---
title: "How a $20K Pilot Became a $30M Deal"
episode: 124
podcast: "The LeanScale Podcast"
publisher: "LeanScale"
guest: "Tim Yandel"
guest_title: "Chief Revenue Officer, Imubit"
date_published: 2026-09-23
date_modified: 2026-09-28
duration: 01:15:36
word_count: 14164
topics: ["enterprise-sales", "forecasting", "revenue-operations", "sales-leadership", "ai-in-gtm"]
canonical_url: https://www.leanscale.team/knowledge/podcast/tim-yandel-imubit-20k-pilot-30m-deal/
source: "LeanScale Knowledge Hub — https://www.leanscale.team/knowledge"
license: "Free to quote and cite with attribution to The LeanScale Podcast."
---

# How a $20K Pilot Became a $30M Deal — Full Transcript

> Episode 124 of The LeanScale Podcast, with Tim Yandel.
> Published September 23, 2026 · 01:15:36 · 14164 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/tim-yandel-imubit-20k-pilot-30m-deal/

## 00:00 — Cold open + intro

**[0:00]** My guest today is Tim Yandell, Chief Revenue Officer at Inubit.

**[0:04]** What makes Tim worth listening to is that he has run both,

**[0:07]** and he is blunt about the trap hiding inside the strategic sale.

**[0:11]** You don't have anything that people kind of grab onto.

**[0:13]** So connecting the two is really the job.

**[0:15]** I rounded up the 30 million from 21.

**[0:17]** I'm just kidding.

**[0:18]** But it was actually 29.4 million.

**[0:20]** When you're fundraising and doing things like that,

**[0:23]** the difference between an 80% growth rate and 2Xing

**[0:26]** is potentially worth tens of millions to your evaluation.

**[0:29]** So it's not a small thing to say, hey, we close this in December versus March.

**[0:35]** What's the big deal?

**[0:36]** You have the chiseled revenue athlete,

**[0:39]** and then you have the more of the chess player,

**[0:41]** or if you will, it might be lazy and fat behind the chessboard,

**[0:45]** but very strategic mentally.

**[0:47]** I know I have like 18 sessions open right now,

**[0:50]** but am I actually doing anything productive?

**[0:53]** Am I actually moving the needle forward?

**[0:55]** Dive as deep as you can,

**[0:57]** but not so deep that you forget what the job you're supposed to be doing.

## 01:08 — Recruiting to software: the perishable asset

**[1:08]** Tim, walk me through how you went from recruiting to closing a--

**[1:12]** I can't believe I'm going to say this number--

**[1:14]** a $30 million deal and what you had to do differently in that type of sale.

**[1:22]** Yeah, thanks for having me.

**[1:23]** I'm looking forward to discussing a little bit more.

**[1:25]** I rounded up the $30 million from '21.

**[1:27]** I'm just kidding, but it was actually $29.4 million,

**[1:32]** but I did do a little rounding.

**[1:33]** $30 million sounds a little bit better than that.

**[1:36]** The journey was a lot of discovery on not only just closing a big deal,

**[1:41]** but just the difference in solution selling,

**[1:44]** which is in the recruiting side of things,

**[1:46]** more of the consultive type of work into you're selling not a person,

**[1:50]** but an actual product.

**[1:53]** And so a lot of learnings there in particular,

**[1:58]** but one in particular is when you're in recruiting,

**[2:01]** you have a perishable asset, if you will.

**[2:03]** You have someone that's on the market for a period of time

**[2:06]** and they're going off the market.

**[2:08]** And so you have this natural critical event

**[2:11]** that surfaces from all your deals that you do.

**[2:15]** The longer you take, the more that Anthony is looking for another job

**[2:19]** and he changes his mind and this is logic sense.

**[2:22]** When you're selling software,

**[2:24]** there is no critical event that's naturally aging.

**[2:26]** So you got to find it within the person you're talking to.

**[2:30]** And once you find it, which is really, really the point of enterprise sales,

**[2:35]** you continue to ensure that you're reminding

**[2:38]** and you're kind of surfacing all of your conversations around that event.

**[2:42]** So that is one of the big things that drives enterprise sales in particular,

**[2:49]** but also just software sales in general and difference on that.

**[2:53]** Ultimately, that was kind of the conversation that led to the $30 million deal.

## 02:57 — The $20K pilot that became a $30M deal

**[2:57]** It started on a pilot, which was a small 20K pilot to prove out the technology is working.

**[3:05]** And then it started to kind of surface the bigger problem in particular.

**[3:08]** And this one was with a global manufacturing company

**[3:12]** that makes all types of products from refrigerators to car parts located in Germany.

**[3:16]** You could probably close down on who that could be.

**[3:23]** But it was specifically computer vision and data labeling in particular.

**[3:28]** And one of the pricing items that they needed to do

**[3:30]** was relevancy in the manufacturing space.

**[3:32]** So they didn't get outpaced by the competitors' parts on self-driving components in cars.

**[3:39]** And so it turned into like a science project at first,

**[3:44]** which is, "Hey, let's test out this cool technology."

**[3:46]** But once it got to the right person with the right message of,

**[3:50]** "Do you want to be a first mover on this, or do you want to be a fast follower?"

**[3:56]** And the benefits of a first mover, because they could answer either way.

**[4:00]** The benefits of a first mover was clearly outweighed why.

**[4:03]** And it turned to be more of a personal kind of achievement

**[4:07]** for the person we were dealing with

**[4:08]** on how they are going to get promoted within their global organization.

**[4:11]** And so it's not just a critical event of,

**[4:14]** "Hey, if we don't do this, then my budget gets pushed naturally."

**[4:18]** It was a personal kind of motivation that ended up being

**[4:21]** like the emotional tenet of driving that deal forward.

**[4:24]** And then you just back it up with ROI after that.

**[4:26]** But that personal kind of critical event is pretty key.

**[4:29]** It's very hard to find.

**[4:30]** And then kind of bringing it back into the recruiting angle,

**[4:33]** personal motivation is what every decision is made out of,

**[4:37]** whether your software or services or recruiting.

**[4:41]** And so rooting that out and kind of marrying it between all of them is pretty key.

**[4:45]** I think you uncovered something I never really heard articulated that way,

**[4:49]** where oftentimes these big enterprise deals are massive career movers for people.

**[4:56]** And if you do a good job and you get implemented quickly

**[4:59]** and show the value that you know your solution can show,

**[5:02]** that can expedite their promotion within the organization.

**[5:06]** And I think that's a huge level.

**[5:08]** I've seen that happen a ton of times with products that I have supported

**[5:12]** in the enterprise phase, where that person becomes a hero

**[5:16]** once they do a full implementation and it goes successful.

## 05:19 — It's not FOMO, it's FOMU — deals lost to no decision

**[5:19]** It could go the other way too.

**[5:21]** Could go the other way too.

**[5:22]** And I think that in enterprise, 85% of deals don't get closed loss to competitors.

**[5:31]** They get lost to no decision.

**[5:34]** And the reason why deals get lost for indecision

**[5:39]** is because it's not FOMO, which I'm sure you've heard.

**[5:44]** It's FOMO, which is fear of messing up.

**[5:47]** And when you're selling to these large organizations that are traditional in nature,

**[5:53]** my motivation at a fast growing technology company

**[5:58]** to get exposure and attention is very different

**[6:01]** at a brick and mortar company that's been around for hundreds of years,

**[6:05]** where it's almost the opposite.

**[6:07]** Attention isn't a good thing, and it depends on the culture as well.

**[6:12]** So it's not always a promotion.

**[6:14]** Sometimes it's like, if you don't do this, if you don't innovate,

**[6:18]** you might actually get replaced by someone who does.

**[6:20]** Like an outsider coming in, like a digital nomad coming from another industry

**[6:25]** into your safe zone.

**[6:27]** So if you're not pushing yourself, it's the other way around, right?

**[6:30]** So it's all what resonates with the individual.

**[6:32]** But I guess the key is find out what that root cause of personal motivation

**[6:38]** and emotional driver is with the right person.

**[6:42]** And that's kind of like finding your champion,

**[6:45]** because you can do that at someone at the wrong level and does nothing.

**[6:48]** But once you do that, then it's no longer your deal.

**[6:52]** It's their deal.

**[6:53]** It's their decision.

**[6:55]** And you're just here to help them out and making sure that they're doing

**[6:58]** all the steps necessary to get the deal done.

**[7:01]** Yeah. It's like you get on the same team as them presenting it to the organization.

**[7:05]** I think whenever you can build that type of relationship,

**[7:09]** they can help move those along quicker.

**[7:11]** Yep. Yep.

## 07:12 — Revenue athletes vs. chess players

**[7:12]** One of the things you're talking about during our prep session,

**[7:15]** you described salespeople who are in high velocity motions.

**[7:20]** And I would put recruitment in there absolutely as a high velocity motion,

**[7:24]** plus the urgency on both sides of the marketplace that you're running.

**[7:28]** You say they turn into revenue athletes.

**[7:30]** So, Juan, I would love for you to define what does a revenue athlete look like,

**[7:35]** and then apply that mindset that you can pick up there and bring to the enterprise world.

**[7:41]** Yeah. If you think about high velocity teams,

**[7:46]** the month ends, the deals go, some of them die, some of them win.

**[7:50]** You learn something with every interaction.

**[7:52]** They're quick, iterative.

**[7:54]** You just have more at bats to refine.

**[7:57]** And almost like the losses don't hit as hard.

**[8:00]** The wins don't mean as much as well.

**[8:03]** But it's like the drug.

**[8:05]** You get the dopamine hits and you get that going.

**[8:08]** And so, I mean, the bullpen environments,

**[8:12]** that's why I have music in the background.

**[8:14]** I grew up in that environment.

**[8:15]** The more stimulation, the better.

**[8:18]** But in an enterprise, you don't have as many at bats,

**[8:21]** and you don't have a lot of lessons to learn from.

**[8:24]** And then, arguably, if you wait to win loss, it's so long.

**[8:30]** If your sales cycle's eight months to 18 months, then how fast are you learning?

**[8:36]** And then if you're also kind of holding on the deals

**[8:38]** that are already lost because of indecision,

**[8:40]** the buyer just doesn't want to tell you that they're not going to go with you.

