The LeanScale Podcast · Episode 122

Your AI Strategy Is a Data Model Problem

Jake Toepel and Anthony Enrico's Updata Partners CEO Summit talk on why a smarter model will never draw you the map: the semantic layer, the context graph, the four-level maturity curve, tokenomics, and a ten-week roadmap that is more than half alignment

Jake Toepel · Chief Technology Officer · LeanScale Hosted by Anthony Enrico
Published Updated 00:45:52 42 min read 8464 words
Executive Summary

The one-paragraph brief, extended

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

Jake Toepel is co-founder and CTO of LeanScale. He and Anthony Enrico gave this talk to a room of CEOs at the Updata Partners CEO Summit, and it resonated enough that they re-recorded the full presentation for the podcast. The thesis is in the title: your AI strategy is not a model problem, a budget problem or a prompting problem. It is a data model problem, and it is the one part of the stack no vendor is going to solve for you.

The talk opens on a question that sounds easy — which of my customers are likely to expand this quarter? — and takes it apart. The AI has to know what a customer is and where the source of truth lives, whether expansion means committed contracts or more usage, and what drives likelihood in your business. Jake's metaphors make the point that more intelligence does not fix this. An F1 car with no map drives for miles in the wrong direction. Einstein hired as a GTM analyst on day one doesn't know which Acme is the real Acme across your marketing automation, CRM and product database. Coaching Usain Bolt does nothing when a toddler runs the second leg. And because every session starts fresh, every day is the model's first day on the job.

Anthony anchors why it matters in yield. In a $20 million plan with a 20% conversion rate, one point of conversion is another million dollars, and a sales cycle one day shorter can pull a quarter of a million dollars into the quarter. His claim is that the value companies can extract from AI today is capped by the data model underneath it.

The fix has two layers. The semantic layer — LeanScale's internal GTM brain — is business logic written down and codified in a repo, GitHub in LeanScale's case, with one owner per metric. Without it, a query that fans out across opportunity line items turns a $10,000 deal into a $30,000 one in the forecast. The context graph connects records across and within systems, and Jake's advice is to start by making the CRM the first context graph. That is also a tokenomics argument: clean associations let an agent hop through data instead of indexing the whole CRM, which matters once the $200 plans that deliver $5,000 of usage end and a $25,000–$30,000 monthly bill lands on the CFO's desk. The rule underneath all of it is the one Jake states flatly: do not let AI author your business logic.

Jake then walks the maturity curve — centralized, resolved, defined, retrievable — from a warehouse and BI layer, through identity resolution and 20 to 30 agreed, version-controlled metric definitions, to cheap retrieval. Anthony argues that building agents is the cheap part once the data model exists; starting with the agent means reverse-engineering a mini data model for every one. Jake adds that it democratized building at LeanScale, down to approving Anthony's pull requests. The deployment plan is ten weeks with five roles, and more than half of it is alignment: what a customer is, what an MQL is, how ARR is counted. The two ways it fails are no single owner per definition and starting with the agents.

Key Takeaways

15 things worth stealing

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

01

A simple question hides several undefined terms

"Which of my customers are likely to expand this quarter?" looks like something you should be able to type into Claude connected to Salesforce, HubSpot and Gong. But the AI has to know what a customer is and where that source of truth lives, whether expansion means committed contracts or more usage, and what actually drives likelihood in your business.

Why it matters: Before judging an AI tool on the answers it gives, list the definitions a question depends on. If your team can't answer them consistently, the model will fill the gaps with confident guesses.

Revenue ExecutivesRevOps LeadersFounders
02

More horsepower won't build the map

Jake admits the team thought, even six months earlier, that the next model release would make everything just work. It didn't. Models are already trained on essentially all public information; what they lack is the context that makes your company unique. An F1 car with no map, an Einstein on his first day, and a Usain Bolt relay with a toddler on the second leg all make the same point.

Why it matters: Waiting for a smarter model is not a strategy. The context problem is categorically yours to solve, and it stays unsolved no matter which model you plug in.

FoundersRevenue ExecutivesRevOps Leaders
03

Every day is the model's first day

Jake describes hiring AI models every single day, with each day as their first day of onboarding. Without a shared foundation, teams stay stuck in a constant cycle of informing the AI, telling it what's going on and bringing it up to speed.

Why it matters: Build the foundation once so any model or tool you bring on operates from the same context, rather than re-onboarding it in every prompt.

RevOps LeadersRevenue Executives
04

The reason to do this is yield from the GTM machine

Companies invest tens of millions of dollars in go-to-market organizations and often don't measure the yield. Anthony's math: in a $20 million plan at 20% conversion, one extra point of conversion is another million dollars, and cutting one day from the sales cycle can pull a quarter of a million dollars into the quarter. Doing both at once compounds.

Why it matters: Tie AI investment to conversion rate and time in stage, not to activity. Anthony's claim is that the value you can extract from AI right now is capped by the data model you have in place.

Revenue ExecutivesFoundersSales Leaders
05

The semantic layer is your business logic, written down and owned

LeanScale calls its semantic layer the GTM brain: business logic and context codified in a repo, GitHub for LeanScale, though a Google Drive folder works. It holds everything from brand messaging and design kits to who LeanScale sells to, what good looks like on each project, and exactly what win rate and bookings mean. You don't need a fine-tuned model or a data science team.

Why it matters: Each metric needs one owner controlling the definition, so CS, sales and marketing work from the same foundation instead of arguing about whose number is right.

RevOps LeadersRevenue ExecutivesFounders
06

Without definitions, a $10,000 deal reports as $30,000

Jake has seen this across multiple clients. Ask for forecasted ARR, and the AI runs simple SQL, gets numbers back and reports success. It doesn't know that opportunity products or usage are fanned out across several line items, so a $10,000 deal shows up as $30,000.

Why it matters: An AI that returns numbers is not an AI that returns correct numbers. Codifying how each metric is calculated, including which records to count, is what prevents confident over-reporting.

RevOps LeadersRevenue Executives
07

Make the CRM your first context graph

The context graph connects the data points gathered through enrichment, events and outreach so the AI isn't guessing which records belong together. Jake frames it as crawl, walk, run and says most companies should start with the CRM: contracts tied to the right opportunities, opportunities to the right accounts, and accounts with the right contact roles.

Why it matters: Knowing what not to connect matters just as much. Internal calls attached to a customer record because someone said the customer's name inflate the picture and need to be fixed before you trust the CRM.

RevOps LeadersCustomer SuccessSales Leaders
08

Tokenomics: the cheap-usage era will end

Six months earlier LeanScale had a token leaderboard and wanted the number to climb; now what matters is output relative to tokens spent. Clean associations let an agent make quick hops through data instead of indexing the whole CRM. Jake calls it a matter of when, not if, providers end the plans where $200 buys $5,000 of usage, and Anthony notes Anthropic and OpenAI are already cutting token limits on some plans.

Why it matters: Fix the data model while usage is still subsidized, so you avoid the fire drill of a first $25,000–$30,000 monthly bill and a CFO asking what gets cut to pay for it.

FoundersRevenue ExecutivesRevOps Leaders
09

Never let AI author your business logic

Jake's firmest rule. A model optimizing for the fastest route will reach for standard industry practice and ship it, which fails for anyone not running "the most vanilla basic lemonade stand SaaS company in the world." Write definitions in plain English first. AI can then help convert a Google Doc into YAML and push it to GitHub.

Why it matters: Never ask the AI to look at your CRM and tell you what a good renewal looks like. That has to come from your historicals and the people working those accounts every day.

RevOps LeadersRevenue ExecutivesCustomer Success
10

Start with the metrics you defend in the boardroom

Setup is cheap: an LLM license and a CRM are enough to start. Don't try to define every metric at once. Jake ties it back to the toughest meetings, the board meetings, and starts with the metrics you'll have to speak to this quarter, then adds the ones that lift conversion or speed up stages.

Why it matters: The owner of a metric should be whoever has to defend it in a board meeting, because they need full confidence in how it was defined. Most definitions should sit with a functional leader, not RevOps.

Revenue ExecutivesRevOps LeadersFounders
11

The maturity curve: centralized, resolved, defined, retrievable

Many companies are at level one: a warehouse and BI layer, but nothing defining where things live. Level two resolves identities, so Acme Inc., Acme Co. and Acme, or Amazon, AWS and Amazon Logistics, map to one canonical key. Level three defines the 20 to 30 key metrics, agreed and version-controlled. Level four makes insight retrievable quickly and cheaply.

Why it matters: The extra-credit version is a vector database or a Postgres database on Supabase alongside the product warehouse. But Jake's advice is that most teams should start by cleaning and associating inside the CRM, where the business already runs.

RevOps LeadersRevenue Executives
12

Agents are the cheap part; the data model is the hard part

Once the data model exists, building agents means asking Claude what agent it can build for a given job and pointing it at the data. Start with the agent instead, and you have to reverse-engineer the data model it needs, ending up with hundreds of mini data models, one per agent.

Why it matters: The payoff is speed and trust: production-grade agents in half a day that can be shared across the company. Anthony's example is the customer health model he couldn't build with 40 CSMs at Emailage without a full data science team.

