absolutely. That that's a great

6:31 question. I think the if you did want to

6:34 read a book about potentially getting

6:36 there, I think the the guy that has

6:38 captured what I felt most accurately and

6:41 we we followed some of what he said and

6:44 it probably saved us six months. Uh his

6:45 name is Rob Snyder and it's called like

6:48 uh the power of pull. Uh and basically

6:51 like

6:51 >> Yeah. So the the mistakes that most

6:53 founders make and I I talked to a lot of

6:55 founders who are in the exact same spot

6:56 as as we were. Uh there's there's a

6:59 couple things that commonly happen. One,

7:02 you have a lot of conviction on what you

7:04 think is the right way to do something.

7:06 So you will kind of force people's

7:08 opinions into what you think is right.

7:11 Uh I have a call uh one of my first 10

7:15 calls for initial product arrow where it

7:18 was the CRO of uh the company Service

7:21 Titan and we have like a friendly

7:23 relationship and he was like yeah I

7:26 would not do what you're doing basically

7:27 like in in the nicest words he's like

7:29 this doesn't really seem like a good

7:31 idea and I ignored that one sentence.

7:34 He's like don't don't sell to CRO don't

7:36 solve this problem we don't really care

7:38 about analytics. I I'll talk about what

7:39 era was in a second, but uh he just said

7:42 it directly and I ignored that sentence

7:44 and I listened to all the positive

7:45 feedback he gave about what we said and

7:48 I was like, damn, he really tried to

7:49 tell us so early on that we were kind of

7:52 going the wrong direction. Um and I

7:54 think it's like your internal biases of

7:56 what you want to be true. Uh you assume

7:59 that what your experience is is what

8:01 everybody else's experience is. And so

8:02 that that's the hard thing to skip out

8:04 of. You have high conviction, but you're

8:06 almost always wrong. uh very few people

8:08 are high conviction and right at that

8:10 stage and if they are they're like the

8:14 um folks who just spun out a tool from

8:16 like Facebook or Uber and then just

8:19 productized it like those are the people

8:21 have conviction because it's it's a

8:22 clear problem. Uh the other thing that

8:24 happens is you focus too much on the

8:26 product instead of the person and the

8:29 problem that person is facing and

8:31 problems almost too g general as well.

8:34 It was a project so we could have this

8:36 like nice to have product which was

8:38 Arrow. Uh Arrow was essentially very

8:41 similar to what we're doing now but

8:42 there were two additional pieces to it.

8:45 >> One we essentially required a data

8:47 warehouse. We assumed that data

8:49 warehouses were going to be the brains

8:51 of an enterprise org and that's where we

8:54 needed to have everything live and

8:56 that's what we needed to pull and source

8:57 from. There's a couple other companies

8:59 that have this this thesis. uh that is

9:01 true but it's a very small number of

9:03 companies that is true for that don't

9:05 have their own uh team to solve it or

9:08 actually know that that is how they want

9:10 to solve it or have that opinion. So you

9:12 have this it's basically a bad business

9:14 decision to to focus on that market.

9:16 >> Um okay so so one thing uh I I've always

9:19 super appreciated people who like give

9:21 you really candid feedback. I actually

9:22 got um super candid feedback on my sales

9:25 process the other day from somebody um

9:27 >> and they were like, "Well, uh you know,

9:29 you really need like a deck and I like

9:32 >> professionalize your sales process if

9:34 you're not just going to be getting a

9:35 bunch of like inbound referrals from

9:37 like your buddies." And I'm like,

9:39 >> "Okay, that's actually really helpful.

9:41 Um that's not the kind of stuff I think

9:43 about." Um

9:44 >> no, absolutely.

9:45 >> Um but I'm curious like what what does a

9:46 like an ideal like team look like for

9:49 you guys? because we have clients who

9:50 use deep line and they're not like super

9:52 technical but I just wonder about this a

9:54 lot from like um I don't know from all

9:56 sorts of angles like um you have to kind

10:00 of understand the basic mechanics of

10:02 deep line to like buy it like would you

10:05 agree with that or or do you think like

10:06 a total like Neanderthal could just be

10:08 like oh I'm going to go deep line

10:11 >> yeah I think the Neanderthalss uh can

10:14 can in fact use deep line

10:17 >> good news for all you Neanderthalss out

10:18 there Yeah. Yeah. The uh the distinction

10:22 I would say is they have to be

10:23 comfortable in a coding agent and kind

10:25 of like letting letting Jesus take the

10:27 wheel of to sorts of like being able to

10:30 say like I'm just going to describe

10:32 something I have trust or confidence

10:34 that it's going to do something and that

10:36 will be in the right direction and then

10:38 I'll iterate and and get to the final

10:39 state. um if that like mental model has

10:43 been captured which is true for both

10:44 like technical and nontechnical folks I

10:47 don't think that's necessarily the

10:48 breakdown of it's basically like how AI

10:50 pilled are they or how how cloudp are

10:52 they uh and if we can get to a really

10:54 good uh we have tons of users who are

10:57 power users who don't understand every

10:58 detail of what's happening but they know

11:00 how to define a test or an output an

11:03 outcome uh to test against

11:05 >> and so I think we definitely skew a

11:07 little bit more towards more technical

11:09 users just because of this like code

11:11 abstraction and being able to commit

11:13 everything to a GitHub repo. That's an

11:15 important feature for more technical

11:17 teams. But the average RevOps person

11:19 probably doesn't care about that yet.