**[8:43]** They're just kicking the can down the road.

**[8:46]** You end up kind of lying to yourself.

**[8:48]** So, yeah, revenue athletes are the ones who are,

**[8:51]** they don't take it personally, they're machines, right?

**[8:53]** They're just chiseled and they're ready to go.

**[8:58]** But they're also not very strategic in nature because of that.

**[9:02]** There's no reason to be.

**[9:03]** I'm not saying that high-velocity teams are dumb by any means,

**[9:07]** but there's pros and cons.

**[9:10]** You have the chiseled revenue athlete,

**[9:13]** and then you have the more of the chess player,

**[9:15]** or if you will, there might be lazy and fat behind the chess board,

**[9:19]** but very strategic mentally.

**[9:22]** So, I think that to avoid that, you have...

**[9:26]** Well, the problem in that is you don't have the urgency

**[9:30]** that a high-velocity seller would have naturally,

**[9:33]** and you kind of can rest on your laurels.

**[9:34]** And as an organization, you kind of sit back on your heels a bit

**[9:38]** because you have time.

**[9:39]** Like, "Oh, we didn't get the proposal out on Friday."

**[9:41]** Well, it's okay.

**[9:42]** We can get it next week.

**[9:44]** The deal's not going anywhere because we have an eight to 18-month sales cycle.

**[9:48]** So, you end up getting lax on that point.

**[9:52]** But I'd argue that, especially this day and age,

**[9:55]** when you're selling an AI solution, of course,

**[9:58]** but when there's so much innovation happening outside,

**[10:02]** it's not just hitting high-velocity low-sale cycle products.

**[10:06]** It's also coming to the enterprise.

**[10:08]** If it's not evident, it's going to be evident very soon.

**[10:11]** And so, if you're not ready for prime time,

**[10:14]** speed is going to come to you whether you like it or not.

**[10:17]** And so, looking at things like how fast does it take to you to get an NDA out?

**[10:23]** How fast does it take internal deal-desk conversations to happen?

**[10:28]** When you look at different metrics you can learn from,

**[10:30]** from a revenue ops perspective,

**[10:32]** how many times are we single-threaded versus multi-threaded?

**[10:35]** Are we at the right level?

**[10:36]** You can have several conversations in a week with a deal

**[10:41]** that doesn't move from stage to stage,

**[10:43]** but now it's likelihood to move from stage three to stage four goes up highly

**[10:49]** because you've engaged eight-plus buyers or eight-plus people in that process.

**[10:54]** So, I think it's all like different tells that you can look from in the data.

**[10:59]** And it kind of comes down to what are you really looking at for efficiency?

**[11:03]** And why you should never accept that it's strategic sales.

**[11:06]** So, let's just go the old-fashioned way and whiteboard things

**[11:10]** and just wait for things to come to us.

**[11:13]** You still have to make sure that you're up to snuff mentally

**[11:15]** and then also physically with the athlete analogy coming back.

**[11:21]** Well, and I think a lot of companies don't realize the opportunity that they can capture.

**[11:26]** Let's take that 12-month sales cycle type of deal.

**[11:31]** If you can compress that to nine months,

**[11:33]** you can make sure you close even more deals within this year

**[11:37]** versus it slipping into the next.

**[11:39]** And then that's stacked up onto your growth rate for that particular year.

**[11:43]** When you're fundraising and doing things like that,

**[11:45]** the difference between an 80% growth rate and 2Xing

**[11:49]** is potentially worth tens of millions to your evaluation.

**[11:53]** So, it's not a small thing to say,

**[11:55]** "Hey, we close this in December versus March. What's the big deal?"

**[11:59]** No, it is a big deal.

**[12:00]** It's a huge deal for your enterprise value.

**[12:03]** And as you know, the longer you let things just wait,

**[12:06]** the less likely it are to close to.

**[12:08]** And then your mechanism is not just...

**[12:11]** It's not land, really, because your addressable market with your big logos is great.

**[12:15]** But the days of closing $30 million land deals,

**[12:19]** it's few and far between.

**[12:20]** Those land deals, even the one I just told you, was an expand deal.

**[12:24]** If you count pilot as a land, right?

**[12:27]** And the most important thing is what kind of expansion flywheel are you building?

**[12:32]** And so, the time to close, it doesn't have to be like...

**[12:35]** Maybe it's 18 months because you're asking for too much upfront.

**[12:39]** Maybe you can close something in 90 days and have like,

**[12:43]** as opposed to 500k pilot or first year deal, you do a 20k pilot.

**[12:49]** And in that 20k pilot, you automatically set them up

**[12:51]** for an expansion into a $5 million deal because of that.

**[12:55]** So, it's all about how you break up your own sales process

**[13:02]** and just try things and be creative with things

**[13:05]** to see what works for the buyer you're selling to.

**[13:09]** Which is an interesting thought because if you land smaller,

**[13:13]** I'm certain the conversion rate of that bigger deal

**[13:17]** is going to be much, much higher if you have an opportunity to prove it out.

**[13:21]** And that should be moved up forward

**[13:24]** than if you tried to land the entire thing in the first go.

**[13:28]** So, I think that land and expand motion in the enterprise world.

**[13:32]** Seeing how you can build that in not only helps you close a little bit early,

**[13:37]** but even the big deal that you have in your head of what it should be,

**[13:40]** that should expedite that potential and improve the conversion rate too.

**[13:44]** Yeah, absolutely.

**[13:45]** And it has some semblance of can you get a higher velocity learning moment at least.

**[13:53]** Having some discipline of saying like, if we're talking

**[13:57]** and you're buying what I'm selling and you say, this sounds great Tim,

**[13:59]** but I need a couple more quarters for whatever reason.

**[14:05]** And so I'm like, okay, sounds good.

**[14:08]** So what's your next, I mean, obviously I'm going to try to convince you not to wait,

**[14:11]** but are you close, you should close loss that deal.

**[14:15]** It's dead, right?

**[14:16]** Because it's two months or three months or two quarters, whatever it might be.

**[14:20]** That's a learning moment.

**[14:21]** So how do we, so the point is, it's like learning close loss.

**[14:25]** And so it gives attention to the actual, you know,

**[14:29]** you know, retro of what you could have done to made you not want to wait two quarters

**[14:35]** and having those moments where you can have some sort of a recognition and learning in earlier ways.

**[14:42]** But a lot of enterprise, I mean, I've done this taking over enterprise teams

**[14:47]** and they have just this, their sales cycle is 18, 24 months,

**[14:52]** but that's only because they don't have the rigor of actually closing things

**[14:55]** when they should be closed, right?

**[14:56]** They just kind of hold onto these weird things and their pipeline meetings.

**[14:59]** And I don't know if it's like a pillow that helps them sleep at night

**[15:03]** or something like that with their big, huge pipeline.

**[15:05]** But if the, if the pipeline is fake, then that's an empty pillow to sleep on, right?

**[15:12]** I don't know if some reps understand how easy it is to see through all of that.

**[15:17]** And nobody goes to president's club on their pipeline.

**[15:20]** Yeah.

**[15:20]** So you might as well close it out, keep it clean and then focus

**[15:23]** on the things that matter and can actually close.

**[15:25]** Yeah. Yeah, I agree.

**[15:28]** What one thing on the speed too, I'm wondering your perspective on this.

**[15:33]** Let's assume, Hey, it's going to take 12 months

**[15:36]** and these little bottlenecks of the NDA, the proposal, scoping out the,

**[15:41]** the POC, if there is one or something like that.

**[15:43]** Let's assume that doesn't ultimately move the needle on the closed date.

**[15:49]** I still think very few things signal competence more than speed.

**[15:55]** So when somebody asks you for a proposal and you can get it to the same day or next day,

**[16:01]** or somebody asks for the NDA and you ship it right away or get it turned around right away.

**[16:05]** I think even just the perception of your company's ability to execute on whatever

**[16:12]** you're trying to sell could really be elevated if you run the process

**[16:16]** really professionally and have speed baked up.

## 16:18 — Diagnosis, not prescription — why urgency backfires

**[16:18]** Yeah. Well, I think what do you, what are you signaling with that?

**[16:23]** I've done a lot of deals like this. You're not the only one, you know,

**[16:28]** and I will help you in that back to that same point of fear of messing up.

**[16:33]** It becomes less of a fear if I'm dealing with someone who's done this many times

**[16:38]** and it's about diagnosis and it's not about prescription.

**[16:42]** It's like, I know exactly what you're going through.

**[16:45]** I've done it before. I can spend more time, you know, and I'm not going to have to push you

**[16:50]** because it's okay, you're going through this stuff, so have all the other 10 other customers

**[16:55]** before you, worried about data wrangling or not being perfect or whatever it might be.

**[17:01]** And so that ends up being like, you end up kind of taking fear away from the deal.

**[17:07]** And so I would actually say if you end up, if you don't do that and if you get into

**[17:12]** advisor mode where it's not about me, it's about you, and then you push urgency,

**[17:19]** you're actually just pushing more fear onto the person who doesn't want to make a decision.

**[17:25]** And that critical moment becomes this like unsurmountable, like fear moment that they

**[17:31]** just can't get past. And so you end up kind of perpetuating a little bit of the problem

**[17:37]** because of that. So I would say it's like, you know, it's not about more urgency,

**[17:43]** it's not about more ROI, that stuff can backfire a lot if you don't get to the emotional driver

**[17:51]** of why this deal or why you, why us, why it works, and it makes sense in an emotional way,

## 17:58 — Stage three is where deals stall

**[17:58]** not just a rational one. Are there any tactical or practical areas in the sales cycle in that

**[18:06]** enterprise world that you think, systemically, some of these companies just are so slow

**[18:12]** at doing X, Y, or Z that you think you could come up, come in and just speed some of those up?

