The LeanScale Podcast · Episode 112

Why Enablement Fails Before It Starts

Cheyenne Griffith on the three conditions a company has to meet before enablement can work, why the SKO launch is the smallest part of the job, and why maintenance is the AI problem that keeps her up at night

Cheyenne Griffith · GTM Enablement Lead · Deepgram Hosted by Anthony Enrico
Published Updated 00:50:54 42 min read 8444 words
Sales Enablement AI in GTM Revenue Operations Sales Leadership
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Executive Summary

The one-paragraph brief, extended

Why this conversation matters — and who should spend the hour.

Cheyenne Griffith is building Deepgram's go-to-market enablement function from scratch — a team of one, less than two months in. Her route there was unusual. She taught fourth and fifth grade math, then the small company behind the learning management system she used in class hired her as a customer success manager. A few roles later she was a CSM at Imagine Learning, where she was invited onto a ten-person enablement team, and after that she built enablement from the ground up at a CRM company. Her thesis is that teaching a seller to sell is the same job as teaching a fourth grader to divide. Teaching one person is easy either way. The hard part is the system that makes it work for a whole classroom or a whole organization.

Most of that system never shows. Anthony puts the lecture or the SKO presentation at maybe five to ten percent of the work. Cheyenne's example is MEDDIC: launch it at SKO and everyone knows what the letters mean. It only becomes real when four more things are in place. The CRM can capture it, the call recording tool can pull it out of calls, leaders make decisions in its language, and someone checks whether more pipeline is moving through the stages and win rates are rising. In the classroom her tool was the exit slip, a quick daily check on whether the lesson landed. Today it is the call recording scorecard. Tailoring by role, she says, is not the hard part. What changes is the messaging, the depth of product knowledge and, above all, how success is measured.

On measurement, a product launch shows how it works in practice. SDRs generate pipeline for the new product and AEs sell it. Customer success engineers, who carry no quota, are measured on the cross-sell opportunities they find. Applied engineers are measured on the calls they support. Those are the lagging indicators. For leading indicators she uses call intelligence: how often reps bring the product up, whether they raise it themselves or only when asked, and whether they handle objections or fold. Before any program she builds an ROI case with conservative, medium and best-case scenarios, for the whole org and for each rep's commission. Afterwards she shows people the results.

She is opinionated about structure. Enablement should report to the CRO. Under RevOps it can slide into a helper function that announces other teams' decisions, and under marketing it can drift away from the front line. The trigger for hiring enablement is not ARR or headcount. Three conditions have to be met first. Founder-led sales must already be handed off to a real sales team. Product marketing needs a strong point of view on who the product is for; without one, enablement ends up doing product marketing too, which she calls too much for anybody. And the leader has to be ready to trust the enabler.

Her biggest AI concern is not slop but maintenance. Deepgram encourages everyone to use AI tools once security has reviewed them, and AEs and SDRs are shipping web apps for prospecting and pricing. When pricing or the ICP changes, those apps go out of date, and it is unclear whose job it is to fix them. She is starting with an inventory of what people have built, and Deepgram is hiring a company-wide head of AI enablement. Her build-versus-buy test follows the same logic: is the tool customer-facing, and what will maintaining it take? She could vibe-code an LMS, but she did not want to maintain one, so she bought Letter AI.

Key Takeaways

13 things worth stealing

The load-bearing ideas, each with the business implication and who should care.

01

The hard part of enablement is the system, not the teaching

Cheyenne frames both teaching and enablement as giving someone the knowledge, skills and tools to do something, then having them apply it — on a discovery call or when halving a recipe. Teaching one child to divide or one seller to sell is easy.

Why it matters: The real work is the system that makes it hold across a whole classroom or organization. Enablement that is judged on individual sessions is being judged on the easy part.

Sales LeadersRevenue ExecutivesFounders
02

Launching MEDDIC at SKO is the tip of the iceberg

After an SKO launch, everyone knows what the letters mean. The program only exists once the environment expects it and monitors it. That means CRM set up to consume the information, a call recording tool configured to pull it out of calls, and leaders speaking the language when they make decisions.

Why it matters: Then you check whether it worked: is more pipeline moving past a given stage, and are win rates rising? Anthony puts the visible presentation at five to ten percent of the job.

Sales LeadersRevOps LeadersRevenue Executives
03

Exit slips became call recording scorecards

In her classroom, a quick quiz after every lesson showed whether the topic had landed. She treats call recording scorecards as the same instrument: frequent formative assessment that shows whether the ship is being steered in the right direction.

Why it matters: Continuous monitoring, not the launch event, is the part of enablement she enjoys most, and it is where program corrections come from.

Sales LeadersCustomer Success
04

Tailoring by role is not the hard part people assume

Teaching an account executive their job is no harder than teaching a customer success manager theirs. It is the same motion across more functions. What she actually tailors is the messaging, the depth of product understanding, and how success is measured.

Why it matters: At Deepgram, the customer success team's materials are aligned more closely with the applied engineering team than with account executives. The line she draws is technical depth, not org-chart adjacency.

Sales LeadersCustomer Success
05

Non-quota roles need creative, but still revenue-linked, measures

For a product launch, SDRs are measured on pipeline for the new product and AEs on selling it. Customer success engineers are not quota-carrying and do not own renewals, so they are measured on mentioning the product and passing cross-sell opportunities. Applied engineers are measured on calls supported.

Why it matters: Everyone likes being tied directly to revenue. For roles further from it, the measure has to be designed deliberately, not borrowed from sales.

Customer SuccessRevOps LeadersRevenue Executives
06

Leading indicators come from how reps talk, not just what closes

Using call intelligence, she tracks how often a new product comes up in conversations. She checks whether reps raise it proactively or only in response to something, and whether they handle objections or fold the moment one appears.

Why it matters: These signals tell her whether the talk tracks are working long before lagging metrics like pipeline or bookings move.

Sales LeadersRevOps Leaders
07

When nothing is obviously broken, pull the thread

Outside a launch, she starts from a metric that is suffering, such as retention, win rates or quota attainment, and peels back the layers. Is retention weak in one industry, among customers on one product, or among customers filing tickets on one issue?

Why it matters: She says Deepgram's entire sales team met quota last year. Anthony's point is that very small gains in conversion, time in stage or sales cycle length still add up to millions at scale.

Revenue ExecutivesRevOps LeadersCustomer Success
08

Sell the enablement program like a deal: an ROI case in three scenarios

Before a program she shows what a conservative, a medium and a blow-it-out-of-the-water improvement would mean for revenue. She does it for the whole revenue org and for each rep's quota attainment and commission.

Why it matters: Afterwards she reports the results back to the team. Early, visible wins are what earn buy-in for the next program.

Revenue ExecutivesSales Leaders
09

Enablement belongs under the CRO

True go-to-market enablement exists to grow revenue through both retention and new sales, so it should report to whoever owns revenue. Under RevOps, she has seen it lean toward a helper function: RevOps builds something and enablement tells everyone about it.

Why it matters: Reporting into marketing can work, since marketing's mandate is also revenue. But she sees a gap between marketing and front-line AEs and CS, and enablement needs its own seat at the table to find the cracks.

Revenue ExecutivesRevOps LeadersFounders
10

ARR and headcount are the wrong triggers for hiring enablement

Readiness depends on the motion. If founder-led sales is still running, you are not ready. She has seen enablement hired to design the move from founder-led to sales-led selling, and does not think it works.

Why it matters: The founder has to have already put trust in the salespeople. The third condition is a leader ready to say, in effect, 'I've achieved this, now I trust you to optimize it.'

FoundersRevenue Executives
11

Without product marketing, enablement becomes product marketing

Product marketing does not need to be sophisticated. At its heart it is someone on the marketing team with a strong point of view on who the product is for and how to talk about it, who will go to bat for that view.

Why it matters: Without that, enablement absorbs product marketing by default, which she calls too much for anybody. She treated a strong product marketing function as a criterion in her own job search.