11:21 They will eventually and that that's

11:22 kind of our bet is more things are going

11:24 to head towards this code first approach

11:27 because uh intuitively it just makes

11:29 sense for agents to be able to

11:31 communicate with each other about go to

11:33 market. They need a common language.

11:34 that code is going to eventually be the

11:36 the right uh form factor for for that

11:39 type of information. Uh code plus

11:41 context in in another format. Um that

11:46 doesn't require someone. So you can go

11:48 in, you can just toss in a prompt.

11:50 Deepline will get you a solution and

11:52 it'll get you potentially the best

11:54 solution uh depending on what you're

11:58 what you're optimizing for. If you're

11:59 optimizing for coverage or uh coverage

12:02 at any cost or cost at a specific target

12:06 of coverage, you have to give it that

12:07 guidance. So, it's how comfortable are

12:09 you with a coding agent uh or an agent

12:11 uh versus how comfortable are you with

12:13 code uh would be the distinction I I

12:16 would make. Um

12:18 does that answer your question?

12:19 >> Yeah. No, it does. it. Um, it also one

12:22 of the other things I wanted to ask you

12:23 about is like

12:24 >> I think you're

12:26 this is an interesting market because

12:27 your total addressable market is

12:28 actually like getting bigger every day

12:31 which is almost like what you want right

12:32 like um when I was working at SIFT um we

12:35 were almost like too early for some of

12:37 the things that we were doing and I

12:38 won't go into all the details but it was

12:40 an AI tool for uh managed service

12:41 providers which is just like IT firms

12:43 and stuff

12:44 >> and they were still like very AI

12:46 suspicious and and I feel like if we

12:49 started it now, not even that long. Not

12:51 even that long later, right? Like 18

12:53 months later, the company started in

12:55 2023,

12:56 >> whatever. Like if it had started in like

12:58 2025,

12:59 >> like I feel like we would have like

13:00 killed it. Um we had other issues other

13:03 than that, but um

13:05 >> yeah,

13:06 >> you know, I wonder like uh

13:08 like what what do you think the total

13:10 addressable market on this is like

13:12 today? Um because I am obviously very

13:16 comfortable in like cloud code and stuff

13:18 but um

13:19 >> I don't know like what what do you you

13:21 tell your investors?

13:22 >> Yeah, I think right now we're seeing

13:24 it's about 20% of the venturebacked uh

13:29 market series BD generally teams that

13:32 are building uh or built their go to

13:35 market motions in the last like year or

13:37 so. uh that market is kind of the the

13:40 prime for this right now because they

13:42 are generally hiring technical folks

13:43 when they're building out their their

13:45 stack to start. Uh or you have to have

13:47 enough engineers within the company that

13:49 one engineer working on go to market is

13:51 not unusual. Uh and that tends to be

13:54 companies like modal cognition, listen

13:56 labs, aoka, these like kind of

13:58 hyperrowth, series A to series B to D is

14:02 is where we're getting a lot of

14:03 traction. And then uh before that they

14:06 tend to not have they might have like

14:08 one AI pled person uh and that's enough

14:10 to get a ton of value out of Deepline,

14:12 but the people are going to get like a

14:13 100x value or are going to be in that

14:16 market. And it generally is about 10 to

14:18 20% of go to market engineers and

14:21 applied AI go to market that like uh

14:24 more technical side of go to market

14:26 engineering and yeah 20% seems like the

14:30 pretty consistent metric that we get to

14:32 uh when we go across kind of all

14:33 ventureback startups. Uh I think it's

14:35 going to keep growing especially on the

14:37 later stage side. I think the the ROI of

14:40 one engineer with very

14:44 um opinionated approaches to go to

14:47 market uh infrastructure is now

14:49 completely outsized. Like the the ROI on

14:52 that person is insane. So you're going

14:54 to get more demand on that side. I think

14:56 series A if you're pre-product market

14:58 fit uh before that there's like systems

15:01 don't necessarily add as much value as

15:03 just like getting out there and doing

15:05 stuff. I think that side uh we won't see

15:08 as much growth on this demographic. I

15:10 think people generally will get more

15:12 technical, but it's not going to be this

15:14 like very more technical archetype. This

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15:52 and thanks for watching the pod. So, um,

