---
title: "Confidence Is a Metric: The Enablement Survey That Ties Training to Revenue"
episode: 149
podcast: "The LeanScale Podcast"
publisher: "LeanScale"
guest: "Chad Trabucco"
guest_title: "Director of Enablement Business Partner Strategy and Activation, Boomi"
date_published: 2026-11-02
date_modified: 2026-11-09
duration: 00:54:19
word_count: 9321
topics: ["sales-enablement", "sales-leadership", "revenue-operations", "ai-in-gtm"]
canonical_url: https://www.leanscale.team/knowledge/podcast/chad-trabucco-boomi-confidence-is-a-metric/
source: "LeanScale Knowledge Hub — https://www.leanscale.team/knowledge"
license: "Free to quote and cite with attribution to The LeanScale Podcast."
---

# Confidence Is a Metric: The Enablement Survey That Ties Training to Revenue — Full Transcript

> Episode 149 of The LeanScale Podcast, with Chad Trabucco.
> Published November 2, 2026 · 00:54:19 · 9321 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/chad-trabucco-boomi-confidence-is-a-metric/

## 00:00 — Cold open + intro

**[0:00]** And when you come at it from that framework,

**[0:02]** and you really are co-building with the managers,

**[0:04]** that's where it's just so fun to enable.

**[0:06]** My guest today is Chad Trebucco, who

**[0:09]** leads enablement, business partner strategy,

**[0:11]** and activation at UMI.

**[0:12]** My starting hypothesis was that a more confident seller

**[0:16]** would be a more effective seller.

**[0:18]** And confidence also gave me an enablement,

**[0:20]** sort of this leading signal, this leading measure,

**[0:24]** that I could influence and control.

**[0:26]** Nothing gave me more influence.

**[0:28]** Nothing helped me advocate for my team

**[0:30]** more than having absolute control, conviction,

**[0:33]** and confidence in the data.

**[0:37]** It was 60% of the calls they were talking about AI.

**[0:41]** But look at this change.

**[0:42]** We've changed this behavior significantly.

**[0:45]** Let's take a look at our ACV.

**[0:47]** And lo and behold, we saw our ACV double over that period.

**[0:50]** I've never done a presentation or walked into a big meeting

**[0:55]** without doing a dry run.

**[0:56]** I think the ones who will succeed are the ones who

**[0:58]** are leaning into that practice.

**[1:00]** And we're already seeing it here.

## 01:09 — The confidence survey: a leading metric enablement can control

**[1:09]** Chad, you've been running a quarterly survey that

**[1:11]** asks reps how confident they feel competitively on product,

**[1:16]** on moving up market.

**[1:17]** Take me back to the first time you ran that survey.

**[1:21]** And what did the answers tell you

**[1:23]** that you didn't already know?

**[1:26]** Yeah, it's a great question.

**[1:28]** So at Glint, this is where we started to run this.

**[1:31]** My starting hypothesis was that a more confident seller would

**[1:35]** be a more effective seller.

**[1:36]** And confidence also gave me an enablement,

**[1:39]** sort of this leading signal, this leading measure,

**[1:43]** that I could influence and control,

**[1:45]** and then connect it to the quarter's revenue results.

**[1:49]** So asking about it regularly over time,

**[1:52]** through this mechanism that I called the voice of sales,

**[1:57]** really gave me a direct view into where sellers needed help.

**[2:01]** And the clearest example of a survey changing

**[2:04]** sort of a decision that came later, sort of an aha for me,

**[2:08]** was when I was at Guru.

**[2:10]** Initially, leadership was prepared to bring in

**[2:13]** a new sales methodology.

**[2:15]** And that was in the discussions before I even started there.

**[2:19]** And when I landed there, I ran this survey,

**[2:23]** brought that idea over to Guru, ran this survey

**[2:25]** within my first couple of weeks.

**[2:28]** And it showed a really immediate gap with the field

**[2:30]** in speaking to one of the core personas, this HR persona,

**[2:35]** which was really core to going larger in accounts

**[2:38]** and selling the full stack across the full company.

**[2:43]** And so that was a critical point for the field.

**[2:45]** And it gave me this lens to come back to leadership and say,

**[2:51]** hey, sales methodology is super important.

**[2:53]** But it won't be as effective if we don't do this persona work

**[2:59]** first.

**[3:01]** And so we did that persona training first.

**[3:03]** I scored the reps on how they played both the seller,

**[3:07]** sort of did this role play.

**[3:09]** But also, I scored them on how they played the buyer

**[3:11]** so that they really engendered sort of the motivations

**[3:14]** of the buyer and started to think like that persona.

**[3:18]** So this really changed our priorities in sort of the cadence

**[3:21]** that we were rolling out.

**[3:22]** And it built trust with the sellers

**[3:25]** so they could see that I was in there--

**[3:28]** I was looking after their impact.

**[3:33]** And I can impact that story a little bit more.

**[3:35]** But that's really where I got started

**[3:37]** in this idea of confidence.

**[3:41]** I think it's unbelievably unique.

**[3:43]** I haven't met an enablement leader

**[3:45]** that has been running it that way.

**[3:47]** But it makes a ton of sense.

**[3:50]** It feels like it unlocks a whole realm of information

**[3:53]** that you wouldn't otherwise have access to

**[3:55]** and really gives you the way to lean in.

**[3:58]** How often are you running the survey?

**[4:00]** Do you kind of cohort it?

**[4:02]** Do you have different surveys for different go-to-market teams?

**[4:04]** Operationally, what does it look like and how do you run it?

**[4:08]** Yeah, operationally, I think I haven't

**[4:11]** run it for different groups.

**[4:14]** It was sort of more general.

**[4:16]** And I think that was by design to really capture--

**[4:21]** I could clean it up on the back end

**[4:22]** and see the titles and different things

**[4:24]** and sort of condense it there.

**[4:26]** When I was running it, the teams were smaller.

**[4:28]** So I really didn't need to specify it.

**[4:31]** But the mechanism was looking back

**[4:34]** at the last quarter of things we rolled out,

**[4:35]** measuring the confidence on the things that we did,

**[4:38]** and then seeing if there's a delta going forward.

**[4:40]** And I think data is so important when you have the trend.

**[4:43]** And so running this quarter in, quarter out,

**[4:45]** beginning of the quarter, minds are fresh,

**[4:48]** sort of take a chance to look back,

**[4:50]** I think was a really critical way to show progress over time.

**[4:55]** And I think that helped me understand,

**[4:58]** are we moving the needle in these certain areas?

**[5:01]** What do I need to surface to leadership?

**[5:03]** We can get a little bit more into the win-loss program

**[5:07]** that we ran.

**[5:08]** But coupling that with this voice of sales

**[5:10]** really gave us sort of the business view, the company

**[5:13]** view, that win-loss level.

**[5:15]** We married that with sort of the voice of the field.

**[5:17]** And that can help us triangulate a lot in terms of the way

**[5:21]** that we bring enablement programs to market

**[5:23]** and really focus on sort of a data-driven approach.

## 05:28 — Surveying managers too, and what to do when the scores disagree

**[5:28]** Are you measuring also at the management level of the team?

**[5:32]** Or is this more of like a field-level survey

**[5:34]** that you're running?

**[5:36]** Yeah, I would also run a confidence survey

**[5:38]** with the managers.

**[5:39]** And that wasn't like, are you confident being a manager?

**[5:42]** I think it was, are you confident in your team's ability

**[5:46]** to do these different things?

**[5:48]** And that gave me just like another way

**[5:50]** to triangulate how the team is approaching things.

**[5:54]** And when those things disagreed,

**[5:56]** I think it was really interesting to probe into that

**[5:59]** and see, hey, the rep's confidence is really high.

**[6:02]** Some ways you want a really confident rep.

**[6:05]** The manager's confidence in that rep or that team

**[6:08]** was a bit lower.

**[6:09]** And so that gave me an opportunity

**[6:11]** to kind of do what we're telling all of our sellers to do.