FoundersMarketing LeadersRevenue Executives
12

The AI risk in enablement is maintenance, not slop

At Deepgram, AEs and SDRs ship web apps that crawl for prospects and build pricing pages, and the whole team may come to rely on one person's pricing calculator. The moment something changes, those tools are out of date.

Why it matters: Her starting point is an inventory of what people have built, so owners can be told when pricing or the ICP changes. Anthony adds that getting a whole company onto something one person built is harder than building it.

Revenue ExecutivesRevOps LeadersSales Leaders
13

Build versus buy: is it customer-facing, and who maintains it?

If a tool is customer-facing, she leans toward buying it from experts. Otherwise she scopes what maintenance will look like: a pricing calculator is easy to keep current, an LMS is not.

Why it matters: She was encouraged to vibe-code an LMS and declined. Siloed AI roleplay tools for SDRs, AEs and CS showed her why messaging and growth over time need one system, so she bought Letter AI.

RevOps LeadersRevenue Executives
Frameworks Discussed

10 named models

Every framework Jimmy names, defined and time-stamped.

The Enablement Iceberg

05:50

The visible part of enablement — the SKO presentation or the classroom lecture — is a small fraction of the work. The rest is the operating environment that makes a program stick and the monitoring that shows whether it worked.

Anthony sets it up by estimating the visible part at five to ten percent. Cheyenne fills in what is underneath: the systems, the expectations, the monitoring and the measurement.

Operationalizing MEDDIC Beyond the SKO

06:29

Treating MEDDIC, a widely used sales qualification methodology, as an environment to build rather than a session to deliver. The CRM captures it, call recording picks it up, leaders use its language in decisions, and its impact is tracked.

Cheyenne's test of success is whether more pipeline is moving past a given stage and win rates are rising — whatever the team set out to achieve when it launched. The episode does not break down the letters. MEDDIC is used as the example of a program whose launch is the smallest part.

Exit Slips to Call Recording Scorecards

08:02

Short, frequent formative assessment after instruction, to see whether learning is landing and steer in time. In the classroom that was a daily exit-slip quiz. In go-to-market it is a call recording scorecard.

Cheyenne calls it 'the same thing, really'. Continuous monitoring is her favourite part of the job.

Lagging and Leading Indicators for a Launch

17:17

Pairing role-specific lagging metrics with leading indicators drawn from call intelligence. Lagging: SDR pipeline, AE sales, customer success engineer cross-sell opportunities, applied engineer calls supported. Leading: product mentions, proactive versus reactive mentions, and objection handling.

She compares the metrics before and after a launch, and uses the leading indicators to decide whether the talk tracks need more enablement.

Finding the Cracks

18:28

When no launch is setting the agenda, start from a lagging metric that is suffering and pull the thread through layers of segmentation until the source appears.

Her retention example splits by industry, by the product the customer chose, and by the ticket issues customers raise. She also uses AI to help triangulate cause and effect.

The Enablement ROI Case

22:24

Before running a program, model its revenue impact in conservative, medium and best-case scenarios, for the revenue org and for each rep's quota attainment and commission. Afterwards, report the actual results.

She compares it to the ROI case you would build when selling something. It gets both her and the team bought in, and showing results afterwards earns the next round of buy-in.

Enablement Reports to the Revenue Owner

25:37

Go-to-market enablement should report to the CRO, because its purpose is revenue through both retention and new sales. Reporting into RevOps risks a helper function, and reporting into marketing risks distance from the front line.

On team design she is less prescriptive. Her own default is to split by role so enablers embed with and are trusted by the teams they serve, rather than organizing by discipline such as instructional design and delivery.

Three Enablement Readiness Gates

30:18

Three conditions have to hold before hiring enablement, rather than an ARR or headcount threshold. Founder-led sales has already been handed off to a sales team. Product marketing has a strong point of view on who the product is for. The executive enablement reports to is ready to trust the enabler.

Enablement hired to design the founder-to-sales handoff does not work. Enablement hired without product marketing ends up doing that job as well.

Inventory Before You Scale AI-Built Tools

36:51

Treat maintenance of employee-built AI tools as an enablement problem. Take inventory of what people have created, notify owners when an underlying input such as pricing or ICP changes, and route promising tools through enablement so they can be scaled.

Deepgram encourages people to use AI tools once security has reviewed them. Cheyenne's concern is that tools built this way quietly go out of date. She has started acting as a light gatekeeper: share a tool with her first so the work does not disappear into a Slack channel.

The Build-Versus-Buy Maintenance Test

45:16

Two questions decide whether to build or buy. Is the tool customer-facing? If so, lean toward buying. What will maintenance actually look like? Build only what is cheap to keep current.

A pricing calculator passes because you just update the price. An LMS fails, which is why she bought one instead of vibe-coding it.

Best Quotes

20 lines worth clipping

Pulled verbatim. Copy or share any of them.

“It's easy to teach one child to divide. It's easy to teach one seller to sell. It is much, much harder to teach a classroom and teach an organization how to do their roles.”
Cheyenne Griffith 05:26
“You launched MEDDIC at SKO. Yay, hooray. Everyone knows what the letters mean.”
Cheyenne Griffith 06:51
“It's really just putting an environment in place and then continuously monitoring that environment as well.”
Cheyenne Griffith 07:50
“So for me now, that looks like call recording scorecards instead of exit slips. But it's the same thing, really.”
Cheyenne Griffith 08:33
“It's not actually any harder to teach an account executive how to do their job versus teaching a customer success manager how to do their job. It's the exact same motion and it requires the exact same things.”
Cheyenne Griffith 09:52
“In this world where everyone is using AI, just knowing what good looks like is half the battle, I think.”
Cheyenne Griffith 14:52
“Very minor improvements on conversion rate and time in stage or total sales cycle can mean millions, tens of millions at scale to how your year turns out.”
Anthony Enrico 21:09
“Here's the ROI of the enablement program that I'm trying to launch. If we're able to increase X by this conservative amount, here's what that will mean for our revenue.”
Cheyenne Griffith 22:41
“This is what it could literally mean for you and your quota attainment and your paycheck, your commission at the end of the day.”
Cheyenne Griffith 23:08
“You all increased by this and here's how much money you made. Like, go team, now listen to me the next time that I tell you to do something.”
Cheyenne Griffith 24:28
“I think that reporting into RevOps is okay. I think I've seen that be a little bit of an issue, just because it can start to lean towards almost like a RevOps helper function.”
Cheyenne Griffith 26:23
“I don't think it's necessarily an ARR or even a team size. It's more about what your motion looks like at that point. So, for instance, people who are still running founder-led sales, you're not ready for enablement yet.”
Cheyenne Griffith 30:33
“What I've seen there is by default enablement becomes product marketing as well. And that's just too much for anybody.”
Cheyenne Griffith 31:52
“The heart of it is someone on your marketing team who has a strong point of view about who your product is for.”
Cheyenne Griffith 32:45
“I see a lot of conversation on LinkedIn and what have you about AI slop. And I'm less concerned about that and more concerned about how we maintain what we're creating.”
Cheyenne Griffith 36:51
“But the second something changes, they become deprecated.”
Cheyenne Griffith 37:32
“Honestly, my biggest challenge right now is both figuring out how we ensure things are well maintained and accurate, and then how do we actually scale AI usage in a responsible way. Far and away my biggest challenge.”
Cheyenne Griffith 39:55
“But then it's like, all right, how do we get the entire company using that now? That's way harder than building the thing in the first place.”
Anthony Enrico 40:59
“Could I vibe code an LMS? Yes. Do I want to maintain it? Absolutely not.”
Cheyenne Griffith 45:34
“If you are interested in making real change and tying the work that you do to the growth of an organization, it's actually a great place to be if you're willing to put in that work and look at the data.”
Cheyenne Griffith 49:33
Practical Advice

What should you actually do?

The playbook, split by the seat you sit in.

Founders

  • Do not hire enablement to design the move away from founder-led sales. Hand off to a real sales team and trust your salespeople first.
  • Ignore ARR and headcount as the hiring trigger. Ask whether your motion is ready to be optimized rather than invented.
  • Before hiring enablement, make sure someone owns a strong point of view on who the product is for and how to talk about it.
  • Be ready to tell the person you hire, 'I trust you to optimize this.' Without that, the role will not work.