**[18:20]** Yeah, I think that stage three, you know, I don't care what sale you're in,

**[18:25]** but it's always stage three. It doesn't matter, it's where the pipeline bundles up.

**[18:32]** But in all seriousness, it's like, I think people rush the first stage is usually discovery call,

**[18:40]** second stage is a demo of the product itself, stage three is like when it's getting into

**[18:45]** the real stuff, right? And there's always this obsession where, you know, moving from stage one

**[18:52]** to stage two to stage three, as quickly as possible, speeds up the deal. When it's not

**[18:59]** necessarily the case where you spend more time on discovery, and less time on like the later stages,

**[19:05]** you know, that's really what matters, to kind of, you know, go slow to go fast kind of thing,

**[19:11]** and setting that up, where you have so many moments of that you can skip through and just

**[19:17]** really find that pain point, finding that critical event at the beginning, why should you actually

**[19:23]** get more stakeholders involved? Because the moment you get more stakeholders involved on your side,

**[19:28]** the more you get kind of out of control of what is actually being said in the narrative, and

**[19:32]** potentially wasting a lot of other people's time as well. So you're almost protecting not only their

**[19:37]** time, but you're architecting the deal of like, of I want you to speak to this person, and you've

**[19:42]** earned the right to speak to them, as long as you bring in another person that you want to speak to

**[19:47]** that matches a little bit of the leveling as well. And so it's a little bit of that chest match back

**[19:52]** and forth of architecting the flow of that. And once it's out of your hands as a seller, and given

**[19:57]** into like the technical side of your organization, you get a lot of folks internally that can, you

**[20:03]** know, crap on your deal before you get that further, then you have to have your stuff ready to go to

**[20:09]** get exposed internally to say not only why should we spend time with it, why should you spend your

**[20:14]** time with a technical persona internally? And how can you convince how can what do I want you to

**[20:20]** actually say, say these three things, don't say these 20 things, right? These are the if you have

**[20:25]** 20 things in your product that are worthwhile, just say no more than three. And these are the

**[20:30]** three things I want you to focus on. And you know that because you've already done your discovery

**[20:35]** ahead of time. So I don't know, I think that that's probably the stage that things stick,

**[20:41]** because once you show everything, then you basically gave everything to the person you're

**[20:47]** talking to that. So that third stage or that technical stage where you're getting more deep

**[20:51]** dive is pretty crucial, because then you pretty much are giving a lot of the control over to

**[20:56]** the buyer at that point in time, because they know everything about your product. And now it's up to

**[21:00]** them. You know, so piecemealing information at the right stage in the right time is pretty critical.

**[21:08]** I think that's an interesting way to think about it, like intentionally titrating the process out

**[21:13]** a little bit. So that way, you can keep the engagement throughout, because I have seen this

**[21:19]** happen too. And I think it's what you're alluding to, like you do an amazing presentation, amazing

**[21:24]** technical review. And then there's going to be a three month process where there's really nothing

**[21:28]** left for you to do. And we're just waiting for decision time, if they're doing technical reviews,

**[21:32]** or whatever red tape they have to go through internally. And then if you're not manufacturing

**[21:37]** ways to engage in a relevant way, I think it could really lose the momentum along the way,

**[21:45]** let alone what other like booby traps are going on behind the scenes on their side, the person,

**[21:51]** your point of contact leaves, new initiatives happen, who knows what could happen. So I think,

**[21:57]** I don't know if you've seen where, okay, we have to manufacture some engagement and urgency,

**[22:02]** you end up having to do that with what information you think is applicable to the person, you know,

**[22:08]** so and and the people and multi threading. And you have to figure out ways to keep the conversation,

**[22:14]** you know, relevant. Otherwise, you're just kind of I've never had I've never had a deal where you

**[22:19]** just say, okay, they have everything they need. And you haven't talked to them and in more than

**[22:27]** 30 days, and the deal as promised, comes in, you know, on time, your inbox and DocuSign is there.

**[22:34]** Yeah, it's like I've been refreshing the DocuSign link for every single day. Don't worry. There's

**[22:39]** nothing else we can do. I mean, that's it. You get that from forecast calls with, with salespeople,

**[22:44]** because it's like they've run out of ideas. You like because you gave them everything, you know,

**[22:50]** you've lost completely control of your deal. And you give that power to folks, because you just

**[22:54]** want to answer everything, all their questions, you know, and you're more on the receiving end,

**[22:58]** as poor as you're not driving the deal at all. So and you missed that whole point, you missed that

**[23:04]** whole, that moment you can play into doing deals, especially critical ones, you miss it because you

**[23:11]** just undervalued your time at the beginning of the sales process by trying to get to the technical as

**[23:18]** quickly as possible. And when you undervalue your time in the deal, then so will the person you're

**[23:23]** talking to and the stakeholders and they just say, okay, so Tim's or whoever the rep is, they're just

**[23:28]** kind of a person that gets people together. They're the scheduler, you know, I really want to talk to

**[23:33]** this person. And I have to go through means for an end is this this seller that I got to talk to,

**[23:39]** because you never developed the relationship, you never became valuable at that point in time and

**[23:43]** just gave it up too quickly. Any and I know it probably depends on every org and exact product

**[23:50]** and everything. But any way or tactics that you recommend slowing the process down so you can go

**[23:59]** fast. I like the way you put it that way, like slow, smooth, smooth as fast, Navy SEAL type of thing.

**[24:03]** But any any tactics you recommend to just help set that environment up?

**[24:11]** I think that it kind of manifests into like a mutual clothes plan in some way, shape or form.

**[24:19]** Once you get to a spot where it seems like it seems like we want to continue this conversation,

**[24:23]** right? I'm not going to like preempt this and say like you need to buy by this date. But you know,

**[24:27]** if we're if you find the critical event and you can find you can tie that to an actual date that

**[24:33]** you can commit to and doesn't have to be like etched in blood by any means. But it's something

**[24:42]** that you can start saying, okay, so this is how I think this can go. What do you think? I mean,

**[24:47]** next call, we talk about this bringing this person work your way backwards almost from the from the

**[24:53]** critical event of like getting legal involved and all that kind of stuff to get that go live date

**[24:59]** actuality in existence. You can even say like I know we said September 1st is the date we want

**[25:04]** to go after. Most likely it's going to slip, but let's just try to hold ourselves accountable to

**[25:09]** what that date is. And then you kind of go backwards from there and it shows kind of what

**[25:16]** we said earlier. It shows that you've done this many times before and you're in complete control

**[25:21]** of how to buy your solution. And it's not like, all right, I'm the buyer, I'm going to put you

**[25:27]** into this buying process of mine, I'm going to vet you with 15 different vendors. And that's

**[25:32]** just the worst spot to be in because you know, you're not going to be able to stand out from the

**[25:37]** competitors or your buying process because you've lost that control. I think it's just being

**[25:42]** intentional and mindful of like, before you talk to what, let's say you do a first discovery call,

**[25:48]** you get this action, you spot exactly who's who in the zoo that makes the decision at that company.

**[25:53]** You say, okay, Anthony doesn't have the budget, but he's going to be a champion. And you kind of

**[26:00]** do like a power and org chart internally with maybe someone else that can think through this

**[26:05]** with you. I'd love to collaborate with someone else. And like, if you're with another rep, say,

**[26:10]** hey, can we just go back and forth and see if we can architect some deals together? And it could be

**[26:15]** early stage for years, but you just go through your org chart, and then you kind of turn that

**[26:20]** org chart into a power chart. Who has the influence and the authority? Who is your business

**[26:25]** champion? Who has influence and no authority based on what you're seeing? What does this person look

**[26:30]** like in terms of similar buyers who bought that? Can you bring that use case to the table and say,

**[26:36]** you sound like a lot like this company. Their challenge was X, this is how they solved it with

**[26:42]** Y. Does that resonate with you? And then you get that kind of, yeah, that seems to be really,

**[26:47]** really interesting. So you just kind of establish credibility that you've seen deals like this

**[26:50]** before, and you saw challenges that are applicable to them. And you go, this is how this deal was

**[26:54]** done. This is how we kind of manifested it. Usually they had trouble at this area. Legal

**[26:59]** was a pain in the ass. How's your legal team? And they're like, oh, yeah, my legal team is a pain in

**[27:04]** the ass too. And you can kind of like, you know, warm that up in that way. So I think it's just kind

**[27:08]** of going through that confidence. And if you haven't done a deal before, if you're a new rep

**[27:13]** at a company, then try to steal someone else's story, you know, and then just act like you've

**[27:17]** done it before as well. And just trying to figure out the steps and the people and pace of that

**[27:21]** process where you can make that. So I think that's, I think it's just kind of figuring out when to,

**[27:29]** when to limit the exploration and get to a spot where you're actually ready to move forward with

**[27:34]** the deal itself. Otherwise exploration and decision and steps could take a long, long time if you're

## 27:43 — Forecasting when every deal slips

**[27:43]** not in front of how many are appropriate for the deal you're trying to do. One thing I want to go

**[27:49]** into that I think is really difficult for teams to figure out is forecasting in the enterprise

**[27:55]** world. I don't know how on earth you forecasted the $30 million deal. I don't know what that looked

**[28:00]** like in your CRM, but how do you, cause this is very different than high velocity. You go back,

**[28:06]** you have all the historical data, you can run your conversion rates, you can run your cycles

**[28:11]** in the grand scheme of things. You're going to be able to keep it pretty tight when you have

**[28:15]** hundreds of deals coming through the door. What's your approach to forecasting when the deals are

**[28:20]** that big? I mean, the deals are going to slip. I think that's what you have to assume, you know,

**[28:26]** at least a quarter. And so even if the seller is great at what they do and their high confidence,

**[28:34]** it depends on who you're forecasting to. If you're forecasting to a board, then you have

**[28:39]** to take into account that if it hasn't slipped once, it's going to slip. And so minimally.