RevOps LeadersCustomer SuccessRevenue Executives
13

A shared foundation democratizes the build

For a long time, Jake was the company's vibe coder and everything ran through him. Once everyone was connected to GitHub with shared design kits, Anthony started submitting pull requests. Jake says he would once have called anyone crazy for predicting he'd be approving Anthony's PRs.

Why it matters: When every builder works from the same foundation, the CTO can trust the output without rebuilding it each time, and anything useful can go to the whole company quickly.

FoundersRevenue Executives
14

More than half the roadmap is alignment

Anthony is explicit that the engineering isn't that hard. The hard part is agreeing on definitions, on the source of truth for each one, and on the owner. What is a qualified opportunity? What is an MQL? What is a customer: the Salesforce field, an ERP account, an invoice, pilot accounts, customers who have given churn notice? How is ARR counted with usage-based products?

Why it matters: Jake borrows Amazon's "disagree and commit": trust the owner, commit to the definition, and bring your insights to improve it rather than defending a private spreadsheet.

Revenue ExecutivesSales LeadersMarketing LeadersCustomer Success
15

Five roles, ten weeks, two ways it fails

The team is an executive sponsor with budget and authority (usually the CRO, maybe the CEO), RevOps as the linchpin, an analytics engineer, a platform engineer, and whoever runs the CRM. The roadmap runs about ten weeks, with more than half spent on alignment before the engineering and agent building start.

Why it matters: The two failure modes are not having a single owner per definition, which is where the wheels fall off, and starting with agent building before the data exists for agents to use.

Revenue ExecutivesFoundersRevOps Leaders
Frameworks Discussed

11 named models

Every framework Jimmy names, defined and time-stamped.

Horsepower vs. Context (F1 Car, Einstein, Usain Bolt and the Toddler)

06:07

Model intelligence and business context are separate problems. Vendors keep adding horsepower; only the company can supply the map. Anthony's summary: more horsepower won't build the map, more intelligence won't give you the context, and making Usain Bolt faster won't fix the toddler leg.

Jake uses three images. An F1 car is a highly tuned machine, but without a map the driver can go miles in the wrong direction. Einstein hired as a GTM analyst doesn't know which Acme is the real Acme across the marketing automation platform, CRM and product database, so he infers the middle. In a two-leg relay, coaching Usain Bolt gains nothing when a toddler runs the second leg, stumbling and getting distracted. The takeaway is to coach the second leg: give the model your context.

Every Day Is the Model's First Day

08:25

You are effectively hiring your AI models every day, and each day is their first. Without a persistent foundation, teams are stuck re-onboarding them over and over.

Jake presents this as an extension of the Einstein example. The goal is to get out of the constant cycle of informing the AI and bringing it up to speed, so that whatever model or tool you bring on runs from the same consistent foundation.

Maximize Yield From the GTM Machine

09:36

The most effective way to get more out of a go-to-market investment is to raise yield: increase conversion rates and reduce time in stage. Small gains compound, and they are the business case for investing in the data model.

Anthony's numbers: in a $20 million plan with a 20% conversion rate, one point of conversion adds a million dollars to the plan, and a sales cycle one day shorter can pull in a quarter of a million dollars, which may decide whether you make the quarter. His argument is that the ceiling on AI value today is set by the data model, so those gains stay out of reach until the model is fixed.

The Semantic Layer (the GTM Brain)

12:32

All of your business logic and context, written down and codified in a repository your agents can read, with one owner per metric.

LeanScale uses GitHub because it's free to start, native to the major LLMs, and easy to share and automate around; a shared Google Drive with the right folder structure also works. Contents range from brand messaging, design kits and the ICP to precise definitions of win rate, bookings and how to value different pipelines and segments. Each metric is a YAML file naming the metric, its owner and its calculation. Changes go through pull requests that notify the owner, who approves or rejects them.

The Context Graph (Start With the CRM)

15:17

Connecting the dots across and within systems, so the AI knows which records belong together when it looks at a person or account. The crawl-walk-run starting point is to make the CRM your first context graph.

Contracts should be tied to the right opportunities, opportunities to the right accounts, and accounts to contacts with defined roles. Add key product and usage data where it's missing. Jake adds the negative case: decide what not to connect, and fix associations like internal calls attached to a customer record just because someone said the customer's name. Semantic layer plus context graph is what turns a response into something a human can act on: the definitions flatten the data into cohorts, and the graph provides the receipts.

Tokenomics: Output per Token

16:38

Measure AI by output relative to tokens spent, not by volume of usage, and design the data so agents can hop between connected records instead of indexing whole databases.

Six months earlier LeanScale had a token leaderboard and wanted it to climb. Now the priority is efficiency, because providers are expected to end heavily subsidized plans. A distilled data model, built with ETL tools such as Polytomic's harbors or by keeping only the key fields instead of 500 custom opportunity fields, gets more out of every token. Jake's warning is the first $25,000–$30,000 monthly bill landing on the CFO's desk.

Never Let AI Author Your Business Logic

21:30

Humans write definitions in plain English. AI may format them (Google Doc to YAML to GitHub), but it must never decide what a metric or a good renewal means.

A model heading for the fastest route from A to B, especially one optimizing on tokens, will reach for standard industry practice and ship it. That only works for the most vanilla SaaS business. Definitions have to come from your historicals and the people working the accounts every day. Jake says AI is not there yet, and he doesn't think it ever will be.

Boardroom-First Metrics and Ownership

22:55

Define first the metrics you'll have to defend in the board meeting this quarter, and make the owner of each metric the person who has to speak to it there.

Jake starts with the toughest meetings, board meetings, and only then adds the metrics that lift conversion or speed up stages. Ownership follows the same logic: whoever defends the number needs full confidence in how it was defined and approves any change to it. Anthony adds that most definitions should sit with a functional leader — the VP of Sales owns qualified opportunity, the VP of Marketing owns MQL — rather than with RevOps.

The Data-Model Maturity Curve: Centralized, Resolved, Defined, Retrievable

26:38

A four-level progression. (1) Centralized: warehouse and BI layer in place. (2) Resolved: identities deduplicated to one canonical key per account across systems. (3) Defined: 20 to 30 key metrics defined, agreed and version-controlled, each naming the column and filters to use. (4) Retrievable: clean associations and distilled data give quick, cheap retrieval.

Jake sees companies investing in data infrastructure earlier, but most stall at level one without defining where things live. Level two is plain deduping; the Acme and Amazon/AWS/Amazon Logistics examples show why a shared key such as domain or CRM record ID matters. Level three is where LeanScale pushes clients, and it's mostly an alignment problem. Level four can extend to a vector database or a Postgres database on Supabase next to the product warehouse, but most teams should start by cleaning and associating inside the CRM, where the business already runs.

Data Model First, Agents Second

30:54

Build the data model once so any agent can run on it. Starting with the agent means reverse-engineering a bespoke data model for every agent you build.

With a strong data model, building agents is the cheap part: you ask Claude what agent it can build and point it at the data. Production-grade, shareable agents take half a day. Agent-first work leaves each agent manually wiring itself to every source of truth, producing hundreds of mini data models. It's also one of the two named failure modes of a deployment.

The Ten-Week Roadmap and Five Roles

41:58

A roughly ten-week deployment staffed by five roles: an executive sponsor (usually the CRO, possibly the CEO), RevOps, an analytics engineer, a platform engineer, and whoever runs the CRM. More than half of the time goes to alignment before engineering and agent building.

The sequence is: agree on definitions, sources of truth and owners; codify and store them; connect and deduplicate the data; then build agents. The executive sponsor provides budget, tools and people's time. RevOps is the linchpin because it already holds much of the business context. Anthony presents the plan as something to copy and tailor. It fails in two ways: no single owner per definition, or starting with agent building.

Best Quotes

20 lines worth clipping

Pulled verbatim. Copy or share any of them.