**[6:13]** And that's do a little more discovery,

**[6:15]** probe a little bit deeper, understand the pain,

**[6:18]** and then tie that to the value

**[6:21]** that we can drive on the backend

**[6:22]** if we really understand what the manager is trying to get at.

**[6:25]** Why do they see that as a lower score

**[6:28]** or lower confidence in that team?

**[6:31]** And then you build a program around that with them.

**[6:34]** And that co-build is just so critical for enablement.

**[6:37]** It really drives things forward.

**[6:38]** And then you can show on the backend,

**[6:40]** hey, we proved this point.

**[6:41]** Here was your pain.

**[6:42]** Here's how we solved it.

**[6:43]** What can we do next?

**[6:47]** - Are there any common insights?

**[6:51]** I'm sure this will depend on the company

**[6:53]** and the market they're competing in

**[6:55]** and all different types of things.

**[6:57]** But since you've been running this for a while,

**[7:01]** are there a few common things that tend to come up

**[7:04]** where people don't feel as confident

**[7:06]** as maybe people would assume that they'd be confident in?

**[7:10]** Is it product knowledge?

**[7:12]** Is it competitive information?

**[7:14]** Is it market knowledge?

**[7:16]** Anything that tends to come up quite often.

**[7:18]** - I really haven't found a common trend

**[7:20]** across companies from the survey data.

**[7:23]** I think it depends on the situation.

**[7:26]** Rep's heads are down.

**[7:27]** They've got a big quarter generally coming up.

**[7:30]** I do find surprises though.

**[7:32]** And I think there are some surprises

**[7:34]** and I think this is more of a gut feel

**[7:36]** and sort of a thematic theme that I've seen

**[7:41]** across companies and that's the fundamentals.

**[7:43]** I think reps realize some of the fundamentals get lost

**[7:48]** in all of the things that we're doing,

**[7:51]** all of the things that we're pushing.

**[7:53]** I think enablement can get lost in,

**[7:55]** well, we trained on that last quarter

**[7:57]** so it should be sort of like standard

**[7:59]** for folks this quarter.

**[8:01]** And that's not always the case.

**[8:02]** I think folks need time to catch up.

**[8:04]** I think folks need time to absorb.

**[8:08]** I have the sales leader that always says it's seven times seven.

**[8:11]** You got to hit them seven ways

**[8:12]** with seven different messages

**[8:15]** for things to really sink in.

**[8:16]** And I think that realization is really true.

**[8:20]** And sometimes that extends to the fundamentals

**[8:23]** of like, are you doing an upfront contract?

**[8:25]** Are you creating five minutes to close the call

**[8:28]** and make sure that you've got your next steps documented

**[8:31]** with the prospect and coming back to those things

**[8:34]** and reminding the team that those fundamentals are important

**[8:38]** and they're reminding them why

**[8:40]** in all of the things that they're doing.

**[8:42]** So it's not necessarily a realization from the data.

**[8:48]** It's more of a gut feel

**[8:49]** and a trend that I've seen across companies.

**[8:51]** - Yeah, and I'm assuming,

**[8:53]** I think some people may think,

**[8:55]** okay, you're all at the enablement program,

**[8:57]** you did the training and now you're all done, great job.

**[9:00]** Well, it's just like anything else,

**[9:02]** maybe like diet and exercise.

**[9:03]** People need to be reminded

**[9:06]** more than they need to be told or taught.

**[9:09]** And also if you're working in a scaling company,

**[9:11]** you're continually adding in new reps

**[9:13]** and cycling and cycling people out, cycling people in.

**[9:16]** And some of the things,

**[9:18]** even though it may sound like you're a broken record

**[9:20]** at a certain point,

**[9:21]** but like you need to keep reminding them

**[9:23]** of those fundamentals.

**[9:24]** So that way when they're in the field,

**[9:27]** it's not that they've just been taught about it,

**[9:29]** but it becomes the muscle memory they use

**[9:31]** in the sales process.

**[9:33]** Are there certain cadences you like to follow

**[9:37]** for training and reminding?

**[9:40]** How do you, 'cause this is a very, very tough job

**[9:43]** to keep the ball moving and all this stuff.

**[9:46]** Is there any schedule that you like to follow

**[9:49]** to keep all this top of mind with the reps?

**[9:54]** - Yeah, I think one thing I've learned lately,

**[9:57]** and I think we can kind of probe into this a bit more

**[9:59]** when it comes to the managers.

**[10:01]** But I think it's really important

**[10:03]** to think about the hierarchy

**[10:05]** in the way that you communicate.

**[10:07]** And I think generally we're all moving so quickly.

**[10:12]** We're building agents, we're rolling things out,

**[10:15]** we're pushing things out,

**[10:16]** enablements sort of on the bleeding edge

**[10:18]** of everything new and moving forward.

**[10:21]** Sometimes we forget that hierarchy of communication

**[10:24]** is really important.

**[10:25]** So I have a standing meeting with all my leaders

**[10:29]** across all of those different roles.

**[10:31]** So the heads of, the VPs of,

**[10:35]** the global heads of every two weeks

**[10:38]** so that I can keep them abreast

**[10:39]** of the things that are happening for their org.

**[10:42]** And then when a new thing is happening,

**[10:44]** we're sort of like getting in front of it,

**[10:46]** giving them comms to share with their managers,

**[10:48]** and then we're proactively sharing

**[10:50]** with their managers as well before those things happen

**[10:53]** so that there's no surprises.

**[10:55]** I think one of the things

**[10:55]** that enablement does have control over

**[10:58]** is no surprises to the manager group.

**[11:01]** And so I'm really pushing that with my team

**[11:03]** and they're working closely with their managers

**[11:06]** because managers have one of the tougher jobs

**[11:08]** in addition to reps.

**[11:10]** And when you create that mantra of no surprises,

**[11:14]** they really do feel like they're in it with you.

**[11:16]** And then you communicate to the field

**[11:19]** that these things are happening,

**[11:20]** this training is happening.

**[11:22]** I also think it's really important to have rituals.

**[11:25]** And when I say rituals,

**[11:27]** I mean a constant team meeting

**[11:30]** that happens every quarter or every month

**[11:34]** within sort of the larger business.

**[11:37]** So we have an enterprise town hall that happens every month.

**[11:41]** That's an important ritual for enablement

**[11:43]** to know about and lean into.

**[11:45]** Then I think there's important rituals

**[11:46]** from a learning perspective.

**[11:47]** And we have this really cool model here at Boomi

**[11:50]** where we do something quarterly.

**[11:51]** There's quarterly training that includes

**[11:54]** the most important things, right?

**[11:55]** Competitive training, product training, pricing training.

**[11:59]** And that is a ritual that reps know

**[12:01]** is gonna happen every quarter, quarter in, quarter out.

**[12:04]** And then there's a sort of a cadence

**[12:06]** and a calendar below that

**[12:09]** that enablement can plug into.

**[12:11]** We spotlight what's great

**[12:13]** and we have these vehicles or these rituals

**[12:16]** at sort of every segment, every region

**[12:20]** that we can plug into that the reps know,

**[12:22]** the managers know what happens during that ritual,

**[12:26]** what to expect.

**[12:27]** And again, that comes back

**[12:28]** to that sort of no surprises mantra.

**[12:31]** I think that just keeps them focused

**[12:33]** on what they need to do

**[12:34]** when these things pop up on the calendar.

**[12:36]** They know why they're being asked to show up.

**[12:38]** They know what they're gonna get.

**[12:39]** They know what they're gonna take away.

**[12:41]** And then there's rituals beyond that, right?

**[12:43]** There's communication rituals in Slack or email.

**[12:46]** And if you keep those consistent,

**[12:48]** you keep a newsletter going of

**[12:50]** these are the things we taught you.

**[12:51]** These are the resources you have.