**[28:46]** And so I think you take that into account. Of course you would want to look at prior data,

**[28:49]** but typically enterprise software companies that I've been a part are really poor at data hygiene.

**[28:56]** To the point we were talking about earlier. And plus it's someone else's data story. So if you're

**[28:59]** a CRO or you're out of RevOps, you're joining a company, the data story that was told before,

**[29:08]** it could be a lot of different things. Like the rigor of closed loss, like I said earlier,

**[29:11]** could be completely out the window. And so that sales cycle is no longer something you can trust.

**[29:15]** So it's like, is it, this deal is set to close in six months, but yet the data says we've never

**[29:20]** closed a deal in six months. It's like, well, does the data tell you that it hasn't closed in six

**[29:24]** months because you've been holding onto opportunities or, you know, and you're just more rigorous.

**[29:28]** So you have to, you got to take into account that deals will slip. I would also kind of be

**[29:35]** relentless on, I mean, I've been forecasting using like gong or otter and having that

**[29:44]** tell me the story of what the behavior of the buyer, the champions are. Are they using language

**[29:50]** itself that is being kind of transposed because you're dealing with a rep that has happy years?

**[29:58]** On the other end, are you dealing with a rep that's super pessimistic that doesn't want to

**[30:01]** put anything in the forecast because they feel like that's kind of, I only put deals in the

**[30:06]** forecast when it's like, illegal. I'm like, well, great, that gives me no visibility into anything.

**[30:11]** So thank you very much. So those are like the opposite of your pipeline stuffers. So I can run

**[30:18]** both ways. And so just like an honest assessment of how, why things are going to close. And I think

**[30:25]** it's you as a sales leader or RevOps leader, depends on that be very black and white objective

## 30:30 — What actually counts as a critical event

**[30:30]** of what needs to happen. What is the critical event? When is that critical event? What happens

**[30:36]** if that critical event is not hit? So if it can move, you know, if it moves a couple of weeks or

**[30:43]** month or two, then, you know, it still can be a critical event. But if the critical event

**[30:47]** can move quarters, it's not a critical event. And there's no consequence of no action. So that's

**[30:53]** what a compelling event is. So it's, it would be nice to have, you know, this, this new thing,

**[30:59]** you know, it'd be nice to have a new car. But do I need to have it? And if I don't have it,

**[31:05]** by this point in time, I'm out of my lease or whatever it might be like, those are, those are

**[31:09]** critical events. And so deals don't get forecasted without a credible compelling critical event.

**[31:17]** And they don't get into best case or most likely without it. So, you know, be rigorous with

**[31:24]** whatever methodology you're using. And ensure that you have, you know, whatever it is, it could be

**[31:30]** spiced, it could be med pick could be whatever it is, but critical event needs to be there.

## 31:36 — "Have you approved a deal this size before?" — how to ask it

**[31:36]** I like that. And it's really clear and tactical for someone to have another one that you've

**[31:41]** mentioned before. I like this as a qualifying question, and I'm curious, best way to artfully

**[31:48]** ask someone you're in a sales process with, but when you ask the buyer, have you ever personally

**[31:54]** gotten a deal this size approved before? And I think that could go one or two ways. It could be,

**[32:01]** yes, of course. Okay, good. Check that box. How do you handle it when they say no? First,

**[32:05]** I want to even how to ask it. How do you ask it where it doesn't sound like it's going to come

**[32:09]** off wrong? And then if they say no, what do you do? Let them, I mean, yes or no question is the

**[32:19]** dangerous question. So I think it's like, tell me about, I'm sure you've closed deals like this

**[32:24]** before. Like, what was the last process you went through that was a similar, similar magnitude in

**[32:28]** terms of price? You know, any learnings from that. And you can usually spot like, let me think.

**[32:38]** Yeah, nothing really comes to mind. It's like, it's okay. This is your first one. No big deal.

**[32:45]** But make it exciting for them. You know, it's a journey that they're on with you. And I think

**[32:48]** that's the end result of you being the shepherd in the sales process or the evaluation process

**[32:58]** is be like, it's fine. Not everyone has, you're new in your role or whatever it might be like, you

**[33:04]** know. So you can commiserate with them and say like, I'm not looking to kind of expose you. I'm

**[33:09]** just trying to figure out business justification is a big thing for any kind of deal. But once you

**[33:17]** hit over $100k, you know, it becomes scrutinized and let alone millions of dollars. I mean, that's

**[33:23]** the whole committee of people you have to be prepared for. And so if you have someone that says,

**[33:29]** I'm going to do the business justification for this, and you're not a part of that conversation,

**[33:36]** that person must be a very sophisticated buyer. And you can even say that it's like, wow, okay,

**[33:39]** you're doing this by yourself. Most people I'd work with, I work with them on the business

**[33:43]** justification because you know, this is a high ticket item. So you must have done a lot of these.

**[33:50]** How many have you done? You know, and you know, you can kind of feel it off from there. So I

**[33:54]** wouldn't say it's a scripted way of asking it. It's just feel it out. But don't be like, have you

**[34:00]** done this before? You know, don't go directly to the chase. No, that's a much more artful way

**[34:08]** of asking the question. And I think I've seen some people going through their qualification list

**[34:15]** and can ask a lot of these things in an off putting way. But I actually like the way you positioned it

**[34:20]** that actually puts them on a pedestal in a way. And it's like, I'm just assuming you have the

**[34:26]** experience. So no problem. I'd love to hear how you did. And I think that's a really good way

**[34:30]** of getting that answer. Yeah, you don't want to put them on a pedestal where they're above you,

**[34:34]** but you want to put them at the level that they're your chat, you're talking with them,

**[34:37]** right? So there's a mutual respect. Exactly. Anything else in forecasting that you can think

**[34:44]** of that just helps you tell the story to the CEO, tell the story to your board during a board meeting,

**[34:55]** tells a story during a fundraise potentially, what types of things do you want to make sure you have

**[35:00]** in your forecast if your deals are of that size? Well, if you're dealing with, well, you mentioned

**[35:06]** quite a few different audiences there. But if you're talking to a board or investor in general,

**[35:15]** I mean, they want to make sure that you have, they want to make sure that you're data centric.

**[35:20]** That's for sure. You can't just be I've done this before, this is my Rolodex. I'm a seller for 20,

**[35:26]** 30 years, you know, that bravado doesn't go very far at all. So you need to have data and a firm

**[35:33]** handle of what the data is telling you. So I've run into traps early and just said, all right,

**[35:39]** I'm a data first CRO, here's the data. It's obvious to me, you know, this is what the this is what it's

**[35:44]** saying. You have to have a story behind the data. Otherwise, you're kind of screwed. They can make

**[35:54]** assertations of what this data is saying, when you don't have like a way a command of it. So it's like

**[36:01]** not going too far into how you've done it. But like, I've broken this data based on cohort date.

**[36:07]** And why am I doing cohort is because I found that doing it this way is not the way

**[36:12]** to kind of get the you know, it's like so it's show a little bit of double clicking.

**[36:17]** Show a little bit of the hey, when I use this close percentage in this in this forecast

**[36:22]** likelihood, this is kind of the way I've discounted a little bit where I've used

**[36:27]** prior quarter slippages. And because this deal hasn't slipped once, I'm assuming that it's a 50%

**[36:36]** close probability at this quarter, because it's most likely going to slip based on the data we've

**[36:40]** had. And so I think it's like, it's the it's the power behind the thought behind the data itself

**[36:47]** on how you're presenting, especially for board that gives them confidence, at least, but listen,

**[36:53]** every board is different. So that's there's not like, I'm not here saying I've got the silver bullet

**[36:58]** for board conversations. It's always something you could take you should take very seriously

**[37:01]** at if you're if you're presenting in front of a board. And if you're presenting in front of

**[37:07]** an executive team, I think it's I think it's less being I found more success when you present a

**[37:18]** forecast by asking and getting clarification from your executive team around the table their input.