Revenue Executives

  • Have go-to-market enablement report to the CRO, with a real seat at the table rather than a messenger role.
  • Ask for an ROI case before each program, with conservative, medium and best-case scenarios, and for a report on actual results afterwards.
  • Keep looking for optimization even when the team is hitting its number. Small gains in conversion, time in stage and cycle length compound at scale.
  • Name an owner for AI enablement across the whole company, not only go-to-market.

Sales Leaders

  • Treat a methodology launch at SKO as the start. Expect it in deals, inspect for it, and speak its language in pipeline reviews.
  • Use call recording scorecards as frequent formative checks rather than waiting for win rates to move.
  • When a new product launches, watch whether reps raise it proactively or only when asked, and whether they hold up under objections.
  • Translate each program into what it means for an individual rep's quota attainment and commission.

RevOps Leaders

  • Set up the CRM and the call recording tool to capture a methodology before it launches, so adoption and impact can be measured.
  • If enablement reports into RevOps, give it a planning role rather than using it to announce what RevOps has already built.
  • Keep an inventory of employee-built tools and their owners, so you can notify them when pricing or ICP changes.
  • Before building internally, ask whether the tool is customer-facing and scope what maintaining it will actually take.

Customer Success

  • For technical customer success roles, align enablement materials with applied or solutions engineering rather than with account executives.
  • Measure non-quota CS teams on product conversations and cross-sell opportunities surfaced from their current accounts.
  • When retention slips, segment by industry, by product chosen and by support ticket type before designing a fix.
  • Rethink the business review for highly technical buyers, who may not want a traditional QBR at all.

Marketing Leaders

  • Establish and defend a clear point of view on who the product is for and how to speak about it; enablement depends on it.
  • Without that point of view, expect enablement to absorb product marketing by default — a load Cheyenne says is too much for anybody.
AI Takeaways

How AI actually changes GTM

LeanScale's signature read on the AI-in-GTM question this episode wrestles with.

The thesis

Cheyenne is a heavy, positive AI user: she scales role-specific content with Claude, uses AI to triangulate cause and effect, and bought an AI-native LMS. But she argues the AI risk that matters for go-to-market teams is not low-quality output. It is the maintenance and adoption debt created when many people build useful tools that nobody owns once pricing or the ICP changes.

Agent & automation ideas

  • A registry of employee-built tools and their owners that flags affected tools when pricing or ICP definitions change and checks whether they were updated.
  • Role-by-role content generation from a single 'what good looks like' outline written by enablement.
  • Call-intelligence monitoring that counts new-product mentions per rep, classifies them as proactive or reactive, and scores objection handling.
  • Retention root-cause analysis that segments a declining metric by industry, product and support ticket issue.
  • A single roleplay environment shared across SDR, AE and CS teams, so messaging stays aligned and progress can be tracked over time.
Operations Takeaways

By function

The same conversation, filtered for RevOps, pipeline/marketing ops, and customer ops.

Revenue Operations

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Pipeline & Marketing Ops

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Customer Operations

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Metrics Mentioned

The numbers, with context

~5–10%
Visible share of enablement work

Anthony's estimate of how much of teaching or enablement is the lecture or SKO presentation, with the operational work underneath.

10 enablers
Imagine Learning enablement team

The team Cheyenne joined for her first enablement role.

Team of one, under two months in
Deepgram enablement headcount

Cheyenne's situation at the time of recording, building the function from the ground up.

Entire team (~20 people) met quota last year
Deepgram sales quota attainment

Cheyenne's example of a team where nothing is obviously broken but optimization still matters.

3
ROI scenarios per program

Conservative, medium and blow-it-out-of-the-water estimates, built for the revenue org and for each rep.

Entities

Companies, people & tools mentioned

Auto-extracted and linked into the knowledge graph.

Companies

DeepgramVoice AI

The voice AI company where Cheyenne is building go-to-market enablement as a team of one, less than two months in. Deepgram sells APIs to highly technical buyers. Its customer success engineers are not quota-carrying and do not own renewals, and applied engineers support calls. Everyone is encouraged to use AI tools once security has reviewed them, and a head of AI enablement is being hired. Cheyenne says the entire sales team, around 20 people at the time, met quota last year. She uses Deepgram's own API to turn podcasts into reading material.

00:17 · 10:18 · 16:14 · 21:27 · 36:08 · 41:44 · 47:36Company →
Imagine LearningEdTech

Where Cheyenne worked as a customer success manager. She became an early adopter of its tools and a mentor to new CSMs, and was then invited onto its enablement team. It was her first enablement role, on a team of 10 enablers that gave her strong mentors to learn the function from.

02:10 · 02:56Company →
LeanScaleGTM Operations

Anthony's firm. He says LeanScale invests significant internal time in taking tools that individual people build to solve real problems and getting the whole company to use them, which he calls harder than building them.

40:42Company →

People

Cheyenne Griffithguest

GTM Enablement LeadProfile →
Anthony Enricohost

Co-founder of LeanScale and host of The LeanScale Podcast.

Co-FounderProfile →

Tools & software

ClaudeAI Assistant

Cheyenne's 'best friend' for role tailoring. She writes a basic outline of what good looks like for a role at Deepgram and uses Claude to scale it out to each role.

Website ↗
Letter AISales Enablement / LMS

The learning management system Deepgram bought rather than vibe-coding one. Cheyenne needed aligned messaging, growth tracked over time, and a link to revenue. She says it generates a lot of content from factual input.

Website ↗
SlackTeam Messaging

Where employee-built tools often get shared in a single channel with no visibility into who adopted them. Also home to the enablement communities Cheyenne follows, including Sales Enablement Collective.

Website ↗
LinkedInSocial Platform

Where Cheyenne sees the AI slop conversation she considers the wrong worry, and one of her main sources for staying current.

Website ↗
Methodologies referenced Role outlines scaled with AIPer-rep ROI framingShare-with-enablement-first for employee-built toolsSegmented retention diagnosis
Related LeanScale Services

Where this shows up in the work

Sales Enablement Build

Stand up a zero-based, sales-academy enablement motion sized to your span of control and sales complexity.

The readiness gates, reporting line, team structure, role-based measurement and ROI case are a blueprint for standing up an enablement function.

AI for GTM

Agents and workflows that multiply operator throughput — the 'make humans superhuman' thesis, operationalized.

Scaling AI usage responsibly — ownership and maintenance of employee-built tools, a company-wide AI enablement owner, and build-versus-buy — is the problem Cheyenne calls her biggest challenge.

Fractional RevOps

Embedded, field-facing RevOps leadership and execution — the operator model Jimmy describes, delivered as a service.

Operationalizing a methodology depends on CRM and call recording instrumentation, and the RevOps-versus-CRO reporting question sits at the boundary between the two functions.

Frequently Asked Questions

Straight answers

Generated from the conversation, marked up for search and AI extraction.

When is a company ready to hire sales enablement?

According to Cheyenne Griffith, who is building go-to-market enablement at Deepgram, the trigger is not an ARR figure or a team size but the state of the sales motion. Three things should already be true. First, founder-led sales has been handed off to a real sales team the founder trusts; enablement brought in to design that transition does not work. Second, product marketing — or at least one person on the marketing team — has a strong point of view on who the product is for and how to talk about it. Third, the executive enablement will report to is ready to say they have built something and now trust an enabler to optimize it.

Why do sales methodology launches like MEDDIC fail after the SKO?

Because the launch is the smallest part of the work. Cheyenne Griffith points out that after a MEDDIC session at SKO everyone knows what the letters mean, but nothing has changed operationally. Making it stick requires an environment that expects and monitors it: a CRM set up to capture the information, a call recording tool configured to pull it out of calls, and leaders who use the language when making decisions. Then someone has to measure whether it is working — whether more pipeline is moving past specific stages and whether win rates are rising.

Where should a sales enablement team report?