**[12:54]** Those rituals really become part of the behavior.

**[12:57]** And I think, you know, it does a couple of things.

**[12:59]** For enablement gives you a lot of places

**[13:01]** to sort of hit that seven times, seven ways.

**[13:05]** But it also for the reps, you know,

**[13:08]** takes the mind's share out of sort of what's happening.

**[13:11]** What is enablement doing?

**[13:12]** What is enablement asking me?

**[13:14]** They sort of know when and where that will happen.

**[13:17]** So they can keep more mindshare on what they do day in,

**[13:20]** day out.

**[13:21]** And that's working with the customers and prospects.

**[13:24]** - I think those sacred rituals are super important

**[13:28]** and giving people, you know, an expectation

**[13:31]** of when they'll be given information,

**[13:33]** which sounds like a really important work stream.

**[13:36]** Are there ad hoc work streams

**[13:38]** that tend to come up in enablement too?

**[13:40]** Maybe more of like a signal based,

**[13:42]** hey, this thing happens.

**[13:43]** So now enablement has to come in and intervene or help.

**[13:47]** Are there any things like that that come up

**[13:49]** and what's giving you the ability to see opportunities

**[13:52]** to lean in and help with the team?

**[13:54]** - Yeah, I mean, it comes back to the data.

**[13:56]** And I think those ad hoc moments are really critical, right?

**[13:59]** A leader will sort of say in those bi-weeklys that I have,

**[14:02]** hey, this is something I'm seeing.

**[14:04]** Enablement's bringing something forward.

**[14:06]** Hey, we were analyzing GONG.

**[14:07]** We were looking at Snowflake.

**[14:09]** We triangulated this problem.

**[14:11]** You know, is this a problem you're seeing?

**[14:13]** How do we address it?

**[14:14]** And I think that's sort of where the fun

**[14:17]** and the art of enablement can come through of like,

**[14:21]** okay, we have all these things on the plate,

**[14:23]** but we need to do this other thing.

**[14:24]** And I think that's where those rituals

**[14:26]** actually become really important.

**[14:28]** 'Cause you can modulate those rituals.

**[14:29]** It doesn't always have to be,

**[14:31]** this product training is always on X.

**[14:33]** Or this window of time is always on product

**[14:36]** or always on competitive.

**[14:38]** And you can re-leverage those windows.

**[14:41]** And I think leaders actually really appreciate

**[14:44]** when you can re-leverage those windows for those ad hoc things

**[14:48]** and plug in sort of just-in-time learning.

**[14:52]** And I always try to tell my team like,

**[14:54]** let's umbrella this, you know, around a common theme.

**[14:59]** So if we're doing product training

**[15:02]** and there's sort of like this ritual of,

**[15:03]** hey, we're gonna level you up around this product training,

**[15:07]** but we get one of those ad hoc requests of like,

**[15:10]** hey, this is a thing we need to lean into.

**[15:13]** You can sort of say, hey, well, this is part of us,

**[15:17]** you know, increasing ACV this quarter

**[15:19]** if you focus on this product training.

**[15:21]** And so you just sort of umbrella these things

**[15:23]** for the reps, the managers as to the why

**[15:27]** and how it fits into the larger context.

**[15:29]** So those ad hoc programs can feel like

**[15:32]** they were part of something larger

**[15:34]** and there's a what's in it for them.

**[15:37]** I think that's always a critical way to connect the dots.

**[15:41]** And then I think the other piece around this ad hoc stuff

**[15:45]** is how are you measuring it?

**[15:47]** How are you sort of showing, you know,

**[15:50]** we're doing this training.

**[15:51]** Here's sort of the way that we're gonna be watching it,

**[15:54]** Gong or other conversational tools.

**[15:57]** And then here's the outcome that we're hoping to drive.

**[15:59]** I talked a little bit about ACV.

**[16:01]** We're hoping to increase ACV by selling more products

**[16:04]** or, you know, more than one product for this initiative

**[16:10]** or this ad hoc request.

**[16:13]** So we're gonna be looking at multi-skew

**[16:15]** and we're gonna see, does that ACV

**[16:16]** or does the percentage of multi-skew deals

**[16:20]** go up over time post-training?

**[16:24]** I think it's really important to measure that

**[16:26]** week over week and then you bring it back to those rituals

**[16:28]** of the syncs with the leaders and the managers.

**[16:31]** So you can show like, hey, we really are in this with you.

**[16:34]** We're looking at it in the same ways

**[16:35]** that you're looking at it.

**[16:37]** And that North Star number that we're all trying to change,

**[16:41]** because of that request,

**[16:42]** something that we're all looking at and working towards.

## 16:47 — Why enablement has to invest in managers

**[16:47]** - One thing that I'm hearing that is really unique.

**[16:51]** I haven't heard a lot of enablement leaders

**[16:54]** spend the amount of focus that you have spent

**[16:57]** on the managers and management layer of the team.

**[17:02]** I think there's a lot of attention that goes on people

**[17:05]** in the field and the reps and individual contributors,

**[17:08]** giving them trained up, monitoring how they're doing.

**[17:10]** But I'm hearing a lot of attention to that management layer.

**[17:14]** Do you have a philosophy around where and when

**[17:17]** and how to invest your time?

**[17:20]** - Yeah, I think what I've learned

**[17:22]** and I was fortunate early in my career,

**[17:25]** particularly at Glint, we had some very seasoned managers

**[17:29]** that didn't need a whole lot of enablement per se.

**[17:33]** They needed visibility.

**[17:34]** And I think that's sort of where the trends were going.

**[17:37]** I think that's why that win-loss program

**[17:38]** was really critical 'cause it gave them

**[17:41]** sort of that company lens and then they were able to see

**[17:44]** how their team was feeling from that voice of sales

**[17:47]** and sort of understand where their team needed support.

**[17:51]** And then they were seasoned enough to be able to lean in

**[17:54]** in those different ways and work with me to do that.

**[17:57]** But I think as I'm realizing, as we move

**[18:00]** sort of into this AI world and teams are scaling

**[18:04]** really, really quickly, I think it becomes

**[18:08]** even more important with these newer managers

**[18:11]** to really enable them on the behaviors that we wanna see.

**[18:16]** And it's creating sort of this foundational layer

**[18:19]** of expectation of how you run your business.

**[18:23]** I think when you have a cohort of newer managers

**[18:28]** that maybe were top AEs that have moved into that role

**[18:32]** or you have a much bigger org, frankly,

**[18:35]** I think that's to your point,

**[18:37]** when do you start to look at managers

**[18:39]** as an area to enable to?

**[18:44]** I think it's that because I have this CRO talk about

**[18:47]** just like a very simple framework.

**[18:51]** We have a written and we have a taught sales process.

**[18:56]** And when the team knows that,

**[18:58]** they'll be much more predictable

**[19:00]** in terms of the outcome that they're driving.

**[19:03]** And I keep coming back to that.

**[19:04]** It's something I think about a lot.

**[19:06]** And when you have a big team,

**[19:08]** you have a lot of new managers,

**[19:10]** it can be very easy to get away from sort of that written

**[19:13]** and taught sales process.

**[19:15]** And so I think that's something to look out for a signal

**[19:19]** for any enablement person or even ops person out there

**[19:23]** is when you see that happening,

**[19:27]** it's really important to come back to the basics

**[19:29]** because if folks are interpreting different things

**[19:33]** about a sales process, you're gonna get different results.

**[19:36]** And I think that predictability is so important,

**[19:39]** particularly in the speed that we're all moving.

**[19:43]** So that would be sort of the way

**[19:45]** that I think about enabling the managers.

**[19:48]** And we can talk a bit more about what does that look like?

