---
title: "How She Runs All of RevOps From the Terminal"
episode: 106
podcast: "The LeanScale Podcast"
publisher: "LeanScale"
guest: "Sarah Madden"
guest_title: "Head of Revenue Operations & Strategy"
date_published: 2026-08-28
date_modified: 2026-09-03
duration: 01:13:40
word_count: 15843
topics: ["revenue-operations", "ai-in-gtm", "gtm-strategy", "sales-enablement"]
canonical_url: https://www.leanscale.team/knowledge/podcast/sarah-madden-fermat-revops-from-the-terminal/
source: "LeanScale Knowledge Hub — https://www.leanscale.team/knowledge"
license: "Free to quote and cite with attribution to The LeanScale Podcast."
---

# How She Runs All of RevOps From the Terminal — Full Transcript

> Episode 106 of The LeanScale Podcast, with Sarah Madden.
> Published August 28, 2026 · 01:13:40 · 15843 words.
> Machine-transcribed and **not diarized** — speaker attribution is inferred, so verify
> attribution against the audio before quoting a specific person.
> Structured breakdown: https://www.leanscale.team/knowledge/podcast/sarah-madden-fermat-revops-from-the-terminal/

## 00:00 — Cold open + intro

**[0:00]** You can, like, drill down into where the data comes from, and then if you have the field of view and someone's shown you how to see the big picture, you can see how that all ladders up.

**[0:09]** Sarah Madden, a.k.a. Smads, is the head of RevOps at Vermont, though, as you'll hear, the title barely covers it.

**[0:16]** She started as employee 64 at Braes, cold-calling accounts as a BDR, until a single waterfall chart in an all-hands convinced her she wanted to spend her career in the data behind the revenue.

**[0:28]** You can hear it. You can hear the anxiety. That's the problem. That's the pain point that we're solving. It's not, "Hey, I can't get all my follow-ups out on time every day." No one says that.

**[0:36]** People say, "I'm up so late at night working on my email, and I feel like I'm always behind." That's the pain point.

**[0:42]** There could be a handful of enterprise deals buried in those emails, so I think those are the type of things where, if you're not using AI, even, let's assume it took the same amount of time.

**[0:54]** Even though you're still leaving money on the table, missed opportunities, missed level of depth to the analysis you're running, you just have such an opportunity to take it to the next level.

**[1:07]** And the last thing that we really anchor on is, if you say something or you do something more than three times, it should be a skill.

**[1:16]** Just think like that for the next 10 days, and you will be shocked at how many things you do and say more than three times. It has been living in my brain rent free for the last two months, and someone told me that.

**[1:25]** Now RevOps is, in my opinion, having the biggest moment of the entire function, because RevOps, I think the backlog of work is almost infinite, and I'm still not keeping up, even with maxing out my cloud account every single day.

**[1:43]** So, I think it's an exciting time, and I think where you've gone, you have some of the most impressive applications of AI in RevOps that I've ever seen.

**[1:56]** Thank you, thank you.

## 02:04 — The waterfall chart that changed her career

**[2:04]** Matt, you said the first thing that got you hooked on ops was watching a waterfall chart in and all hands. What was it about that moment that made you walk up afterward and think, "This slide is the job that I want?"

**[2:19]** Yeah, it was pretty much exactly that. I can still tell you where I was sitting in the room of the all hands meeting when I saw this happen.

**[2:28]** And I think what stood out to me at first, when I first saw the chart, I'm like 24 years old, 23, I definitely don't know what a waterfall chart is, and I don't know what these floating bars mean in the middle of the page.

**[2:37]** But as our CRO at Braes, Miles Cleager, who's walking through what each bar meant and how they stack on top of each other, and he stops at expansion and upsell, and he talks us through how that happened and the products, he gets to churn, talks through how that happens, and paints this whole picture.

**[2:52]** And I see just looking up at that stacked bar chart, I'm like, "Oh my God, you have all this information because I put the right closed loss reason on that closed loss op."

**[3:03]** And I thought it was literally the coolest thing that you can drill down into where the data comes from, and then if you have the field of view and someone's shown you how to see the big picture, you can see how that all ladders up to at the time Miles was talking through.

**[3:17]** So I think we were shifting away from having account managers to more CS-based because our only churn was from a product that went out of business.

**[3:25]** And he's explaining this on how it makes sense because account managers have a slightly different focus, and CS has a slightly different focus, and that's what the business needs.

**[3:32]** And I was like, "Oh my God, this is how you build a business. This is so cool. This is why you collect data. This is why it's important to fill in fields, even when they're annoying, so that someone like Miles can stand up here and say, 'This is how we're going to drive the business, and this is how we're going to get the most out of it.'"

**[3:45]** You guys in every single different way.

**[3:47]** And that was very cool because I could see on the floor as an individual contributor, but then at the same time I could see how it all lattered up and how that actually drives the business.

**[3:56]** I can still picture the colors on every bar chart from that waterfall. It was really nice.

**[4:03]** I love that. I have a very similar, I call it a spider bite moment, like when you go from a normal human being to a superhero ops person. And for me it was the first time seeing a growth model and GTM capacity plan.

**[4:16]** And I was like, "Oh my gosh, you can see into the future with this model and everything you would take to go from where we are today to where we want to be."

**[4:25]** And that was the moment I was completely hooked to. So walk me through what happened. You see the chart in a meeting? What was the story after that and how you got into it?

## 04:35 — From BDR to ops: "this is the job that I want"

**[4:35]** Well, so at the time when this all hands happened, I was a BDR at Braze. I was already talking to the team there and saying, "I love generally what I'm doing, but I don't want a book of accounts. I look around. I don't want to be an AE. There's got to be something else on GoToMarket.

**[4:51]** I see the slide and I walk up to miles after and I'm like, "This is the job that I want." I don't even know what job it is, but like whose ever job it is and is involved in this, that's what I want.

**[4:59]** And that's when I got introduced to, or spent more time with our VP of Operations, Oliver Bell at Braze at the time. And someone was explaining to me, "I don't think you really want to go into operations. It's a lot of Excel time. You're on the phone with customers. It's really exciting and really engaging."

**[5:15]** And I was like, "No, I don't think you understand. I think being in Excel and doing the lookups is way more fun and way more engaging. Actually, that is the right path for me."

**[5:23]** So that was the first time that I started to see, "Oh, there's actually a whole career around Excel that's not being an accountant."

**[5:30]** And that really started to click things into place. Like my first, honestly, the only class from college that I really have a strong memory of is the class in freshman year when we learned how to do Excel.

**[5:40]** And it was called Omos 121, and I learned all my formulas, all my pivots, and it was so exciting. And then every year after that, I would do the Coachella spreadsheet.

**[5:49]** I would do the March Madness spreadsheet, like anything that requires a system or a spreadsheet. My friends and I just went to Paris two months ago. It's 2026, and I refuse to use any of the expenses splitting softwares because I want to make my own spreadsheet.

**[6:02]** They hated it, but I've always been drawn to that. And if I can be in a system and a spreadsheet in the database, it's so much fun because that's what underlies everything in RevOps.

**[6:12]** Everything we do ends up coming from a system, which is pretty cool.

**[6:15]** Yeah, I always like asking people who are in ops, "What is your personal finance management strategy look like?"

**[6:21]** And it's almost always custom-built, hand-grown, artisanally made spreadsheets because it's like, "Yeah, there's all these apps, but it doesn't do these very nuanced things that I want it to."

**[6:31]** So I just build it myself.

**[6:35]** And now, I think, now RevOps is, in my opinion, having the biggest moment of the entire function because in Go to Market, it's really the team that is being looked at to lead the charge on AI and have a definition of what good looks like and build these things that can actually scale.

**[7:00]** It's one thing to do some vibe-coding fun things for yourself, but we're tasked to do the job of building things that can be handed to the entire team as well as scaling what RevOps is doing.

## 07:12 — A $20K consultant budget, a $200 Cursor licence

**[7:12]** So I love one of the stories that you shared in our prep session, too, about you being underwater in your ops role, needing some support, looking for a consultant budget, but then getting a cursor license instead.

**[7:27]** Yeah, now it's funny because now I have the resources and the skills to actually do it. It wasn't so funny at the time, but when I first started at Vermont, again, I was the first hire, so we had some infrastructure built in Salesforce and HubSpot.

**[7:41]** Not a lot. Not a lot of it was repeatable. And we were coming up on some big renewals, and I needed to basically get my arms around our renewal tracking.

**[7:50]** We didn't have a great, great form of renewal tracking, you know, things that slipped or we missed deadlines. So that was the thing that I was really diving into was how can I take this Google Drive folder of like 500 different contracts, PDFs, all in different formats, all with different names of products, like everything that could be different about these PDFs was different.

**[8:08]** They were all named differently in the folder. They were amendments. They were renewals, all different types of things. Some were MSAs. And I had to go through there, figure out exactly the contract line items that we had, and make sure that all of that was reflected in Salesforce on like a subscription, subscriptions object connected to the contract.

**[8:24]** And I'm sitting there thinking, okay, I can do all the Salesforce stuff. I know how to build all this. It's the backfilling that's going to kill me like this is going to take forever. I don't know any other way besides just doing doing the damn thing and like going through every single PDF and hopefully at some point it picks up.

**[8:39]** We've all been there. And that's when I said to my co founder, I was like, Listen, if you give me contractor support, I can probably get this entire thing done in under two months, I can do this part of building and then I can outsource this part, you know, the PDF part.

**[8:54]** And my co founder said, Well, why can't cursor do that? And I was like, I don't know what cursor is. So I don't know why cursor can't do that. And then we get that we get into this back and forth. He's like, I'm going to give you a cursor license first.

**[9:04]** It's like $200 a month, you know, because of course, I quoted something around like 20k for two months to bring on someone to help me with this work. And he says, I'll give you a cursor license, go figure it out, see if you can access it in terminal.

**[9:16]** And this whole conversation, I'm like, what's cursor? What's terminal? I don't know what you are even saying to me. So I'm not really sure how to respond. And of course, I didn't have granola at the time. So I didn't have a transcript that I could run through Claude and like get some help on what just happened in the conversation.

**[9:30]** So he gives me a cursor license, I did some googling, saw a lot of words that I don't really understand. And he got on the phone with me like the next day or something. And we sit down and, you know, he's showing me I'm not even in applications where the whole thing is black, right?

**[9:43]** Like chrome windows, right in settings panels, this whole thing is new to me. And we're sitting there and he shows me like, look, you see down there where the cursor is blinking? That's the text box. It's the same thing as in chat GPT or is in Claude.

**[9:54]** So all of a sudden, I'm realizing like, oh, this is kind of the same thing. It's just a different layout. And then I keep asking questions like, oh, well, how do I do this? How do this?