Cheyenne Griffith strongly prefers that go-to-market enablement report to the CRO, because its purpose is growing revenue through both retention and new sales. She considers reporting into RevOps workable but has seen it turn enablement into a RevOps helper function that simply tells everyone about what RevOps has built. Reporting into marketing can also work, since marketing's mandate is revenue too, but she sees a disconnect between marketing and front-line account executives and customer success. For team structure as it grows, her default is to split enablers by the roles they support so they embed with those teams and earn their trust.

How do you measure enablement for roles that do not carry quota?

Design role-specific measures that still connect to revenue. For a product launch at Deepgram, SDRs are measured on pipeline for the new product and account executives on selling it. Customer success engineers, who are not quota-carrying and do not own renewals, are measured on how often they discuss the new product with customers and how many cross-sell opportunities they pass on. Applied engineers are measured on the number of calls they support. Cheyenne Griffith notes that everyone likes being tied directly to revenue, so measuring roles further from it takes more creativity.

How do you build an ROI case for an enablement program?

Treat it like the ROI case you would build when selling a product. Before launching, Cheyenne Griffith shows what a conservative, a medium and a best-case improvement in the target metric would mean for revenue. She builds that view for the entire revenue organization and also for each rep — what it could mean for their quota attainment, paycheck and commission. After the program, she reports the actual results back to the team. That gets both her and the reps bought in, and early visible wins earn buy-in for the next program.

What leading indicators show whether a new talk track is working?

Cheyenne Griffith uses a call intelligence platform to track three things after a launch: how many times reps bring up the new product in conversations, whether they raise it proactively or only in response to something the customer says, and whether they handle objections well or fold as soon as one comes up. Those leading indicators sit alongside lagging metrics like pipeline generated and deals closed, and they show whether the talk tracks need more enablement well before the lagging numbers move.

What is the biggest AI risk for enablement and go-to-market teams?

Cheyenne Griffith argues it is maintenance, not AI slop. When sellers are encouraged to build their own AI tools — prospecting apps, pricing pages, pricing calculators the whole team relies on — those tools become outdated the moment pricing or the ICP changes, and it is rarely clear whose job it is to update them. Her starting point is taking inventory of what people have built so owners can be notified of changes, asking builders to share useful tools with enablement first so they can be scaled, and giving AI enablement a company-wide owner.

Should an enablement team build its own LMS with AI or buy one?

Cheyenne Griffith was encouraged to vibe-code a learning management system at Deepgram and chose to buy one instead, selecting Letter AI. Her test for build versus buy has two questions: is the tool customer-facing, in which case buying from experts is usually better, and what will maintenance actually look like? A pricing calculator is easy to maintain because you just update the price; an LMS is not. She also wanted aligned messaging and a way to track growth over time back to revenue, after seeing separate AI roleplay tools for SDRs, AEs and customer success that did not talk to each other.

Timeline

Jump through the conversation

Click any chapter to open it in the transcript.

00:00Cold open and intro 00:56From fourth-grade math teacher to GTM enablement 04:04Teaching a seller to sell is teaching a kid to divide 05:50What's actually under the iceberg 08:02Exit slips became call recording scorecards 08:59What actually changes by role, and what doesn't 15:07Measuring a product launch across four teams 18:00When the launch is over: how to find the cracks 19:52What a QBR looks like for a technical buyer 22:24Building the ROI case for an enablement program 25:07Where enablement should report, and where it shouldn't 29:42When is a company actually ready for enablement 31:32The product marketing prerequisite 35:27AI in enablement: what's working and what's risky 37:32Who owns the tool when the pricing changes 43:17Build vs. buy: why she refused to vibe-code an LMS 45:16Cost of maintenance as the deciding test 49:33Advice for anyone considering enablement
Full Transcript

The whole conversation

Broken into chapters, searchable, verbatim from the audio. Speakers inferred (not diarized).

Transcript as markdown ↓ Whole episode as markdown ↓
00:00Cold open and intro

0:00 Honestly, my biggest challenge right now is like both figuring out how we ensure things are well maintained and accurate and then like how do we actually scale AI usage in a responsible way, like far and away my biggest challenge.

0:17 My guest today is Cheyenne Griffith, who is building the go-to-market enablement function from the ground up at DeepGram, one of the leading voice AI companies.

0:26 Right now, DeepGram is in a really good spot. It's one of those places where the issues are not obvious, right? Like sometimes you start a new job and you're like, "Oh, I have a lot more to do." And here, it's less obvious. And so that's been fun for me to figure out.

0:43 Well, I think it's really important to stay plugged in as much as you can, whether it's podcasts, whether you're converting those podcasts into a transcript and reading them or getting plugged into those communities.

00:56From fourth-grade math teacher to GTM enablement

0:56 Cheyenne, you started teaching fourth and fifth grade math. Walk me through how a math teacher ends up building go-to-market enablement at an AI company.

1:10 Lots of happy accidents. So I've always been kind of an early adopter, I guess, which is great. I like to learn and I like to experiment with things.

1:24 So one of the things that I used pretty heavily in the classroom was a learning management system. And I ended up, as you mentioned, being pulled in by them to be a customer success manager. Tiny learning management system, tiny local company, actually.

1:43 I didn't even know. I thought like every teacher in the country was using this learning management system and they were not, but it was still a good first experience in the software world.

1:54 So I did customer success there for a couple of years and it was a startup. So doing customer success also meant doing account management and doing cold outreach and doing all the things.

2:10 And eventually, after a couple of roles, moved into a much, much larger company as a customer success manager at Imagine Learning.

2:20 And similarly, started being an early adopter of some of the tools there and just kind of becoming a mentor to other CSMs as they came on board.

2:30 And eventually the enablement team just said, hey, come join us, which I was delighted and so excited to do because I really, I thrive on feeling like I'm helping people.

2:43 And I think that's what drew me to teaching in the first place. And that's what has drawn me to enablement.

2:48 So, you know, them saying like, you can really help these people that are coming on board to our company was like, okay, I'll do it.

2:56 So that was my first experience in enablement. And it was a much, much larger team that I had since been on. We had 10 enablers there and so it was really good to have strong enablement mentors and people to really learn the function from.

3:11 And then right after that pivoted completely to CRM. So my first experience kind of outside of my little ed tech bubble. And it was very, very different experience, but ended up kind of building that function from the ground up there and stayed there for several years.

3:31 And then I've since kind of done the same thing at a couple of companies. And so now I'm at deep Graham, which is the best decision I have ever made. And yeah, so started a couple of months ago and have been starting to build out the engine here as a team of one for the moment.

3:50 I love it. I love how it's just organically following things you're passionate about things that you like and things that you enjoy. I think it's a great way to carve out your career. I'm curious, though, I think something that I find really interesting.

04:04Teaching a seller to sell is teaching a kid to divide

4:04 You mentioned teaching sellers how to sell. It's really similar to teaching a fourth grade or how to divide. What are those similarities from like classical elementary education to enablement programs at fast growing SaaS companies?

4:20 So, you know, ultimately, I view my job and the job of a teacher or giving someone the means to do something that's it at the end of the day. So a lot of the times that means is through learning and knowledge, of course, but it's also through tools and different things like that.

4:39 But at the end of the day, having someone understand the concept, understand how something is done and then go out and actually apply that in the world, whatever that means, whether it's on a discovery call or when they need to divide.

4:55 They need recipes a lot in elementary school. So when they need to divide to, you know, make a recipe smaller, whatever the case may be. It's really the same. The principles of understanding, you know, this is the knowledge that I need.

5:09 These are the skills that I need. These are the tools that I need to do a job.

5:14 That's really all there is to it, actually. And just like making sure the hard part of the job in both teaching and enablement is making sure it's systematic, I think.

5:26 You know, it's easy to teach one child to divide. It's easy to teach one seller to sell. It is much, much harder to teach a classroom and teach an organization how to do their roles.

5:39 So I think that's where the challenges really come from, less the actual like teach someone to do something and more so the systems that you put in place to make sure that it can kind of continue.