15:54 one thing and, uh, I'm sure you guys

15:56 always get like comparisons to Clay or

15:58 whatever, so I won't belabor the point

16:00 there, but like, um,

16:02 >> so they have like the whole like GTM

16:03 engineering thing, and I've obviously

16:05 like leaned into that for for various

16:07 reasons, like

16:08 >> branding, marketing. I think it's a good

16:10 I think it's a good uh, you know, it's a

16:13 good way to simplify a complicated

16:15 concept. And you talk about like GTM as

16:17 code, but I always think like you know

16:19 like sales and marketing really can't be

16:22 like reduced to code. Like it's a

16:25 >> it's a you know you're trying to form

16:27 like an emotional sort of like

16:29 connection between two people so that

16:30 they can like come to the truth or

16:32 whatever and see like hey is this a good

16:34 beneficial transaction for like both of

16:36 us. And obviously getting contact

16:39 information and stuff like that is very

16:41 important like I this is stuff I do all

16:43 day right. Um,

16:44 >> yeah,

16:45 >> but this may be too esoteric of a

16:47 question, but like how do you think that

16:49 deep line is helping people like get to

16:52 that like faster? Like

16:54 >> I mean you can even describe a

16:56 interesting data workflow or something.

16:58 But like my experience here is that um

17:03 all this like AI stuff, cloud code,

17:05 cursor, whatever, like all the stuff

17:07 that I do, like you can get 90% of the

17:08 way there. I'm I'm back in I'm back

17:11 doing like full cycle sales at Apparo

17:13 now and I'm like, "Okay, dude. I've

17:14 spent so much time doing all of the

17:17 rigomearroll like data stuff and now I

17:19 actually have to like

17:20 >> talk to people again like very jarring."

17:24 Um

17:24 >> yeah.

17:25 >> Uh how do you see it like being in

17:28 service of that? because that's like

17:29 whenever I'm thinking about like GTM

17:30 tools I'm like okay

17:33 >> I 90% of the stuff I can do I probably

17:35 don't even need whatever like whiz pays

17:37 for like right and so maybe um if uh

17:41 >> if you're like a full cycle seller like

17:44 how would Deepline help you and and do

17:45 you have like full cycle sellers using

17:47 deepline like to a large degree or is

17:48 that still like a small percentage of

17:50 your like customers?

17:51 >> Yeah, I would say it's relatively small.

17:53 Um, and it kind of goes back down to

17:55 that like threshold of series B like

17:59 what what problem is the GTM team or GTM

18:02 engineering team solve uh for a company?

18:05 And after a certain threshold when you

18:06 have more sellers uh when every minute

18:10 that like 10 sellers is spending on a

18:12 problem uh now compounds faster than

18:15 than it does at an earlier stage that

18:17 like post series B 50 sellers 100

18:20 sellers uh that's where the systems get

18:22 way more important and I think that's

18:24 that's where the ROI of like the GTMS

18:26 code the more infrastructure based

18:28 approach of hey like a pre-all research

18:31 there's some nuance like by different

18:33 groups of the the

18:34 But you don't need to be the best seller

18:36 in the world to do a really good pre-all

18:38 research automation that saves your team

18:40 time. Uh and if they can save 20 minutes

18:42 per call and you're just frontloading

18:44 the information, uh 20 minutes times 100

18:46 sellers, uh that that is impactful. So

18:50 uh before that, I think the GTM muscle

18:52 and knowing how to build relationships

18:54 and actually being focused on all right,

18:57 what is the the use case pain point uh

19:00 what is the angle that we're going to

19:02 enter with? I think earlier stage that's

19:04 way more crit uh critical uh because you

19:07 don't like systems are to build

19:10 repeatable processes uh before the

19:13 process is fully repeatable. You need

19:14 more muscle around how do I find the

19:16 repeatable process and so it's it's kind

19:19 of like a before and after is how I view

19:21 it. Um before we do have folks who just

19:23 run the entire cycle on deepline because

19:25 we have all your CRM integrations I run

19:28 our entire sales motion on deepline. all

19:30 our follow-ups, everything is drafted,

19:33 kind of gives me the approval process.

19:35 Uh, I think what we've seen work well on

19:37 that end is human in the loop approvals

19:39 of basically just draft everything for

19:42 me and get me like 80 90% of the way

19:44 there and then I go in provide feedback

19:46 or or make the the final approval before

19:49 something gets done. So whether that's

19:50 updating the CRM or sending a message

19:53 with like notes from a call, uh, all of

19:56 those are are just do the work, let me

19:58 review. Um, but I would say that's

20:01 probably like 10 to 20% of our customers

20:03 uh versus like 80% are one central

20:06 person building for a larger uh set of

20:08 sellers.

20:09 >> Okay, this is something else I've been

20:11 thinking about like with like Muse and

20:13 Gro Muse is like having its like moment

20:15 instinct. Um, and I'm like very Grockbot

20:18 pill and all that kind of stuff. Um

20:22 what is the benefit uh or sorry not not

20:26 I wouldn't say benefit but like do do

20:28 you foresee this is actually like two

20:30 questions really like do you foresee

20:32 like a future where deepline is just

20:35 another like API that people are calling

20:37 from like a centralized orchestration

20:40 agent or do you see it as something more

20:43 where where you're going to utilize like

20:45 not the UI is like the wrong word

20:46 because I guess I guess you guys do kind

20:47 of have a UI even in the even in the

20:49 terminal or whatever.