**[37:26]** And it's not the Tim show. It's not the CRO show saying this is my forecast. Look at how beautiful

**[37:31]** it is and how likely it is to close. It's a our forecast as an executive team. It's a I am just

**[37:37]** like the tip of the spear getting one angle from the sellers, but you manage a team and you manage

**[37:42]** a team. And so some people on your team are on calls as well. You may be on calls as well. The

**[37:47]** CEO might be engaged a couple call. What's your read? You know, do you think we're reading this

**[37:51]** this deal correctly? Or how would you forecast this? I think that's the that's how I've seen

**[37:56]** more success. And you can get and I find myself, you know, recently in the past six months, even

**[38:04]** you get in. If you don't do it in a collaborative way, you kind of get defensive about it

**[38:09]** naturally. You know, and so people poke questions like, I mean, Anthony, you're not you're not in

**[38:14]** these deals. Like, why are you asking me questions about my forecast? You know, it's like this is

**[38:19]** it's almost like you find your ego getting into it. It's like, like, this is my deal. Do I go into

**[38:23]** your like product roadmap? And do I say I actually do, but whatever. But do I poke holes in it?

**[38:30]** I'm like, yeah, I guess they do. But you know what I mean? Like, you get a little defensive

**[38:34]** on it. So just watch yourself. And if you go into it with a collaborative spirit, you find yourself

**[38:38]** being less defensive, because what do you have to be defensive about? It's like, you're forecasting

**[38:43]** what these sellers have told you. So it's like, why should you have pride and ownership of what

**[38:48]** you've been handed? You do your diligence, you put your rigor on it. But ultimately, don't take it

**[38:53]** personally when someone starts to poke holes in it. Well, it sounds like product didn't invite you

**[38:58]** in to have some recommendations on the roadmap. So that's that's their fault, I think. Yeah. I mean,

**[39:03]** invite. Yeah. I just shoe more myself into these like, let me just be a fly in the wall in your

**[39:09]** roadmap session. Let me just hear what hear what you're getting through. Yeah, we should be shipping

**[39:13]** these things 10 times faster. I don't know what's going on around here. Yeah, well, it's always it's

**[39:18]** always the caveat with product, which is like, it's like, oh, you want this? Well, then this is going

**[39:22]** to go. It's like why everything is a trade off, right? So you want the sandwich, then you're not

**[39:26]** going to be able to have a drink with it. I'm like, everything is a trade off. So I think that's

**[39:31]** super important to get to flip it around because the CRO position, oh my goodness, that that is the

**[39:38]** hardest job with the most risk in all startup world. And usually it feels like they're on an

**[39:47]** island expected to just go make magic happen, go make it rain and makes a bunch of money and

**[39:53]** go do it. And if you don't do it, it's all your fault. But I would love when I've seen some CRO's

**[39:59]** just get like destroyed when they're isolated and put in their own. And just like you said,

**[40:05]** start to get defensive and start like, yeah, take it as a personal attack. But I've seen some CRO's

**[40:12]** turned into a real collaborative effort and then puts the right amount of pressure on everybody

**[40:16]** else. Like, hey, yeah, product gets involved in big deals or CFO needs to come in to get some

**[40:23]** special type of pricing going on for this or make it figure out a POC or form something new. And

**[40:28]** the CEO needs to take ownership on some strategy that we're having. So when that happens,

**[40:35]** I think it's so much more productive and then you're all focused on the right things. Hey,

**[40:40]** how can we just do the right things that give us the best shot at winning?

## 40:44 — More internal selling than external selling

**[40:44]** I 100% agree. I think it's also might be a lesson between the high velocity seller and the

**[40:50]** enterprise seller, which is you have more internal selling to do than external selling,

**[40:57]** getting the team aligned on what you're trying to do. And kind of mentioned to it earlier, but

**[41:02]** you don't get a gold star and say, oh, wow, so this is a deal that Tim just closed by himself

**[41:09]** and he got no help ever. And if anything, if I'm a board member or an executive that says,

**[41:16]** okay, so no one else sniffed this deal out, then I'm actually more concerned. I have more concern

**[41:21]** in this deal than I previously did because it was done with one person as opposed to several.

**[41:25]** So if it works against you, then why not be collaborative on this stuff? And if you're

**[41:33]** buying something that has a significant value, they're buying you as a company, not just a

**[41:39]** product. And that partnership goes a lot further than just what they're buying today. So the

**[41:43]** confidence in the people behind the product is key. So you're kind of like showcasing within

**[41:50]** without it being like a, you know, exploration, endless exploration, be articulate about who

**[41:58]** on the executive team you want to bring in based on the size of the deal and what their role would

**[42:02]** be. And that's applicable to that. And so you're not doing this deal by yourself, you know, and

**[42:06]** you're doing it in a way where you can have a collaborator and map the power in the company,

**[42:12]** leverage them to say like, Hey, I think you got along with Joe at this company and you kind of

**[42:18]** match their persona a little bit. So why don't you, you know, develop that one-to-one relationship,

**[42:23]** Anthony, and ping that person. And this is what I would do. So you're kind of like a puppeteer,

**[42:27]** right? Behind your own kind of team. I mean, it just happened yesterday. We had a workshop with

**[42:35]** potential customer that, you know, of course is taking some time. It's in legal right now. And so

**[42:39]** it's been in legal for the last three months. You know, we did like a product roadmap workshop

**[42:44]** session with their product person as well. And so I'm like, you guys jammed a little bit on that

**[42:49]** conversation. So, you know, my head of product, I'm like, why don't you send them a text or an

**[42:54]** email and saying, Hey, we'd love to kind of go a little bit further on this conversation if you're

**[43:00]** up for it. And it helps build momentum and keep that momentum while legal is doing what, who knows

**[43:06]** what they're doing right now, but not signing my contracts. So, you know, you can be architecting

**[43:11]** that way. They're out there eating bonbons, just not caring. Yeah, looking at their massive stack

**[43:18]** of contracts to go through, you know, it's like, wow, it's getting really big right here. It's,

**[43:22]** I wonder how big it can go. Good time for me to go on vacation. This is

**[43:27]** exactly. No, I think, I think that's really helpful in turning sales into a team sport. And

**[43:36]** that's a good way for people to think about it too. Like the more velocity, the more individualistic

**[43:40]** it can likely be. And then the more enterprise, the more team oriented that whole process really

**[43:45]** needs to be one component of the team. I think a lot of people have when they're thinking of

**[43:52]** departments like rev ops, I think there's a lot of index and orientation to the velocity sales

**[44:00]** type of environment. And I think a lot of the work they do tends to become obvious there.

**[44:06]** I've done rev ops and enterprise environment, so I have a good idea. But from your perspective,

## 44:11 — RevOps as a force multiplier: the Slack deal desk

**[44:11]** where has rev ops helped the enterprise motion the most? And where are you using rev ops to

**[44:19]** get the most leverage out of your team? Oh, I mean, like, rev ops has always been my secret

**[44:25]** weapon, partly because I hate doing rev ops myself. And so, you know, you look at, you know,

**[44:30]** what brings you joy and what brings you frustration and identify that's usually a strength and a

**[44:36]** weakness. So you might think that you're good at rev ops, but if it brings you no joy, it's probably

**[44:40]** because you can't just admit to yourself that you're just not rev ops material. They're a

**[44:44]** force multiplier. And if you treat them like, you know, data wranglers or just a means to an end,

**[44:52]** then that's what you get. But they're a strategic lever on how to advance your business. And just

**[44:56]** because they can't do it in turn rates or turn rates on like high velocity metrics and just

**[45:01]** manage it that way and give me a whole of the data story so I can tell it when I board, then

**[45:06]** you got to have a thought partner in that area where it's almost like, am I thinking of things

**[45:10]** the right way here? How kind of systems internally can we build in rev ops to make us more effective?

**[45:17]** My rev ops person is the person that makes it a reality. Is there a way where we don't have to do

**[45:23]** weekly deal desk meetings that last two hours? Like, what can we do? What can we get ahead of

**[45:30]** time? And what's one way we can use Slack and just make sure that everything goes through deal desk

**[45:35]** appropriately, where we don't have to do CPQ. We don't have to do any of that kind of stuff.

**[45:38]** We just build like some sort of a system that says, all right, Tim, it's you need to look at

**[45:43]** this portion of the deal because it's a commercial thing. And then it goes to this person who's in

**[45:49]** product and this person that's in like services. And then it goes ultimately to the CEO to

**[45:54]** to look through. And then, you know, just explain that problem. Like we have a fully articulated

**[45:59]** deal desk motion on Slack where it's just like, I just get pinged and it says approve yes or no.

**[46:04]** Here's what I need to know without actually opening the entire contract, although I can,

**[46:07]** if I want to see the whole deal. But if I need to kind of get back an approval matrix, then,

**[46:13]** then, you know, he designed a system that just does that. So systems thinking is kind of the

**[46:19]** the way I look at it. It's like, I need a systems thinking person where I can look at the data,

**[46:25]** of course, and talk about strategy. But like, you know, come to the table and say like, he's the

## 46:29 — Measuring internal SLAs and building revenue athletes inside

**[46:29]** one, my head of RevOps, Jack Volkoff, you can look him up on LinkedIn. And I hope no one recruits

**[46:35]** him because of this podcast. But he comes up with the ideas of like, hey, I just was thinking,

**[46:40]** I'm like, wouldn't it be interesting to measure the response time on SLAs that we have on legal

**[46:46]** requests? And I wonder if we can kind of build a little bit of a trend saying like, you know, hey,

**[46:50]** this month, we've gone down from three days to two days, or this many hours to this many hours. And

**[46:57]** so that's a that's a way to kind of get, you know, revenue athletes within your own organization. And

**[47:03]** so, yeah, I would think it's not just, it's not about buyers themselves. The end buyer isn't the

**[47:10]** isn't the only mechanism for measuring RevOps. It could be internal signals that you can make sure

**[47:16]** that you get into like, you know, rigor and get into a spot where you're offering a customer a

**[47:22]** great experience, because the buying process and the way that they get back to a customer about

**[47:28]** certain things is programmatic, systematized. And you're kind of taking the creativity to another

**[47:34]** level where it's something that's predictable. So yeah, I think RevOps is super crucial.