05:50What's actually under the iceberg

5:50 Yeah. And I think a lot of people when they're looking at teaching or enablement, the tip of the iceberg stuff is seeing the lecture in the classroom or seeing the presentation at the sales kickoff.

6:02 But that's got to only be like five, 10 percent of it. What else in enablement? I think it's one of the most misunderstood departments and go to market.

6:11 What else is really living underneath that operationally that a lot of folks just aren't seeing?

6:18 A couple of things come to mind. I would say the first thing is just making sure that the environment is set up correctly for them to then be able to do whatever it is that you talked about for SCO at SCO.

6:29 Right. So if you introduced medic, for instance, I love medic, by the way, a lot of people don't. And so that's another conversation.

6:40 I'd love to talk about medic. I'm a really big dork. It's one of the most popular qualification methodologies any of our customers use. And it's popular for a reason. Yeah, it works for a reason.

6:51 But anyway, so you launched medic at SCO. Yay, hooray. Like everyone knows what the letters mean. But actually creating an environment where you are expecting that people are using medic, where you are monitoring whether people are using medic.

7:07 And most importantly, back to my favorite thing, data, where you are actually tracking does this work for us? Does this make sense?

7:14 And so it can be really basic things like making sure that your CRM is set up to consume that information, making sure that whatever call recording tool you're using is set up to easily glean that information from calls.

7:29 But then also making sure you're actually using that to make decisions and that you're speaking that language on a regular basis.

7:35 And then finally, like, if you launch medic, well, is it working? Are we now, you know, pushing more pipeline past X, Y, and Z stage? And are we now actually, you know, increasing our win rates or whatever it is that we set out to do when we launched medic?

7:50 So it's really just putting an environment in place and then continuously monitoring that environment as well. And that's my favorite part is that kind of continuous monitoring piece.

08:02Exit slips became call recording scorecards

8:02 And again, it's similar to in the classroom, like one of the things that was really in vogue when I was a teacher was we call them like exit slips.

8:12 And it was like every single day after you teach something, you give them a little quiz and you just continuously monitor how they're doing on whatever the topic is.

8:22 And just getting those like quick formative assessments of how people are doing really regularly really helps to kind of see if you're steering the chip in the right direction.

8:33 So for me now, that looks like, you know, call recording scorecards instead of exit slips. But it's the same thing, really.

8:41 No, I think that's I think it's really important because I imagine in the classroom, you're seeing, okay, I'm teaching these subjects and then you get some pretty concrete feedback to see if they got the questions correct or not if the students are understanding.

8:53 And I think I know a portion will probably get it right away and then a portion need it really tailored.

08:59What actually changes by role, and what doesn't

8:59 And I know that has to be the case and go to market to where, especially if you have 20 sellers, 100 sellers, you have the CSM team, you have different functions. There's like a lot of different roles and personalities to tailor around.

9:13 What's your approach to tailoring to make sure that everyone gets the type of information they need?

9:21 This is a really good question because anytime I've ever been asked about this, people assume that it's really hard. They assume it's the hardest part of the job in many cases when you are in true like go to market or revenue enablement versus just pure sales enablement.

9:41 They're like, how do you manage to do that for all these different roles? And I hope this isn't a cop out, but it's still kind of the same thing as being a teacher.

9:52 It's not actually any harder to teach an account executive how to do their job versus teaching a customer success manager how to do their job. It's the exact same motion and it requires the exact same things.

10:07 You're just handling more functions now. So it starts with a deep understanding of your role and a deep understanding of the product that you're supporting.

10:18 DeepGram has been such a fun transition for me because I've been in SaaS for so long and really we're dealing in APIs. So that's been a really fun transition of what does learning and selling and talking about an API look like versus SaaS.

10:35 But once you know like this is my job and this is the software or API or what have you that I support, it's all kind of the same.

10:44 So this is one area where I've really I have relied pretty heavily on AI for this area because I can create like that basic outline of this is what good looks like here at DeepGram when it comes to this role.

10:59 And then I can you know really rely on my best friend Claude to help me when I create something basic to like scale that out to different words based on what good looks like in their work.

11:11 I call mine Claudio. I usually say my best friend Claudio built this for you. So here you go.

11:17 I was really into Claude Monet when I was a kid. So Claude really like feels right to me even though Claude has very very little to do with you know impressionistic art still nice association.

11:35 Every time I'm typing in that prompt I'm just thinking of a nice painting.

11:40 Yeah, I am. It's yeah weird association but I'll take it.

11:46 Well, on the personalization front, I imagine there's like a few avenues you need to personalize on one the presentation of data, maybe how you measure, maybe assets that you create or artifacts that you give.

12:01 What are what are some of the things that you do specifically to tailor a big message that's going out to the whole company for a job role and if somebody is leading enablement giving the recommendation of okay how tailored and custom do you go.

12:19 Yeah, I do think to some extent it depends on the work in the specific roles so this is another case where deep gram has been really fun to learn and I think this is a trend in a lot of companies now where your customer success team is now technical account managers

12:36 or our customer success team is customer success engineers, and that role in general has become a lot more technical I think in the last couple of years.

12:45 And so, a deep gram specifically that's one thing that we've really leaned into is ensuring that the customer success team has a deeper technical dive. So we actually like more closely align their materials with our applied engineering teams materials and our app

13:02 sales team runs pre and post sales engineering. So, we're actually aligning those more closely than we are like the a and the CS materials.

13:15 So yeah, what what I would tailor is typically like our messaging right like how do you speak to a customer about whatever it is that we're learning about.

13:24 Definitely tailor, you know, our product understanding so our app and team needs to have a deeper understanding of the product than our account executive so we're going to get a lot more technical there.

13:35 And then, definitely I think the most important thing because this is always going to be the most important thing to me is how we measure it. Right, so that's that's so key is, you know, what I want a customer success engineer to be able to do with information

13:51 and ultimately what good looks like in their role is very different from what I want an account executive to be able to do with information. And that is part of the challenge of go to market enablement is I think like we are.

14:05 Everyone's comfortable saying like we want our sales to increase by X amount, but it's a little bit less comfortable to say, you know, we want our retention to look like this or we want, you know, our request for app inch to look like this

14:22 or we want to launch more forward deployed engineers or whatever the case may be it's, it's a little less comfortable because everyone likes to be tied directly to revenue, me too.

14:33 So you have to get a little more creative when it comes to how you're measuring things as well.

14:39 But yeah, I think ultimately just understanding.

14:44 And we talked a little bit about this just understanding what good looks like in their role is the most important thing and it

14:52 brings me back to that idea of just understanding what good looks like in general and how we were talking about like in AI like in this world where everyone is using AI like just knowing what good looks like is half the battle I think.

15:07Measuring a product launch across four teams

15:07 Yeah, it makes a ton of sense. I would love to hear about the metrics that you put on each role to understand if the enablement is moving the needle.

15:18 And also, this might be a little bit less structured but what data are you looking at to inspire new enablement programs as well.

15:29 Yeah, now I'm excited. So I, this will actually, this will all be public knowledge by the time this episode goes out but I'm going to use a specific example which is where we're preparing a product launch right now.

15:43 And so right now it's a secret but soon it won't be. But we've been preparing a product launch and so that's very much what's on my mind right now is like how are we going to measure the success of this product launch.

15:54 And so, for our account executives, it's, it's, and for SDRs it's pretty clear, right, like we want our SDRs to generate pipeline relevant to this new product that we're about to launch, and we want our sales team to sell this new product that we're about to launch, not very complicated.

16:14 And for our customer success engineer team here at DeepGram specifically you know they are not quota carrying they are not responsible for renewals but obviously they're still an integral part of our revenue organization.

16:25 So for them, it looks like, you know, creating opportunities for this new product right so they're actually kind of acting as pipe generation because they are mining their current customer base to find those new opportunities.

16:38 And that's what I'm looking for you know how many times did you speak about this in your conversations with your customers, and how many opportunities were you actually able to pass over for you know across sell.

16:49 For our applied engineers you know it's something like how many calls were you able to support right so still tied to revenue because ultimately those calls are tied to revenue and how much we sell, but it starts to get further away.