20:50 Um,

20:51 >> but like how do you see Deepline a year

20:53 from now? Uh, assuming that um the AI

20:57 doomers aren't right and uh

20:58 >> Yeah.

20:59 >> Yeah. We survive. We survive

21:01 >> toasters. Yeah.

21:02 >> Yeah. Yeah. I think what I'm already

21:04 seeing and feeling I feel like there

21:06 there's a couple companies I look at. Uh

21:08 so owner.com is one where they're

21:10 generally like 6 to 12 months ahead of

21:12 everybody else. And then I also look at

21:13 like my personal usage behavior and like

21:15 where I'm I'm getting value. And what

21:17 we've seen pretty consistently is I use

21:20 chat, uh, codeex, cloud code, grockbot,

21:23 instinct, whatever. I'll try all of

21:25 them. Uh, and I never have to set up an

21:27 integration because I just add the

21:28 deepline CLI and then I'm done. And that

21:30 has every possible go to market

21:32 infrastructure tool uh, that I need. I

21:34 never have to log in. It's all just like

21:36 that one off. Uh, and it's a shared

21:38 backend. So let's say I I do have a

21:42 particular workflow like um enrich this

21:45 user and add to the CRM and I have a

21:48 very particular way of uh doing that.

21:50 What information I think is useful or

21:52 important? Are they hiring GTM

21:54 engineers? Uh how many RevOps people do

21:57 they have on the team? Did they just

21:58 fund raise? Those types of signals are

22:00 important for my enrichment but might

22:02 not be for anybody else. So I have a

22:03 play. I can say add this company to the

22:06 CRM in any of the interfaces. uh and it

22:09 will do the same thing every single time

22:10 because that play is is predefined. So

22:13 if we have a a customer where they want

22:16 the same kind of set of steps to be

22:18 taken for every rep uh or every

22:20 individual end user, it's a very

22:23 distributed set of agents on one central

22:25 set of deterministic and

22:27 non-deterministic workflows. Uh and all

22:29 the integration in O is handled

22:31 centrally. So

22:33 >> for like yeah for our less technical

22:35 listeners um

22:37 >> I'm wondering so I I

22:39 >> and maybe for me too because I I have an

22:41 idea about how this works but so you

22:42 have the deepline CLI which is like

22:44 installed on your computer which is just

22:46 a way to think about is just like a

22:47 little application that interfaces with

22:49 deep line on your on your PC or whatever

22:51 right

22:52 >> and then um for the other coding agents

22:55 like how would they know to go call the

22:58 deep line like as a tool or or whatever.

23:01 the deep line.

23:03 >> So yeah, so we we have an API, an MCP

23:06 CLI. We have like infinite number of

23:08 ways you can access uh the platform. Uh

23:11 how do they know you when you install

23:13 it? We kind of just say check deepline

23:15 first. Uh either in your like in your

23:18 config, agents MD, something like that.

23:20 Uh and then we have skills that teach

23:22 any of those agents how to use the the

23:24 tool correctly uh and how to package up

23:27 asks. Uh the way I would kind of uh view

23:30 it in it's just an MCP. It's the same

23:33 thing as like an MCP that you use for

23:34 something else, but instead of just

23:36 notion or just HubSpot, it's all 106

23:40 integrations that we have. Uh and it

23:42 will if you set up the integrations in

23:45 in our platform and say, "All right, I

23:47 want to add HubSpot or Adio." Uh as well

23:49 as our LinkedIn ads audiences and Google

23:52 Ads audiences, all of those are just

23:54 managed integrations. So it's basically

23:56 just one MCP that fans out to hundreds

23:59 uh that you no longer have to think

24:01 about did I connect this one uh who

24:03 should have access to which ones. All of

24:05 that is centrally managed.

24:07 >> Okay. But you have to tell your codecs

24:09 or whatever that hey when I run when

24:13 >> well this is what I've done. I'm just

24:14 wondering if this is the the best

24:15 practices

24:16 >> like uh

24:18 >> so like cloud code and cursor they have

24:20 like all of the

24:22 >> API keys and everything that I use and

24:24 then um

24:25 >> I have like a very large like context

24:27 file with explanations when to call

24:29 these tools and this is pre-loaded into

24:31 every session or whatever so that it

24:33 kind of has like some directions but um

24:35 but you're saying that you have to tell

24:37 Codeex for example hey when I'm doing

24:39 like GTM stuff like I want you to go

24:42 call deepline because it has all these

24:44 plays, right? Is that kind of like what

24:45 you're saying?