“The model is already trained on all the publicly available information that's ever been created in history. It's a mind boggling amount of information. But what it doesn't have is the context and insights that make your company unique.”
Jake Toepel 05:43
“But an F1 car, if you don't give the driver a map, he's going to have no idea where to go, right?”
Jake Toepel 06:21
“He doesn't know which ACME is the real ACME across all of your different systems.”
Jake Toepel 07:04
“You're hiring these AI models every single day. Every single day is their first day that you're onboarding them.”
Jake Toepel 08:25
“More horsepower isn't going to build the map, more intelligence isn't going to give you the context, and then making Usain Bolt run faster isn't going to solve the toddler leg.”
Anthony Enrico 09:12
“If you're in a $20 million plan with a 20% conversion rate, increasing the conversion rate by one point will give you another million dollars in the plan.”
Anthony Enrico 10:32
“The ceiling of what value they could be extracting out of AI right now is completely capped and limited by the data model they have in place.”
Anthony Enrico 11:42
“So now a $10,000 deal looks like a $30,000 deal in your forecast.”
Jake Toepel 15:05
“We had a big token leaderboard and all we wanted to see was that number keep climbing. And now what we want to see is the output relative to the number of tokens.”
Jake Toepel 16:38
“It's a matter of when not if. We know that these providers are going to pull the rug out on these gravy train max plans that, you know, for $200, you get $5,000 worth of usage.”
Jake Toepel 18:33
“So an account that has 150 touch points looks great until we start to look and say, no, those are support tickets that haven't been answered.”
Jake Toepel 20:11
“Do not let AI author your business logic. It is not there yet.”
Jake Toepel 21:30
“Unless you are running the most vanilla basic lemonade stand SaaS company in the world, that is not going to work for you.”
Jake Toepel 21:53
“But the ones that you really want to make sure you have confidence on are the ones you have to defend in the board room.”
Jake Toepel 23:17
“If you would have told me six months ago, even that I'd be approving Anthony's PRs, I would have told you that you were crazy. But here we are.”
Jake Toepel 33:42
“Literally half of this is an alignment problem. So the engineering here is not that difficult.”
Anthony Enrico 34:53
“What is a customer? And how do I know? Is it this field that says customer on Salesforce? Is it they have an account in our ERP? Is it that they've had an invoice?”
Anthony Enrico 36:29
“If you've ever walked into a meeting and tried to defend a number that you don't have context on, that is not a fun razzle dazzle game.”
Jake Toepel 39:48
“The biggest one is not having a single owner for definition. That's really where the wheels fall off on this.”
Anthony Enrico 43:13
“Semantic layer, write down your definitions, find a good place to store it that you can point your AI to. Context graph, connect the dots of your data between systems, even within systems.”
Anthony Enrico 44:07
Practical Advice

What should you actually do?

The playbook, split by the seat you sit in.

Revenue Executives

  • Before asking AI a business question, list the definitions it depends on (customer, expansion, likelihood) and check whether your team agrees on them.
  • Frame the AI investment as yield: a point of conversion and a day off the sales cycle, compounded, rather than a count of AI activity.
  • Sponsor the effort with real budget, tools and carved-out time; typically that sponsor is the CRO or CEO.
  • Assign each metric one owner: the person who will defend that number in the board meeting.
  • Practice disagree-and-commit on definitions: commit to the owner's version and improve it, rather than defending a private spreadsheet.
  • Get ahead of token costs now, before subsidized plans end and a five-figure monthly bill lands on the CFO.

RevOps Leaders

  • Start the semantic layer with the 20 to 30 metrics leadership defends in the boardroom, not every metric ever calculated.
  • Write definitions in plain English first; use AI only to convert them into YAML and push them to a repo.
  • Store each metric definition with its owner, the column to use and the filters to apply, and route changes through pull requests the owner approves.
  • Make the CRM the first context graph: contracts to opportunities, opportunities to accounts, accounts to contacts with defined roles.
  • Resolve identities to one canonical key, such as domain or CRM record ID, across every system before trusting account-level AI answers.
  • Remove bad associations too, such as internal calls attached to a customer record because someone mentioned the customer's name.
  • Give agents a distilled data set (key fields only, via a governed layer) rather than raw access to hundreds of custom fields.

Sales Leaders

  • Own and document what counts as a qualified opportunity; don't leave it to RevOps or to the model.
  • Check forecast queries for fan-out across opportunity products or line items before trusting AI-generated ARR numbers.
  • Measure the payoff in conversion points and days removed from the sales cycle.

Marketing Leaders

  • Write down one definition of an MQL, agree on it, and stay consistent with it.
  • Change the MQL definition through a reviewed change the owner approves, for example tightening over-qualification quarter over quarter.

Customer Success

  • Settle what a customer is: the CRM field, an ERP account, an invoice, pilots, accounts that have given churn notice.
  • Classify touch points as good or bad before using touch-point volume as a health signal, because 150 touches can be 150 unanswered support tickets.
  • Build customer health and expansion signals on the shared data model instead of an ad hoc analysis each quarter.
  • Define what a good renewal and a bad renewal look like from your own historicals rather than asking AI to infer it from the CRM.

Founders

  • Don't wait for the next model release to fix answers that are wrong because of missing context; that is yours to solve.
  • Start with what you already have: an LLM license and a CRM are enough to begin.
  • Sequence the work as definitions, then data, then agents, and expect more than half of a roughly ten-week effort to go to alignment.
AI Takeaways

How AI actually changes GTM

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

The thesis

A smarter model will not fix answers that are wrong because of missing context. The value a company gets from AI in go-to-market is capped by its data model: a human-authored semantic layer of owned definitions and a context graph of properly connected records. With both in place, agents become cheap, trustworthy and token-efficient.

Agent & automation ideas

  • An expansion-likelihood agent that answers from agreed definitions of customer, expansion and the drivers of likelihood.
  • A deal-risk agent that weighs touch-point sentiment and separates unanswered support tickets from healthy engagement.
  • A customer health agent built on the shared data model, flagging problems early and teeing up likely expansions.
  • A forecasting agent that follows the codified ARR and bookings definitions, avoiding line-item fan-out.
  • A deduplication and identity-resolution agent that maps variant account records to one canonical key.
  • A definition-change reviewer that routes pull requests on metric YAML files to the named owner for approval.
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

$1M
Value of one conversion point

In a $20 million plan with a 20% conversion rate, increasing conversion by one point adds another million dollars to the plan.

$250K
Value of one day off the sales cycle

Reducing the sales cycle by one day can pull roughly a quarter of a million dollars of revenue into the quarter, in the same $20 million plan example.

$10K deal reported as $30K
Forecast inflation from fan-out

When opportunity products or usage fan out across line items, a naive AI query over-reports a $10,000 deal as $30,000 in the forecast.

$200 for $5,000 of usage
Subsidized AI plan economics

Jake's description of the max plans he expects providers to end.

$25,000–$30,000
Expected monthly AI bill after subsidies end

The first monthly bill Jake warns teams will have to explain to their CFO if they haven't optimized their data for tokens.

150
Touch points that looked healthy

An account with 150 touch points looks great until they turn out to be unanswered support tickets.

500
Custom opportunity fields

The kind of field sprawl Jake doesn't want AI digging through; a distilled set of key fields gets more out of each token.

20–30
Key metrics to define

The number of key metrics LeanScale pushes clients to have defined, agreed and version-controlled at level three of the maturity curve.

4
Maturity curve levels

Centralized, resolved, defined, retrievable.

About 10 weeks
Deployment timeline

The copyable roadmap, with more than half of it spent on alignment.

5
Roles needed

Executive sponsor, RevOps, analytics engineer, platform engineer and the CRM owner.

Half a day
Time to deploy an agent on a solid data model

Production-grade, shareable agents once the data model is in place.

40
CSMs Anthony managed at Emailage

Spread around the world and serving hundreds of customers, with no reliable customer health model.

10
Pre-built agents in the giveaway

Included in the resource pack alongside the presentation and the metric definition worksheet.

Entities

Companies, people & tools mentioned

Auto-extracted and linked into the knowledge graph.

Companies

LeanScaleGTM Operations

Jake and Anthony's company. Internally it runs a semantic layer it calls the GTM brain on GitHub, moved from a token leaderboard to output per token, and let non-engineers such as Anthony ship agents and automations through pull requests. The talk closes with LeanScale's resource pack, its MCP (playbooks, benchmarks, studies and podcast transcripts) and a diagnostic offer.

12:32 · 17:40 · 33:19 · 34:19 · 44:58Company →
Updata PartnersVenture Capital / Growth Equity

Host of the CEO Summit where Jake and Anthony first gave this talk to a room of CEOs, before re-recording it for the podcast.

00:00Company →
EmailageRisk & Fraud

Where Jake and Anthony worked together before LeanScale. Anthony ran customer success there for part of his time, with 40 CSMs worldwide and hundreds of customers, and found a reliable customer health score almost impossible without a full data science team. Jake uses the same 40 CSMs to argue that undefined terms aren't a new problem AI invented.

31:41 · 37:47Company →
PolytomicData Integration / Reverse ETL

An ETL tool LeanScale is partnered with and uses internally. Its harbors model distills approved data into a governed layer with its own context layer and skills, so agents only see approved data and anyone who connects runs the same skills on the same data. Anthony mentions its founder and CEO giving an upcoming conference talk.

24:30 · 25:17 · 29:48Company →
AmazonE-commerce / Marketplace

Used twice by Jake. First as an identity-resolution example: Amazon, AWS and Amazon Logistics can share a domain, so an AI may look at AWS when it should look at Amazon. Then for its value of disagree and commit, which he recommends for metric-definition meetings.

27:49 · 29:16Company →
AnthropicFrontier AI

Named alongside OpenAI as a provider already starting to cut token limits on some plans, part of the argument that subsidized AI usage will end.

17:54Company →
OpenAIFrontier AI

Named alongside Anthropic as a provider already starting to cut token limits on some plans. Its next model launch is the kind of release Jake says teams wrongly expected to make everything just work.

05:31 · 17:54Company →

People

Tools & software

ClaudeAI Assistant

The everyday AI client in the talk: teams handing out Claude licenses to push usage, the expansion question typed into Claude connected to the CRM, and the easy half of the work, asking Claude what agent it can build once a data model exists. The giveaway deck can be converted to Markdown and dropped into Claude.