17:04 So that's those are some specific things that I'm looking at right now where I'm comparing you know what does this look like today and then after launch next week, what what does this start to look like and how does this grow over to name.

17:17 And then those are our big picture metrics you are lagging indicators and then for me I'm constantly looking at our leading indicators as well so I'm using our call intelligence platform to see how many times have they brought up this new product and conversation and when they do,

17:34 are they doing it proactively or are they doing it as a response to something. And when they do, are they then you know handling objections well or are they folding the second that something occurs.

17:44 So I'm looking at things like that to understand you know are the top tracks that we created working and things like that to see if we need to better enable on how we have those conversations and ultimately how we sell that particular product.

18:00When the launch is over: how to find the cracks

18:00 And so, it's a lot of fun. And that's obvious right like we have a product launch so it's very obvious to me that this is what we need to do when it comes to enable that but the second part of your question was, you know, when this product launches over and this

18:14 has kind of been my whole role since I started at deep gram was this product launch to my big product. And so, I don't want to be lost at sea in two weeks when the product launches over and I'm like, what should I enable on now.

18:28 So, that's what it gets even more fun and when you start to, you know, look for the cracks right.

18:38 And so you hear here are metrics on one thing or another whether it's customer retention or win rates or quota attainment or what have you, starting there and then like peeling back the layers to see where did the improvements come from.

18:53 So, if our retention is suffering, is it suffering in a particular industry, or is it suffering in customers that chose a particular product or is it suffering with customers that, you know, push tickets on this particular issue.

19:11 So, following that thread of like when we have a metric that suffering or less than ideal. Where does that thread take us when we start to pull back the layers and so that's something that's always been really really fun to me and that's another area where I've been

19:25 able to really lean into AI to start to better triangulate like the cause and effect of the things that we're doing.

19:34 So, for instance, right now, deep grim is in a really good spot. Like, I love it. I'm so happy because it's, it's one of those places where the issues are not obvious right like sometimes you start a new job and you're like, Oh, I have a lot more to do.

19:52What a QBR looks like for a technical buyer

19:52 And here it's less obvious and so that's been fun for me to figure out but one of the things is we, we sell to really technical people.

20:02 And so we don't do a lot of business reviews, because these people are super technical and they're like, whatever I just want to like play with the code.

20:10 Please. And so we're trying to create conversations on the customer success team where we can start to better understand our customers metrics for success and how we retain them ultimately and how we keep them happy and keep their accounts growing.

20:29 And so that's been a fun challenge to figure out like what is a QBR look like for someone really technical versus someone like in the CRM space who is in sales themselves and has done a million of these.

20:42 So that's a fun challenge I'm working on right now.

20:45 But yeah, it's been more difficult to find the cracks, which is a good problem to have.

20:53 Yeah, I imagine once things are in business as usual, you don't have a big product launch, a big SKO coming up or something where the whole organization is really changing, being proactive and looking for those opportunities to get those gains.

21:09 I think one of the things people don't have a strong appreciation for is very minor improvements on conversion rate and time and stage or total sales cycle can mean millions, tens of millions at scale to how your year turns out.

21:27 So I think looking for all of those little winning edges across a certain rep over here, a CSM over there, really add up in the grand scheme. It's optimization exactly because, you know, Brad, I think the entire team met their quota last year.

21:46 Every single person on the team. Really? Stunning. How many reps? That's insane.

21:51 I don't know. At the time, I was just looking at this yesterday. At the time, I was around 20. So it's a small team, but still.

22:00 I don't know if I've seen a team do that. Unless you're at, like, anthropic.

22:05 Yeah, yeah. So, Brad, but, yeah, so, like, people can walk in and say, like, there's nothing wrong here and there may be nothing wrong here, but there's still so much optimization to take place to ultimately grow our ARR.

22:24Building the ROI case for an enablement program

22:24 And that's what makes it fun. And then being really explicit about that, too, when you start a program or some sort of enablement effort, being really explicit about what this could potentially mean for the team.

22:41 And so it's similar to, like, an ROI that you would do if you were selling something, right? Like, here's the ROI of the enablement program that I'm trying to launch. If we're able to increase X by this conservative amount, here's what that will mean for our revenue.

22:58 Here's my, like, medium estimate. And here's, like, if we blow it out of the water and increase it by this amount, then this is what this could mean for our revenue.

23:08 And then I want to make it really personal, too. Like, I do that both for the entire revenue org, but then also, like, for each rep. Like, this is what it could literally mean for you and your quota attainment and your paycheck, your commission at the end of the day.

23:22 So being really explicit about it both helps me till it grilled me and get me excited about what I'm doing. But the same for the rest of the team, right? It gets them excited and it gets them bought in to say, okay, I don't really think that much about, you know, how I bring up this specific thing on calls.

23:43 But when you tell me that it could increase my win rates or increase whatever and that those are going to compound and compound and compound, people get a lot more excited.

23:56 And then the last thing I'll say on that particular topic, I'm just getting all excited and nerdy now.

24:05 That's what this podcast is for.

24:07 Yeah, in enablement. I think the other thing, and I talked about this in my interview because they asked me straight up, like, how do you get buy-in?

24:16 So that was part of what I said. But also, it's showing that off after the fact, too, and making sure that you are following those results and then saying, hey, remember that session we did?

24:28 You all increased by this and here's how much money you made. Like, go team, now listen to me the next time that I tell you to do something.

24:37 So, yeah, you have to have some early successes in order to get that buy-in for sure. But staying grounded in the metrics helps a ton.

24:46 Yeah, I think getting that buy-in upfront with the investment and enablement and showing the math behind the results, hey, if we can make these efficiency and effectiveness improvements, we can elevate the team to here.

25:00 Or even, hey, you're planning on tripling your sales team. I mean, even just maintaining some of these metrics would be a huge win at scale.

25:07Where enablement should report, and where it shouldn't

25:07 Yeah. So I would love your take on the best way to structure an enablement team. So there's early stage where it's like, hey, we have someone with an enablement title. That's great.

25:21 Yeah. As the teams grow, as things get more complex, what other type of roles do you like to have on the team? And then where do you like having this department report into? Is it reported to RevOps, directly to a CRO, products sometimes?

25:37 I love this question. I love this question. I'm very opinionated about this. So I've seen, you know, enablement report into many different functions.

25:49 I personally very strongly feel that it should report into the CRO, ideally. And, you know, again, like there is this difference between sales enablement versus like true go to market enablement.

26:04 And that's what I've done in my last few orgs is that true go to market enablement function and that especially should report directly to the person responsible for revenue, because that's what we're trying to do at the end of the day is increase our revenue, both through retention as well as increasing our sales.

26:23 So I do think it's a report into revenue. I think that reporting into RevOps is okay. I think I've seen that be a little a little bit of an issue, just because it can start to lean towards almost like a RevOps helper function, right?

26:46 Like we're doing this, you go tell everyone about it. We're doing this, you go tell everyone about it. And I do think it needs to have that seat at the table, especially for someone like me who is so passionate about like measurement and finding those cracks.

27:00 Like I want to do that work. I don't want to be told what to do. So for me, I want to report directly up. And then, you know, I've seen reporting into marketing a lot as well.

27:11 And I think that can work just because that's ultimately the mandate of marketing as well is to grow revenue. But I do think that there's a bit of a disconnect between marketing and the front lines when it comes to AEs and CS and things like that.

27:27 So yeah, CRO is definitely ideal for me. And then the other piece of your question was like, how do you build an enablement team out? And I think this one definitely more depends on the org. I'm a little bit less opinionated about this one.

27:43 You know, as I mentioned, I think that enablement at its heart is not really any different based on, you know, who you're enabling, right? So I've seen a lot of orgs do it by function.

28:00 So you now have CS enablement and you have sales enablement and maybe you have sales engineering enablement, SDR enablement, what have you.

28:09 I think that could work really well for some organizations, especially as those teams get really, really large and start to need more specialization when it comes to the content that is important to them.

28:21 But I think that very much depends on what your product is at the end of the day and what your sales motion and your retention motion ultimately looks like.