**[10:01]** And he's like, stop asking me ask the chat bot. So eventually I was like, okay, I get it. We keep moving for about an hour. And then I realized, okay, there's a lot here. Let's let me let this settle. Let's regroup in a day in a day or two.

## 10:15 — Being refused help was the unlock

**[10:15]** And we set time for Friday. It was like Friday for an hour. And I'm getting ready five minutes before, of course, I want to prep before my co founder gets on the phone. And I'm sitting there. I'm like, okay, I'm gonna ask him this question. I'm gonna ask him this question.

**[10:25]** And I'm like, wait, he's just gonna tell me to ask the chat bot. So why do I I'm not gonna wait for him to get on the phone. I'm just gonna start asking the chat bot and instantly cursor and I start going back and forth. I don't even know what model I still don't even know what model I was on in cursor at this point, I had one folder on my desktop that had every single project I'd ever worked on.

**[10:42]** It was a mess. And I am going back and forth with cursor. And then I eventually slack my co founder. I'm like, Shreyas, you know what? I don't think I need you because I don't know what are you gonna do just sit here, watch me type to this chat bot. Like, I think I figured it out. I get the idea I can I can do it.

**[10:55]** And he goes, that's good, because I'm getting on a flight. I wasn't going to join anyway. And I was like, okay, I get it. I get how much we can do ourselves now. And that like both of those things like getting the cursor license, and then being told, yeah, I'm actually not going to help you because you don't need help.

**[11:11]** You sit down and you can figure it out was the perfect forcing function for me, because it forced me to go in with no assumptions on how anything worked, because I didn't know how anything worked.

**[11:21]** And I asked every question like really honestly, and I didn't have any crutches to turn around and be like, well, what do you think? How should I say this? I just had to talk to the computer, which was crazy for a few months.

**[11:32]** And then I realized like, what could be built? I gate I was asking cursor like, okay, here, I have this project, I've got this PDF folder. Here's how I'm going to go through it. And cursor said, Well, why don't you just give me the link to the Google Drive folder, dude, I can still picture this on my computer screen.

**[11:45]** And I was like, just the link. And I give it to cursor and it starts telling me, you know, you've got 450 contracts in here, blah, blah, blah, blah, blah, blah. It wasn't perfect. Of course, this was almost two years ago now.

**[11:57]** But it was the most impressive thing that I'd ever seen. And I was like, oh my god, if you can read a PDF of contracts, you can read a PDF of event attendees. And you can read a PDF of all these other things of sales collateral, all of that is possible.

**[12:10]** And as soon as I took that one, keep calling it a non technical use case, because I will like to stay thinking that I am non technical.

**[12:17]** As soon as I realized, oh, there's a pattern here in terms of like what I can give it and what I can get out and then how I can act on it. That was the initial foundation that I really started building on when it came to what is AI capable of regardless of what tool I'm using.

**[12:30]** So that was a really big turning moment. Yeah.

## 12:33 — The infinite RevOps backlog

**[12:33]** Yeah, and I think you're gonna have to reevaluate that definition of technical I think a lot of us are. But I think there's something so dangerous about someone in rev ops just getting completely weaponized with AI, and realizing, I think the level of curiosity just expand so much because

**[12:53]** there were so many things that I've always wanted to do that I just couldn't do because I was held back by bandwidth capacity. It's like, oh my gosh, I want to do this analysis, but I need a whole like date engineering team in order to do that or I want to be able to model this out in order to build a model that's going to be like eight hours in Excel.

**[13:10]** I'm not going to spend my entire day doing that's not worth doing it. But I had a list of 10 million things that I would love to be able to do that I just could never get to.

**[13:20]** So that's why at least in rev ops, I know there's some jobs that are absolutely going to be impacted by AI. But rev ops, I think the backlog of work is almost infinite, and I'm still not keeping up even with maxing out my cloud account every single day.

**[13:35]** So I think it's an exciting time. And I think where you've gone, you have some of the most impressive applications of AI in rev ops that I've ever seen.

**[13:48]** Thank you. Thank you. Yeah, I think, I think back to your point on, you know, bandwidth and stuff like our job at the core is prioritization, not just for ourselves and for our team but for also the rest of the business, which means we have to be the most ruthless

**[14:01]** prioritizers in the business, which means there's always going to be stuff on our backlog, there's always going to be stuff that we don't don't do. And then the other flip side of our job is pattern recognition and seeing further out than right now.

**[14:14]** So there's always going to be things on the list and to your point like if we can start coming up with ways to get 10% of my time back so that I can explore some of these things that are further for more forward looking or have been on my backlog because I'm not sure if I can quantify it being a priority.

**[14:29]** Now I can quantify and be sure it's not a priority, or it will flip my mind be like oh my god I did not realize how much this is blocking. Now I can reprioritize, which is a gift, like being able to dip into all the things we've always wanted to do, and be able to prioritize

**[14:45]** better so that we're working on better things, I think is a huge benefit of all of the AI.

**[14:50]** But yeah, thank you. Thank you for your comment about like good applications. Go ahead. Fully agreed, fully agreed. Well, I know you prepared some demos today or walking through some of the things you've built.

**[15:03]** Man I think anybody in RevOps is just going to love this. I hope so. I hope so and I have prompts on GitHub for like the skills that you know you can't really replicate and share with someone else I've got prompts that we can share.

**[15:15]** We can download themselves. I thought I'd go through a few real like RevOps go to market workflows that we've done or maybe I'll start by explaining kind of how we think about creating skills when to create skills, what buckets we're categorizing them in.

## 15:29 — The three buckets: context, process, infrastructure

**[15:29]** Then I think that will make sense on like the RevOps skills that we've really built. And then we have a whole other set of what we call infrastructure skills that are all about helping us maintain this new system that we now have similarly to how you have like maintenance days for Salesforce or upkeep for your key

**[15:45]** and core platforms and systems. We're treating all of our AI platforms the same way as that we're already thinking, obviously we're thinking about tracking, but we're also thinking about how do we maintain the system for each person and for each of us over time.

**[15:57]** I can go through, let me pull up. So let's talk through a few of the different patterns that we found at Vermont. I'll start by saying, certainly none of this is exhaustive, and this is just the patterns that we've seen in our work and I'm sure we're missing things so I'd love

**[16:11]** to add to our buckets. But like any operator I work better with tags and categories than just like a big blank white space. So the first thing after we got I'd say like maybe the RevOps team had done about a dozen skills ourselves.

**[16:24]** We didn't have any plugins yet. It was just individual skills, individual MCPs connected. And I'd say the rest of the team at Vermont, I'll talk a little bit more about our building approach too.

**[16:35]** But the rest of the team, let's say across our 25 to 30 people on go to market, everyone had created at least two skills, probably. They've used code a little bit they've used codecs.

**[16:46]** We're probably working most of their time in co work, and then some other people are working in code and codecs. So we're already a pretty advanced group, or a familiar and a comfortable group, we're all at different levels.

**[16:57]** We have a nice baseline but we're all at different levels. So at this point when me and my team said okay we need to stop and look at everything that we've built, where's it coming from, where does it live, is it in the same GitHub repo like just organization across the board.

**[17:09]** The first thing we did was we took all the skills, probably about 70 skills in our go to market repo, fed that right into Claude and I said, tell me what's in here.

**[17:18]** Help me categorize them, move them into groups, explain to me what they mean, do different ones have different permission sets like just understanding what we had already done.

**[17:26]** And a few patterns came out for us so when I look at the skills I group them into three different buckets in terms of what they can do for us, or like what their purpose is.

**[17:37]** So there's one set of skills, that's about surfacing context, right like your email inbox scanner, it surfaces information to you that you probably would have done otherwise.

**[17:46]** You maybe have a scheduled task that scans the market or scans for competitors, all of that is surfacing information that if you didn't have AI, you could probably go out and do it yourself.

**[17:55]** It may not be the same quality or this as exhaustive but you could do it yourself. That's really helpful because it gives us time back, it gives us information in the right way and exactly the right way that you consume it better than how I consume it.

**[18:06]** So that's surfacing context. The second one is where we get into process, and that's where we actually give a skill an entire end to end process or a couple of combination of skills, a whole process that the skill is now expected to do.

**[18:18]** And I do not have to do that process at all. Those are some of the rev up skills I'm going to talk about later.

**[18:23]** And then the third bucket is infrastructure right now. So, how do we maintain a healthy terminal, how do we maintain a hygienic folder and file structure, I don't know I'm not a software engineer, I have no idea.

**[18:35]** I just had one massive folder that was titled the name of the one project I ever worked on and everything was in there for like 12 months. So, how do we as not being a senior software engineer as not being technical, I don't know what I don't know.

**[18:49]** So how do I build a whole set of skills that compensate for my blind spots and my gaps. So that's infrastructure. That's my favorite bucket at the moment because of how much I've been in code and codecs but I won't, I won't spend too much time on there.

**[19:02]** There's other a few other things that kind of go into how and when we build skills that was very clear coming out of this analysis.

## 19:09 — The rule of three, and listening for the anxiety

**[19:09]** We've got a few three rules that's centered around the number three. One is if you are doing a process that goes for anyone across the team if you're doing a process that requires you to go into more than three tools, or three for your more.

**[19:22]** That means we need to rethink the workflow. I don't know I don't know what the problem is I don't know if there is a problem, but we need to stop and say, you're clicking too much you're going into too many windows your context switching.

**[19:31]** This does not have to be this way, help me understand what's trying to what's trying to happen. When I'm sitting down with our, you know, F D E's or F D P M's our account managers, and they're talking to me on how they're like you can hear it you can hear the anxiety.

**[19:45]** That's the problem. That's the pain point that we're solving. It's not, hey, I can't get all my follow ups out on time every day. No one says that people say I'm up so late at night working on my email and I feel like I'm always behind.

**[19:56]** That's the pain point that we have to follow and that's the one that we usually get to Claude. So we'll say, okay, Caitlin has to go into 14 different tools to pull something for a QPR deck, and she's going to pull the same thing every time.

**[20:08]** Well if every one of those tools somehow connects into AI, and then she does the same thing every time that's just a skill, that's just instructions. So can we turn that whole thing into a skill, or can we take the biggest time suck and turn that into a skill.

**[20:20]** So that's our approach we're looking for things processes that someone more than one person on the team follows that way we can get as much breath as possible.

**[20:28]** We have to go into more than three tools to complete the process or to get the full value or to understand it. And then the last thing that we really anchor on is if you say something or you do something more than three times, it should be a skill.

**[20:43]** Just think like that for the next 10 days and you will be shocked at how many things you do and say more than three times, it has like been living in my brain rent free for the last two months and someone told me that.