ChatGPTAI Assistant

Paired with Claude as the tools companies are moving from maximizing usage of to using optimally; a new ChatGPT model is one of the releases teams expected would make everything just work.

SalesforceCRM

One of the CRMs an AI might be connected to when asked the expansion question, and one candidate source for what counts as a customer (a field that says customer on the account).

HubSpotCRM

Connected alongside Salesforce in the expansion-question example, and a source of campaign data that ETL tools can blend with Gong calls, Clay data and CRM data into a unified model.

GongRevenue Intelligence

The transcript source in the opening example and Jake's example of a tool that has done sentiment analysis well for a long time. Touch points arriving through email or Slack don't carry that sentiment by default.

ClayGTM Data / Enrichment

Enrichment data that ETL tools can blend with HubSpot campaigns, Gong calls and CRM data into a distilled model for AI to query.

GitHubDeveloper / Code Hosting

Where LeanScale keeps its semantic layer: free to start, native to the major LLMs with clean connectors, private or shared, and easy to automate around. Metric definitions live there as YAML with owners who approve pull requests, and connecting the whole team to it is what let Anthony start shipping PRs.

Google DriveFile Storage / Collaboration

Jake's lower-tech alternative to GitHub for housing the semantic layer, as a shared drive with the right folder structure. A Google Doc is also where he suggests first writing definitions in plain English.

SupabaseDatabase

Jake's example of a cloud database, running Postgres, that could host a vectorized database alongside the product warehouse at level four of the maturity curve. He treats it as extra credit.

PostgreSQLDatabase

The database Jake mentions running on Supabase for the extra-credit retrieval layer next to the product warehouse.

VascoSemantic Layer

Introduced by Anthony as a go-to-market platform that forces you to build your semantic layer and gives you the context graph in one. Setting it up produces both, and you can then point your AI at Vasco to ask questions.

Methodologies referenced Metric definitions as codePlain English first, AI formatting secondIdentity resolution to a canonical keyTouch-point classification and cohort analysisDistilled data layer for agentsTen-week deployment
Frequently Asked Questions

Straight answers

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

Why does AI give confident but wrong answers to go-to-market questions?

Because it lacks the business context the question depends on, not because the model isn't smart enough. LeanScale CTO Jake Toepel and co-founder Anthony Enrico use the question "which of my customers are likely to expand this quarter?" to show it. To answer, the AI has to know what counts as a customer and where that source of truth lives, whether expansion means committed contracts or more usage, and what drives likelihood in that particular business. Models are trained on essentially all public information but not on how your company defines and runs things, so they fill the gaps with plausible guesses. In one example Jake has seen across multiple clients, an AI forecast counted opportunity line items separately and reported a $10,000 deal as $30,000.

What is a semantic layer in GTM?

A semantic layer is a company's business logic and context written down and codified where AI agents can read it. LeanScale calls its own the GTM brain. It holds precise definitions of metrics such as win rate, bookings, MQL and ARR, along with context like the ICP, product catalog and brand messaging. LeanScale keeps it in GitHub, with each metric as a YAML file naming the metric, its owner and its calculation; a shared Google Drive with the right folder structure also works. Each metric has one owner, typically the person who has to defend it in a board meeting, and changes go through pull requests that the owner approves. Humans write the definitions in plain English, and AI only helps format them.

What is a context graph and where should a company start?

A context graph connects records across and within systems so an AI knows which data belongs to which account, person or deal instead of guessing. Jake Toepel recommends a crawl-walk-run approach that starts with the CRM as the first context graph: contracts tied to the right opportunities, opportunities to the right accounts, and accounts to contacts with defined roles, with key product and usage data added where it's missing. Deciding what not to connect matters as much, such as internal calls attached to a customer record because someone mentioned the customer. Clean associations also save tokens, because an agent can hop through connected records instead of indexing the whole database.

Should AI write your metric definitions?

No. LeanScale's rule is "Do not let AI author your business logic." A model optimizing for the fastest route will fall back on standard industry practice, which only fits the most generic SaaS business. Definitions such as what a good renewal looks like, what counts as a customer or how ARR is calculated have to come from a company's own historicals and from the people working those accounts. AI's appropriate role is formatting: turning a plain-English Google Doc into a YAML file and pushing it to a repository such as GitHub where agents can read it.

What are the stages of AI data-model maturity for go-to-market?

The talk describes four levels. Centralized: a data warehouse and BI layer exist, but nothing defines where things live. Resolved: identities are deduplicated to one canonical key, such as domain or CRM record ID, so Acme Inc., Acme Co. and Acme, or Amazon, AWS and Amazon Logistics, aren't confused. Defined: the 20 to 30 key metrics are defined, agreed and version-controlled, each naming the column and filters to use. Retrievable: clean CRM associations and a distilled data layer give quick, low-cost answers, optionally with a vector database alongside the product warehouse. LeanScale pushes clients to reach the defined level and advises most teams to start by cleaning and associating inside the CRM.

What is tokenomics and why should revenue leaders care?

Tokenomics means measuring AI by output relative to the tokens spent rather than by raw usage. Jake Toepel says LeanScale once kept a token leaderboard and wanted the number to climb; now it optimizes output per token. He expects providers to end heavily subsidized plans, where roughly $200 buys $5,000 of usage, and warns that teams that haven't prepared will face a first monthly bill of $25,000 to $30,000 to explain to their CFO. A clean data model reduces cost because agents follow connections between records and read a distilled set of key fields, instead of indexing the entire CRM or hundreds of custom fields on every query.

How long does it take to deploy a semantic layer and context graph, and who needs to be involved?

About ten weeks, according to LeanScale's roadmap, and more than half of that is alignment rather than engineering: agreeing on definitions, sources of truth, owners and tools before the technical work and agent building start. Five roles are needed: an executive sponsor with budget and authority (usually the CRO, possibly the CEO), RevOps as the linchpin between teams, an analytics engineer, a platform engineer, and whoever runs the CRM. The two most common failures are not having a single owner for each definition and starting with agent building before the data model exists.

Why build the data model before building AI agents?

Because agents are the cheap part once the data exists. With a solid data model, a team can ask an assistant such as Claude what agent it can build and point it at the data, and ship production-grade, shareable agents in about half a day. Starting with the agent means each one has to connect manually to every source of truth, which amounts to reverse-engineering a separate mini data model per agent. A shared foundation also spreads building across the company: at LeanScale, non-engineers now build agents and automations the CTO can trust because they all run on the same definitions and data.

Full Transcript

The whole conversation

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

00:00Why we recorded the Updata CEO Summit talk

0:00 So Jake and I were at the UpData Partners CEO Summit the other week and the presentation really,

0:08 really landed. It was a room full of CEOs. We presented on the idea that your AI strategy

0:15 is really a data model problem. And we felt like it resonated so well that we wanted to record the

0:21 presentation, go through it, and then just share it with the audience and all of you.

0:26 So relevant in the market right now where everyone's just throwing out Claude licenses,

0:32 trying to increase their usage where they can and try to maximize the value that they get in return

0:37 from that token spend. And I think it's transitioning now from how much can we do

0:44 with these solutions like chat GPT and Claude to how optimal can we use them going forward.

0:50 And summarize everything, semantic layer, write down your definitions, find a good place to store

0:56 it that you can put your AI to, context graph, connect the dots of your data between systems,

1:02 even within systems. Man, once mythos comes out, once chat GPT launches their new model,

1:08 this is going to change everything. More horsepower isn't going to build the map,

1:12 more intelligence isn't going to give you the context. And then making Usain Bolt run faster

1:17 isn't going to solve the toddler leg. If you're in a $20 million plan with a 20% conversion rate,

1:23 increasing the conversion rate by one point will give you another million dollars in the plan.

1:30 Do not let AI author your business logic. It is not there yet.

1:46 So Jake, thanks for being my wingman out in DC and then my wingman for this as well.

1:53 And I'm really excited to get into it. Yeah, same here, man. Like you said,

1:58 this is just so relevant in the market right now where everyone's just throwing out Claude licenses,

02:00"Which of my customers are likely to expand this quarter?"

2:04 trying to increase their usage where they can and try to maximize the value that they get in return

2:10 from that token spend. And I think it's transitioning now from how much can we do with these

2:17 solutions like chat GPT and Claude to how optimal can we use them going forward. So this is kind of

2:25 the first step in that. And I'm really excited to take this out to the broader market with you.

2:30 Awesome. Awesome. Well, let's dive into it. We're going to go through the same presentation we went

2:34 through in the crowd. So we'll just go through the slides. We also have a few giveaways at the end.