**[47:42]** I've always liked when I've seen really good duos with CROs, heads of RevOps,

**[47:48]** and they kind of turn into your chief of staff a little bit, maybe like your COO of the startup

**[47:54]** that you mentioned. And I love the way you put it, they turn your strategy into reality, and they

**[48:00]** can execute against it. And I think a lot of the leverage too, if you can help your sales team

**[48:07]** reduce that sales cycle a little bit, increase conversion rate a little bit, hold a little bit

**[48:12]** more pipeline than they could before, and be a little bit more efficient, that leverage compounds

**[48:18]** pretty quickly, even with a small sales team. And yeah, I think you keep it lean, keep your sales

**[48:24]** team fed really well, keep their pipeline healthy, and not turn into this bloated sales org if you

**[48:31]** have RevOps in order. Yeah, I mean, if you have like a, if you have a seven stage sales cycle,

**[48:37]** a sales process, and you incrementally every quarter improve each one of those stages by 1%,

**[48:44]** you know, and you look at that over a year, you're making some significant impact. And just because

**[48:49]** you don't see, you know, if high velocity of deals, I mean, that those rates really add up.

## 48:56 — Baseball, Moneyball, and the long season

**[48:56]** I am a baseball fan. And not because I just like the sport itself, because I like going to games,

**[49:03]** I mean, outside, and you know, it's turned into a good thing with my kids. But because baseball is so

**[49:08]** frickin long, the season is so long, there's so many games, and it's the only sport that you,

**[49:13]** even the best teams in baseball, they lose more than 50 60 games a year. And so they've, they

**[49:20]** they've experienced failure. And then every team that wins the World Series goes through a period

**[49:25]** of time in the season, where they've just sucked, you know, and there's there's that drought. And

**[49:31]** it's kind of how you get out of that drought that really defines your season. And I feel like that's

**[49:38]** a good analogy for business, especially in the enterprise space, where, you know, it's you got

**[49:45]** to learn, you got to improve, you got to take your losses, and you got to kind of learn from them,

**[49:49]** and you got to keep on going, because it's a long ass season ahead. And it's not about just burning

**[49:53]** out in a month, and just kind of making your your number in a quarter, it's about the whole,

**[49:58]** whole year. And in most cases, it's multi years. And you know, it's a significant test of time.

**[50:05]** I think it's a great metaphor, especially just saying discipline to the fundamentals as you go

**[50:09]** through. And even when you're doing the right thing, sometimes bad things happen. So you have to

**[50:15]** kind of roll with that as you go along. Yep, exactly. And so your rev ops, and enterprises

**[50:20]** like moneyball, right, it's kind of like, look at all the stats and look at all of it, the different

**[50:25]** components of like, it's not just three point percentage, and how many threes that you got to

**[50:29]** do, but like, walk rate on base percentage steel, I did this this war metric that it's going around,

**[50:36]** which is wins above replacement, which I'm, I still don't quite understand how they do that.

**[50:40]** But that's a metric as well. But it's like, it's pretty cool stuff. So there's countless ways to

**[50:46]** break down that game and stats and numbers that a lot of folks don't necessarily appreciate.

**[50:52]** Yeah, I've kind of become obsessed with it. Because like, I ran red ops for three companies,

**[50:57]** then at lean scale, we've, we've done engagements with hundreds of companies. And I think you just

**[51:04]** see when you see those conversion rates go up a little bit, when you see time and stage reduce a

**[51:09]** little bit, when you see, hey, let's get rid of a couple sellers that really aren't producing,

**[51:15]** and then amplify the ones that are doing a really good job, like these little micro improvements

**[51:22]** all across the go to market life cycle just add up to so much. I don't think people realize like,

**[51:27]** if you're on a $20 million plan and assume you have enough pipeline to feed it, if you can

**[51:32]** increase your conversion rate by five points, that could mean another $5 million into your

**[51:39]** overall year. So the numbers get pretty big pretty quickly. And just being like a blood hound,

**[51:46]** looking for those areas that can get improved, we'll just keep that thing going. Yep. Yep.

## 51:51 — The data and the story

**[51:51]** It's a force multiplier. One thing I want to make sure we get to the data in the story.

**[52:00]** If you have one, you might as well not have anything. You really need both to come together

**[52:05]** really well. My CRO that I worked with that company, he would always say, if you torture

**[52:12]** the data enough, it'll tell you anything you want it to. And that was kind of his phrase around it.

**[52:17]** But I think tell me more about that and some of the venues that you need to be prepared for too.

**[52:25]** Well, we went to the board conversation. I think that's one of them. I mean, if you don't connect,

**[52:29]** if you have the story with no data, then there's no story that's relevant. If you have the data

**[52:34]** without the story, then you don't have anything that people kind of grab onto. So connecting the

**[52:40]** two is really the job. And, you know, one of the things that you can get to an example of like,

**[52:49]** you know, 40 to 60% of losses are due to no decision. And then if you don't have a story

**[52:58]** as to what that signals, then what does that mean? It's like, so why? Okay, so great. So 40 to 60 of

**[53:07]** your percent of your losses are moving to no decision. And if you don't have a compelling

**[53:11]** reason or a few different theories as to why that is and how you're going to fix it,

**[53:17]** you're on the wrong path. And not only the board conversations, like, I mean, at the end of the day,

**[53:20]** who cares? It's like, are you doing the right job? Are you looking at the data at the right way?

**[53:25]** Are you double clicking to say, okay, so how do we kind of fix that? And what are the reasons why

**[53:32]** that is the case? What are we doing, not doing in the discovery call that we could be doing more?

**[53:36]** Okay, let's try that. Now, how do we measure whether that whether we're on the on the right

**[53:42]** path? And how can we do that in a quick way, where we don't have to wait six months to see if we did

**[53:48]** the right thing to begin with? What are the metrics we're looking for? And so you kind of like double

**[53:53]** and triple click into that and say like, okay, well, then and this is where you need, where I need at

**[53:58]** least someone who is who is inquisitive and can interrogate the data, not to tell a better story,

**[54:05]** but what you're trying to really solve for. And what are you trying to measure improvement on?

**[54:10]** And the data is the data. So then you make your assumptions as to why that is. And then you make

**[54:14]** some points as to how to fix it. And then you get to how are we going to measure improvement,

**[54:19]** which is somewhere we can iterate quickly on. We don't have to wait too long for that data to come

**[54:24]** back to know that we're on the right path or the wrong path. So we can kind of pivot necessarily.

**[54:30]** That's hard. It sounds much easier on a podcast to do than in a white boarding session,

**[54:40]** not only to come up with those metrics, but come up with those gates of measurement to say,

**[54:44]** when do we expect to see results of whether it did anything or not? And so if it's two weeks,

**[54:50]** is it a month? Let's make sure we have that kind of concrete agreement amongst us, whoever's in this

**[55:00]** decision tree. And then at that point at a time, we do either do more of it or less of it based on

**[55:04]** what it's doing. Because in the enterprise sales cycle, as you mentioned, you may not know what

## 55:14 — Leading indicators and measurement gates

**[55:14]** you're doing is working in the closed one metric. What are you measuring to see if what you're doing

**[55:22]** is having an effect? Is it just further up the funnel? Are there more subjective things that

**[55:29]** you're taking a look at as well? What are some things that you've had experience with where you

**[55:34]** say, hey, yeah, this is giving me leading indicators that that change we made in enablement,

**[55:38]** that change we made to positioning is actually working? I took over marketing for a bit. By the

**[55:44]** way, if you want to have the hardest job out there for relevancy, I feel bad for CMOs. So CMOs are

**[55:52]** pretty tough. So at least I have a scoreboard that everyone knows on CMOs. It's like I have

**[55:59]** a scoreboard, but people believe it is another story. But anyway, so when I took over marketing,

**[56:06]** it was the theory of like, okay, so paid search is the way that every marketer gravitates to,

**[56:13]** as to how they're getting the lead volume, which I fundamentally think has been completely disrupted

**[56:19]** based on AI, but whatever. And so we went through a theory of like, let's just organically write,

**[56:25]** this is maybe a year ago, year and a half ago, when LLMs were kind of, now everyone's doing it, but

**[56:32]** let's write 10 to 15 popcorn pieces a week of content. And these are like top 10 things that

**[56:42]** manufacturers do in this industry that has, you know, have maybe a little bit to do with us,

**[56:47]** but not like it's not our pitch, right? And let's run it for a month. And then, you know,

**[56:54]** you get the traffic rates, and you can just look at it very, very explicit, like saying,

**[56:58]** I don't have to have leads or opportunities be the thing we're solving for. Right now,

**[57:03]** I'm just trying to say, do they give people more to the website? And then that gate was successful.