24:46 >> Uh yeah. Yeah. Effectively, if you if

24:49 you just say uh run this, I want to pull

24:52 data from people data labs, uh it will

24:55 most likely find deepline because we

24:57 have that context on on the CLI of uh

25:01 which tools. If you want to be 100% sure

25:03 that it's going to call deepline, you

25:04 can say use deepline or uh use one of

25:06 our skills and then it will uh find the

25:09 best plays. It'll find the right info

25:10 from there. Uh but basically the we have

25:13 a play and the goal is to get it to

25:15 trigger that play. It can be off a

25:16 keyword. It can be use deepline 2. Uh or

25:20 deepline GTM there. There's a couple

25:23 different ways you could trigger it. Uh

25:25 the goal is just to get it yeah get the

25:27 agent to try using deepline or check if

25:30 deepline solves this problem. Uh, and so

25:32 you I have run into issues where like oh

25:35 it'll try the HubSpot MCP first and I'm

25:37 like oh wait always use deepline for

25:39 HubSpot because it's already there and

25:41 it's a CLI it's much faster. There's no

25:43 like uh limits on how much data I can

25:46 upload or download from it. So I I have

25:48 to give it that context going forward.

25:50 Uh because some of the agents like

25:51 Rockbot specifically is one where it

25:54 will default to the MCP first uh a

25:56 native MCP. So, we need to tell it

25:58 instead of always defaulting to the

26:00 native MCP, go to deepline first.

26:02 >> Okay. Interesting. Um, are you good to

26:04 go for five more minutes?

26:05 >> Yeah. Yeah, I'm good.

26:06 >> Okay, cool. Perfect. Um,

26:09 okay. Next question. Um, if one thing

26:13 that I've struggled with like at

26:14 companies that I've worked at

26:16 >> is just trying to get people to like

26:18 adopt like new tools. like um

26:22 gosh, this is going to sound bad, but

26:23 like when I was at when I was at Aerops

26:26 um I don't want to sound salty about

26:27 AirOps like

26:29 >> but uh you know um

26:32 trying to figure out the best way to say

26:34 this, but there was there was there was

26:36 a an instance in which some new people

26:40 had been onboarded and they assumed that

26:42 I'm like GTM AI guy or whatever. So

26:45 they'd ask me questions which I was

26:46 always very humbled by that they would

26:47 come to me for like ask me questions or

26:49 something but you know I was like hey

26:51 you know you should like set up the

26:52 HubSpot uh uh API I can get you a

26:55 readonly key and you can install into

26:57 cloud code and they're like

26:59 >> how do you do that? And uh like Jesus

27:02 Christ like

27:03 >> what are we doing here guys? Um,

27:05 >> yeah.

27:05 >> Um,

27:07 >> do you have any like sort of advice for

27:09 maybe like a RevOps person or maybe that

27:11 one

27:12 >> AI pill sales guy in the org to like

27:15 help them like get these tools adopted

27:19 because I'm on the same page like the

27:22 leverage that you get from this kind of

27:23 stuff whether it's deepline or any of

27:24 this other stuff like um

27:26 >> is so outsized versus the one day of

27:29 banging your head against the wall that

27:30 it really takes to to learn this stuff.

27:33 And I I do think that like using AI

27:35 tools requires sort of like a different

27:37 mental model in middle managerial

27:40 skills. Uh interestingly enough, um

27:42 there's some study which anybody can go

27:44 look up probably that the people who are

27:46 like effective with AI are the ones who

27:48 have like management skills. Um so uh

27:52 that's an interesting stat. But like how

27:55 do you think about maybe somebody who

27:56 wants to sell I'm just going to give you

27:58 a really soft here like if you want to

28:00 sell deepline internally but uh you

28:02 don't know you're not sure like if you

28:04 can get these adoption from your team

28:06 like maybe what's like some way to to

28:09 encourage that for for people. Yeah I

28:12 don't know open-ended question.

28:13 >> Yeah I I think there's a bit of

28:15 psychology here of like you and I are

28:18 we're I'd probably describe us as like

28:20 tinkerers. like we are interested in

28:21 trying things and just seeing how it

28:23 works and and testing new things out.

28:25 80% of the uh employees at a company are

28:27 not they do not care about the new tool.

28:30 They would rather not onboard a new tool

28:31 if they can avoid it. What I've seen

28:33 pretty consistently work is two two

28:35 kinds of approaches. One is uh just

28:40 focus on doing things where they work

28:43 today. Like just avoid the adoption

28:44 problem entirely and say uh the central

28:47 team is going to populate the

28:49 information you need in Slack or

28:51 Salesforce or uh what like text you

28:54 something like whatever is the least

28:58 different from what they're doing today.

28:59 Just take that on to the the central

29:01 team and that is going to have the

29:03 highest adoption that's going to have

29:04 the highest ROI over time. it is hard to

29:06 figure out exactly what the best option

29:08 is all the time. Uh I am usually the

29:10 joke I make is I'm usually wrong on like

29:12 what I think the best solution is going

29:14 to be. I'm like going into a company

29:16 this it's going to be Slack at this

29:17 company. Slack is going to be the main

29:19 way we can communicate with reps and

29:21 then it's definitely Salesforce or

29:23 Salesoft or something else. Uh so it's

29:25 often hard just to like pick the best

29:26 option, but centralizing it and getting

29:28 it to a rep without having to actually

29:31 have them do anything is is always going

29:32 to win here. Um, and you can't like

29:35 force someone to be curious about these

29:37 types of things. And so it's it's like

29:39 what just gets the job done and and

29:42 centralizing is going to win that most

29:43 of the the time. Uh, you what you'll

29:46 find is like 20 to 30% of uh reps are

29:50 actually tinkerers and they are actually

29:51 interested in doing this stuff. So 70%

29:54 will get the value, 30% are like, oh, I

29:56 want to add this or change this and then

29:58 just give them the tools to adopt. like

30:01 you you can't really uh force curiosity.