2:38 So if you hang on for the end of the podcast, you'll have a QR code where you can go download

2:45 a lot of the materials that we have access to here. And then just you can get everything going

2:52 in your company. So first couple things we're going to go through. We're going to really anchor

2:56 this into why this is important. So this again, in the context of revenue operations, marketing

3:03 operations, go to market for B2B SAS and AI companies, we all inherently have the FOMO of

3:11 like, hey, we need to be implementing AI. We know it's important, but let's remind ourselves of the

3:18 why. Then we'll go into what it actually is and what we're talking about, break it down in a really,

3:25 really detailed manner, show you the art of the possible. So once you have a really strong data

3:29 model in place, what are the type of AI agents and workflows you can build and work on? We'll give

3:34 you a full roadmap on how to deploy it, how to set it up in your company. We'll give a quick reminder

3:39 of why it's important, and then we'll have the giveaways at the end as well. So before we fully

3:45 get started, I think this was one of the inspirations. It was asking a super on paper, simple

3:52 question, which of my customers are likely to expand this quarter? Which seems like a really

3:59 natural thing. You would just type in a cloud and be like, hey, I'm connected to Salesforce,

4:03 I'm connected to HubSpot. It even has access to, you know, Gong for my transcripts. I should be

4:09 able to ask this and just hit go. And then I think what happens that I think we don't appreciate

4:16 is there are a lot of layers to this question and a lot of things that the AI is going to need to

4:22 know like, what is a customer? It seems like a really simple question, but where is my source

4:29 of truth for what a customer is and what it isn't? What does expansion mean? Are we talking about

4:37 committed contracts? Are we talking about more usage? What do we mean by expand? And then what

4:42 drives likelihood? What in your world means a company is likely to expand? So all of those things

4:51 are struggles an AI model will have if you're trying to ask this question. So Jake, on the

5:01 presentation, this was I think my favorite part, you going through the metaphors, because I think

5:05 it helps anchor like how wait, shouldn't the AI just be able to figure this out? But anyway,

5:10 I'll kick it to you to go through some of these. Yeah, absolutely. And a lot of this, you know,

5:15 is lessons learned the hard way, as Anthony was alluding to asking a simple question, the AI sees

5:21 all of this data and all this information. But again, it doesn't really have the understanding.

5:26 And we're going to talk a lot about that. And a lot of the times, what we thought,

5:31 even six months ago, was man, once mythos comes out, once chat GPT launches their new model,

5:38 this is going to change everything. It's just going to work. And what we found is that's just

5:43 not the case. The model is already trained on all the publicly available information that's ever

5:49 been created in history. It's a mind boggling amount of information. But what it doesn't have

5:55 is the context and insights that make your company unique, how you run your business, how you operate,

6:01 everything you need to guide it to that next stage. And we really think of this like an F1 car,

6:07 it is a highly tuned optimized performance machine. That's what these providers are bringing to these

6:15 LLM models. They're best in class, best in breed, and they're making incremental gains on things

6:21 like coding in different areas. But an F1 car, if you don't give the driver a map, he's going to have

6:28 no idea where to go, right? We could be driving in the complete wrong direction for miles before

6:35 we realize, hey, we need to course correct here. So a lot of what we talk about today is going to

6:39 be how you build that map in a very, very simple way. Another one that I really love, I really love

6:47 this one, is you could hire the smartest person that you've ever met. And let's say you haven't

6:52 met them. We'll use Einstein in this example. He comes in day one as a GTM analyst looking at all

6:58 the information in your CRM. He doesn't know what to make of it. You ask him what deals are at risk.

7:04 He has no idea. He doesn't know which ACME is the real ACME across all of your different systems.

7:09 You've got ACME Inc. in your marketing automation platform, ACME Co. in your CRM, and just ACME in

7:15 your product database. Are those the same client? Are they different? How was he supposed to infer

7:20 that on his first day? And that's what these models do. They just make up the middle and figure out the

7:26 path along the way. We're going to show you exactly how you steer them in the right direction. So when

7:31 you hire Einstein that first day, you bring on the new model, whatever rolls out next, it has all of

7:38 the information needed to be successful. And then lastly, I love this one as well. Anthony and I both

7:45 have toddlers at home. So this one, this one hits deeply. You could have the fastest runner in the

7:51 world in a two leg sprint. The first leg is run by Usain Bolt, whoever the fastest fan alive is

7:57 nowadays. You're not going to make incremental gains by coaching him when the second leg of the

8:03 race is being run by a toddler. What we see here is again, tripping, falling, stumbling over itself,

8:09 getting distracted by other things and running down a weird path where you're chasing them and

8:13 trying to pull them back to what you want them to focus on. Again, you need to coach that second

08:17Why this matters: yield from the go-to-market machine

8:19 leg. You need to steer the toddler in the right direction. One more that I'll throw out here is

8:25 essentially the Einstein example. You're hiring these AI models every single day. Every single

8:31 day is their first day that you're onboarding them. So what we're going to show you is how you get

8:36 out of the onboarding constant cycle of informing the AI, telling them what's going on, bringing

8:44 them up to speed and really operating from a consistent foundation. So again, regardless of

8:49 the model of the tool that you're bringing on, everything is operating off of the same foundation.

8:55 Yeah, and I think just to reiterate what you've said, there's just so many people. I was kind of

8:59 in this camp too, where it's like, oh, the model is going to get better and do the work for me.

9:05 It's like, no, categorically, just by the sheer definition of what it is we're talking about,

9:12 more horsepower isn't going to build the map, more intelligence isn't going to give you the context,

9:17 and then making Usain Bolt run faster isn't going to solve the toddler leg. So I think just making

9:24 sure people know that, oh, this isn't something that the model will just solve for me is really

9:30 important. And then why is this important? Okay, we're all in go-to-market, we're in revenue

9:36 operations roles, CROs, CMOs. Why do we even need to be deploying in the first place? And I think

9:43 for us, it really all comes back to one thing, which is maximizing yield from your go-to-market

9:50 machine. A lot of these companies, I know, Jake, you've seen a ton of them, they're investing

9:57 millions, they're investing tens of millions of dollars into these massive machines and

10:03 organizations that are designed to go out and get revenue, make bookings, grow customers,

10:08 convert deals. And a lot of times, companies really aren't even measuring what the yield

10:13 of this investment is bringing. And the most effective way to get more production out of

10:21 the investment you've made in your go-to-market engine is to increase yield. So increase your

10:26 conversion rate, reduce your time and stage. If you do this really well, I know people understand

10:32 that the gains can be really massive. Sometimes I think people forget the magnitude. If you're

10:39 in a $20 million plan with a 20% conversion rate, increasing the conversion rate by one point

10:47 will give you another million dollars in the plan. And reducing the sales cycle by one day

10:54 can help cycle in a quarter of a million dollars of revenue, which could be the difference of making

10:59 your quarter or not. So I just wanted to share, I think this is people, they know it's important,

11:06 but sometimes I think forget the magnitude. And especially if you combine both of these at the

11:11 same time. So when we're talking about leveraging AI to get more out of your go-to-market and why

11:17 you should invest in a robust data model in order to do that, this is why. It's how can I increase

11:23 my conversion rate by a couple points? How can I reduce my sales cycle by a couple of days? And if

11:28 you can do both of those at the same time, the results are really going to compound. I think

11:33 unfortunately what people are missing right now is they're not getting everything out of the models.

11:42 The ceiling of what value they could be extracting out of AI right now is completely capped and

11:48 limited by the data model they have in place. So I think all of those potential conversion rate

11:54 improvements, time and stage improvements, really are being lost until you get this data model

11:59 problem figured out. Okay. So now we know kind of why it's important and seen some numbers behind

12:05 it, which is pretty illuminating. When you think about those just small incremental gains and how

12:10The semantic layer, or what we call the GTM brain

12:11 much they add up to over time, I think it's super important to show exactly how you do this and how

12:16 we see clients getting started with this. I think also there's a perception in the market that

12:23 we need to fine tune a model or we need data science to come in and build kind of a custom

12:28 distilled version of some of these models that are unique to our business. When in reality,

12:32 it's much, much simpler than that. So first and foremost is the semantic layer. And here at lean

12:39 scale internally, we call this our GTM brain. Essentially all this is to boil it all down and

12:45 make it nice and simple is all of your business logic, all of your context written down codified

12:52 in some sort of repo. We use GitHub internally. It's widely distributed. You can start for free,

12:59 totally easy to set up and it integrates with all of these different LLMs nice and cleanly. They

13:04 know exactly how to use it, but you can also use something like Google drive to house this.

13:08 Wherever makes the most sense for your team and your agents to be able to access this data

13:13 is where it should ultimately live. The main thing here, there's no real limits to what you put into

13:20 this GTM brain semantic layer. We have everything from our brand messaging, our design kits,

13:27 who we sell to and who we don't, what products we have on the shelf today,

13:31 what good looks like to us for each individual project that we run. And then we also have where

13:37 to find key business insights and really defining all of those at a super fine granular level.

13:43 So this starts just as simple as saying, what does win rate mean at our company? How do we classify

13:50 bookings and what value should we be looking at across different pipelines, across different

13:56 segments, whatever that looks like unique to your business should be documented and codified here.

14:02 The key thing that I'd really like to point out, and I'll talk about it a little bit later as well,

14:06 but having one owner for these metrics is massive. You need to have one person who's really controlling

14:13 the narrative on each of these. And that's to avoid many cooks in the kitchen and CS not buying

14:19 into the way that sales is operating or marketing is operating. Everybody should be working again out

14:24 of this consistent foundation. We've seen this across multiple clients where we ask a question,

14:30The $10,000 deal that reports as $30,000

14:32 what's my forecasted ARR for this quarter? Super simple, nice and clean. The AI goes out,

14:37 hits your back end to look at your product usage and start doing some forecasting.