**[19:50]** How are we doing that?

**[19:51]** Why is that an aha for me?

**[19:54]** - Yeah, well, and I think a lot of it too

**[19:56]** comes down to reinforcement.

**[19:58]** It's one thing to teach the process,

**[20:00]** put it on paper, like you mentioned,

**[20:02]** and teaching is more than a single session.

**[20:06]** I have young kids, I could tell them to do something,

**[20:08]** but usually it requires a little bit of reinforcement,

**[20:11]** not saying sales reps are children,

**[20:12]** but there's some commonalities between the two.

**[20:17]** And I think if you do a really, really good job

**[20:19]** of enabling the managers,

**[20:22]** then they can help with the day-to-day reinforcement

**[20:24]** when they're coaching their reps,

**[20:26]** when they're digging deep into a deal,

**[20:28]** making sure that, hey, yeah, we're following the process

**[20:30]** that we all agreed on, gives us the best chance of winning,

**[20:35]** then that investment can compound throughout the whole team,

**[20:38]** especially as you're scaling.

**[20:40]** - Your point is so well taken that, hey,

**[20:42]** we've agreed upon this because this is the best way

**[20:46]** for us to accelerate deals, close deals.

**[20:50]** And when you come at it from that framework

**[20:52]** and you really are co-building with the managers,

**[20:54]** that's where it's just so fun to enable

**[20:57]** because it becomes less enablement, less enforcement,

**[21:01]** and really it becomes empowerment.

**[21:02]** And I think that's a framing

**[21:04]** that I really like to anchor into is like,

**[21:07]** how can we empower these managers?

**[21:09]** How can we empower these reps to carry

**[21:12]** what great looks like forward?

**[21:14]** I mean, I think that's the game that we're in.

## 21:17 — Green lights, coach camps and always-on coaching

**[21:17]** - Specifically, what cadence do you set up

**[21:19]** with the managers and how do you like to enable them?

**[21:22]** Are you helping them come up with the methodologies?

**[21:25]** Are you getting things on paper for them?

**[21:27]** Are you producing materials for their team?

**[21:29]** Are you surfacing the insights through transcripts

**[21:33]** or the confidence survey?

**[21:36]** What are all the ways where like tactically,

**[21:39]** okay, this is how I prepare a manager

**[21:41]** to help manage their teams

**[21:43]** from an enablement perspective?

**[21:45]** - Yeah, it's all of those, right?

**[21:48]** It's the written process, right?

**[21:51]** If you can't measure it, you can't document it,

**[21:54]** and it's not gonna be as important,

**[21:55]** and it's not gonna be consistent.

**[21:56]** And so we've done a lot of work

**[21:59]** to take the signals that we see in our data

**[22:02]** that move deals from one stage to the next, the quickest.

**[22:06]** What are those, we call them the green lights.

**[22:09]** What are those green lights that happen at every stage?

**[22:12]** What are the things that have to happen?

**[22:13]** What are the behaviors, the outcomes, the activity?

**[22:18]** 'Cause it isn't always the sort of,

**[22:20]** oh, well, this stage takes 20 days,

**[22:22]** this stage takes 40 days, let's measure that.

**[22:25]** It's really the behaviors that underlie that,

**[22:27]** the things that are happening that drive that

**[22:29]** that are so important.

**[22:31]** So we've sort of codified those green lights

**[22:34]** into this framework

**[22:35]** that we're then training all of the managers on,

**[22:38]** it's documented, and it's built into their rhythm.

**[22:40]** It's built into their calendar, their cadence

**[22:43]** of what their week, what their day looks like.

**[22:47]** And I think we've had a lot of success sort of spelling out,

**[22:52]** these are the things that you should be doing

**[22:53]** and looking at in a week in, week out,

**[22:57]** in almost a calendar format.

**[22:58]** So we're sort of building in that framework

**[23:01]** of this is what our process looks like,

**[23:03]** and this is what your process should look like as a manager.

**[23:06]** And then we're creating these sort of rituals.

**[23:09]** I have a person that I work closely with

**[23:12]** who's running this, used to be on my team,

**[23:14]** has been elevated into this role

**[23:16]** to focus exclusively on managers.

**[23:18]** And he calls these things coach camps.

**[23:21]** And it's a really interesting ritual

**[23:23]** to bring the managers together

**[23:25]** to talk through that ritual, that framework.

**[23:30]** What is it looking like in practice?

**[23:31]** And there's some surveys that go on prior,

**[23:34]** there's some analysis that go on prior

**[23:35]** so that the topics are really relevant

**[23:38]** and they have an opportunity to talk through as a team.

**[23:41]** And I think that peer-to-peer learning can be so critical

**[23:45]** both at the rep level, but also at the manager level.

**[23:48]** And this gives them sort of that forum

**[23:52]** to learn from one another, some of the newer managers,

**[23:56]** to learn from those who are more seasoned.

**[23:58]** Some of the newer ones might be more apt

**[23:59]** to understand the latest tooling.

**[24:01]** And so they're teaching those who've been there longer

**[24:05]** and have more of a standard way that they go about things.

**[24:09]** And so it becomes this wonderful cross-pollination.

**[24:13]** So there's sort of the documentation,

**[24:16]** there's the peer-to-peer learning

**[24:18]** and sort of those focused time.

**[24:20]** And then sort of the third thing that I think

**[24:22]** is really critical, especially now

**[24:24]** with all of the tooling that we have from an AI perspective

**[24:28]** is we're building agents, we're building alerts

**[24:32]** into that daily flow, into Slack,

**[24:36]** into specific areas within Salesforce

**[24:40]** that are alerting the managers

**[24:41]** on those opportunities to coach.

**[24:43]** And I think we haven't talked too much about coaching,

**[24:45]** but that's what managers can be good at.

**[24:49]** Most of them have sat and seen.

**[24:51]** Most of them have seen a lot more opportunities

**[24:55]** than their reports.

**[24:57]** And I think creating some signal in all of the noise

**[25:00]** of these are the two things you can do.

**[25:03]** This is the one priority that you want to coach to

**[25:07]** for this particular rep based on these things

**[25:10]** that have happened, based on the framework

**[25:12]** that we've established, based on the process

**[25:15]** that we've established, based on this call or that call,

**[25:19]** and kind of pulling all those things together, right?

**[25:22]** The framework, the peer-to-peer learning

**[25:26]** and sort of like that condensed time

**[25:27]** to sort of learn and explore.

**[25:29]** And then this kind of always on coach,

**[25:32]** that's something we're leaning into a lot more

**[25:34]** sort of exploring now.

**[25:36]** And I think there's a lot of opportunity with AI

**[25:39]** to make that happen in ways

**[25:42]** that we haven't been able to do before.

**[25:46]** - I love that.

**[25:47]** I think the one that sticks out to me the most

**[25:49]** is the coach camps and getting managers, coaching themselves.

**[25:53]** Again, we think a lot about how enablement is for the reps,

**[25:57]** for the people on the front lines.

**[25:59]** And I think the managers get left out of this quite often.

**[26:02]** And by the way, often you're getting managers

**[26:04]** that were just a rep a couple of days ago,

**[26:06]** and now they're put in this position

**[26:07]** to go lead all these teams.

**[26:09]** And it's new for them too.

**[26:11]** There's a new job that needs to be done,

**[26:13]** ways in which you can manage best practices they can follow.

**[26:16]** And then all of the insights

**[26:17]** that you can help give them ideas like,

**[26:18]** hey, did you know you could coach your rep

**[26:21]** over here on this thing that should help them

**[26:23]** and nudging them in the right direction?

**[26:24]** I mean, it's unbelievably helpful.