**[20:52]** Turns out, almost every part of your job you could turn into a skill. I've done about 10% of them, the ones that were most comfortable with, and that we have the most control over.

**[21:02]** But as soon as you start seeing that pattern, you realize, oh, running a tool evaluation is something I do more than three times, doing a tool renewal and the business case and the memo and getting stakeholder buy in.

**[21:14]** There's actually an SOP that I follow, even if it's just in my head.

**[21:18]** And then you start to realize, oh my god, if I just wrote that whole thing out, could Claude do it end to end.

**[21:23]** Yes. The answer is yes.

**[21:26]** The answer is almost always yes. And if you're not sure, ask Claude and then it'll be yes. Exactly.

**[21:32]** The answer is try. The answer is ask first.

**[21:36]** No, I think that's a really good framework to think about because if you're going throughout your day and just being thoughtful about logging, hey, these are the things that I'm doing, the actions I'm taking.

**[21:47]** I really like that threshold of if you're doing something three times or more, then it should be a skill and also navigating multiple applications.

**[21:59]** I think that's a big one, too, because I think one blocker, at least as of now in July of 2026, a lot of people have is like, oh, I didn't realize I could connect all these MCPs or I could push data through with a CLI and I can bring it all in with one skill.

**[22:16]** So I think those are really good benchmarks to start saying, OK, start making the list of the things that you want to build and make. And if you don't know how to do it, just ask Claude.

## 22:28 — Slack is a data lake

**[22:28]** Just ask Claude. Just start. Just say, Claude, go through my email. What's something I've said more than three times. What's something I've done? Go through Slack.

**[22:34]** I think that's another thing, too. I don't know if we talked about this in our prep session, but someone I was speaking to this woman, Piper Martz, at one of our workshops over the weekend, one of the cloud workshops that we host.

**[22:45]** Piper said something about systems thinking and how systems thinking. I mean, we've all talked about this in the last few months.

**[22:50]** Systems thinking is going to be a core element, especially for like non ops and non operator people learning how to think in systems.

**[22:56]** I mean, we were born thinking in systems. So now being able to take frameworks like this or rules of three or whatever it is and share it with other people and then be able to say, like, this is how we look for patterns.

**[23:07]** We look to find what's the trigger action or what's the outcome or what's the decision we're making. Those can all surface patterns.

**[23:14]** And then once you get into that zone and you realize, oh, Slack isn't just our messaging app, it's a data lake.

**[23:21]** There's actually all of this qualitative data that I never would have had access to if I couldn't just scrape Slack.

**[23:29]** So once you start seeing your tools, which are your systems, you see notion, you see your call recorder, your email and drive, all of a sudden you're like, oh, my God, I see how this can all work together.

**[23:38]** And that's when people really start to light up, which is my favorite part.

**[23:42]** Can I share one that we use that it highlights the use of Slack.

**[23:48]** So we have tons of engagements and we're working with a number of fast growing B2B SAS and AI companies.

**[23:56]** And we have a shared Slack channel with all of them.

**[23:59]** And that's where most of the work is happening.

**[24:01]** So we have a shared Slack channel.

**[24:03]** Then we have all the transcripts.

**[24:05]** So we built a more like a data warehouse to have all the transcripts that we were going to organize them by client, things like that, instead of the automations to get the pipeline of transcripts moving.

**[24:17]** And then we have our PM system.

**[24:18]** So all the tasks and projects that we're doing for our customers.

**[24:23]** Never have I been able to understand the health and sentiment across our customer base until I connected all of our Slack channels, all the transcripts.

**[24:34]** And then our entire project management system all into one customer health agent workflow system that goes, looks at everything and then categorizes which ones are in good health, average health or poor health.

**[24:48]** That would have taken a data science team of 20 and a whole team of engineers to build before.

**[24:55]** And now that one took me like an hour to find.

**[25:01]** I mean, how many times have we done and calculated customer health scores till I'm blue in the face and as the, you know, the caveat and the footnote is always like, well, there's also qualitative stuff that we can't really account for.

**[25:13]** And we don't really know how to include here.

**[25:14]** And we have, you know, a section that's vibes and it counts as 10%.

**[25:17]** Like those days are over.

**[25:19]** How cool is that for customer health?

**[25:22]** I almost always just relied on CSM sentiment because it was the, it was like, that's as close as we're going to get because every product related thing had its caveat.

**[25:33]** It's like, oh, they're still ranting.

**[25:34]** They're super happy.

**[25:35]** They did testimony with us, but they're not using the product.

**[25:37]** It's like, okay, fine.

**[25:38]** Forget it.

**[25:39]** Just tell me what's going on.

**[25:42]** But now we can actually see all the relevant data and do something useful with it.

**[25:48]** It's really cool.

**[25:49]** And the analysis that we can now do on like, you know, when one comment is mentioned in the sales cycle or this piece of content happens after this kind of demo with this stakeholder, it materially moves a deal faster.

**[26:00]** Like, let's be real.

**[26:01]** No way I was ever going to find an insight like that from a pivot table that was not ever going to happen.

**[26:05]** And I probably wasn't going to work hard enough to find it.

**[26:07]** Now we can.

**[26:08]** And that's really cool.

**[26:09]** And now we can make a custom piece of collateral for every customer who walks through if we just make it a skill.

**[26:14]** It's cool.

**[26:15]** Yeah.

## 26:16 — The data enrichment bake-off in 20 minutes

**[26:16]** Let me walk you through some of our RevOps team skills and that way we can talk a little bit more about like the process.

**[26:24]** So I want to give a little bit of context.

**[26:26]** This is like a good RevOps story on how every single one of these true process related skills RevOps came about.

**[26:33]** We were doing an evaluation on data enrichment providers.

**[26:37]** Right.

**[26:38]** And we were doing a data test to compare against the data we had in Salesforce, the data we had from our existing providers against potential ones that we were going to move to.

**[26:47]** You know, the onus was on me.

**[26:50]** I had to send an email to all of the people that we were evaluating saying here's our data set from Salesforce, 500 accounts, 500 contacts.

**[26:57]** And when we've had to do that before, I have to go through and say like, OK, this percentage is going to be like dirty and bad data.

**[27:02]** This percentage is going to be good data.

**[27:04]** I'm going to do 60 percent are number one ICP, 40 percent are second ICP.

**[27:09]** I'm going to do 10 percent international.

**[27:10]** Like you try and come up with all these different weights and then eventually you just say, you know what, I'm just going to randomize this because this is so much work to get a really good data test manually.

**[27:19]** And at some point you can't spend more than like two hours on that spreadsheet.

**[27:22]** So I was getting I was preparing myself.

**[27:24]** I was like, God damn, I'm going to have to go in and do this.

**[27:26]** And then I thought, wait a second.

**[27:28]** I think I just did something with code where it looked at a CSV.

**[27:32]** So I thought, OK, if code can look at a CSV and I know it can make files, so I know it can make a CSV and I just installed the Salesforce CLI, I don't even know what that does yet.

**[27:41]** Is there a way that code could give me a spreadsheet so that I don't even have to go into Salesforce?

**[27:46]** That would be the dream.

**[27:47]** So I took that whole question and I said that to Claude.

**[27:50]** And of course, you know, before you can even like process the response coming back, it's like, oh, sure, Smads, no problem.

**[27:56]** Let me pull these account owners. And it started repeating back to me all of that stuff that I had in my head about ICP Mix, Dirty Clean Data, International US, whatever it was.

**[28:06]** And all of a sudden I was like, oh, my God, this is crazy.

**[28:10]** I can't believe this is possible.

**[28:12]** And again, you know, you see the patterns and I'm like, wait, this is basically my whole job, right, being in tools or being in a spreadsheet and then connecting things elsewhere.