14:42 And what it does is it runs some very simple SQL. The SQL responds with data and the AI says,

14:48 nice, I did it. I got some data. This looks good. These are actual numbers. I can return this to the

14:54 end user. What the AI doesn't understand is the nuance in your CRM or in your data warehouse,

15:00 where we're looking at opportunity products or product usage, and it's fanned out across

15:05 multiple line items. So now a $10,000 deal looks like a $30,000 deal in your forecast.

15:12 You're over reporting over estimating. And that's just one very small example of what we see day in

15:17 and day out. Now the context graph, again, to boil this all down and make it super simple for everyone.

15:24 All this is, is connecting all of the different dots that you have, all of the different data

15:28 points that you've gathered through enrichment, through events, through outreach, whatever that

15:33 may be. It's so important that you have this data model defined so the AI isn't guessing which

15:40 records are associated to which. We really think of this in a crawl, walk, run format. And we think

15:46 most should just start with making their CRM their true first context graph. All of the data

15:52 should be there already. If it's not, bring in key product data, key usage insights. Whatever is

15:59 missing to make it a complete picture of your organization, that should be tied back to your

16:00Tokenomics, and when the gravy train ends

16:04 source of truth, which we ultimately think should be the CRM. So it's just making sure your contracts

16:11 are associated to the right opportunities, which are associated to the right accounts,

16:15 which have the right contact roles defined so that the AI can go in and very quickly understand

16:21 what an account looks like, all the key players in the game, what a good renewal looks like, what a

16:26 bad renewal looks like. If it's disparate and disconnected, you're going to get overinflated

16:32 or underinflated numbers and not be able to address the root issue. There's also an aspect of this

16:38 that comes down to tokenomics. Again, going back to six months ago, we had a big token leaderboard

16:44 and all we wanted to see was that number keep climbing. And now what we want to see is the output

16:48 relative to the number of tokens. So we're really looking at this from an optimization perspective,

16:54 where your AI isn't going to have to index your entire CRM every time. If it has these connections,

17:00 it makes very easy hops through the data. Instead of saying, here's this opportunity, can you go look

17:05 at all the usage data behind this? Now it has to index this entire database and try to piece

17:11 together exactly which of the custom objects are tied back. So this is where we see extreme value

17:17 in getting your CRM dialed in. When cloud force rolls out, as we've seen with the native connector

17:22 and all the skills that they've baked in, that's not going to save you on the token side if your

17:26 CRM doesn't have the good quality associations to meetings booked to the tickets filed. All of that

17:34 is so, so important to again, building that holistic picture of what's going on inside your company.

17:40 Yeah, I think a lot of people don't realize. So you're mentioning like, yeah, lean scale,

17:44 we were token maxing all day and a great time is fun. I think a lot of creativity, but

17:54 we definitely are going to have to get more efficient. You know, anthropic opening eye,

17:58 they're already starting to cut how, what your token limits are within some of their plans.

18:04 So understanding, okay, how do I make this a more efficient process? It's kind of like a nice to have

18:10 maybe six months ago in the future. This is going to be unbelievably important. And I think your

18:18 CFOs are going to be all over this. So laying the foundation early now. Okay. We got the semantic

18:24 layer in place, got the context graph set up. Um, there's different levels to this too, but

18:29 getting that done early is going to save people a lot of money.

18:33 A hundred percent. And as I always say, it's a matter of when not if we know that these providers

18:40 are going to pull the rug out on these gravy train max plans that, you know, for $200, you get

18:46 $5,000 worth of usage. And they know that they have all the insights on that usage and they are

18:53 going to start cranking up the dial. So to your point, if you address this now, while you're still

18:58 on the gravy train, it saves you from the fire drill, two, three, four, who knows how many months

19:04 from now, when you get that first 25, $30,000 a month bill and have to go explain to your CFO

19:10 exactly why you need to cut budget in other areas to support this overinflated AI usage.

19:17 If I were to guess, it's going to be one quarter post IPO from either open hair and drop pick or

19:24 whoever. So again, to tie it back and a little bit, I guess I'm a pessimist, so I used which deals are

19:31 at risk instead of which deals are going to expand, but just to tie it back to a core business question

19:37 that, you know, each and every one of us probably have questions about and have plugged into one of

19:41 our LLMs in the past. So before it really started to look at how many touch points are on this

19:49 account, right? And so a healthy account might have X number of touch points, but what it doesn't

19:55 understand is the sentiment behind some of those touch points. Tools like Gong are great at this.

20:01 They've been doing this for a long time. Sentiment analysis is so important, but when stuff comes in,

20:06 let's just say through email, through Slack, you're not necessarily going to get that insight

20:11 straight out of the box. So an account that has 150 touch points looks great until we start to

20:18 look and say, no, those are support tickets that haven't been answered, right? We need to start to

20:23 classify what good touch points look like, what bad touch points look like. And that's where the

20:28 semantic layer comes in is it really flattens this out to say, what are all the really good

20:33 opportunities looking like? What are all the really negative ones looking like? So we start to do this

20:37 cohort analysis and really break down the data into these identifiable buckets that can then be

20:43 modified over time. So this isn't something that's permanent set in stone. You can always modify this,

20:49 but without it, you're really operating from a very vanilla assumptions-based inferred model,

20:55 no confidence behind it. Now the context graph that comes in with the additional receipts.

21:02 So that's going to tell you exactly why certain things happened, why certain touch points were

21:07 negative, how many of those in the ecosystem there were, and then putting that all together,

21:09Never let AI author your business logic

21:12 the semantic layer in the context graph in the response is something that a human can actually

21:16 take action on. And that is the key. When a human can take action on the insights given from an LLM,

21:23 that's again, when we see the maximum value coming from those tokens. Now, a key here,

21:30 do not let AI author your business logic. It is not there yet. And I don't think it ever will be,

21:38 as we've alluded to, it can be the best, most performant model in the world. That is going

21:43 to take the fastest route from point A to point B, especially as it starts to optimize on tokens.

21:48 It's going to say, yep, what are standard industry practices? Boom, ship it. We are good to go.

21:53 Unless you are running the most vanilla basic lemonade stand SaaS company in the world,

21:59 that is not going to work for you. What you need to do is just start writing it down in plain

22:04 English. Just start putting pen on paper. Start typing it out in a Google doc where AI can help

22:11 is putting it into a format that's good for GitHub and good for agents to access. It can turn it from

22:16 a text document into a YAML file, get all of that aligned, and then push it to GitHub. But what you

22:21Start with the metrics you defend in the boardroom

22:22 don't want to do is ask it, hey, go look at my CRM and tell me what a good renewal looks like. No,

22:26 no, no, no, no. That all needs to come from your insights, your historicals, and your team that are

22:32 working these accounts day in and day out. So as we've talked about, I mean, setting this up is

22:38 pretty cheap. You can basically get started with your current stack. If you have an LLM license

22:43 and you have a CRM, you're pretty much ready to go. Just start with the basics. Don't try to get

22:49 every possible metric that you've ever calculated done at the same time. Focus on the ones that

22:55 matter the most. And I always tie this back to the toughest meetings, the board meetings.

23:01 That's what I always try and tie it back to is focus on those metrics that you know you're going

23:06 to have to speak to in this quarter. Then we can start to build the ones that add additional juice,

23:11 help us move the needle on certain conversion metrics, or move things out of a stage faster.

23:17 Those are all great. But the ones that you really want to make sure you have confidence

23:21 on are the ones you have to defend in the board room. So I always try and emphasize getting that

23:27 first set of metrics done codified and with a set owner is so crucial going forward.

23:34 Then we start to look at ways to optimize the spend. And I think that's where the tokenomics

23:38 come in and getting really clean data. So you're not going through and indexing your entire CRM

23:45 every single time. And there's a lot of tools that can help in this space as well.

23:49 ETL tools are now coming up with these unique ways of surfacing data in a blended fashion,

23:56 where, again, you can pull in your campaigns from HubSpot, your gong calls, your clay data,

24:01 and your CRM data to form a unified model that you're not bringing into your CRM.

24:07 Or it's a distilled version of that. So only the key fields that matter to your company

24:11 when you're doing forecasting. And I'm not having my AI, again, dig through 500 custom opportunity

24:18 fields that we see. It's like a very distilled set to get the most juice out of those tokens

24:23 that you're spending. Yeah. And I know there's quite a few tools that are coming out. One we're

24:30 partnered with closely, Polyatomic. I think that's a really good option with their data harbors

24:35 model so they can support this. I know their founder CEO is going to be giving a talk

24:43 at OpStar coming up. So I think that's a good option. And I'm sure we're going to see more

24:48 of these too as time goes on. I think this is going to be a huge need for a lot of companies

24:54 that are trying to maximize the value of their AI and data model. 100% and have some sort of

25:00 middleman because we see that all the time of the fear of connecting an LLM directly to your CRM.