**[26:28]** One thing I think a lot of enablement teams struggle with,

**[26:34]** and I'd love your insights and feedback on this,

**[26:37]** is how to articulate the value of enablement.

**[26:42]** And oftentimes when you're wanting to add headcount,

**[26:47]** expand the team,

**[26:49]** it's under a lot of scrutiny from the CFO, the CEO.

**[26:54]** I think sometimes the CRO intuitively understands

**[26:56]** where the investment is,

**[26:57]** but how are you articulating that value

**[27:01]** to advocate for more investment and enablement

**[27:04]** as the company grows and scales?

**[27:06]** - Yep.

**[27:07]** I mean, it's the best when a CRO intuitively gets that.

**[27:10]** I think those are the next areas to work.

**[27:12]** - Sometimes they need help backing it up too.

**[27:14]** Like you gotta work then with the business case with the CFO.

**[27:17]** - Totally, totally.

**[27:18]** Yeah, like you said, it's sort of a gut level,

**[27:21]** but when you can speak their language,

**[27:22]** I think that's when it makes it the most fun

**[27:24]** and it just becomes a no-brainer.

**[27:27]** I really, I come back to this idea

**[27:30]** of leading and lagging metrics.

**[27:32]** And every time I've been able to do this,

**[27:34]** every time I've found a way to capture a leading metric

**[27:40]** to the outcomes, the revenue outcomes

**[27:42]** that the business or the CRO, CEO wanna drive,

**[27:46]** I've found success in my career.

**[27:48]** And those leading metrics can be something as simple as,

**[27:52]** are we seeing gone mentions,

**[27:54]** conversational intelligence mentions go up post-training,

**[27:59]** measuring that over time

**[28:01]** and seeing sort of the behavior change

**[28:04]** that enablement caused and then correlating it.

**[28:08]** It's not always causation,

**[28:09]** but correlating it, by the way, we saw this thing change,

**[28:13]** we saw this increase.

## 28:16 — AI mentions from 20% to 60% of calls, and ACV doubled

**[28:16]** When I was a guru, it was right at the cusp

**[28:19]** of chat GPT coming out and there was this explosion

**[28:23]** of like AI this, AI that, what does it mean?

**[28:26]** And we really needed to make our team conversant

**[28:28]** in AI language.

**[28:29]** There was always, there had already been AI built

**[28:33]** into the system, but we needed to make the team

**[28:35]** more conversant in what is AI for guru?

**[28:40]** How are we thinking about it?

**[28:41]** What are we doing?

**[28:42]** And so we ran this training series of trainings

**[28:46]** to kind of like bring them up to speed on,

**[28:49]** what's the latest?

**[28:51]** What is the product level capabilities with regards to AI?

**[28:55]** We want you to be proactively talking about this more.

**[28:59]** So we measured that and we measured it.

**[29:01]** I think it was something like 20% of the calls

**[29:04]** that they were having at the time,

**[29:07]** that was sort of our baseline included AI,

**[29:10]** some measure of AI in there.

**[29:13]** And after this training, we saw it go up

**[29:15]** and we actually saw it go up.

**[29:17]** It's such a steep curve within two to three months

**[29:20]** that it was 60% of the calls they were talking about AI.

**[29:25]** So I was able to sort of come back and say,

**[29:27]** well, look at this change.

**[29:28]** We've changed this behavior significantly.

**[29:30]** Let's take a look at our ACV.

**[29:33]** Let's take a look at how our deals are progressing.

**[29:36]** And lo and behold, we saw our ACV double

**[29:38]** over that period of time.

**[29:40]** So it's conversations like those that make a real difference

**[29:44]** to building that investment,

**[29:46]** to building more headcount, to articulating.

**[29:50]** If we can do this, imagine what we can do over here.

**[29:54]** And I think it comes back to that reporting, right?

**[29:56]** Like those rituals.

**[29:58]** If you're constantly sort of sharing,

**[30:00]** hey, this is incrementally how we've changed things.

**[30:03]** This is how it rolls up to the top line number

**[30:05]** that you're the North star that you're most concerned about.

**[30:08]** If you're constantly doing that,

**[30:10]** it doesn't become this like big ask

**[30:13]** and there's not this like,

**[30:15]** I've got to present this business justification.

**[30:17]** You may have to, it depends on the company,

**[30:19]** but it becomes a lot easier if incrementally over time,

**[30:23]** you've constantly been sharing,

**[30:24]** hey, we've added this many QOs

**[30:27]** based on this training that we've done

**[30:29]** or in correlation with this training that we've done.

**[30:32]** And it's showing up in sort of the bottom line number

**[30:36]** of the deals that we're now closing.

**[30:38]** When you can do that over time,

**[30:41]** it makes those conversations much easier,

**[30:44]** much more streamlined

**[30:45]** and kind of a no-brainer for everybody.

## 30:48 — One point of conversion = $1M

**[30:48]** - I also don't think some people understand the magnitude

**[30:51]** of what increasing conversion rate

**[30:54]** or increasing ACV can do and what it can be.

**[30:58]** I'll give an easy example.

**[31:00]** If you're on a $20 million booking plan

**[31:03]** and let's say you have a 20% conversion rate,

**[31:06]** so you need $100 million to build a pipeline to get there.

**[31:11]** On the same pipeline with the same reps,

**[31:13]** with the same pricing, with the same everything,

**[31:15]** if you don't change a single other thing,

**[31:17]** but you improve conversion rate by 1%,

**[31:20]** you'll add another million dollars of bookings

**[31:22]** into the plan.

**[31:24]** - Yeah.

**[31:25]** - One small minor improvement can pay for enablement

**[31:32]** over and over again.

**[31:34]** And by the way, that's the opportunistic approach to it.

**[31:37]** If you don't make these investments,

**[31:40]** the same math works the other way.

**[31:42]** - Yeah.

**[31:43]** - If you start to experience drift with your new reps

**[31:47]** not performing as well as what the experienced reps are

**[31:50]** and that conversion rate starts to dip down,

**[31:52]** you could be losing millions of dollars as well.

**[31:55]** So I think the teams that can articulate

**[31:58]** the numbers really well,

**[31:59]** I know it's not always fun selling yourself

**[32:01]** and constantly advocating for what you're doing.

**[32:06]** And you don't have to take whole credit for it,

**[32:08]** but you do have to say like,

**[32:11]** I don't know the exact number that's attributed

**[32:13]** to everything I did,

**[32:14]** but I do know we influenced it and it's correlated.

**[32:17]** And there's immense value in keeping the yield

**[32:21]** as high as possible with your team.

**[32:24]** I also think there's an interesting note in there of like,

**[32:29]** you're also taking reps off the field

**[32:32]** or out of the field to do enablement.

**[32:35]** And so I think there's like an implicit justification too

**[32:39]** and enablement has the responsibility to say,

**[32:42]** here's the impact of that time investment

**[32:45]** that I'm requiring from your team, from your managers.

**[32:49]** I think it also goes to that point too.

**[32:51]** And if you're constantly telling the leadership,

**[32:55]** the managers, here's how we're measuring it,

**[32:57]** it is changing, we're going from 20% to 60%.

**[33:02]** Like that investment becomes much easier,

**[33:05]** that time investment becomes much easier.

**[33:07]** The reps understand why.

**[33:09]** I think enablement can be sometimes

**[33:12]** it's so important to provide context.

**[33:14]** I talked about that no surprises idea.

**[33:17]** This helps bring down sort of that,

**[33:20]** why am I doing this thing?

**[33:21]** Why is enablement asking?

**[33:23]** You can build that trust over time

**[33:25]** by constantly measuring it.

**[33:28]** - What's been the biggest challenge

**[33:31]** across your career in enablement

**[33:34]** that if you were to give any advice to somebody else

**[33:38]** going down the same path,

**[33:39]** you could maybe help prepare them for.

**[33:43]** - Yeah, I think it really revolves

**[33:45]** around this measurement idea.