**[28:20]** I can do that from terminal.

**[28:21]** Oh, my God.

**[28:22]** So then we refine the spreadsheet.

**[28:23]** We get it better.

**[28:24]** I get like contacts, accounts and leads.

**[28:25]** We did everything.

**[28:26]** I really fine tuned like the percentages and the weights.

**[28:30]** I felt so good about it.

**[28:31]** I double checked with my pivot table.

**[28:33]** Everything looked good.

**[28:34]** Sent it back to a few of the data providers.

**[28:37]** One of them said, oh, actually, you can run the data test yourself.

**[28:40]** You can upload it into the platform.

**[28:42]** I was like, great, I can do it myself.

**[28:43]** Love it.

**[28:44]** I'll just do my V lookups, compare, you know, the data accuracy, the fill rate, all that stuff.

**[28:49]** I log into the platform and I see they have an API key.

**[28:52]** I was like, oh, wait, I can put an API key.

**[28:56]** Not pasted in a terminal, but there's something with API keys in terminal.

**[29:00]** And then I went back to terminal or went back to cursor at this point and I was like, if

**[29:03]** I gave you the API key, that means you could just pull the data and then you could match

**[29:07]** it against the CSV and then you could do the analysis, right?

**[29:10]** I was like, yeah, of course, just give me the API key, you idiot.

**[29:14]** So then I go through this.

**[29:16]** I'm like, okay, drop it in.

**[29:18]** And within like 15 minutes, I had done the data test.

**[29:21]** It was crazy.

**[29:22]** The whole thing was done.

**[29:23]** And then I said, okay, the data quality isn't that great or it's better, whatever it was.

**[29:28]** Wait, you also have access to email.

**[29:30]** You have access to ramps.

**[29:32]** You know how much we're spending on our current tool.

**[29:34]** You have access to Notion.

**[29:35]** So you know in our documentation library what docs rely on this kind of data.

**[29:40]** You have access to Slack.

**[29:41]** So if I wanted to scrape Slack and see somewhere where the AEs are saying this data sucks,

**[29:47]** I could compliment that onto my analysis and say actually there's a lot of evidence that

**[29:51]** people don't want this provider for whatever reason.

**[29:53]** And we can also pull Salesforce to actually pull and see, you know, are these numbers

**[29:58]** going to convert?

**[29:59]** And when we do occult calls, it can convert to the right number.

**[30:01]** Are we getting the right data?

**[30:03]** The whole thing was done in like 20 minutes.

**[30:05]** It was insane.

**[30:06]** And then Claude put together this like PDF overview of the entire thing.

**[30:09]** And you've sat through these data test reviews with providers before.

**[30:13]** It takes three days to run the test.

**[30:14]** No fault of their own.

**[30:16]** They run the test.

**[30:17]** They come back.

**[30:18]** They walk you through the PDF.

**[30:19]** And I'm like, yeah, yeah, yeah, yeah, just give me the headline number.

**[30:22]** Anyway, I sit there with Claude.

**[30:24]** We run that one.

**[30:25]** And then I'm like, wait, we have three other to evaluate.

**[30:26]** And we just go through the same process.

**[30:28]** And we check RAMP.

**[30:29]** We compare it against, you know, the current provider spend.

**[30:32]** I'm like, go check G2.

**[30:33]** See if there are more reviews.

**[30:34]** And I'm just trying to think of like all of these tools that I have access to, how could

**[30:37]** they enrich my decision on which provider to move forward with without me doing any

**[30:43]** work?

**[30:44]** I'm like, okay, I'm going to do this.

**[30:46]** I'm going to do this.

**[30:47]** And I'm like, okay, I'm going to do this.

**[30:48]** And I'm like, okay, I'm going to do this.

**[30:49]** And I'm like, okay, I'm going to do this.

**[30:50]** And I'm like, okay, I'm going to do this.

**[30:51]** And I'm like, okay, I'm going to do this.

**[30:52]** And I'm like, okay, I'm going to do this.

**[30:53]** And I'm like, okay, I'm going to do this.

**[30:54]** And I'm like, okay, I'm going to do this.

**[30:55]** And I'm like, okay, I'm going to do this.

**[30:56]** And I'm like, okay, I'm going to do this.

**[30:57]** And I'm like, okay, I'm going to do this.

**[30:58]** And I'm like, okay, I'm going to do this.

**[30:59]** And I'm like, okay, I'm going to do this.

**[31:17]** And I'm like, okay, I'm going to do this.

**[31:18]** And I'm like, okay, I'm going to do this.

**[31:19]** And I'm like, okay, I'm going to do this.

**[31:20]** And I'm like, okay, I'm going to do this.

**[31:21]** And I'm like, okay, I'm going to do this.

**[31:22]** And I'm like, okay, I'm going to do this.

**[31:23]** And I'm like, okay, I'm going to do this.

**[31:24]** And I'm like, okay, I'm going to do this.

**[31:25]** And I'm like, okay, I'm going to do this.

**[31:26]** And I'm like, okay, I'm going to do this.

**[31:27]** And I'm like, okay, I'm going to do this.

## 31:28 — The tool eval skill, and shifting work to stakeholders

**[31:28]** eval skill. So that now when our head of marketing, let's say

**[31:32]** cross beam, for example, our renewal of cross beam is coming

**[31:34]** up, we take the tool eval skill, the head of marketing kicks it

**[31:39]** off. So I don't even have to do it anymore. She'll kick it off

**[31:42]** and say, Okay, we're about to renew cross beam, or should we

**[31:44]** renew cross beam, go through it, it scrapes cross beam notion

**[31:48]** slack, all of these data sources, puts it together, finds a

**[31:51]** best next alternative and then puts together, well, before it

**[31:54]** puts together the notion doc, there is a persona of me in the

**[31:57]** skill that like interrogates the budget owner, are you sure you

**[32:00]** need this? Is there another way you could do this just like, as

**[32:03]** if I were in the room, and then the final copy they create or

**[32:06]** Claude creates a one pager from notion and then that gets pushed

**[32:10]** to the rev ops channel. And it says smads and Evelyn who's our

**[32:13]** head of finance, there's a new tool renewal proposal or tool

**[32:17]** eval proposal, take a look and then we get feedback. And then

**[32:20]** from there, that's that's now how we process our tool renewals

**[32:22]** and evals is crazy.

**[32:25]** I think what's also really relevant for this one in

**[32:27]** particular is the go to market tech landscape is just exploding

**[32:32]** with new tools every single day. And there are some fantastic

**[32:37]** point solutions that would fit your exact process. But it's

**[32:42]** very difficult to keep up. I mean, this is literally all

**[32:45]** lean scale does every single day, we have hundreds and

**[32:49]** hundreds of tools that we've managed. And it's still hard for

**[32:52]** us to keep up. And every single day on product hunt, we have a

**[32:56]** product hunt feed into slack, like letting us know any new go

**[33:00]** to market tools. Yes, absolutely. And every single

**[33:04]** engagement we do, we run into new tools that we hadn't heard

**[33:06]** of before. So when you're sitting in one organization, and

**[33:13]** you have one tool to renew a couple tools to renew, I mean,

**[33:17]** it's almost impossible to do without AI powering it. So you

**[33:21]** can know, here's all the solutions. Here's all of our

**[33:24]** processes and things that we actually need and things that

**[33:26]** matter to us. Are there certain regions of data you need or

**[33:29]** whatever? And that's huge.

**[33:32]** Yeah, it's, it's a big, it's a big lift off of us. And I think

**[33:36]** what's also interesting, you know, I like grew up in rev ops,

**[33:40]** being under the assumption that like, we are here to make it so

**[33:44]** effing easy for the sellers to sell anything they need that

**[33:47]** does not involve them selling and talking to a customer, if

**[33:51]** they say they need it so that they can bring in more customers

**[33:54]** and support more customers and bring in more business smash,

**[33:56]** you better go do it. Right. And in a good in a good way, in a

**[33:58]** way that it really pushed me to think about how easy can I make

**[34:01]** it for my stakeholders, whether I'm asking you to respond to a

**[34:03]** slack message, or I'm asking you to update your pipeline, how

**[34:05]** easy can I make it. And now we have these tools that can help

**[34:08]** make it easier or even take the burden off of them. Or in this

**[34:12]** case, with the renewal and eval, I'm actually shifting the burden

**[34:14]** to them. I don't know if I've ever really done that in rev ops

**[34:17]** where I say, No, I'm not going to do this work, you're going to

**[34:19]** do this work. So that's like an interesting thing. I haven't

**[34:23]** decided how much I like yet. So far, it's been useful. We've run

**[34:27]** three renewals through it. And we've run, I think maybe like

**[34:30]** three or four brand new tools through it. And it's worked

**[34:33]** every time. And we're really happy with it. So

**[34:37]** Amazing. What else? What else are you deploying into the field

**[34:41]** that's making your ops team do what you can do?

## 34:44 — Pipeline Ops: evidence, not autofill

**[34:44]** We've got Okay, so I want to talk about the pipeline ops

**[34:48]** plugin that we just released. And there are a few skills in

**[34:51]** there. And then I want to

**[34:52]** hang on, can I pause on there? You're the only other person I've

**[34:56]** heard use the term pipeline ops. Oh, really use it. We use it

**[35:00]** here at least here all the time. And as like, it's kind of like

**[35:02]** marketing ops for like a subset of more like specific and some of

**[35:05]** it leads into rev ops. But anyway, just I like I love the

**[35:09]** term.

**[35:10]** I like the term and I think it's really clear. It's better for me

**[35:14]** to say who's managing pipeline ops. It's not as clunky as like

**[35:17]** who's the op owner who's responsible for updating this.

**[35:20]** And you know, in most of our orgs, it's not just the sellers

**[35:22]** who own an opportunity, it might be ams or ftpms or account

**[35:27]** managers, whoever it is. So I don't like to just group and say

**[35:29]** like the seller the account manager or the ops owner. So we

**[35:33]** really defer to saying pipeline ops is the task like the job

**[35:37]** that needs to be done. But yeah, I'm glad you like it too. So we

**[35:41]** this pipeline ops skill, well, it's a series of skill is a

**[35:44]** plugin that we just released two or three weeks ago to the sales

**[35:47]** team. And the impetus for this all started with obviously the

**[35:52]** AEs, we have a very lean team, we have a really healthy

**[35:55]** pipeline. And obviously, that means we're not going to have

**[35:57]** the healthiest or the most hygienic pipeline, it's going to

**[36:00]** get stale because that's a lot to maintain for our AEs. We do

**[36:03]** have some level of like fields being updated from our internal

**[36:06]** call recorder and like other tools. But you still need to get

**[36:09]** opportunities into the pipeline. We have some automated ways to

**[36:12]** do that. But our process doesn't always follow the same thing

**[36:14]** every time. And more often than not someone needs to create an

**[36:17]** opportunity like from their inbox or from their calendar, not

**[36:19]** through automation. So to do this to make this as easy as

**[36:23]** possible, we came up with a series of skills starting with

**[36:27]** new opportunity created. That's one skill and I'll walk you

**[36:31]** through what it does. But it's I mean, you can figure it out new

**[36:33]** opportunity created, then we have a separate skill that picks

**[36:35]** up once the off has been created. And that actually changes the

**[36:39]** opportunity stage. And within that this is my favorite part

**[36:43]** within the actual pipeline movement skill, we of course

**[36:47]** connect to the internal call recorder, your email, your

**[36:49]** calendar, like everywhere that you would get the information

**[36:51]** from in order to update your pipeline. And instead of AI

**[36:55]** actually writing any of those fields or making changes to any

**[36:58]** of those fields, AI only surfaces back the evidence for

**[37:02]** each field. So let's take like the economic buyer or the

**[37:04]** champion or legal process, whatever, Claude isn't going to

**[37:07]** surface and say, Hey, Anthony, here's what I think you should

**[37:10]** put in that free text field. Yes or no, and I'll push it over.