28:31 I've also seen it be more by, you know, the type of enablement function. So things like you've got someone who is in charge of instructional design and they're kind of creating slide decks and creating courses in the LMS and things like that.

28:45 And then you've got someone who's responsible for delivery. And then so more about what that person is an expert in when it comes to enablement.

28:55 I think that can work as well, depending on the org. I would say, again, for me personally, if I'm going to build out a team, I do think the easiest way to start is just bifurcating by roles and allowing people to like really embed themselves into that org.

29:13 And I think that's the piece of it that's really advantageous is, you know, you get really close to the CS team, you start to embed yourself into what they do, and they really come to trust you versus an instructional designer who people are not necessarily going to come to trust and see is their source of truth.

29:32 So that's that's what I tend towards, especially like as a word grows larger in those particular arenas.

29:42When is a company actually ready for enablement

29:42 What's your thought on, and maybe I'll go earlier stage, so they don't have enablement yet.

29:48 And let's say we would like this company to not totally hit a wall and then decide to get enablement, they want to be a little bit on the proactive side around it.

29:58 What kind of gauge do you have to say, this is when you should be bringing enablement and and this is, or maybe framed another way, any ratios to like GTM spend or revenue or headcount where, hey, if you cross these thresholds, you need enablement and see.

30:18 Yeah, you know, I think about this a lot because I think I've seen seen people be brought in far too late and far too early as well.

30:28 So it's something I thought about a lot for myself, even when I'm considering new roles.

30:33 I don't think it's necessarily like an ARR or even a team size. It's more about what your motion looks like at that point. So, for instance, people who are really like still running founder led sales, you're not ready for enablement yet.

30:52 Like you need to figure out what you actually want your sales team to look like and how you're going to hand over the reins to them before you ask someone to enable.

31:04 So I've even seen it be an attempt to transition between founder led sales and true sales led sales.

31:11 And I think that transition really needs to already have taken place.

31:15 So they're leaning on an enablement person to come up with that program. Exactly. And I don't think that works.

31:25 I think you need to have already put some trust in your salespeople before you bring someone in to enable them.

31:32The product marketing prerequisite

31:32 And then another piece I would say is strong product marketing fit and also a strong product marketing function.

31:42 I've seen enablement come in without that product marketing in place.

31:47 And so you don't really have a point of view yet on what you're selling. Right.

31:52 And so what I've seen there is by default enablement becomes product marketing as well.

31:57 And that's just too much for anybody. I want to hang on that one for a second, because I think a lot of people don't know what good product marketing looks like.

32:07 And so if you have an opinion on that and to look for that, to say like, hey, you should probably have these things going on before you really invest in enablement, what would that look like?

32:19 Great question. So this was like very much a criteria in my job search was like, I need to validate that they have strong product marketing in place.

32:30 And it's like, I love product marketers. They're the best partners in the world.

32:37 So as far as, you know, looking for what good looks like again, I think it's just like the heart of it.

32:45 Even if it's not like very sophisticated yet, if it's not a function that's really built out, the heart of it is someone on your marketing team who has a strong point of view about who your product is for.

32:59 Right. And so that's how it goes back to like product market fit.

33:02 Like I really strongly believe that our product is for this type of company or this type of person in B2C, which I've never worked in.

33:11 But that sounds like a whole different thing. Right.

33:15 But this is who our product is for. And this is the way that we want to speak about our product.

33:19 I think as long as you have like a strong point of view about that and someone who is ready to like actually go to bat for that point of view as well as like the bare bones of what you need in place.

33:32 If you're still trying to figure that out or you have someone who is maybe not willing to back that up yet, then I'm not ready to join you yet.

33:44 I'll go elsewhere.

33:47 Yeah. Call me when you're ready. Yes. Yes. Yeah.

33:51 Those are some good thresholds. So founder led sales has been passed down.

33:54 You have a proper operating sales team. You have product marketing in C or at least somebody filling the functions of that that has strong opinions about ICP and who the products for any other things that are like you should have this in place before you throw on the enablement accelerant.

34:11 Yeah. The last thing I would say is just, you know, whoever ultimately that function is going to report up to.

34:19 And I think it should be the CRO. But whoever it is, you know, that's a little a little less important.

34:26 But that person is just ready to put trust into an enabler is really what I look for.

34:34 So someone who is ready to say, I have done this, this and this with my team.

34:42 Here's what I've achieved so far. And now I need someone to come in and optimize that.

34:47 Right. Whatever that looks like. I trust you to optimize that is what I'm looking for.

34:55 It's going to sound like I'm Braille nosing here and maybe I am, but I love my boss and, you know, he I've been here for like not even two months.

35:06 And he said, that's fine. I trust you like 20 times and music to my ears.

35:13 So that's that's the last piece is someone who is willing to say that's fine. I trust you.

35:20 I think that's so important in any role and who you're reporting to tends to dictate your experience more than anything else.

35:27AI in enablement: what's working and what's risky

35:27 So I think that's super valid. I think something that has come up quite a bit, especially in the enablement front is pretty heavy use of A.I.

35:41 Some of it's good. Some of it's bad. What have been really helpful and productive applications of A.I. in the enablement space and what are some things that are creating risk in the function?

35:56 Another fun question. So, you know, this is another cool thing about deep gram, which is like, well, actually, I love you deep gram, but maybe there are some issues that are caused by this, too.

36:08 I'll tell you what they are. But, you know, deep gram, like, gives everyone free reign when it comes to using A.I.

36:16 Like, as long as we've done security review of it, you are encouraged to use it. All right.

36:22 And so that's one of the things that's been really cool is just this encouragement to explore and use it.

36:29 But it does create problems, too. And they're aware of this. We're all working on solving it.

36:34 But, you know, I think it's less about my personal usage and more about how the team is using it and ultimately ensuring that all of these amazing things that people are doing are sustainable.

36:51 So I see a lot of conversation on LinkedIn and what have you about, like, A.I. Slop. And I'm less concerned about that and more concerned about how we maintain what we're creating.

37:04 So we have so many amazing people. It's a really quite technical team, even down to like our account executives and our SDRs that are shipping websites that do things, right?

37:17 They're shipping web apps that, you know, crawl for prospects. And they're shipping web apps that create really amazing, you know, pricing pages that we're sending out to customers and different things like that.

37:32Who owns the tool when the pricing changes

37:32 But the second something changes, they become deprecated. And that's my biggest concern is, like, whose responsibility is that you've created this really cool tool to go in and update the pricing of this one particular product, because every person on the team is now using your pricing calculator.

37:51 And whose responsibility is it when our ICP changes to go in and fix your prospecting tool? And that's what makes me really nervous.

38:01 So it's amazing things. And I'm so glad that people are empowered to create their own things because I think that's going to make them better at their jobs and more bought in.

38:09 And it's going to help them throughout their entire careers. But I'm really nervous about maintenance.

38:16 So, you know, for us right now, like, we're literally just trying to take inventory is where that starts. Right. And start to create some systems where we can at least track what people are creating so that when things change, we can notify them.

38:34 Right. Oh, we know you have a pricing calculator. Here's this pricing change and we can monitor whether or not they've updated it. Things like that.

38:42 So the solution will evolve, I'm sure. But that's like the big problem on my plate right now that I'm trying to solve for because I don't I don't want to discourage people from creating really cool job aids.

38:54 But I do want to figure out how I can make sure that they're accurate.

39:00 And then the people who make really good ones. How do we share that with the rest of the team, too? I think I've seen that issue a little bit, too. Like, oh, it's like creativity. But like, how do I use Anthony's cool little thing that he built over there and then like share it and update data across things?

39:16 It's like that last mile. Turn this into an enterprise tool stuff. That's for sure for teams to do because right now it's like, you know, somebody should something amazing and they just send it in like one Slack channel.

39:29 I'm like, I don't know who adopted that. And I don't know how they're using it. And so, yeah, it's been a challenge. And so I've started to be like a little bit of a gatekeeper about it.

39:44 So like, if you create a really cool tool, share it with me first so that I can help you scale it so that all of that hard work you did is not just like traveling into the ether.