**[33:47]** I don't think there's ever been a place

**[33:48]** and I've been at places that have been very sophisticated

**[33:52]** in terms of the way they measure,

**[33:55]** in terms of the RevOps teams that they have.

**[33:59]** I don't think there's ever been a place

**[34:00]** where enablement has had enough

**[34:04]** cache or speed to be able to measure

**[34:09]** the things that they want to measure

**[34:11]** as quickly as they want to measure them.

**[34:13]** And to keep a real beat on that.

**[34:16]** And so I guess what I've learned is you have to be creative.

**[34:20]** You have to find a way to get dirty with the data.

**[34:24]** Enablement isn't always sort of

**[34:26]** come from a background of data.

**[34:28]** They don't come from a background of

**[34:30]** how do these things work?

**[34:31]** How do these revenue systems come together?

**[34:33]** But you've got to find a way to get creative

**[34:35]** to measure those leading outcomes,

**[34:37]** to measure what matters to enablement.

**[34:40]** Because that's the only way that you'll speak to leadership.

**[34:42]** If you can connect those to the revenue outcomes

**[34:44]** that sort of matter to them, that's the only way.

**[34:48]** And so sometimes it's, hey, this data is directional.

**[34:52]** Here's how I found it.

**[34:53]** Here's how I'm measuring time to first deal.

**[34:56]** May not be the perfect way.

**[34:58]** But I'm gonna measure it over time

**[35:01]** and it will change with the business.

**[35:03]** But it is directional.

**[35:04]** And what we're seeing on the other side,

**[35:06]** this correlation, is that these reps are ramping quicker

**[35:10]** than they were before.

**[35:10]** And I measured the before the same way.

**[35:13]** I've had to do this at every single company

**[35:15]** is just scratch my head, get dirty with the data,

**[35:19]** figure it out.

**[35:20]** And I think that becomes not only

**[35:23]** that's been a challenge in my career,

**[35:25]** to find that at different companies

**[35:27]** and have to do that myself.

**[35:29]** I've also found it to be the strongest accelerant

**[35:34]** to my career at each company.

**[35:36]** When I have that voice and I can stand behind the data

**[35:39]** and say, here's how I measured it.

**[35:40]** I know it inside and out.

**[35:42]** I've worked with RevOps.

**[35:43]** Or I figured this out myself

**[35:45]** and it's correlated with what RevOps is doing.

**[35:47]** And these outcomes are showing up in the correlation.

**[35:51]** It's been such an accelerant to what I do,

**[35:55]** both in my career,

**[35:57]** but also in my advancement within that company.

## 36:00 — The enablement data cockpit

**[36:00]** - Let's get specific, 'cause I agree with you.

**[36:02]** Whenever I have had control over the data,

**[36:06]** which I started LeanScale in 2021

**[36:08]** before that I ran RevOps for three companies,

**[36:11]** nothing gave me more influence,

**[36:13]** nothing helped me advocate for my team more

**[36:16]** than having absolute control,

**[36:18]** conviction and confidence in the data.

**[36:23]** As a head of enablement,

**[36:24]** what are those metrics that matter?

**[36:27]** If you had your ultimate data cockpit,

**[36:30]** what are the standard things every enablement person

**[36:33]** should be measuring and monitoring?

**[36:36]** And then maybe what are some of the unique ones

**[36:38]** that may pop up in different scenarios?

**[36:40]** - I'll throw out a couple that I think are really, really fun.

**[36:43]** I've talked a lot about conversational intelligence.

**[36:46]** I think traditionally it's been like,

**[36:48]** are these things mentioned?

**[36:50]** Are we tracking?

**[36:51]** Are they saying these things that we've taught them?

**[36:55]** I think that's a very easy one to measure.

**[36:58]** - The prerequisite for that, I'm curious.

**[37:00]** So you would want to first codify the things

**[37:05]** you want the reps to be talking about.

**[37:07]** And coming up with,

**[37:09]** hey, these are the things that we want to make sure

**[37:11]** are happening on every single call.

**[37:13]** That way you can measure that, right?

**[37:16]** - Yeah, you can do that.

**[37:16]** You can also do it after the fact.

**[37:19]** And it can be a little more ad hoc to your point.

**[37:21]** Sometimes enablement's moving quickly.

**[37:23]** You get something out the door.

**[37:24]** What's great about sort of a lot

**[37:26]** of these conversational intelligence tools

**[37:28]** is you can look back.

**[37:29]** You can scratch your head and you say,

**[37:31]** these were the things we were training on,

**[37:33]** codifying those.

**[37:35]** And let's look back and see,

**[37:37]** was that happening before, to what degree?

**[37:39]** And what's happening now?

**[37:41]** I think when it comes to sort of like

**[37:43]** sales methodology behaviors,

**[37:44]** absolutely, yes, you're so spot on, Anthony.

**[37:47]** Yes, we need to codify those,

**[37:49]** plug those into these systems and say,

**[37:51]** over time, what's happening?

**[37:53]** With the ways that we're asking reps to go to market.

**[37:56]** So that's certainly one is measuring at that level.

**[38:00]** Where I found some other interesting areas to measure

**[38:04]** is Slack, I think a lot happens in Slack.

**[38:07]** One thing I've measured in my career is like,

**[38:10]** we roll something out, there's confusion.

**[38:13]** I'm measuring like the number of repeat questions.

**[38:17]** And now with AI, you can ask your LLM,

**[38:20]** like how often in this channel

**[38:23]** are we seeing repeat questions show up

**[38:25]** or questions that are similar?

**[38:27]** You run a training and you say,

**[38:29]** now are these repeat questions continuing to happen

**[38:32]** at the same rate that we had before?

**[38:35]** I think that's a really interesting barometer.

**[38:37]** It's a very interesting barometer

**[38:39]** for the subject matter experts

**[38:40]** who are answering in that channel.

**[38:42]** You can reduce that by running a training and say,

**[38:44]** by the way, I've made your job a little bit easier.

**[38:47]** You're not answering the same level of questions,

**[38:49]** but for the field as well,

**[38:51]** they're now asking questions

**[38:53]** and I've seen this trend happen at multiple companies.

**[38:55]** When you reduce the repeat questions

**[38:58]** in Slack and email and Jira, wherever,

**[39:00]** you start to see that the questions become

**[39:02]** much more deal specific, much more nuanced.

**[39:05]** And to me, that's a sign that like,

**[39:07]** hey, you've done the foundational training.

**[39:10]** Folks have the sort of common understanding

**[39:13]** about the different things that you need to do,

**[39:16]** but they are asking much deeper questions.

**[39:18]** They're thinking about these problems

**[39:20]** at a much deeper level,

**[39:21]** which is what you want them to be doing.

**[39:23]** - Those make a lot of sense.

**[39:24]** I'm wondering if there are any other measurements

**[39:27]** that you wanna make sure you're capturing

**[39:29]** for your enablement cockpit

**[39:31]** and also the ones that are articulating value

**[39:33]** for enablement as well.

**[39:35]** - Yeah, I'd like to tell a story just like,

**[39:38]** I think it's important to be measuring sort of how,

**[39:43]** from a competitive lens, how are things landing?

**[39:46]** I think nowadays there's probably a weirder competitive lens

**[39:50]** for a lot of companies that are kind of upstarts

**[39:52]** where the competitor is billed versus buy.

**[39:56]** And so that becomes a new unique area to lean in,

**[40:00]** especially for some of the AI native companies.

**[40:02]** But when I measured competitive win rates

**[40:05]** as a part of that win-loss program,

**[40:07]** that was something we did quarter in and quarter out.

**[40:10]** Here's our top five competitors.

**[40:12]** Are we seeing them show up in deals?

**[40:14]** And this was like pre-gong, pre-anything.

**[40:18]** This was pretty dirty spreadsheet that we were running,

**[40:20]** but we had a sales kickoff coming up

**[40:23]** and the initial direction was like,

**[40:25]** let's just do more sales training.