**[37:14]** Claude will say back, Hey, here are four bullet points of times

**[37:17]** when someone's explicitly quoted that, you know, Caitlin is the

**[37:21]** economic buyer. And it's written in a way that like you can't

**[37:24]** really copy and paste it. And also we have a rule in that you

**[37:26]** can't copy and paste and Claude's not going to push it

**[37:28]** over. You the human needs to rewrite this in some way. And

**[37:32]** that's our way of including some human element like some human

**[37:34]** judge in the loop. A lot of people have a lot of success

**[37:37]** with like updating all of their fields and Salesforce on

**[37:39]** opportunities. That's awesome. We're not ready for that. We

**[37:42]** didn't want to do it. We want more human in the loop and we're

**[37:45]** not really afraid of slowing down a whole agentic process to

**[37:49]** make sure that we have people checking things. It's also

**[37:52]** helpful for the AEs so they stay on top of you know, all of their

**[37:55]** opportunities that they're running. That's one of my

**[37:57]** favorite because it really shows that we're not just relying on

**[38:03]** AI to do something for us. Like I think I was reading an article

**[38:06]** recently, I'll have to find it about how you can take your AI

**[38:10]** work and your work that you're doing with AI, if you removed AI,

**[38:13]** would you still get the same output? And if you still get the

**[38:17]** same output, then AI has only just made it faster for you.

**[38:20]** That's not really redesigning your workflow. Redesigning your

**[38:23]** workflow is sitting down saying, Okay, my problem statement is

**[38:26]** that I need a really clean opportunity pipeline with as

**[38:28]** little work on someone else. And as accurate as possible. I can

**[38:32]** get accuracy from tools, I can use AI and skills so that it's a

**[38:36]** low lift. And then I know I can trust it because I have a log of

**[38:39]** every field that was updated and why as an admin. Now I have a

**[38:43]** whole new set of like process that I can take, I can say

**[38:46]** actually, I can make a skill that triggers at the end of the

**[38:49]** day. And it goes through their calendar and it checks to see

**[38:51]** if there are calls with people that don't have an opportunity

**[38:54]** in Salesforce. And it will prompt them and say, Hey, should

**[38:56]** you put this opportunity in Salesforce? Let me help you

**[38:59]** update it. And let's check the call to make sure that you're

**[39:01]** putting it in the right stage. And you're matching against our

**[39:04]** entrance and exit criteria. Easy.

**[39:08]** Yeah, and I do like what you said about between efficiency and

**[39:12]** effectiveness, focus on effectiveness, how do you do

**[39:15]** more? How do you make it higher quality? A lot of the things

**[39:19]** that we're doing, they don't necessarily have to be done

**[39:21]** faster. But there are a lot of opportunities to do things

**[39:25]** better. And I think that opens up a ton.

**[39:28]** Yeah, yeah. And then that's how we're doing the pipeline ops, we

**[39:32]** also added kind of on top of the pipeline theme, we added a

**[39:36]** missing opportunity scanner. So you know, sometimes

**[39:39]** opportunities don't get into the pipeline when they should. And

**[39:42]** once upon a time, I used to be a sales ops analyst, and I would

**[39:45]** literally look through people's sellers calendars, and then

**[39:47]** follow up and say, Hey, you haven't logged the meeting in

**[39:50]** Salesforce, can you do it? This was before we were using gong

**[39:53]** and everything else. Now we don't have to do that. And we

**[39:58]** have all these tools that can make it so much easier. And we

**[40:00]** don't have to be involved. I don't have to be the nagger

**[40:02]** anymore. Not I hope I was in the first place. But now we have

**[40:05]** these tools that can do things for us. And it just completely

**[40:07]** changes the way that we should even approach a problem

**[40:09]** statement and like who should complete it. So there's a lot of

## 40:12 — Importing a lead list: a day becomes 40 minutes

**[40:12]** a lot of good stuff. Let me walk you through this import lead

**[40:15]** list one because I think this is like the best biggest pain of

**[40:20]** every rev ops person's experience. I have shared this

**[40:23]** with a few rev ops people. And when I walk them through it,

**[40:25]** their eyes light up. And I'm like, don't worry, I will send it

**[40:27]** to you. So anybody who wants it came out after we did the tool

**[40:33]** renewal and evals and realizing like, okay, the all of these

**[40:35]** steps, all these tools, these are just instructions, we can put

**[40:37]** them in a skill. A few days later, I'm going through the

**[40:41]** typical importing a lead list right from a webinar. We have

**[40:44]** one great one webinar partner in particular, they always have

**[40:47]** like 500 leads, they allow free email addresses, I don't like it,

**[40:51]** you know, there's always a misspelling in the email,

**[40:53]** someone's name, whatever. Of course, we usually go through

**[40:56]** that I try to clean it up, I command find hotmail and iCloud

**[40:59]** and all that stuff, and try to clean it up so that I can match

**[41:02]** it to do bit get into Salesforce get into the campaign and set

**[41:05]** the campaign member status. That's the whole process that

**[41:08]** we're trying to do. Of course, I have to go into data loader, the

**[41:11]** CSV, I don't know, maybe I'll check something in the data

**[41:14]** enrichment tool, I'll go into Salesforce. And I'll get

**[41:17]** interrupted five times that it will end up taking me the entire

**[41:19]** day to actually get through this. And there are so many spots

**[41:22]** along this process, we're like, if the member status isn't right,

**[41:24]** or isn't marked as responded, that throws off lifecycle

**[41:27]** reporting. So I have to be really on top of it, or whoever

**[41:31]** on my team is doing it, we need to be really in sync, and we

**[41:33]** really have to have the process written down. So this is just a

**[41:36]** high problem area of importing lead lists, given the way that

**[41:39]** we were set up about a year ago. At this point, I'm like, okay,

**[41:43]** we just did the data enrichment thing with the CSV, we've got

**[41:46]** to be able to do something with the import lead list, I download

**[41:49]** a Google Sheet, save it as a CSV, it's just sitting in my

**[41:51]** downloads folder, I'm not even going to move it. And I say to

**[41:54]** Claude, check out that list. That's in my downloads folder,

**[41:58]** this is an event or a webinar we just had, you can go to notion

**[42:01]** to the marketing calendar to find all the details on that

**[42:03]** event. You know, take a look and let me know what what you see.

**[42:07]** And then I said, you know, it's very impressive. It says there

**[42:10]** are three people who spelled dot com instead of dot com. Someone

**[42:14]** you know, didn't put their last name, but I can infer it from

**[42:15]** their email, like all of the things that a human I would have

**[42:17]** done, instantly done for me, and everything's filled in the CSV.

**[42:22]** Then we talked through what are we gonna do about the free email

**[42:24]** accounts, I said, Can we use the lucha API key again, all of a

**[42:27]** sudden, they're all enriched to find if there's a work email,

**[42:29]** everybody has a work email, and titles filled in like all of a

**[42:32]** sudden, I'm like, Oh my god, I just got three hours back in the

**[42:36]** last eight minutes. That's crazy. And then the process just

**[42:40]** keeps building on itself. And I realized, oh my god, you can

**[42:43]** make a campaign in Salesforce. Actually, if you go to the

**[42:45]** documentation library in notion, you will see the exact SOP and

**[42:48]** the naming convention for our campaigns. You'll also find the

**[42:52]** Google Sheet that has a map of our campaign member statuses,

**[42:55]** and how to add them. All of a sudden, the campaigns created,

**[42:58]** and the campaign member status is created. And then the only

**[43:00]** thing left to do is to get into Salesforce. So we run D dupe, we

**[43:03]** match, we create, everything kicks off, and the whole process

**[43:07]** has taken, it now takes about 40 minutes. And we have a revops

**[43:10]** analyst and he can run like up to four in a day. It's, it's

**[43:14]** crazy. I don't know how else to say it. It's wild.

**[43:16]** Well, and, and even in this case, so huge efficiency pains,

**[43:21]** potentially worth way more is the uncovering process that you

**[43:25]** have on those free emails. Oh, yeah. You would have just thrown

**[43:29]** them away. Otherwise, how many times have I just deleted them

**[43:32]** from this? I'm like, yeah, we're not finding these and they're

**[43:34]** not going to Salesforce. So oops, no more. Not a problem

**[43:38]** anymore. Then there might be who knows there could be a handful of

**[43:41]** enterprise deals buried in those emails. So I think those are the

**[43:45]** type of things where if you're not using AI, even let's assume

**[43:51]** it took the same amount of time, even though it won't, you're

**[43:54]** still leaving money on the table, missed opportunities,

**[43:58]** miss level of depth to the analysis you're running. You

**[44:02]** just have such an opportunity to take it to the next level.

**[44:05]** Exactly. And I just I try to think I think I had a one of my

**[44:09]** managers, Dan Walsh, when I was at BuzzFeed, he would always say

**[44:12]** something would be really proud of something. And he'd be like,

**[44:14]** Okay, yeah, what do you have to do to double it? I'd be like,

**[44:18]** double it. I'm just so proud of what I just did. What do you

**[44:20]** mean double it? Or he'd say the same thing and be like, well,

**[44:23]** how about how are you gonna cut it in half now? And I'm like,

**[44:25]** I'm just proud of where I got. But always having that mind of

**[44:27]** like, well, what if what would have to happen for it to be like

**[44:32]** kind of cooler or more intense, more excellent. And I think

**[44:37]** having that in the back of my head being like, well, Claude,

**[44:40]** you tell me what more can we do? What better research can we do?

**[44:43]** That is the curiosity that keeps pushing you and to keep asking

**[44:46]** Claude to get more out of it.

## 44:50 — The tech stack, and no MCP means no relationship

**[44:50]** Curious, just because I'm a connoisseur of GTM tools, what

**[44:54]** does the tech stack look like? And are there any tools that

**[44:57]** you're super excited about right now?

**[44:59]** Yeah, our tech stack is, let's see, we've got a lot of the

**[45:03]** usual suspects. So we have Salesforce, HubSpot, Outreach.

**[45:08]** We use Lucia for data enrichment, we use store leads,

**[45:11]** store leads provides like e commerce data, we sell to e

**[45:13]** commerce companies. Store leads, we use glyphic, they just

**[45:17]** changed their name to Airspeed though. So Airspeed we use as our

**[45:20]** call recorder. We of course use Slack, obviously the AI tools,

**[45:25]** we use Spotdraft as our contracts management tool. We

**[45:29]** don't have a CPQ system, I built and configured a some

**[45:33]** lightweight something between Salesforce and Spotdraft that

**[45:35]** serves as our CPQ solution. We use Stripe. What else do we

**[45:40]** have tools wise? That's about it. We used to be on Webflow for

**[45:46]** our website, but we cut that to build our website on Cloud Code.