25:06 How do you control the data that it has access to? How do you make sure that reps aren't stealing

25:11 each other's accounts and overriding the ownership? There's all of these dilemmas that need to be

25:17 solved. And you alluded to one, Polyatomic is a great tool. We use it internally as well. And

25:23 it allows us to really bifurcate systems and only allow the agent to access the data that we've

25:29 approved. So again, we're distilling it down into this harbor. And then the harbor actually has its

25:34 own context layer so you can put skills in there. So then anytime anyone connects to that, they're

25:40 running the same consistent skills, the same consistent output on the same consistent data.

25:46 I think consistency is kind of the name of the game here. Yeah, another platform too. And it'll

25:52 kind of fit this maturity curve. I know you'll go through it a second. But Vasco. Vasco is a really

25:57 good go-to-market platform that pretty much forces the function of building your semantic layer and

26:04 will give you the context graph all in one. So as you go through the motions of setting up Vasco,

26:09 you get two for one and giving that setup. And then you can point your AI just to Vasco and ask

26:14The maturity curve: centralized, resolved, defined, retrievable

26:14 the questions you need to ask. So it's I think a couple of good options there. And I think there's

26:21 more to come. And I think hopefully it'll make this process a little bit easier in the future too.

26:28 Totally, totally. Yeah, and tracking to go is so important. There's just so much functionality

26:34 out there that I think most teams haven't quite started exploring yet that's going to be really

26:38 exciting over this next quarter. So on the maturity curve side, I think this one's interesting.

26:45 There's definitely a shift happening right now. I know a lot of the companies that we used to work

26:49 with, you know, we're evaluating a data warehouse, they might have like one little cluster that

26:55 they're tracking their product usage in, but no CRM data flowing between the two. And we're seeing

27:01 that shift earlier and earlier in the growth stages to where companies are investing pretty

27:06 heavily in this data infrastructure early on, because they know the value down the line of

27:11 tying this all together. So really what we're seeing is a lot of companies are at this centralized

27:16 level one zone where they have the BI layer, they have the data warehouse, they've got all

27:21 the infrastructure in place, but we still haven't defined where everything lives throughout that

27:28 ecosystem to build that confidence with the AI. So that's when you move to level two, resolve those

27:34 identities, really flatten out your duplicate problem. I know, I know it's a problem for

27:39 everybody. It's a problem for us. We've actually developed agents and tools around this because

27:43 it's just such a prevalent thing of duplicates, misaligned data, right? I'll go back to the ACME

27:49 example, but even something like Amazon, you've got Amazon, you've got AWS, you've got Amazon

27:56 logistics. There's so many different options in that one given account that it gets really hard

28:02 to tie that all together or the AI is looking at AWS when it should be looking at Amazon because

28:07 the domains are the same, really flattening that out, getting to that canonical identity model is

28:13 huge. And I know I'm using a lot of fancy words there, but all that really means is deduping your

28:18 CRM, getting one consistent key to identify an account, whether that's the domain, whether that's

28:23 the record ID and the CRM, just making sure you have that across all your systems. So that flows

28:29 all the way to the data warehouse. That's where we get to the definition metric. That's where you go

28:34 through and say, if you're looking for win rate, here's the column you should look at and here's

28:39 the filters you should apply. We're going to talk a little bit more about what that looks like,

28:42 but I think this is where we're really trying to push our clients to, is getting them to this point

28:48 where they have all their 20 to 30 key metrics defined, agreed upon, and version controlled.

28:56 Now the agreed upon part is big and Anthony's going to talk a little bit about that as well,

28:59 I'm sure, but getting that alignment is really the core problem. Sometimes difficult discussions

29:05 need to be had. We work with a ton of different companies. I think all of them recognize revenue

29:11 just a little bit differently. So it's really important that you come in and just define those

29:16 owners, define what these mean to you. And going back to the Amazon example, one of their values

29:22 is disagree and commit. And I think that's so important to bring into these meetings,

29:27 trust the owner, even if you say, no, no, no, no, we've been using this spreadsheet over here and

29:31 our calculations look much better. Well, that's great, but let's try this. Let's commit to this

29:37 and build on this foundation and bring your insights in. Let's get to an ultimate foundation

29:42 that we all agree upon. Level four, we move into the retrievable. So that's where a lot of the

29:48 polyatomic harbors we talked about getting really good, clean associations in your CRM. So you're

29:53 not indexing the entire database every single time is so important. This really comes down to

30:01 highly retrievable, quick insights that don't cost a lot of spend. That's the next evolution. And

30:07 again, you can get really advanced in this with the extra credit mode, going with a vectorized

30:12 database that sits alongside your product warehouse. You can even do this in a cloud

30:16 database, something like super base, using like a Postgres. But really, we think most should just

30:22 start cleaning and associating in their CRM. That's where you're running your business today.

30:28 That's where you're going to get the most juice out of all of the teams are working out of that

30:31 platform. They don't need to connect to an additional database. And ultimately, you'd

30:36 probably write a lot of this info back from that vectorized database to your CRM. So we really try

30:42 to focus on using the tools you have today and getting the optimal usage out of them when it

30:46 comes to AI. And this is a lot of work. It's not super easy to get all this set up. And I think

30:54 it's really the hard part. If you think about, okay, there's two different camps. There's get

30:58 the data model set up. And then there's build the agents, build the workflows. I think building the

31:04 agents and workflows is so easy. That's the cheap part. If you have a great robust data model, all

31:10 you have to do is ask Claude, hey, what type of agent can you build me for XYZ? Yeah, point to

31:14 this data set. So when you do have the data models set up and everything ready to go, that's when,

31:23 okay, yeah, we can line up all the sales agents, the marketing agents, CS agents,

31:28 all the rev ops agents that we need to spin up. You can do things like forecasting. You can count

31:34 on the forecasting analysis it's providing. One of the biggest things, so Jake and I, before we

31:41 found our way back at LeanScale, we worked at a company called Emailage. And I, my first half at

31:49 that company, I actually ran customer success. And I had 40 CSMs all around the world. We had

31:57 hundreds and hundreds of customers. And it was almost impossible to get what every head of CS

32:05 wants customer health. And it's because you're dealing with so much qualitative data, you're

32:10 dealing with so much data, and there's so much analysis and sentiment to try to read that is

32:14 nearly impossible. You'd need like a full data science team just to do it. But now if you get

32:19 your data model set up, you can get a very robust customer health model and something you can rely

32:25 on. It can help identify problems early on. It can help tee up companies that are likely to expand

32:31 so you can maximize those opportunities. But there's just so much you could do. And a lot of

32:35 these just won't take very long once you have a data model that can support it. If you're trying

32:40 to start with the agent first, inevitably, you're just going to have to go reverse engineer the data

32:45 model it needs to run, rather than, okay, why don't we just build this whole thing out that we can

32:51 then run any agent on. You'll be able to deploy agents in half a day, ones that are production

32:59 grade, you can share with your entire enterprise, they're scalable, reliable, trustworthy, where if

33:05 again, if you just keep going to let's build the agent first, it's going to have to manually

33:10 connect to all of the different sources of truth, you're going to be building hundreds of many data

33:14 models for every agent you want to spin up. And just to double down on that point, just real quick.

33:19 Yeah, I think it also democratizes the build. And for me as a CTO, that's so important, because for

33:26 a long time, it was like, Jake is the vibe coder of this company, right? Like, if we need to do

33:31 anything, it's got to run through Jake. But after we've built this out, and we've gotten everybody

33:36 connected to GitHub, and we have these design kits, Anthony's thrown in a ton of PRs. I mean,

33:42 he is cranking stuff out, like, if you would have told me six months ago, even that I'd be approving

33:46 Anthony's PRs, I would have told you that you were crazy. But here we are. And it's amazing.

33:52 It's awesome. And I know I can trust the output. I don't need to go back and reinvent the wheel

33:57 every time. And so for us, it's really democratize the build of these, where each individual person

34:02 can build their own agents or build their own automations with the confidence that it's

34:07 operating again on that same foundation. So just to double down on how important it's been to us,

34:08Half of this is an alignment problem

34:13 me personally, if I'm being honest, but it can be so impactful across organizations.

34:19 It really has been impactful. And it has unlocked a lot of builders at LeanScale to be able to

34:26 build something, like you said, that's built on data that you can trust and the results it's

34:33 giving you you can trust and the way it's working. But also, then it's very easy to say, okay,

34:38 that's awesome. Let's now get that exact same thing into the hands of the entire company

34:42 so they can use it too. I think once you make the investment, you'll definitely see the value.

34:49 So I want to go through how to deploy it. Okay, how are you going to actually get there?

34:53 And Jake alluded to this earlier, literally half of this is an alignment problem. So the engineering

35:02 here is not that difficult. It's something that I'll walk through the types of roles you'd likely

35:08 want to lean on to get it done. There's a little bit of technical work to do, of course. But most

35:14 of this is, okay, can we get on the same page? Can we all agree on what the definitions mean? Can we

35:19 agree on what the source of truth is for all of these definitions? And then can we agree on the

35:24 person who owns what this definition is? And if you can do that, then okay, now let's codify this

35:31 and house this somewhere. And then let's make sure our data is connected meaningfully and clean it

35:36 up, deduplication, all that stuff. Then you can go have fun building agents. But I don't want to

35:42 diminish the fact that the hard part of this, like most things in life in general, is going to be

35:48 alignment and communication between the teams. So starting with the semantic layer, the way

35:54 you might want to think about it is, okay, every metric, every definition has to have an owner.