**[40:28]** But because we were measuring this competitive win rate,

**[40:30]** I saw over time that we had this persistent decline

**[40:34]** against two of our biggest competitors.

**[40:36]** And I think maybe this is a key insight for enablement too,

**[40:39]** of bringing programs forward based on that data.

**[40:43]** But I was able to sort of bring this data to our CRO

**[40:45]** and say, hey, this isn't just an isolated event.

**[40:49]** This is a trend, a pattern we've seen

**[40:51]** across successive quarters.

**[40:53]** Is there something we can do at kickoff

**[40:55]** that focuses here?

**[40:57]** And because I had the data,

**[40:59]** we were able to sort of make that case.

**[41:02]** And what we did was we did sort of this,

**[41:05]** peer-to-peer training at sales kickoff.

**[41:07]** We had some reps come up,

**[41:09]** talk about what they'd done, what they'd done differently,

**[41:12]** or even just their process for beating these competitors.

**[41:16]** And sometimes it's so helpful to have reps speak out.

**[41:20]** They're learning themselves like,

**[41:21]** oh, hey, I did this thing kind of well.

**[41:24]** I should probably replicate that on my own deal.

**[41:26]** Like enablement can sometimes be the teach back,

**[41:30]** but it also makes it more attainable for the field.

**[41:32]** I think like sometimes it's so hard

**[41:35]** to kind of like picture this training as helping me.

**[41:39]** But if you have a rep speaking to that,

**[41:42]** it really can put it in the sort of lens of,

**[41:45]** oh, I can do this too.

**[41:46]** This is attainable, this is achievable.

**[41:48]** The long way to say like, after this training,

**[41:51]** we watched the competitive win rates

**[41:54]** against those two competitors.

**[41:56]** We focused on our top two.

**[41:58]** And that following quarter,

**[42:00]** we saw our win rate go up 10 points

**[42:03]** against one competitor and 15 points another.

**[42:06]** And this wasn't a competitor

**[42:07]** that we were competing against one, two times.

**[42:11]** So your point of like that incremental change

**[42:14]** being a huge outcome.

**[42:15]** We had six figure sort of ACV deals,

**[42:19]** or our ACV was about six figures

**[42:22]** or in the six figure range.

**[42:23]** So that change, that 10 to 15 point percentage change

**[42:28]** made a huge impact on what we were doing,

**[42:32]** what we were bringing in,

**[42:33]** but it also gave enablement again,

**[42:35]** sort of that further momentum and that cache to say,

**[42:38]** here's the data that I saw, here's what we did,

**[42:41]** and here's the outcome.

**[42:43]** Now let's do more.

**[42:45]** - And let me remind anyone listening,

**[42:46]** that's without adding another rep,

**[42:49]** without adding product capabilities,

**[42:52]** without doing more marketing,

**[42:54]** without making another dollar investment anywhere else,

**[42:59]** those gains are massive.

**[43:01]** So I think just especially once the team is at scale,

**[43:06]** these yield changes,

**[43:09]** these yield shifts can mean millions and millions of dollars

**[43:13]** and really getting your team efficient

**[43:16]** and running really, really well.

**[43:18]** - I have a question 'cause I think this is probably

**[43:22]** one of the most misconstrued aspects of hiring

**[43:27]** and bringing salespeople in.

**[43:29]** There's this concept of ramp,

**[43:31]** and people will throw out the term,

**[43:33]** well, when are the salespeople gonna be ramped?

**[43:35]** And I think a lot of people have

**[43:36]** a million different definitions for what that is.

**[43:41]** From your perspective as an enablement professional,

**[43:44]** what does a fully ramped salesperson mean

**[43:48]** and how do you get them there?

**[43:50]** - Yeah, I think you gotta see the behaviors.

**[43:53]** You gotta see someone who's,

**[43:55]** you take a look at what reps are consistent

**[43:58]** quarter in, quarter out.

**[44:00]** They're showing the same sort of output consistently,

**[44:04]** which sometimes at some companies can be very easy to see

**[44:09]** because not a lot are doing that.

**[44:11]** They have these bumps and lumps.

**[44:12]** So it's looking at that and then it's spending time

**[44:15]** understanding what are the behaviors that sit behind that?

**[44:18]** How often are they on the phone?

**[44:21]** How much are they self-sourcing to create their own pipeline?

**[44:24]** What are they doing from sort of a brass tacks

**[44:28]** foundational perspective?

**[44:31]** And you're looking to see what do their calls look like?

**[44:35]** Are they following these certain behaviors

**[44:36]** that we've agreed upon?

**[44:38]** And it's maybe tweaking some of the processes that you have,

**[44:41]** then it's enabling to that and you spell that out.

**[44:44]** You say, very clearly in the onboarding,

**[44:47]** this is what top reps do.

**[44:49]** Here's the data.

**[44:51]** This is what you're expected to do.

**[44:53]** This is how you're expected to inspect your own pipeline.

**[44:56]** This is how you're expected to re-qualify.

**[44:59]** Week in, week out, this is how you're expected to run

**[45:03]** the give get sort of conversation throughout the process

**[45:06]** from day one to the end of a sales cycle.

**[45:10]** So I think it's looking at those behaviors

**[45:12]** and then working back.

**[45:13]** I also think it's really important to work

**[45:15]** with the leadership and understand

**[45:17]** what is time to first deal?

**[45:19]** What does ramp look like to them?

**[45:21]** Because you can come up with as many metrics as you want

**[45:24]** or any sort of framework, but if it doesn't land for them

**[45:27]** and there's not sort of a consensus or agreement

**[45:30]** at that level, you're always gonna get into

**[45:33]** sort of these knife fights at the end.

**[45:35]** And I've seen different measures,

**[45:37]** different measures of what time to first deal looks like.

**[45:40]** And then one other thing that I've done

**[45:43]** and I think is a really interesting way to look at this

**[45:45]** is sort of a leading metric to that

**[45:50]** is not looking at time to first deal,

**[45:52]** but looking at time to fourth or fifth deal.

**[45:55]** Are the reps creating momentum?

**[45:57]** And that can be an early flag, early signal

**[45:59]** to those managers where you can provide intervention

**[46:03]** at that stage if you're not seeing that period of time

**[46:07]** accelerate happen within sort of the window

**[46:10]** that you would expect.

**[46:12]** And you're not just looking at time to first deal

**[46:13]** and saying, great, they close their first deal.

**[46:15]** But what momentum are they creating?

**[46:17]** And I have found once they sort of break the seal,

**[46:20]** they can start creating their own momentum.

**[46:23]** But if something wobbles within that sort of first few deals,

**[46:28]** you can provide intervention and make sure that

**[46:31]** they are on track to achieve the behaviors

**[46:33]** that you want them to achieve for a fully productive rep.

**[46:38]** - Let me rephrase what I'm not hearing.

**[46:41]** Ramp does not mean they're trained on the product

**[46:44]** and ready to do a demo.

**[46:46]** - Yeah, yeah, yeah.

**[46:48]** - Which I think a lot of people are like,

**[46:50]** train them on the product, walk through the pitch deck,

**[46:54]** they're ready to go.

**[46:55]** First one, two weeks, lock and load.

**[46:57]** We have a ramped rep and it's like, no, no, no, no, no.

**[47:00]** There is so much more that goes into it

**[47:02]** before you have confidence that this person can reliably

**[47:06]** and continuously hit their quota and produce for you.

**[47:09]** - Yeah, I think I'll just add one more note to that.

**[47:13]** When I found the most success in thinking about onboarding,

**[47:17]** it's not, to your point, shoving a bunch of stuff at them

**[47:21]** and saying, this is the latest and greatest,

**[47:22]** go figure it out.

**[47:24]** It's building it around the sales process

**[47:27]** so that a rep knows, okay, I got a deal.