**[45:49]** So there are some like we've demoed a lot of tools, we've

**[45:52]** done a lot of POCs with tools, we tried Artisan for like the

**[45:55]** AISDR work, we were on zoom info for a while, we demo Cognizant

**[46:00]** or to the POC with Cognizant. But right now we're running a

**[46:03]** pretty lean tech stack, honestly, because we're we're

**[46:06]** actually building again, most of our stuff. We're doing a POC or

**[46:10]** demoing some deep line data right now, we use clay pretty

**[46:13]** extensively. We've used saber in the past for some insights

**[46:19]** tracking, I really like their stuff. But yeah, we're really

**[46:22]** just buying data at this point, with the exception of like a

**[46:25]** HubSpot and a Salesforce probably, and then trying to

**[46:28]** make as many of our own products as we can. And that

**[46:32]** makes sense.

**[46:33]** No makes a ton of sense. I think now more than ever, like you

**[46:37]** mentioned the CPQ, we've built custom CPQs for customers as

**[46:40]** well. As if it's lightweight, there's a certain amount of

**[46:43]** complexity where say, hey, no, let's go with a proper one. But

**[46:46]** I do think it is a really interesting time for that build

**[46:50]** versus buy discussion. Are there any tools that you feel like

**[46:53]** are kind of on the chopping block or maybe categories of

**[46:57]** tools? You don't have to name specific ones exactly.

**[47:01]** I mean, any tool that doesn't have an MCP by now is not a tool

**[47:04]** I'm looking to have much relationship with honestly.

**[47:08]** Especially like, if I have to go into your tool to use it, I'm

**[47:11]** not going to use it. And I'm not going to demo it probably.

**[47:14]** And that's regardless of category. I don't care. I mean,

**[47:17]** I think that goes for my personal life too. Like I run

**[47:19]** my personal life out of terminal the same way I run my work life

**[47:23]** out of terminal. So I mean, I installed like the WOOP MCP and

**[47:27]** the Apple Music MCP recently, like I'm a freak, honestly. So

**[47:30]** if you don't have an MCP, if you don't have a CLI, like I

**[47:33]** don't see myself relying on you or seeing you as a really strong

**[47:37]** partner. That's probably the first part. I am curious to see

**[47:43]** what's going to happen with some of the conversational

**[47:44]** intelligence. And I'm like, kind of split on what's going to

**[47:47]** happen with it. So we love our transcripts. And we really use

**[47:52]** our transcripts more than we use any of like the insights that

**[47:56]** come from a lot of what what the platform will analyze for us.

**[48:00]** We really reference like specific keywords or when

**[48:02]** something specific was said at the point that a specific person

**[48:05]** joined a call. There's a lot of specifics that we look for in

**[48:09]** our transcripts. So I am trying to think if the transcript is

**[48:13]** the most valuable part to me right now, I certainly am not

**[48:16]** going to go build a conversational intelligence tool.

**[48:17]** I'm not trying to compete with Gong that will not provide us a

**[48:19]** competitive advantage. There's no point in doing that. But I

**[48:23]** have re I have shifted my focus in terms of what do I actually

**[48:27]** need from this whole system and like what's happening. I'm not

**[48:31]** even totally convinced you need video and all of your call

**[48:33]** recording. That's kind of a hot take. A lot of people like the

**[48:35]** video. I don't think it's necessary. If you have the

**[48:38]** transcript, if you're able to detect sentiment and tone based

**[48:41]** off of the transcript or some other way. I think that's all

**[48:44]** you need. I don't know what that means for the future of

**[48:46]** conversational intelligence, but I know that it means I'm not

**[48:49]** relying on it as much. It is more of just a mechanism to

**[48:53]** capture the transcripts. I'm trying out Google meets a little

**[48:57]** bit more right now. I'm trying to learn the Gemini

**[48:58]** transcription service. Again, I'm not trying to rebuild

**[49:01]** anything. I think it's really important that we focus on you

**[49:04]** build your first MVP to prove that this is something that you

**[49:06]** should go buy. But then you just buy we can buy we as the

**[49:12]** companies have a little bit more leverage in terms of I don't

**[49:14]** want to sign a full year contract. Maybe I'll sign a nine

**[49:16]** month contract or six month contract. POCs are back so you

**[49:19]** don't have to commit in the same way. That's how we're going

**[49:22]** about it. We'll build our own MVP first. If it feels like it

**[49:24]** will be that much more valuable, then we will go and buy

**[49:27]** something. But we usually go through a few iterations to be

**[49:30]** sure we know what we want before we end up buying anything.

**[49:34]** Yeah, I'm with you on that. We use fireflies. Nice. Fun fact,

**[49:39]** our COO, who's also my childhood best friend, but our COO was the

**[49:46]** first hire at assembly AI. And they run the back end of so many

**[49:51]** speech to text on if you know assembly then that's cool. So

**[49:57]** sometimes we pick our products because he might still have some

**[50:01]** level of investment there. But I think on the on the

**[50:06]** conversational intelligence, I agree. I think I want to run it.

**[50:10]** I want to run the intelligence my own way anyway. So as long as

**[50:14]** I have a good transcript, and the only time you need video is

**[50:17]** if you need to actually see something. But I think most if

**[50:20]** you're demoing tools, even most of it has less to do with what

**[50:25]** the UI is and or do with what the workflow and data

**[50:29]** capabilities are. So totally do you need to see it?

**[50:34]** I don't know. I'm not I'm not I'm not convinced yet. But times

**[50:38]** before I'm usually wrong. So we'll see.

## 50:42 — Building a RevOps team now

**[50:42]** Well, it's gonna change a ton as we go. But another thing that I

**[50:45]** think I'm curious your take on building a rev ops team with

**[50:49]** these new capabilities. What are the roles look like? I mean, I

**[50:53]** used to have like an army of analysts, I used to have people

**[50:56]** dedicated to adminning a tool. How are you thinking about

**[51:01]** building your rev ops team with everything today?

**[51:05]** I, the first thing I'll say, I mean, I, I have mostly worked at

**[51:09]** early stage startups where headcount is not a privilege we

**[51:12]** always have or budget that we can tap into. So when it comes to

**[51:17]** building out a team, I will always start by saying people

**[51:20]** follow pain. So whatever your pain is where you're spending

**[51:23]** time where you can't recreate a workflow with AI, that's

**[51:27]** probably where you need to hire first. Now when I think about

**[51:30]** skill sets, and the profiles that are naturally going to

**[51:33]** change because of the what our work is, and like honestly, what

**[51:36]** our job is, is very different. Some of the fit, I mean, roles

**[51:40]** wise, and I think the future of the rev ops, or one of the

**[51:44]** futures I see happening is, there becomes a little bit more

**[51:47]** of a bifurcation in terms of the strategy and the process and the

**[51:50]** enablement, I think enablement is going to have a research too,

**[51:52]** because we're spending all our time building stuff, creating

**[51:55]** products, making sure people understand what is happening,

**[51:58]** the information that's being fed to them, I think enablement is

**[52:00]** going to have the next resurgence after rev ops, or

**[52:03]** maybe we'll bring them along with us. But enablement is

**[52:06]** going to be huge, I think that we're going to see a lot of

**[52:08]** really strong enablement leaders that have been, maybe we're

**[52:11]** early to enablement, like in the B2B in the tech space, the last

**[52:14]** 10 years, and now they're going to merge, especially the AI

**[52:16]** pilled ones, I think are gonna be really, really powerful at

**[52:18]** the orgs that they're at. But again, the process, the

**[52:21]** strategy, even blurring, you know, with like forecast

**[52:24]** management, that's still a little bit of a people skill,

**[52:27]** working with the sellers working with the sales managers,

**[52:29]** understanding where you're waiting your deals, I see all of

**[52:31]** that as being like the traditional rev ops that stays

**[52:35]** data analytics, systems, tools, automations, I suspect that

**[52:40]** will move towards tech teams, data teams, I don't know if the

**[52:44]** rev ops team or the go to market engineer is going to end up

**[52:46]** reporting to the VP of data, I don't know. But I see similar

**[52:50]** patterns in the type of work that's happening. Obviously,

**[52:53]** here at Vermont, like I manage most of the tech stack, it

**[52:56]** wouldn't be that much of a leap for me to add like the other

**[52:58]** five tools here. So you can see how someone who's been in go to

**[53:01]** market engineering, you know, if you are a data analyst, I said

**[53:04]** this actually last week to my team, like we are, we're

**[53:07]** basically a data integrity team that's really good at

**[53:09]** automations and tools, right? Because everything that the

**[53:12]** business runs off of, it's our job to give the business what it

**[53:15]** needs to make decisions today. Almost all of that comes from a

**[53:18]** system. And those systems are built on the processes and the

**[53:22]** strategies and the rules that we have set. That is so much work

**[53:25]** that I could see it staying with someone else, especially as some

**[53:28]** of these like AI companies are growing exponentially. And then

**[53:31]** you really have a more technical team could be go to market

**[53:34]** engineers could be someone like me, I still consider myself

**[53:37]** non technical, but like that sounds very interesting. Working

**[53:40]** with the data and analytics team being closer, you know,

**[53:43]** especially with all these usage based businesses and consumption

**[53:46]** pricing, like the data warehouse is also a go to market tool, it

**[53:51]** captures metering and it captures rate cards and usage, it

**[53:53]** calculates billing, it dictates the rev rec schedule, it has a

**[53:57]** lot. So it's not a big leap to say, actually, the people who

**[54:00]** have been managing 60 to 80% of the tech stack, and who have

**[54:04]** also been responsible in communicating how to use it,

**[54:07]** maybe we should also give them the other technical tools that

**[54:10]** we also own, because all of that reporting gets fed in

**[54:13]** together. So that's where I see like this AI pill technical

**[54:17]** aspect of rev ops growing, and the softer more people elements,

**[54:23]** and really the first line of defense for rev ops before we

**[54:25]** know what to build, I see that staying as a little bit of a

**[54:27]** separate thing.

**[54:29]** You know, what I've seen as a, as a trend recently that I think

**[54:33]** would align with your hypothesis is seen a few heads of rev ops

**[54:37]** move into a COO position. And in that COO position, it would be

**[54:43]** very natural to say, Okay, well, I have a VP of rev ops, maybe

**[54:47]** maybe product ops or engineering ops and then but within one

**[54:51]** executive owning the entire tech stack infrastructure of the

**[54:54]** company.

**[54:56]** Totally. That's I think that's going to happen. It's not that

**[54:59]** many more tools. And when you think of like, who has the most

**[55:02]** experience, again, in communicating how to use a tool,

**[55:04]** how to uncover it, but also what tool we should use how to manage

**[55:08]** it, the privacy concerns within a tool, I could see it really

**[55:11]** following falling, and being, you know, consolidated into one

**[55:15]** team for sure.