30:04 It's it's some people are going to have

30:05 it, some people aren't. Uh but that

30:06 doesn't mean they're not great sales

30:08 reps. Uh the other pattern, so that

30:11 that's kind of one pattern I've seen

30:12 work. The other one that I've seen

30:15 worked well and this worked really well

30:17 at companies that I thought would take

30:19 really long to adopt AI and it was just

30:23 start showing them examples uh but make

30:26 them all optin examples of hey like uh

30:30 here's a automated email that we're

30:32 sending to like two reps and here's what

30:34 you have to do to set it up but uh we're

30:36 not going to do that for you. You just

30:37 tell us if you want it and we'll help

30:39 you set it up. And uh there was this one

30:41 like uh more legacy company that sells

30:45 into an extremely legacy industry like

30:47 as legacy as you can think uh like World

30:49 War II legacy uh

30:51 >> some buggy manufacturing.

30:52 >> Yeah. Yeah. Exactly. So let's go with

30:54 manufacturing as the the target. Um and

30:56 the sales reps are like older. They

31:00 don't want to change anything. Uh but

31:02 when we started showing them like

31:04 pre-drafted

31:05 research emails with custom landing

31:07 pages, they're like, "Oh my god, this is

31:09 this is fantastic." They went and all

31:11 signed up for their own cloud accounts

31:13 and like started doing things and you

31:16 just kind of have to like peique the

31:17 interest and examples are consistently

31:20 the the best way I've seen to do that.

31:22 And that's why we love our like

31:23 lightning talk stuff which you were one

31:24 of the first you were the first speaker

31:25 at the first one for the record of

31:28 people really like the imagination is

31:30 really what we're trying to to get

31:33 across of broaden your horizons on

31:35 what's possible show all the things that

31:37 are possible and then people will tend

31:38 to say like oh I could use X for my case

31:41 or this might actually solve my problem

31:43 over here and then there's a little bit

31:45 more interest uh generated. So like if

31:48 you want adoption, if that's your number

31:50 one priority, uh remove humans from the

31:53 equation and just do it for them. But if

31:55 you want to actually peique curiosity

31:57 and interest, uh demo days, examples, uh

32:00 just kind of show like an AI internal

32:03 demo day every week at a company is

32:05 going to have more ROI there than uh

32:08 giving everybody access to all the tools

32:10 uh because they they just don't know

32:11 where to start. And I I think we got

32:13 this from our original platform, Arrow,

32:15 where we had a hosted managed agent,

32:17 kind of like cloud code in the cloud,

32:19 that sat on top of your data warehouse.

32:21 And the number one piece of feedback I

32:22 always got is uh we'd had a couple

32:25 recipes that you could press buttons

32:26 for, but every person when they saw an

32:28 open chat box would be like, "Okay, now

32:30 what? What do I do?" And I'm like,

32:32 "Yeah, just type in your problem." And

32:33 they're like, "Well, I have a hundred

32:34 problems. I don't know which one to type

32:35 in." And people just go blank when they

32:37 see a blank box. And I think there's

32:39 some psychology around this of there's

32:41 just too many options and then you just

32:43 panic and crumble and don't know what to

32:45 do. So if you just give someone claude

32:47 and say go do anything, they're not

32:49 going to know what to do. But if you

32:50 give them five examples that they saw in

32:52 a demo last week, they're like oh yeah,

32:54 I need this one. This one would solve my

32:56 problem. Uh and it just gives them

32:58 something more tactical to grab on to.