**[57:08]** Yes, it does. Okay, cool. So let's look at lead volume. Is that increased as well? No, it didn't.

**[57:13]** Okay, well, then that probably has to go with content and the quality of the content itself,

**[57:17]** and maybe call to action, so you can play around with it there. So what probably you're trying to

**[57:22]** solve, it's not the whole thing, to your point of like small improvements in the wholesale cycle

**[57:27]** need to be it. So if I'm improving this point of the sales process, then what am I looking at,

**[57:34]** as far as a success, it could be like, I want to, we're going to extend the discovery period of time

**[57:39]** to two to three calls from one call. And because of that, we think it's going to impact either the

**[57:45]** next session, or maybe it's the stage three, what I was talking about. And so the time horizon for

**[57:52]** that is we expect that to be 60 days. And so that's our kind of line in the sand to kind of go

**[57:58]** forward from there. So I think it's really applicable to like, what you're trying to solve

**[58:03]** for. And if it's close loss to note, like how do we get things to move in stage three faster? It's

**[58:10]** not like more do more things in stage three, as the only answer, it could be a answer, it could be a

**[58:16]** answer to do. And you could have a theory to say, yeah, let's do more things in stage three. But it

**[58:20]** could be like, well, let's look at the other things. And let's part in interrogating the data that I

**[58:23]** think is valuable, where it's like, if I have an opinion, or I come, all right, Anthony, I have an

**[58:28]** opinion, stage three, win rate or duration of that stage itself needs to be needs to be improved.

**[58:38]** So really reduce the sales cycle from stage two to stage four, this is how we're going to do it.

**[58:42]** We're going to have a new demo or whatever workshop that we're going to introduce here.

**[58:47]** And without someone that can kind of check me to say like, okay, that's one element of doing it,

**[58:51]** but but can we look at the stage before? Or have we looked at the stage before that not accepting

**[58:56]** the first kind of solution as the solution. So you have a problem, you should have several solutions

**[59:02]** to that problem. And they all could be right. And don't do all of them because you want people to

**[59:07]** measure which one was actually effective, right? So we're going to say, let's start with this one.

**[59:11]** And because we feel like it has the shortest learning cycle. And so that's the one you pick

**[59:16]** with. And then, you know, it's a do we have an agreement that this is the measurement that we

**[59:20]** want to get to. So I don't know, that's kind of the the internal negotiation that you do through

**[59:27]** these things. And again, I feel like a lot of this stuff is much easier said than done, you got to be

**[59:31]** very rigorous, and kind of be mindful of this stuff, almost like put like a little banner in your home

**[59:36]** office that says, you know, don't accept the first data story that you have try to interrogate multiple.

**[59:43]** No, it's very difficult to do in real time, especially because you were mentioning, like,

**[59:48]** often, if you're trying to do an experiment, that you're going to change one factor and see how it

**[59:52]** goes. Sometimes you don't have the luxury of just waiting. So you might have to do three factors at

**[59:56]** once. Maybe you don't do 10, but you have to do a couple things. And then you need to bring in some

**[1:00:01]** judgment, like, okay, do we think it had an effect, the data says this, but what do we think drove the

**[1:00:07]** biggest impact? So, but I think just even having that approach of, I'm not gonna wait to see what

**[1:00:13]** close one is, let's start looking for leading indicators. Let's lead with a hypothesis. Hey,

**[1:00:18]** we think this thing will affect this other thing. Let's do it, commit to it, and then measure it,

**[1:00:24]** and then come back and did it work? I don't know. Maybe we need to change it. Yeah, yeah. But yeah,

**[1:00:30]** as you mentioned, easy to say in a podcast. It's tough to do it real time every day in the field.

**[1:00:36]** Yeah, it's try to be as black and white as you can, you know, I think that the best part about

**[1:00:40]** data is you can you shouldn't be in love with the solution that you put in place. You can be very

**[1:00:45]** objective with it. And, and again, easier said than done, but if you're like so positive about

**[1:00:54]** this changing it, then you kind of you have to try it. But but just watch your enthusiasm for this

**[1:01:00]** fixing it. You know, because you might be like, Oh, no, I definitely think it's going to work. And

**[1:01:04]** then you're gonna you can interrogate the data in a way that's like, Oh, no, I think it's working,

**[1:01:08]** but it's not actually doing the conversion that we said it was going to do. So, you know,

**[1:01:14]** be objective. I've had to walk that one back a million times. And then my excuse goes, well,

## 01:01:18 — AI in go-to-market: the internal app store and the scrutinizer agent

**[1:01:18]** it's good for the brain. So let's just keep doing it. So the other thing that's obviously creating

**[1:01:23]** lots of leverage, lots of noise is AI and go to market. And there's so many different applications.

**[1:01:29]** What are you seeing being effective ways of leveraging AI? And maybe what are some

**[1:01:35]** ineffective ways to? Yeah, I mean, we're in the AI industry ourselves, that's what we sell. And so

**[1:01:40]** it's kind of an interesting, you got to dog food it a little bit and kind of be kind of AI native.

**[1:01:46]** And so we don't use our own solution for go to market. Unfortunately, that'd be kind of cool.

**[1:01:50]** So we are leveraging all types of things to build different solutions internally. So even like

**[1:01:58]** rebuilding, we have like an internal app store, where we've had folks within the organization

**[1:02:05]** be able to kind of build different skills and apps that solve challenges. And I think one of the cool

**[1:02:12]** things about that is connecting the dots on like someone from another department. And if you don't

**[1:02:17]** go into like, here's a skill that fixes my problem. But this is kind of what I did to build it is

**[1:02:25]** sometimes the most interesting thing that I can see, like there was one example where someone's

**[1:02:29]** like replacing an internal tool, I'm not going to say what the tool is, but it's like a collaboration

**[1:02:34]** software that we use for quite some time. And he's like, I think we can actually replace it,

**[1:02:42]** because part of the problem is, you know, filling out this collaborative software is some of the

**[1:02:47]** issue. And so if we have a listener agent, which is on Otter, all of our internal calls are being

**[1:02:53]** recorded, as well as external calls, we have so much information we're sitting on. We have Slack

**[1:02:58]** as a tool, we communicate exclusively internally, because we're a global hybrid company. And so all

**[1:03:03]** the information is there. And so it's not a matter of just like, you know, setting the different tasks.

**[1:03:09]** So he created an agent that automatically creates the tasks and builds this collaboration thing and

**[1:03:14]** does automatic updates. And that's not noisy in Slack. And one of the reasons I picked this one in

**[1:03:21]** particular is because I said, like, how do you make this not noisy? Because I build these bots

**[1:03:26]** all the time, or these agents, and half the time I turn them off, because they annoy the hell out of

**[1:03:31]** my sales team. And, and he has this like, he talked about like a listener agent, and then like a

**[1:03:39]** scrutinizing agent, and then before it goes even to him, they talk to each other. And so you have a

**[1:03:44]** guy, you have an agent that scrutinizes the listening agents, the listening agent kind of pulls up,

**[1:03:49]** here's everything that happened this year, it's everything that we should have posted. And then

**[1:03:54]** the scrutinizer basically just like, calls bullshit on half the stuff before it actually go. I'm like,

**[1:03:58]** that's a brilliant thing to do. He had a better way of saying it like, than scrutinizer or bullshit

**[1:04:03]** artists. But I like that description. Well, that's what I titled my agents. I called them, you know,

**[1:04:10]** dummy and smart, I don't know. But, but you end up kind of having these workflows, you say, I can

**[1:04:16]** build that same logic in all of my workflows. And my man, so I think that internally, not everyone's

**[1:04:25]** going to do this, right? So but internally, by creating an avenue of folks that do that have a

**[1:04:30]** curious mind and have that builder mentality, and have that in and provide like an avenue for people

**[1:04:38]** to publish what they've done. So people can can not only just reuse it for what they need to do,

**[1:04:43]** but repurpose it and and build it and make it their own. And further it in another function is super

**[1:04:49]** cool. So I think that there's so many different cases where you can create more work for yourself

**[1:04:56]** and more insights. And are you actually doing anything with that stuff? Like, so there's a lot

**[1:05:00]** of busy work you're doing, but AI is supposed to make make you more efficient. So is it making you

**[1:05:05]** more efficient? I think questioning that aspect of it is pretty, pretty key. But ultimately, like,

**[1:05:13]** it's a way for me to be more effective than ever before by just making sure that I'm consistent

**[1:05:20]** with my management style and, you know, and, you know, you're making canonical docs and what you

**[1:05:25]** want to stand for and making sure you check yourself and you're in on decisions you make,

**[1:05:30]** make sure it's fair and consistent with whatever you did. And if I'm deviating, then I need to call

**[1:05:35]** it out. So there's like coaching mechanisms that you can use internally to make you a better leader.

**[1:05:41]** So I don't know, I think that my I can go on and on about all the different ways of deploying it.