**[55:16]** And the go to market data is the messiest data. It's the most

**[55:19]** difficult data to work with. I mean, if you look at product and

**[55:22]** engineering data, or financial data or agent, that data is so

**[55:26]** clean, and so easy to work with. So we've already done things on

**[55:30]** hard mode, we might as well just go get the easy stuff too.

**[55:33]** Yeah, seriously, that's crazy to think that like the ERP would be

**[55:36]** easier than I believe it. Yeah, I think when I know building out

**[55:42]** the team to and like some characteristics, one thing that

**[55:45]** I've been thinking a lot more about recently is you especially

**[55:49]** like we're in these fast growing orgs, we're in the age of AI, a

**[55:52]** lot of teams are relatively flat, like our or get Vermont, I

**[55:56]** have a team, but we're essentially a flat org for the

**[55:58]** most part, which is really exciting. And it means you can

**[56:01]** be a manager, but you're also expected to be an IC, which is

**[56:03]** great, because I love to build and I love to be doing my work.

**[56:07]** But the, the importance of building out loud, I think is

**[56:11]** even more important, because no one's going to come in and check

**[56:14]** on you, everyone is running a million things on their own, you

**[56:17]** need to be constantly updating and communicating. This is what

**[56:20]** I'm spotting. This is what I'm building. This is my approach.

**[56:23]** Even just last week, I shared something we've a shared AI

**[56:25]** enablement channel where we all just drop in like, this is what

**[56:27]** I've learned, or this is what I'm doing. And I dropped in, honestly,

**[56:31]** I was talking to myself more than I was talking to anybody

**[56:33]** else. But I was like, this is how I decide when to use code

**[56:35]** versus codecs. And in the middle, I'm like, I don't know if

**[56:37]** this is right. But this is how I'm choosing it. And this is

**[56:40]** what's making me say that. And then we'll just end up having a

**[56:42]** whole conversation from that. So being able to say, this is what

**[56:46]** I'm doing, I don't know if anybody's listening, I don't know

**[56:48]** if this matters to anybody else. But it was helpful for me. I'm

**[56:51]** gonna at least try to share it. I think that's really, really

**[56:54]** important for the next several years in particular.

**[56:57]** Well, in the spirit of sharing, I know you prepared a couple

**[57:00]** demos, I'd love to see a few things in action. Maybe we do

**[57:05]** need video for this one, maybe the transcript won't just

**[57:07]** suffice.

## 57:09 — Infrastructure skills and the 50% context rule

**[57:09]** Fair enough. Alright, so I've got a few different skills that I

**[57:14]** thought I would share. I'm going to start with some skills. So

**[57:18]** again, I operate mostly in terminal, I manage my email from

**[57:21]** terminal, most of my slack, anything that comes to me, I try

**[57:25]** to start from terminal, even if I take it somewhere else. So I

**[57:28]** actually don't work in the terminal app, I work in CMUX.

**[57:31]** It's really nice, because you can have like lots of different

**[57:33]** quadrants. And then I have different workspaces along the

**[57:35]** side. So what you're seeing here, it is terminal, it's just

**[57:38]** in a different UI. So I'll come in here and I'll open up Claude,

**[57:41]** Claude code. And the skills that I'm gonna walk you through

**[57:44]** today, because I think these are the ones that are easiest for

**[57:46]** many people to grasp, because it's like a shared process, I'm

**[57:49]** going to go through some skills that fall into what I consider

**[57:52]** the infrastructure bucket. So to give you a little context on how

**[57:55]** we got here, this is me and probably April or May. I'm

**[58:00]** realizing, okay, nothing out of my folder structure is correct.

**[58:03]** None of my file structure is correct. Every time I think

**[58:06]** Claude remembers not to use an m dash, it sends me an m dash in

**[58:09]** the next next message. I was having all this frustration. And

**[58:12]** I went to call and I said, What do you need from me in order for

**[58:15]** you to work exactly or near exactly as I expect you to? And

**[58:19]** we went through all these things tone and voice, folder

**[58:21]** structure, what to push to GitHub, what's for, you know,

**[58:24]** personal work or personal folder that might be on my desktop,

**[58:26]** whatever. And from that, that's where we built all of these

**[58:30]** infrastructure skills. So a few of them before I even start

**[58:33]** getting into it, I want to pull up here and show you right down

**[58:37]** here, you'll see I added this usage bar, or I call it a status

**[58:40]** bar at the bottom. So I met with a friend of mine who's a go to

**[58:44]** market engineer. And he told me something that changed the way I

**[58:48]** think about how to run my sessions. He said, you should

**[58:50]** never run a session past 50% context, because that's when

**[58:53]** Claude and even codex really starts to degrade. So I said,

**[58:57]** Okay, great. How do you know when you're at 50% context? And

**[59:00]** he said, Oh, you can just ask Claude, I was like, I'm not gonna

**[59:02]** ask Claude. Instead, I'm gonna create a breadcrumb for myself,

**[59:05]** where I'm going to add a marker here. So I'm going to say, let

**[59:08]** me just say, Hey, Claude, and let's see if we can get it

**[59:11]** running, because then there's a little status bar that will load

**[59:14]** here, and it'll show you how much usage. Here we go. So just

**[59:18]** pulling this up, just x out of that is showing me that I've

**[59:22]** already used 8% usage for what's in this chat in this session. So

**[59:26]** now I know when I get to 51%, I got a clear context and I got to

**[59:29]** start a new session. So that became my next friction point,

**[59:32]** right? So first, it was the clearing context at the right

**[59:35]** usage amount. So I created this little breadcrumb for myself, a

**[59:38]** visual guide to know when to switch. Now I want to make

**[59:41]** clearing context as quick as easy as possible. So in order

**[59:44]** to do that, I'm going to pull something up this we might want

**[59:47]** to demo output podcast prep. I'll explain this skill after. But

**[59:53]** what I'm going to pull up here is we're going to pretend that

**[59:55]** I'm in the middle of a session where I am preparing for this

**[59:59]** podcast interview. Because of course, when Anthony reached out

**[1:00:01]** to me, I think, send me an email, probably send me an email

**[1:00:05]** or send me a LinkedIn DM, that hit my work email. So I go into

**[1:00:08]** Claude here and I say, Hey, I just saw an email come in from a

**[1:00:11]** LinkedIn DM from someone talking about a podcast sounds really

**[1:00:13]** interesting. Can you take a look at it? I can't remember if Claude

**[1:00:16]** can actually read the email or the inbox from the email, but

**[1:00:21]** that's the idea. And that's like how I try to work. So here you

**[1:00:24]** can see, let's pretend I'm right in the middle of this session,

**[1:00:26]** right here, where I'm like, Okay, Anthony, and I are going to

**[1:00:29]** talk about robots greatest hits, let me scrape, you know, our

**[1:00:32]** projects dash or projects database, make sure I'm prepared

**[1:00:35]** with everything that we need. Let's see. Anthony's share

**[1:00:38]** Google Doc with me, yada, yada, yada. Okay, great. I created this

**[1:00:41]** doc, I feel really prepped. I'm at 10% context, let's just

**[1:00:44]** pretend that I'm at 51% context now. And before I prep, you know,

**[1:00:48]** my talk track, I want to clear context. So in order to do that,

**[1:00:52]** make that really easy, because I'm not a senior software

**[1:00:55]** engineer, I don't know how to make sure that Claude always

**[1:00:58]** documents every decision we made, or writes a really clean hand

**[1:01:00]** off doc, so that the next time I come in, and I want to work on

**[1:01:03]** prepping for this podcast, I can just pick up right where I left

**[1:01:06]** off, and I don't even need to lose a beat. So that's what I was

**[1:01:08]** trying to solve for, right, because I constantly need to

**[1:01:11]** clear context. So the first thing I did was I created this

## 1:01:14 — Wrap and pickup: 250 times a month

**[1:01:14]** skill, it's called wrap, you can see here, it's called end of

**[1:01:16]** session wrap summarizes what was decided and built updates, a hot

**[1:01:19]** cache and creates a compact handoff doc. So every single

**[1:01:23]** time I am in a session, and this goes for my personal life and my

**[1:01:26]** work life, I use CMUX for both. I'm done with a topic or maybe

**[1:01:31]** Anthony, I'm prepping, and I'm gonna go for lunch, and I'm gonna

**[1:01:33]** close this session, I'll come here and I'll say wrap. Right?

**[1:01:37]** And I think it might respond to me and say there's nothing to

**[1:01:39]** wrap here, because technically, we didn't make any changes. But

**[1:01:43]** actually, hold on. Let's do yeah, let's do Okay, update, the

**[1:01:48]** podcast got pushed to Friday, let's just make a change. So

**[1:01:53]** before I actually wrap the session, now I'm going to make

**[1:01:56]** this change so that it has something to wrap. But in this

**[1:01:58]** wrap skill, it's going to update, you can see this, see this

**[1:02:01]** handoff, Anthony podcast, MD, this is the file that created the

**[1:02:05]** first time I was working on this podcast prepped. So it created a

**[1:02:09]** file. And that's how when I come in, I'm like, hey, let's pick up

**[1:02:12]** that project. I will just say, hey, pick up Anthony podcast.

**[1:02:18]** Okay, update. Sorry, it's not good. I'm in plan mode right now,

**[1:02:24]** because I'm trying to think of ways to maintain my spend a

**[1:02:27]** little bit better. So I default to plan mode all the time. But

**[1:02:31]** here, it's going to update a dock. These are some of my hooks

**[1:02:35]** that are in place to stop bad things from happening. But here

**[1:02:40]** we go handoff files are owned by wrap, let me invoke it

**[1:02:42]** properly. So now because I just said, okay, an update to this

**[1:02:45]** project is that the podcast is happening on Friday, it's

**[1:02:48]** updating the dock. Now as it wraps this whole session, it's

**[1:02:51]** going to go through and run through a few other skills that

**[1:02:54]** I have. Like for example, I have a PM plugin that updates all of

**[1:02:58]** our projects in notion for the RevOps team creates new

**[1:03:01]** projects, creates problem statements, gathers context on a

**[1:03:05]** project before we launch it. And then here we go. This is exactly

**[1:03:08]** what it looks like. So session wrapped what we did picked up

**[1:03:11]** the Anthony podcast recording got pushed to Friday. And then

**[1:03:15]** it shows me here, these are the files that we actually wrote

**[1:03:17]** documents every decision we made here, anything that I said, Oh,

**[1:03:20]** we'll have to do that in the future. And now it's time for me

**[1:03:23]** to clear context. But before I hit clear, I need to know

**[1:03:27]** exactly how to start this conversation again. So I'm going

**[1:03:29]** to copy, I'm just going to copy this, go clear, it's going to

**[1:03:33]** clear, we're back to zero, and I'm going to paste and it picks

**[1:03:37]** up Anthony podcast exactly where we were 10 seconds ago, and the

**[1:03:41]** whole thing's gonna load, it's gonna say picking up the session,

**[1:03:43]** this is where you left off, it was moved to Friday, and it'll

**[1:03:46]** take you know, I don't know, probably five or 6% of our

**[1:03:49]** usage. And that's how I pick up immediately between sessions. So

**[1:03:53]** I'm always staying on the strongest version of Claude, I'm

**[1:03:56]** not degrading over time as I get into like 70 or 80%. And then

**[1:03:59]** I'm practicing this amazing, I guess, engineering hygiene by

**[1:04:05]** documenting everything in exactly the right way, so that I

**[1:04:07]** can move really quickly. This is one of my favorites. I when I do

**[1:04:12]** like look at my skill count, I have used wrap and pickup, I use

**[1:04:16]** them about 250 times a month, which is pretty crazy.