36:04 And on the sales side, we need definitions on what a qualified opportunity might be.

36:09 On the marketing side, oh my goodness, I can't tell you how many different definitions of a

36:14 marketing qualified lead I have seen. You need to figure it out for your company. So write it down,

36:20 agree on it, and then just stay consistent with what an MQL is in your company. Customer success.

36:26"What is a customer?" and other questions nobody agrees on

36:29 I've run into this so many times too, which would probably be shocking to most people. What is a

36:33 customer? And how do I know? Is it this field that says customer on Salesforce? Is it they have an

36:40 account and our ERP? Is it that they've had an invoice? Do we count pilot accounts as customers?

36:46 Do we count customers that have put in a churn notice still as customers? Or do we wait until

36:51 the churn time comes? What is a customer here at this company? You'd be surprised at how many

36:56 different definitions you can get on that. And then there's all kinds of company-wide ones like

37:00 what's annual recurring revenue? For those who are listening, most of your company is valued on ARR.

37:07 That's just the way people value companies, especially early on. So what is the definition?

37:15 How do you articulate what your ARR is? Especially if you have usage-based products and a usage-based

37:20 service too. So anyway, getting this all on paper, codified, and then stored in one spot,

37:26 super important. Now I'll kick it to Jake to go through quickly, just technically, like okay,

37:34 where does this live? But again, most of it's going to be that alignment. Totally, totally.

37:41 And just to double down there, this isn't a new problem. This isn't something that AI invented

37:47 with this lack of definitions around an organization. As you alluded to earlier at emailage,

37:51 having 40 CSMs around the world, if we didn't onboard them properly and we just threw them

37:56 into the wild, do you think they'd be successful? Probably not. So this is just really highlighting

38:02 the importance of getting this stuff on paper because again, you don't want to be Adam Sandler

38:07 in 51st states playing the same video every morning for your AI and trying to tell them exactly what

38:13 bookings means to you. So not a new problem, just AI has definitely accentuated the need for it

38:18 across all these different business units. So the semantic layer, I promise I'm not going to make

38:24 you look at too much code here. Sorry if you just threw up in your mouth a little bit. This is

38:29 YAML on the right and then just a simple folder structure on the left. So as I talked about

38:33 earlier, we use GitHub for this. It's very native to all these LLMs. There's nice clean connectors.

38:39 It's free to set up, free to use. You can house things privately. You can share them amongst the

38:44 team. Very easy to configure, very easy to add automations around as well. So we're big fans of

38:49 using GitHub for this, but you could even use Google Drive with the correct folder structure

38:54 in just a shared drive format. So on the left is just that exact folder structure. It's the

38:59 semantic layer first, the different models that we have, all of the different entries and metrics

39:04 that we would want to capture. And one example of a metric is on the right there. So this is

39:09 the YAML file. You'll see the metric at the very top. In this case, we're looking at win rate.

39:13 The next line is the owner. And this is so important. We got a great question when we

39:19 presented this live of how we think about who should be the owner. Ultimately, we're going to

39:24 talk about some of the roles that are involved in this as well. But RevOps is kind of becoming that

39:30 pioneer of change when it comes to AI and being kind of the first AI enabled team,

39:36 making sure that we're rolling it out responsibly. But ultimately, your owner per metric, and I go

39:41 back to this time and time again, is who's going to have to speak to it in a board meeting? Who

39:48 is the owner of what that metric means? Because if you've ever walked into a meeting and tried to

39:52 defend a number that you don't have context on, that is not a fun razzle dazzle game. Let me

39:57 tell you, I've done it a couple times. I'll never do it again. It is not fun. You start sweating.

40:03 So whoever is going to be speaking to that number should have full confidence in exactly how we

40:07 defined it, how we got there, what it means to us, and be able to back that up. They also approve

40:13 any changes. So like I said, and Anthony alluded to, there's tons of different ways to qualify MQLs.

40:19 You can change that quarter over quarter. If you say, "Hey, we were over-qualifying a little bit.

40:23 We want to tweak it down." Perfect. Submit a PR. Because the owner is in that metric defined in

40:29 the code, they're going to get a notification to let them know, "Hey, so-and-so just submitted a

40:34 new PR. They want to update the win rate metric. What do you think of this?" They can pick and choose

40:39 and say, "Yeah, yeah, yeah. I really like that new lead scoring model." Or, "No, no, no. I don't want

40:43 to change. We always want to MQL hand raisers." Whatever that looks like, they have a chance to

40:49 interject and then stay in the loop as well. Because as we've alluded to, they're going to

40:53 be speaking to these metrics. So super important that you just start writing these down. I know

40:58 the code makes it look a little bit aggressive, but really you just need to start documenting this.

41:06 Okay. The context graph. I'm not going to spend a ton of time talking about this one.

41:11 Really, what I want you to understand is this is just connecting the dots in your CRM. But as

41:17 important as it is to connect the dots, it's also just as important to say, "What are we not going

41:22 to throw into this mix? What are we not going to tie together because we don't want that insight

41:26 or it doesn't belong in this individual context graph?" So I think taking some time to really look

41:32 at those associations, understand where you need additional, where the gaps exist today,

41:37 and then where maybe things are overinflated as you click into some of those calls and you see

41:42 internal calls being associated to a company record because they mentioned their name,

41:47 those types of things that need to be flattened out and fixed

41:50 before you have that full confidence in your CRM as your first context graph.

41:58 So I can hop in here. There's a handful of roles. The ones I really want to focus on,

42:00Five roles, a ten-week roadmap, and how it goes wrong

42:03 you have to have an executive sponsor to push this through. There needs to be some budget

42:07 put here. You're going to need some tools. You're going to have to carve out people's time to make

42:10 sure people know that this is important. So whoever that is, typically it's going to be your CRO,

42:14 maybe even your CEO. Like Jake mentioned, RevOps is going to be a huge person to lean on. They are

42:20 already owning a lot of the business context and I think they are a perfect linchpin between the

42:28 teams to pull all this together. Now, if you have an analytics engineer and platform engineer on the

42:34 team, I think that would be fantastic as well. And then whoever's running your CRM. So if somebody's

42:38 running your CRM, that's a person that you're going to want in the room when you're making

42:42 these decisions. If we were to space it out, everything's going to look a little different.

42:47 What does your data environment look like, et cetera. But in general, you should be able to get

42:51 this done in about 10 weeks. And if you notice, more than half of it is mainly alignment on

42:58 definition, semantic layer tools you're going to use. And then it moves into the engineering side

43:03 and the agent building side. But this is a 10-week roadmap that you can copy for your organization.

43:08 And I think Taylor for your needs. A couple of things, ways this could go wrong. I don't

43:13 want to harp on all these too much, but I think the biggest one is not having a single owner for

43:18 definition. That's really where the wheels fall off on this. So, hey, your VP of sales

43:22 owns what a qualified opportunity is. Your VP of marketing owns what an MQL is. I wouldn't have

43:28 RevOps own many of these. I think most of these will live with a functional leader. And then one

43:36 that we highlighted starting with the agent building. It's like, yes, you can try to build

43:40 all the agents you want, but at the end of the day, they all need data to access. So,

43:44 sequencing this is really important. And then just a reminder, hey, if you do this right,

43:50 if you invest in the data model, you build the agents and you start to shave off a few days of

43:55 the sales cycle, improve conversion by a couple points. These results continue to compound. And

44:02 this is where you make the investment back. Just to strip the jargon and summarize everything.

44:07 Semantic layer, write down your definitions, find a good place to store it that you can point your

44:12 AI to. Context graph, connect the dots of your data between systems, even within systems.

44:19 Just make sure the AI knows when you're asking a question and it goes to a particular person

44:21The giveaway

44:23 or account, it knows what other data is connected to that. And if you think about it that way and

44:30 make it pretty simple, I think you'll go pretty far. And then the last thing, this giveaway,

44:34 this is all for you. So in here, you're going to get this presentation so you can download it,

44:38 PDF PowerPoint, convert it to Markdown and throw it into cloud, whatever you want to do,

44:43 you can have it. You'll also get the metric definition worksheet that you can work with

44:49 your team. This should give you a head start. We have 10 pre-built agents that you can download.

44:54 Now, none of them are going to be that effective unless you invest some time in your data model,

44:58 but you're going to have them. And then also a way to stay connected with LeanScale. We actually

45:06 put everything into our MCP. So if you go to leanscale.team, you can get connected to that.

45:12 We have our playbooks, we have benchmarks, we have studies, we have podcast transcripts,

45:19 if you want to know what CROs and CMOs are actually talking about. And you'll have all

45:24 of the materials from here. And then if you're interested, we can also offer up a diagnostic

45:31 to take a look under your hood and see where we can help. So I hope this was helpful. Jake,

45:37 thanks for being my wingman as always. And I hope this helps whoever's listening,

45:42 invest what they need to into getting their data model ready to get the most out of their AI.