32:59 >> So that's super interesting. Um we're

33:01 we're almost out of time so I'll

33:03 >> have this one last uh discussion point

33:06 but so I had uh started about think I

33:09 had thought about doing my own SAS um

33:12 which is a very maybe cliche I don't

33:14 know um at some point and um it was

33:16 going to be like a Salesforce uh tool

33:19 for um just all kinds of stuff. Uh it

33:22 was the concept and you're anybody who's

33:24 listening to this is welcome to steal

33:25 this. Um, I'm not going to start the

33:26 SAS. Um, I decided it would be eaten by

33:30 the frontier models eventually, so I

33:31 didn't think it was a good idea. But,

33:33 um, the the concept was essentially like

33:35 a context repository for like your CRM

33:38 because like everybody has all these

33:40 like crazy, you know, variables and

33:42 custom fields and custom workflows and

33:43 it was going to go ingest all that

33:45 >> and then it was going to interview you

33:47 though like in the beginning. Um like

33:48 there would obviously it would work out

33:50 of the terminal and stuff but the first

33:51 thing it would do is be like hey you

33:53 have like this Salesforce flow like

33:54 what's I don't understand it like what's

33:56 the purpose and I would want it tagging

33:59 metadata into fields so that when APIs

34:02 or or whatever uh were calling these

34:04 fields like it would have some kind of

34:06 context on it. Um I'm just curious like

34:09 I'm just throwing this out there like uh

34:11 >> do you think that um a guided like

34:14 interview process would almost be like a

34:15 better onboarding experience because

34:17 that the open chat box like

34:19 >> like canvas uh thing it's it's a problem

34:22 that like every sort of PLG tool has and

34:24 I guess I would categorize like deepline

34:27 >> as like uh PLG and so so anyway my

34:30 question is like

34:32 >> what maybe for other like PLG founders

34:34 out there since I'm now categorizing you

34:36 as PLG Maybe erroneously, I don't know.

34:39 >> Yeah. No, no, that's fair.

34:40 >> What do you What sort of like advice do

34:42 you have for them to I don't know for a

34:45 better product experience and like the

34:46 age of AI and the blank slate era?

34:49 >> Yeah, I mean we are testing that uh

34:52 pattern right now. Like that is that is

34:54 something that we're looking into

34:55 because the the way I've thought about

34:58 it is fastest time to value like what is

35:01 that aha moment? And so that that

35:04 creates this kind of bifurcated

35:06 experience of okay well we want power

35:08 users to be able to get to something

35:09 useful as quickly as possible and we

35:11 don't want to like get in their way but

35:12 if you don't know what's going on we

35:14 also still need to get those folks

35:15 across the finish line and we can

35:17 prioritize experiences and say like all

35:19 right well we're going to make it really

35:20 easy to move fast but also like give you

35:22 this exit path. Um

35:25 there there's kind of this concept of

35:27 the golden path of like the e what are

35:29 you expected to do at every single step

35:31 and make that very clear and visually

35:32 clear and when you have an open box it's

35:34 not clear. So we've tried recipes, we've

35:37 tried tried these prompts and doesn't

35:39 really land. Uh and then the other piece

35:41 of feedback we get a lot is can you help

35:43 me set up my context folder? Uh and the

35:46 thing about deepline is we don't

35:47 actually need a context folder. like we

35:49 can get most of what we need in runtime

35:51 from uh your website or maybe your local

35:54 files. If you've already run prompts in

35:56 that folder, we're probably going to get

35:57 all the information we need. Uh but

36:00 that's some everybody like wants that

36:02 step of make sure I'm doing this

36:04 correctly. And so there's there's this

36:05 like confident and trust problem that

36:07 we're we're also seeing and the guided

36:10 experience solves kind of both of those

36:12 of where do I start and is my entire

36:15 like workspace correct for this? Do I

36:17 have all the pieces I need to be

36:18 successful here? And the short answer is

36:20 you probably are without realizing it.

36:22 Uh but people want that like second

36:24 level of of validation that yes, we have

36:26 confirmed that you are good. Um and then

36:28 the first one uh we'll we'll see how it

36:31 pans out. We're we're launching it soon.

36:33 So I think I'm I'm bullish on it for a

36:36 particular type of user and bearish on

36:38 it for uh like you I think would be

36:41 annoyed in the process. I think

36:44 >> you would be annoyed. So, how do we like

36:46 let you exit it or skip it? So, it

36:48 becomes like yes, it's going to add

36:49 value, but like how do we make sure it's

36:51 the right person and the right value uh

36:54 that that we're delivering? And I I do

36:56 think just PLG has changed remarkably.

36:58 And we were I'm I'm going to go out on a

37:01 limb and say we're probably the first

37:02 cloud code native company where you

37:04 could not use us if you were not using

37:06 cloud code uh in like March or whatever.

37:08 Um and the the benefits there are

37:11 onboarding is really fast. Time to value

37:13 is incredible. You don't have to

37:14 actually understand anything about the

37:16 platform to get value. Uh the hard part

37:18 is we have very little UX surface area

37:20 to teach someone about what we do. Uh

37:22 you have what you give back to cloud

37:24 code and or codeex or whatever and that

37:28 is limited uh and it's noisy. So it's

37:30 going to show a bunch of code. You might

37:32 give some feedback in there, but it's

37:34 just like you don't have the surface

37:36 area that you had 10 years ago in

37:37 productled growth. Uh you don't have the

37:39 UI that you can guide people to. We have

37:42 power users of our platform who

37:44 literally never log in to the UI. They

37:46 just do everything through the terminal.

37:47 And I was like, "Oh yeah, we launched

37:49 this product." And he's like, "Yeah, I

37:51 don't look at the UI. You have to tell

37:52 me in the terminal or I'm never going to

37:53 see it." So it's education is now way

37:56 harder. Uh you don't own as much surface

37:58 area. And both of those are constraints

37:59 that we have to optimize around. Uh, but

38:01 you now have this magical guided like

38:04 Clippy that will help you get started on

38:06 any problem. So, what's the right

38:09 experience there? I don't think I've

38:10 seen anyone nail it. Uh, I I personally

38:13 don't like the really guided onboardings

38:14 also. So, I think we're we're biased in

38:16 some ways, but I do think it's something

38:18 along those lines, but maybe a lighter

38:20 weight version of that.