**[1:05:47]** But I'm in, I'm in Claude, more, more hours than I care to admit, in terms of how we and I'm

**[1:05:55]** hammering things through. And for me, I've this is the funnest I've had at building stuff, because

**[1:06:00]** I don't have to know, I don't have to do things that I have no idea how to do like, like, back to

**[1:06:05]** the building mentality, I still need my systems thinker, though I'm not trying to replace that

**[1:06:09]** person by any means, because that brain is much different than my brain still, regardless of what

**[1:06:14]** AI in between human in the loop is centered. So we kind of balance each other out on things that

**[1:06:21]** things that can work. And it's cool. It's cool stuff. Oh, my gosh. Well, you're talking to like,

**[1:06:26]** one of the most AI pill people over here token maxing, I was one of the first people on open

**[1:06:32]** Claude getting a server rack of Mac minis in my house here. And all that money gone to waste.

**[1:06:40]** 100%. It was fun, though. But I think what you there was a point where I had to go,

**[1:06:49]** am I just messing around here? Like, I don't have like 18 sessions open right now. But am I am I

**[1:06:55]** actually doing anything productive? Am I actually moving the needle forward? And I found like, I was

**[1:07:01]** like, I don't really know what this is to like, oh, my gosh, I'm like doing 16 hours a day. I can't

**[1:07:05]** even like get out of the terminal here. And now I'm like, Okay, we're sober about it. There's like

**[1:07:09]** 10 things I have to do every day. And Claude can make sure I do them really, really well. There's

**[1:07:14]** some really important things that we have to do for our customers. There's some real important

**[1:07:18]** processes that we have to run. But it's like five things. And now we can just take a look at unstructured

**[1:07:23]** data really well, that's really difficult or boring to manipulate before. Now we can just make

**[1:07:27]** sure we're not missing anything. And I think when you get into that mode where you're like, okay,

**[1:07:32]** yeah, I have some like, five to 10 supercharged processes that are consistent, I'm iterating on,

**[1:07:39]** but all the core jobs are still the same. So like doing a podcast, before AI, I still had to prep

**[1:07:46]** with the guest, make a storyboard, meet with the guest, send follow up, get everything written on

**[1:07:52]** social media, turn it into external content and then post. So the job isn't different. Now I can

**[1:07:58]** just do some of it a little bit faster and a little bit higher quality. Yeah, exactly. But I am, I

**[1:08:04]** think it, you know, it's funny, it's things you said is whittling it down to actual decisions you can make

**[1:08:09]** is the key thing. And I've known this for quite some time, even going back when I was in college,

## 01:08:15 — The TGI Fridays menu and why less is more

**[1:08:15]** I worked at TGA Fridays. And so TGA Fridays before, right after I'm in the server. Oh,

**[1:08:24]** you're in there. You're in there. Yeah, there you go. Hard knocks. But they had a huge initiative and

**[1:08:30]** it sticks with me to this day. I haven't been to a TGA Fridays in a long time, but I'm assuming their

**[1:08:36]** menu is like this, but their menu used to be a huge book. And then you had the flair and all

**[1:08:42]** that kind of stuff. It was a lot. So they just went through a whole rebrand when I joined,

**[1:08:46]** they took their menu down from, you know, I don't know, I think it was like the cheesecake menu,

**[1:08:50]** which is like 60 pages of stuff. And they turned it into two sides, one's drinks and one's food.

**[1:08:55]** And the food was, you know, appetizers, entrees, desserts, whatever it might be. And they had like

**[1:09:00]** five things of each. And what that kind of signals and they had tons and tons of research is like,

**[1:09:05]** if you have so many options, you're stressing the person out. And then they end up saying like two

**[1:09:11]** things. They end up kind of like, oh, they flipped through the menu and it's just this one. Or they

**[1:09:14]** just asked the server, what should I get? Because they don't, as much as we want more information,

**[1:09:20]** we don't actually want more information. We just want to make the right decision. And so when you

**[1:09:25]** think about that, tying it back to go to market and how you help people through the buying process.

**[1:09:31]** The idea isn't like, Anthony, we had a great conversation about our technology,

**[1:09:34]** cool, I'll send you some materials and I send you 12 different things to look at.

**[1:09:40]** I'm not going to, you're not going to look at them. But if I give you one thing to look at,

**[1:09:45]** you're going to look at it. And if I demo 20 different features,

**[1:09:49]** none of them are going to resonate. But if I send three different features that I think are impacting

**[1:09:53]** to you, then I actually am catering that. So how can you take this human psychology and going back

**[1:09:59]** to recruiting, you have to know human psychology to be a good recruiter. If you don't, you're going

**[1:10:03]** to be a sucky recruiter. And so human psychology is how people make decisions in general. And so

**[1:10:10]** by doing that, you need to make sure you really fall in love with human behavior,

**[1:10:16]** human decision making, and ensure to cater that experience to them by not more as more, right?

**[1:10:24]** Less is actually more and more impactful, and you'll become more memorable because of that.

**[1:10:30]** Do you know what my favorite dining experience is?

**[1:10:33]** Don't tell me Cheesecake Factory.

**[1:10:36]** Omakase.

**[1:10:37]** Oh, there you go. Yeah.

**[1:10:39]** I just want to be told what we are having for dinner. You know the products better than I do.

**[1:10:44]** Just have the chef serve up whatever is best here. I love walking in and not needing to make

**[1:10:50]** a decision. I'm like decision fatigue throughout the whole week. I can't even choose one more

**[1:10:55]** thing. So if you can just lay out all your best stuff for me and I can enjoy it, that's my favorite

**[1:11:00]** way to go to dinner. Oh, I understand. Yeah, it's totally great, especially if these like just,

**[1:11:05]** I'm trying to have a great experience. And they're like, how hungry are you? I'm like,

**[1:11:09]** perfect question. Yes, it's always high. So just get it going. As hungry as you've ever seen.

**[1:11:18]** No, but I think tying it back to AI though, it's like, oh my goodness,

**[1:11:23]** you can just spin yourself in circles for hours, days, weeks. And it feels productive. It feels

**[1:11:30]** like you're doing a lot like the TJ Friday's menu, the Cheesecake Factory. Those menus stress me out,

**[1:11:34]** by the way, too. It feels like it's more valuable because you have more things on it,

**[1:11:39]** but it, but it's not. It's what's valuable is being intentional, the curation of everything.

**[1:11:46]** It's so important. And I think after probably everyone needs to go through their like discovery

**[1:11:52]** phase, like just dive deep, just go get lost in cloud for a little bit. But when you come out of

**[1:11:56]** it and the dust settles, then it's like, okay, I still have the same job that I have to do.

**[1:12:03]** And a lot of it's not replacing any of the work that I have to do, by the way, it just kind of

**[1:12:06]** like created more work for me. And now just be intentional about how you use it and then

**[1:12:11]** get the leverage out of it. Yeah, exactly. That's that's really it. But yeah, dive,

**[1:12:15]** dive as deep as you can, but not so deep that you forget what the job you're supposed to be doing.

**[1:12:24]** It feels like a lot of people are in like the third level of inception and they don't even

**[1:12:28]** remember what they're doing anymore. Yeah, they forget the world that they're in. Yeah,

**[1:12:32]** it's, it's crazy. But you know what, I think that what it's all it's just supporting that we're

**[1:12:39]** going to find humans are find more things to do and then how to change jobs for themselves and

**[1:12:45]** whatnot in the process. So I mean, I wouldn't be like the social media manager that existed is

**[1:12:51]** no longer a job, right. And so you can be fearful about that. Well, now it's replacing social media

**[1:12:58]** jobs. But then you think about, well, how long is the job social media manager been existence?

**[1:13:03]** Not very long. So that in itself is a new concoction of what we can do. And there'll be new

**[1:13:09]** jobs that we come across and those wonderful get replaced as well. And so onwards we go.

**[1:13:16]** Yeah. And at the core of it, it was probably still like every business needs to build product

**[1:13:22]** or build a service, deliver it, internal operations, sales, marketing. Yeah. Like

**[1:13:30]** doesn't matter. Whatever, whatever was dressed up on the top, like social media manager, like,

**[1:13:35]** okay, you're still the marketer, probably project manager, probably like those type of roles. And

**[1:13:40]** there's just gonna be other things. Now you're managing AEO or something. And yeah, like if you

**[1:13:45]** had that experience, it's still gonna be transferable to other things. Yeah. Just dive in. Don't be

**[1:13:49]** fearful, right? Just dive in and figure it out. Otherwise you might be the one being replaced

**[1:13:55]** and you're going to have to do it without a job. So, so just dive in while you're while you can.

## 01:14:00 — Wrap

**[1:14:00]** 100%. Well, Tim, this has been awesome. Thank you for everything you shared. I really,

**[1:14:08]** really appreciate the insights on all things enterprise because I think it's a very difficult

**[1:14:13]** game to play. I haven't met anyone yet who's closed a $30 million deal. That's like entire

**[1:14:19]** company's worth of revenue, which is incredible. And I'm happy that we got to go through that story.

**[1:14:24]** And I really liked the perspective on how to leverage RevOps in that environment too,

**[1:14:28]** because it just has such a brand of being high leverage in that high velocity environment.

**[1:14:34]** But arguably you might even get more out of a RevOps team in that enterprise environment.

**[1:14:39]** And I think knowing how to deploy that and then all things AI, I think it obviously here to stay.

**[1:14:46]** So get plugged in with it. Start using it. Don't be afraid. Probably going to get lost in the

**[1:14:54]** journey, but just come back up and get your feet on the ground and keep trudging forward with

**[1:14:57]** whatever the work you were doing. So anyway, appreciate having you on the podcast today.

**[1:15:03]** Before I let you go, just best way to get in contact with you and the current company you're

**[1:15:08]** working at now. LinkedIn is probably the best way to reach out. So otherwise that's tim.yandel@imibit.com

**[1:15:18]** is my email. So curious to hear anything. Anyone who wants to reach out with more would be great.

**[1:15:25]** Well, thank you so much, Tim. Appreciate it again and can't wait to see what you do next.

**[1:15:31]** Thanks, Anthony.