**[47:29]** What do I do next?

**[47:30]** And you create this sort of like,

**[47:32]** you orient and you speak their language, frankly,

**[47:36]** for how they think about their work.

**[47:39]** When you orient the onboarding program process

**[47:44]** around the sales process or the sales journey,

**[47:47]** it becomes much easier for them to quickly recall,

**[47:50]** oh, this is what I learned about,

**[47:54]** what I need to do with an SQL.

**[47:56]** Or this is how the process happens

**[48:00]** when I move it to propose.

**[48:02]** These are the resources that I need during this.

**[48:04]** This is the actions, the behaviors, the exit criteria

**[48:07]** that I need to achieve.

**[48:09]** It gives them sort of that lens to be able to recall,

**[48:13]** which is so important 'cause they're drinking

**[48:14]** from the fire hose at that first few weeks.

**[48:19]** And if you can orient them,

**[48:20]** that awareness pays off in dividends.

**[48:25]** - I think it's an excellent frame of reference

**[48:28]** that you have for describing how to get somebody to ramp.

## 48:32 — AI role play: stretching before the sprint

**[48:32]** This would not be a podcast in 2026 if I didn't ask you,

**[48:37]** how are you leveraging AI in enablement?

**[48:41]** And what is the most modern approach to enablement today?

**[48:47]** - Well, gosh, it's changing every day.

**[48:50]** There's more capabilities.

**[48:52]** There's more things I'm like hearing about,

**[48:54]** learning about, have access to.

**[48:57]** I'm doing some really interesting analysis

**[49:00]** by connecting to a lot of our data sources,

**[49:02]** our data warehouses to really analyze call data,

**[49:06]** understand how that's happening outside

**[49:08]** of some of the systems that we've traditionally used.

**[49:11]** In my old win-loss days when I had a spreadsheet

**[49:14]** and I was downloading it and running pivot tables,

**[49:16]** this was like the pipe dream and I'm now living it.

**[49:18]** So it's so much fun.

**[49:20]** And I would say like to anybody who's in enablement,

**[49:23]** like just get out there, explore, try new things,

**[49:26]** get creative.

**[49:27]** But the thing that I've seen kind of come online recently

**[49:31]** and a lot of companies are leaning into it,

**[49:33]** and I think it could be really, really interesting,

**[49:35]** is sort of this sense of role play.

**[49:38]** There are now ways and companies that are running,

**[49:43]** that have these platforms that are ingesting a ton of data,

**[49:46]** a ton of like methodologies, your own methodologies,

**[49:50]** your own call data to prepare for calls.

**[49:55]** And this could be anyone from a rep to an SDR

**[49:59]** to even CS running QBRs.

**[50:02]** And I think this idea of being able to practice

**[50:05]** outside of live deals.

**[50:09]** And we all know how critical it is to close live deals

**[50:11]** right now in 2026.

**[50:13]** Like you don't want to be wasting your pipeline,

**[50:16]** sort of figuring it out.

**[50:17]** This comes, you know, this goes

**[50:18]** to our onboarding conversation.

**[50:20]** Like you want reps to be able to practice multiple times

**[50:23]** and work out the kinks.

**[50:25]** And then you want to create the behavior

**[50:27]** where reps are doing this, you know, prior to calls.

**[50:30]** They understand the call they're going into,

**[50:32]** and they're able to practice just like you would

**[50:35]** for a big speech, right?

**[50:36]** You would practice, you know, with someone.

**[50:40]** You'd look in the mirror, you'd practice that.

**[50:42]** And I think the opportunities to do that now with AI

**[50:45]** are so critical.

**[50:46]** I had a sales leader who said, you know,

**[50:48]** this is the same thing as like stretching

**[50:51]** and working out the hammies before you go for,

**[50:54]** you know, a sprint.

**[50:55]** And I'm really sort of excited to see where this space goes

**[50:58]** and how realistic it can get

**[51:00]** and how forward thinking it can get, you know,

**[51:02]** bringing in, you know, the calls that are already

**[51:05]** on your calendar and prepping you

**[51:06]** for those specific personas, those specific transcripts.

**[51:10]** I think that can be a really exciting area.

**[51:13]** And once reps sort of see the value of it,

**[51:15]** I think it is a new space, so it's challenging.

**[51:17]** I think the ones who will succeed

**[51:19]** are the ones who are leaning into that practice.

**[51:21]** And we're already seeing it here of who me,

**[51:23]** the ones who are doing that are our top performers.

**[51:27]** And they are our top performers because they're still hungry.

**[51:30]** They still have that chip on their shoulder

**[51:32]** to make this happen, to get out there, to be resourceful,

**[51:35]** to take every opportunity to get better

**[51:38]** and sharpen that axe every day.

**[51:40]** Well, I think it's a really exciting time to leverage AI.

**[51:43]** And especially in the role-playing sense,

**[51:44]** I mean, I've never done a presentation

**[51:47]** or walked into a big meeting without doing a dry run.

**[51:51]** And I think being able to do dry runs at scale

**[51:54]** because you don't need a loop in a million people

**[51:56]** in order to do it effectively,

**[51:58]** I think is gonna be fantastic.

**[52:00]** And like you said, the reps that take advantage of it

**[52:02]** will show in their performance.

## 52:06 — Wrap

**[52:06]** But Chad, thank you so much.

**[52:08]** This has been an absolute masterclass in enablement.

**[52:12]** I think it's one of the most misunderstood parts

**[52:15]** of operations and go-to-market

**[52:18]** and exactly what does good look like in here.

**[52:20]** And I think you've laid out a really, really strong roadmap

**[52:23]** first showing how to lay the groundwork

**[52:26]** to get the data that you need to make decisions

**[52:29]** and advocate for the proper amount of resources

**[52:31]** that you need to do a good job.

**[52:33]** So we're looking at increasing the yield,

**[52:35]** whether it's conversion rate, ACV, moving velocity,

**[52:39]** moving things through the funnel quicker.

**[52:41]** And as we mentioned, small increments and improvement

**[52:44]** can have massive outsized gains

**[52:47]** and the equation also runs the other way.

**[52:50]** So this is not only in an area to invest in

**[52:54]** just for opportunities,

**[52:56]** but also to mitigate downside risk as well,

**[52:59]** especially as you're growing and scaling.

**[53:01]** You're gonna be adding tens and tens of reps

**[53:04]** as you're growing, as you're building fast.

**[53:07]** And it requires a lot to get one of those reps

**[53:10]** ramped and onboarded.

**[53:12]** And again, ramping does not mean

**[53:14]** they're trained on the product.

**[53:15]** It means they're predictably reliably closing deals,

**[53:18]** hitting their quota, producing at the rate

**[53:20]** you expect them to.

**[53:21]** So Chad, just thank you for everything here,

**[53:24]** excited for people to listen,

**[53:26]** excited for this to be on LeanScale's MCP

**[53:28]** so people can query anything from the conversation.

**[53:31]** And I can't wait to see what you do next.

**[53:36]** - Oh, well, thank you, Anthony.

**[53:37]** This has been so much fun.

**[53:38]** I love that the enablement worlds

**[53:41]** and the RevOps worlds are coming together

**[53:43]** in this conversation.

**[53:44]** I think that's where this space is going.

**[53:47]** And I love that we get to talk about it

**[53:49]** and you can tell I'm super passionate about it.

**[53:51]** So I wanna see these worlds come together more

**[53:54]** and this is a perfect opportunity for that.

**[53:56]** And like I said, this has been such a fun,

**[53:58]** thoughtful conversation.

**[53:59]** So thank you for your questions.

**[54:00]** And if anybody out there has any questions for me,

**[54:03]** like I love this stuff.

**[54:05]** It is so fun to talk about

**[54:06]** and learn from the community of RevOps and enablement.

**[54:11]** So always feel free to reach out.

**[54:13]** I'm happy to chat at any point.