39:55 So we're working on it. But that is like, honestly, my biggest challenge right now is like both figuring out how we ensure things are well maintained and accurate.

40:07 And then like, how do we actually scale AI usage in a responsible way? Like far and away my biggest challenge.

40:16 Yeah, that's really interesting. And I think that's a whole new realm where enablement can lean in.

40:22 People probably weren't thinking about that. Like, hey, who's going to help our team use AI? One, teach them how to do things in a meaningful, efficient and compliant or safeguard way.

40:34 And then two, how do we sift through all of that to find the nuggets of gold that then we enable? That's a pretty big job.

40:42 I know because we we invest quite a bit of time into that internally here at LeanScale because we have people shipping things all over the place and like unbelievably cool stuff that somebody built and was creative and solved a real problem that we have.

40:59 But then it's like, all right, how do we get the entire company using that now? That's way harder than building the thing in the first place.

41:07 And it is not, I mean, obviously, this is true for everyone. But, you know, when I started doing enablement however many years ago, I didn't think I was going to be like figuring out how to properly ship AI tools, right?

41:25 And like worrying about how we're using it. But I guess nobody thought about how we were going to use AI, period.

41:31 So, but I think what I will say is I think for a lot of people that is still not on their radar and it absolutely should be like tomorrow.

41:44 So yeah, and then, you know, the other thing is like, does that fall under traditional, you know, go-to-market enablement? And what we have decided to do is hire ahead of AI enablement and I'll partner very closely with them on, you know, what that looks like.

42:01 But ultimately, you need someone to own that for the entire company, not just go-to-market. So it's absolutely an important go-to-market function, but it's an entire company issue. So it has to touch more than just enablement, for sure.

42:16 Yeah. Yeah. It's a huge, it's a huge problem that I know companies are doing everything they can to solve. I'm curious, since you're training on so many AI tools and helping people get enabled there, are there any go-to-market tools that are catching your eye recently?

42:32 Ones that you're really, really enjoying, whether it's specific to the enablement team, like to help run enablement or just tools you see your teams love using?

42:45 Yeah. Honestly, I, they are building so many things internally that we're, we're like solving all of our own problems. So I don't have a ton of guidance or advice when it comes to like external tools.

43:02 Because yeah, people are so inventive and so ready to create that we are solving so many of our problems that would have been traditionally solved by purchasing a software we're doing it ourselves.

43:17Build vs. buy: why she refused to vibe-code an LMS

43:17 I will say one thing that I did not DIY and I was asked to and encouraged to, and I said, no, thank you, was a learning management system. You know, part of what I've seen at DeepGram and other companies is people are spinning up so many tools.

43:37 And one of those that I saw a lot was like an AI roleplay tool, creating these really great roleplays that then just lived in a silo and in a vacuum. So we had like SDR roleplay tool and then an AE roleplay tool and a CS roleplay tool, and they don't talk to each other at all.

43:52 And so that was kind of worrisome for me. So that's, that's part of why I chose to not try to vibe code an LMS and ultimately choose one because we really need to be aligned on our messaging and we really needed a way to like show growth over time and ultimately track that to revenue.

44:11 So I did choose to purchase an LMS. So I will shout out letter AI is who we chose to use for that. And it is a really cool tool that is utilizing, you know, a lot of really cool AI functions made my life a lot easier because it generates a ton of content for you just based on like your factual input.

44:34 So been really cool for me personally. But yeah, we're solving a lot of things internally.

44:40 It's a very interesting time for that buy versus build conversation that comes up and I am seeing a lot of building.

44:49 So I know we are doing a lot of building. There's a handful of things where I'm like, no, I need this to be production grade and there's security clients that I have to really be mindful of.

45:00 There's like a couple of categories where I want the pros to do it. But there are so many things that you can just build on your own that it's really trimming down what the stack looks like.

45:11 It is. And I think it comes in all of your internal tools. Well, yes, actually.

45:16Cost of maintenance as the deciding test

45:16 But I think what it comes down to is like what you said, right? Like compliance and things like that. I think the way I think about it is like, is this customer facing or not? You know, if it is customer facing, then I think we probably do need to buy in most cases and hand that off to experts.

45:34 And then again, it also goes back to maintenance. That was a huge thing for me. Like, could I vibe code in LMS? Yes. Do I want to maintain it? Absolutely not.

45:44 So that's that's the other piece for me when determining like whether or not something should be built versus bought is like, what will maintenance look like?

45:53 And so I'm trying to really carefully scope out what that maintenance will actually look like and what the lift is there. And, you know, for like a pricing calculator, that's easy.

46:02 We just update the pricing. No problem. That maintenance is fairly simple. For an LMS? No, not so much.

46:10 Yeah, I think cost of maintenance is a good way to think about whether you should build or buy two. For sure.

46:16 I'm curious. There's so much to keep up with in this space. We're in tech. We're in go to market. We're deep in AI. Where are some areas you go to stay fresh, do your own learning? What resources are you consuming to keep you as current as possible?

46:38 Yeah, I love I love this part of my job, and I do consider part of my job for sure. And I do it on company hours for sure, because it's part of my job.

46:51 You should. Yeah, that's actually really important. Would your boss not want you learning? And is that hour not worth it? Anyway, yes, you should be.

47:01 Exactly. Yeah, but, you know, for enablement specifically, there are a couple of communities I'm part of sales enablement collective and sales enablement squad as well.

47:11 So they're on Slack, and I'm just like constantly trolling them and seeing what people are working on. Obviously, LinkedIn is huge. And then podcasts. Yeah, love podcasts.

47:23 Right. I like to I'm weird, though, I like to read information, which is is weird because I work for, you know, speech to text and text to speech API company.

47:36 And so it's really funny, like part of what happens here is people will use our APIs to create a podcast like, hey, this is the new product update, listen to this podcast.

47:48 I'm like, no, I cannot for the life of me sit and listen for 10 minutes. So I use deep gram to turn everything into reading material. That is my default. So I love podcasts, but I read them.

48:03 Oh, I love that. You have the optionality to put it in whatever mode that you that you want to get some information in. Yes, I'm like, give me that transcript. I guess I'm just impatient. I think it's the biggest thing. Or like, I will 100% be putting it on 1.5 X if I am going to listen to it.

48:20 Well, I think it's really important to stay plugged in as much as you can, whether it's podcast, whether you're converting those podcasts into a transcript and reading them or getting plugged into those communities, too, because I don't think there's one central source of truth to learn all of this from.

48:35 So you really have to work with multiple sources and start to come up with your own opinions. But Cheyenne, I really appreciate everything that you shared. I think anybody who's thinking about going into enablement, thinking about onboarding enablement or sitting in an enablement role right now will have so much to learn.

48:52 And I really appreciate the perspective you bring from the classroom into the role, and then how you should structure the team, where it should report, the metrics you should be measuring and the things that inspire you to help make the go to market organization more efficient and more effective.

49:08 I think there's so much learned from it. So I appreciate everything you shared on the podcast and I can't wait to watch what you do next and follow Deep Brand.

49:17 Yes, we have got some exciting stuff coming up.

49:22 It's, you know, at the end of the day, like that's that's the best part of the role is like seeing the things that you work on come to fruition. So I'm super excited about it.

49:33Advice for anyone considering enablement

49:33 And, yeah, you know, you mentioned people considering enablement and, you know, in the sea, like, if that's what drives you, like, do it, right, like, it, I think it can be seen as this like little support role this person who does sessions like no if you are interested in making real

49:56 change and tying the work that you do to the growth of an organization. It's actually a great place to be if you're willing to put in that work and look at the data.

50:10 You can absolutely see the difference, both in the results and just in how a team is operating when you have great enablement and see for sure. Totally agree. Or if you're a fourth grade math teacher, maybe consider a quick career change.

50:27 Yes, let me know. I'll help you out. It's not that hard.

50:34 Well, Shane, thanks again and can't wait to see how your product launch goes and what you do next.

50:39 Yeah, thank you so much. It's been fabulous. I appreciate it.