**[1:04:20]** Well, and also not just the technical aspect of running

**[1:04:24]** these, but I think there's still a human element to running your

**[1:04:27]** workflows and agents and running your sessions. And there's

**[1:04:31]** something calming about saying, Okay, I am done with this. And

**[1:04:37]** also, like I know that everything that I was working on,

**[1:04:41]** I can go pick up again, where if you're just running like hundreds

**[1:04:45]** of random sessions, you're looking to go back in, if you

**[1:04:48]** start a new one, you're gonna kind of like re prompt the

**[1:04:51]** entire process all over again. So it's just good PM practice as

**[1:04:57]** well.

**[1:04:57]** Exactly. And to go back to the like three, you say it three times,

**[1:05:02]** when I first came up with the wrap skill, I think I cleared

**[1:05:07]** it. But when I first came up with the wrap skill that came out

**[1:05:10]** of me saying to Claude, I don't want to ask you to do the same

**[1:05:14]** things every time. If you need to update the readme and you need

**[1:05:16]** to update the memory doc, I need you to know to do that by

**[1:05:19]** yourself. I'm not going to sit here and remind you I need one

**[1:05:22]** word to invoke it. And that's when Claude was like, wait,

**[1:05:24]** that's what a skill is. So then we turn this into a skill, I have

**[1:05:27]** another skill, I won't go through all of them. But I'll

**[1:05:28]** show you. I have oh, it's the plugin is called the skill

**[1:05:32]** factory. But I have the skill factory has multiple skills

**[1:05:36]** within it. And the skill factory is all about like when I spot

**[1:05:39]** bugs in my skills, I capture a bug. So it logs a bug. And then

**[1:05:43]** I'll go q fixes. That's where it is. Hold on. Change them. Okay,

**[1:05:52]** so apply fixes. This is the skill that reads through all of

**[1:05:56]** the logs of the bugs and other skills, and then goes through

**[1:05:59]** and checks how to fix them. So this is like an infrastructure

**[1:06:01]** skill where they're meant to make sure that I'm getting the

## 1:06:05 — The core tools tracker for silent failures

**[1:06:05]** most out of Claude. Another one, this core tools down here, I

**[1:06:08]** have some, you know, like a chief of staff that runs every 20

**[1:06:10]** minutes or so. And I keep kept getting from a chief of staff,

**[1:06:13]** like you don't have any new emails, you're good. And then I

**[1:06:15]** realized four hours later, the Gmail MCP had broken or, you

**[1:06:19]** know, wasn't connected. So in order for that to not happen, and

**[1:06:22]** for me to not be, you know, misled by Claude, I created this

**[1:06:26]** core tools tracker. So if any one of my five tools, like email,

**[1:06:30]** calendar notion slack granola are offline, I know about it. I

**[1:06:35]** also have a recurring MCP heartbeat to check to make sure

**[1:06:38]** that I have what I need. We've created a lot of these skills

**[1:06:41]** that really just like work along beside you. And again, why I

**[1:06:45]** like sharing these is because no matter what you're doing in

**[1:06:48]** terminal, these skills will be valuable for you. And it's

**[1:06:50]** something that you can start building on.

**[1:06:53]** I'm a big fan of that core tools one that you mentioned,

**[1:06:56]** because there are so many times where I'm running something and

**[1:07:00]** yeah, one of my tokens expired or something. And now it's not

**[1:07:04]** connected to that. And it's trying to run it without it or

**[1:07:08]** so, especially if you have any routines or ongoing workflows

**[1:07:13]** that are scheduled. There's so many times I have routine set up

**[1:07:17]** that just don't work, right? And then I have to go in and manually

**[1:07:21]** do it. So it's a huge vein. I'm stealing this one. I hope that's

**[1:07:24]** okay. All yours. Let me show you a few other ones. This one I

**[1:07:27]** added recently, this only works in Claude codex doesn't expose

**[1:07:32]** it. But this is how much I've spent in this session. And then

**[1:07:35]** this right here is my rolling 30 day average. I'm not really

**[1:07:38]** sure how accurate it is. So don't quote me. But then I don't

**[1:07:42]** know if I want this one. I don't know if this is a good one for

**[1:07:45]** me. It's helpful for me. And I use these to, you know, spend

**[1:07:51]** ones in conjunction with the model. And it's helpful to just

**[1:07:54]** see like what spikes bright price, like when I scan through

**[1:07:58]** notion that spikes price a lot, but when I write to notion, it

**[1:08:01]** doesn't take up as much. But when I scan through slack, it

**[1:08:03]** doesn't take up as much usage. So by adding in the model down

**[1:08:07]** here, I, again, it's still on me to do the changing of the model,

**[1:08:11]** but I have these visual cues and visual reminders for me to not

**[1:08:15]** forget things that I need to get better at or gaps that I have.

**[1:08:18]** Like I haven't spent or more recently, I've been spending

**[1:08:21]** time trying to diversify my models. But this is this was the

**[1:08:24]** first step I was like, let me at least understand what I'm on

**[1:08:27]** when I'm on it. That was part one. We've got a few other ones

## 1:08:32 — The RevOps operating system and releases

**[1:08:32]** that I'll just show you we created this ruse rev ops

**[1:08:36]** operating system. This is a plugin with a series of skills

**[1:08:40]** that are all internal team management for our team. So

**[1:08:43]** before we start a project, we will always write a problem

**[1:08:47]** statement similar to like a product team, you start with a

**[1:08:49]** user statement, a user journey, what's the impact, we'll do the

**[1:08:52]** same thing, you know, you want me to import a lead list, I'm

**[1:08:56]** going to create a problem statement first. And then from

**[1:08:58]** there, we'll generate a project. From there, then we will scope

**[1:09:02]** the project, then we will actually make the tasks that are

**[1:09:04]** related to the project, and then we will actually execute on it.

**[1:09:07]** So we went through, let me see if I can go through a few of

**[1:09:10]** these. For example, this new project skill. So this new

**[1:09:15]** project creates the actual problem statement in notion that

**[1:09:20]** lives in one database, that page is related to our projects

**[1:09:23]** database, this skill creates projects for us and it follows

**[1:09:27]** the same instructions, scan slack for context scans granola

**[1:09:30]** scans all of our tools to add to the problem statement that we

**[1:09:34]** surfaced, then it generates the problem, the project itself in

**[1:09:39]** notion for me, like right in the format that we need, that it

**[1:09:43]** generates the tasks, it does everything for us. And we'll do

**[1:09:46]** I think I've got another one in here about sprints. But we

**[1:09:50]** operate on the sprint schedule. So you can see here, when I will

**[1:09:55]** post that we have a new RevOps sprint starting and like, what

**[1:09:58]** are we working on this week, I'll start by drafting with the

**[1:10:01]** RevOps sprint launch. And we'll have one for the wrap. We also

**[1:10:05]** have this other one called RevOps releases where again, we

**[1:10:08]** try to operate as much of a as a product team as possible. So

**[1:10:11]** whenever you know product ships a new feature, they will post

**[1:10:14]** like ship shipped in the ship channel. We had FOMO we want to

**[1:10:18]** do the same thing. So now in our RevOps slack channel, once we

**[1:10:21]** release a project and you know, there's a difference for our

**[1:10:24]** stakeholders, we'll do a RevOps release, we have some pictures,

**[1:10:27]** it creates you know, a short little memo that goes in notion

**[1:10:30]** it's linked to the project, it's linked to the documentation.

**[1:10:34]** Anybody who wants to learn about a project that we released is

**[1:10:36]** going to have all these different artifacts to work off

**[1:10:38]** of and we approved all of the language that goes in them.

**[1:10:41]** That's what we do from terminal from these skills, but we did

**[1:10:43]** not manually write them. And we certainly did not have the time

**[1:10:46]** to go get all the context to build it out and get the right

**[1:10:48]** project.

**[1:10:52]** These RevOps ones are good. This is also where we have, let me

**[1:10:54]** show you our pipeline ops. So that's what I was talking about

**[1:10:57]** earlier. New pipeline review them, add a contact to a

**[1:11:02]** specific campaign, review your pipeline before you go into a

**[1:11:05]** pipeline meeting. So we've got all these different, you know,

**[1:11:09]** habitual routines that our team is doing. And we're trying to

**[1:11:12]** really perfect the process and the framework for that skill for

**[1:11:15]** us before we start building out like even more agents that you

**[1:11:19]** know, are external facing as well. This is a way that we're

**[1:11:21]** using to manage our blast radius with a lot of these AI

**[1:11:25]** capabilities is we're really focusing on what is the internal

**[1:11:28]** stuff that we feel confident about and then we will expand to

**[1:11:30]** more things.

**[1:11:33]** Smads, this is fantastic. I really appreciate you walking

**[1:11:36]** through these and sharing them. And I think the biggest takeaway

**[1:11:41]** is how you're approaching the infrastructure component of your

**[1:11:45]** agents and workflows and making sure the MCP is connected, are

**[1:11:49]** we consistent with how we're, how we're launching these agents

**[1:11:53]** or building these capabilities. And I think that's where the

**[1:11:56]** teams that are making the investment in that component of

**[1:12:00]** AI are going to start to really, really run fast and make a big

**[1:12:05]** gap between the ones that are not.

## 1:12:07 — Treat agentic infrastructure like Salesforce

**[1:12:07]** I agree. And I think I said this a little bit earlier too, but we

**[1:12:10]** need to think of these platforms and these tools and what they

**[1:12:14]** can do for us in the same way as bringing on a Salesforce. This

**[1:12:17]** is now a cornerstone of your tech stack. And we have

**[1:12:20]** maintenance days, we have code freeze periods for Salesforce,

**[1:12:23]** we have blackout dates, all of that is probably going to end up

**[1:12:27]** also applying to the company wide agentic infrastructure, as

**[1:12:30]** well as your own personal operating system. And if I want

**[1:12:33]** to make sure that my team is pulling the right context for a

**[1:12:36]** project or writing the right type of problem statement, all I

**[1:12:39]** got to do is write a skill. And then we use it.

**[1:12:45]** Amazing. Smads, thank you so much for being on the podcast

**[1:12:50]** today and sharing everything. I love the story of seeing that

**[1:12:54]** waterfall chart, getting the spider bite and finding your way

**[1:12:57]** into ops and then all of the things that you're doing on the AI

**[1:13:00]** front really, really pushing the limits and sharing a standard of

**[1:13:03]** what good looks like for RevOps. So thank you for being here. And

**[1:13:08]** I can't wait to see what you build next and hope that you can

**[1:13:12]** share some of these with audience as well.

**[1:13:14]** Definitely, definitely. I will include a link to my GitHub where

**[1:13:17]** I have, whether it's the actual skill or the prompts that you

**[1:13:19]** can just download and use and then you have to share it with

**[1:13:22]** someone else. That's the rule. You can't just keep it to

**[1:13:24]** yourself. We got to share.

**[1:13:27]** Too generous, too generous. Thank you again.

**[1:13:29]** No, thank you for having me. This has been awesome. I will

**[1:13:31]** geek out anytime. So thank you. Thank you for having me.