38:22 >> Super interesting. We could we could

38:24 chat about yeah in the age of AI for

38:26 forever because it it really has like

38:28 it's broken down all of the

38:30 >> traditional sort of uh I don't know

38:33 pathways for adoption that product

38:37 designers would would rely on to like

38:39 get a conversion or or you know upsell

38:41 people later on. And um yeah it's super

38:46 super annoying like because it's super

38:47 annoying for me when I get the product

38:49 got on boarding experience or whatever.

38:51 Yeah. um for for obvious reasons, but

38:54 it's like but if you're a product

38:56 designer or a CMO who wants somebody to

38:59 like get this stuff into your brain like

39:01 what do you just like oh no they don't

39:03 have to do the onboarding experience

39:05 like you know it's a really difficult

39:07 decision like I think people are having

39:08 to like wrestle with from like a product

39:09 design standpoint and um

39:12 >> yeah we'll we'll see what happens uh but

39:14 yeah I'll let you know how it goes.

39:16 Okay, cool, man. Well, thank you so much

39:18 for you're you're my first guest on what

39:21 are the chances.

39:22 >> Yeah, I don't know. This wasn't by

39:24 design. You just in um did this

39:27 I I was like, dude, I should have

39:28 blocked off my calendar for the podcast.

39:30 No podcast before 11 a.m., but

39:34 >> sufficiently awake for this one. So,

39:36 >> perfect. Appreciate it.

39:38 >> So,

39:38 >> I'll do later one next time. Yeah,

39:40 after.

39:40 >> No, we'll definitely have to do a part

39:42 two. Um got a season two planned. So, I

39:45 booked all of season one. Now, I'm

39:47 booking season two, which is gonna

39:48 happen later on in the year.

39:50 >> Yeah, that looks like a week. Very fast.

39:53 >> Also, I'll probably have a sponsorship,

39:57 but if you want to sponsor season two,

39:59 let me know.

40:00 >> Yeah, we'll talk.

40:01 >> Um, anything you want to leave the

40:03 audience with? Uh, any lightning talks,

40:05 anything coming up? Obviously, your your

40:07 stuff's going to be in the show notes,

40:08 but anything you want to pitch before

40:10 you go?

40:11 >> Yeah. Um, nothing top of mind. We just

40:14 had our lightning talks last week. Uh

40:15 we'll have another one in November. Uh

40:18 or late late October, early November. Uh

40:20 most likely New York one more time and

40:23 then SF for the next one. We try to do

40:25 these pretty often. If you have talks

40:26 that you think are interesting or things

40:28 you want to show off, uh this is these

40:30 are community events. So, uh always love

40:32 submissions. Uh, and if you want to try

40:35 out Deepline, uh, we have, uh, a promo

40:38 code I can share for this podcast

40:40 specifically, uh, which will probably be

40:43 Apero, uh, or Ben at Fine, whatever you

40:47 want to call it. We'll edit it later.

40:49 Put that in in post. Okay.

40:50 >> Uh, yeah, we can we can do some credits

40:53 for uh, your your listeners here. And,

40:56 uh, yeah, if you guys have any feedback

40:57 on the product, always excited to hear

40:59 from uh, folks.

41:01 >> Awesome, man. Well, uh, thank you so

41:03 much everybody. Go try out Deepline and,

41:06 uh, talk soon.

41:07 >> Appreciate it.

41:08 >> Yep. Bye.

Episode 1 of the Apero Advisors podcast. Jai Toor built Deepline so GTM work in Claude Code, Cursor, or Codex can look like a few lines of code: find a contact, write to the CRM, send the email, with drafts and approvals before anything ships. Ben, back in full cycle sales at Apero, pushes on what still needs a human: trust, messaging, and the emotional work of selling. They compare DIY terminal stacks to Deepline recipes and MCP, where ROI shows up after Series B when dozens of sellers multiply every hour spent on data and ops, and why PLG onboarding for agent native tools is mostly a blank chat box problem.

Notes

  1. 01

    Jai frames GTM as code when you abstract CRM, enrichment, and send steps, but keeps human in the loop on drafts and final approval before anything customer facing ships.

  2. 02

    Deepline targets post Series B teams where seller time compounds: one GTM engineer with strong infrastructure can support many reps; pre PMF teams still win by talking to buyers, not over building systems.

  3. 03

    Ben's live stack is Claude Code plus APIs; Deepline is the hosted path to the same outcomes with less wiring, including MCP and CLI hooks for coding agents.

  4. 04

    Agent native PLG breaks classic UI guided onboarding: fast time to value, almost no surface to teach the product, so guided setup and context validation matter for buyers who want confidence before they run workflows.

  5. 05

    Full cycle sellers can get most outbound mechanics from AI, but the last mile is still conversations, relevance, and judgment about who is worth a call.

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