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Revenue Operations

From Gut Feel to GTM Gold: Using AI to Design Pain-Based Sales Territories

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In most companies, territory design is a high-stakes, low-data mess. It’s rushed. It’s political. It’s reactive. It’s the reason reps roll their eyes and RevOps teams dread Q4. In this tactical and eye-opening session, Kevin Davis (CEO + Founder of BoogieBoard), Doug Bell (Fractional CMO and Co-host of Cannonball GTM), and Jessica Watts (VP of Sales at Fundraise Up) break down a radical new approach: using AI to segment territories by pain - not just size or location - and empowering RevOps to build equity, messaging, and growth into every book.

From sourcing high-quality data with generative AI to deploying custom balance goals and territory scorecards, this is one of the most actionable workflows we’ve seen for territory design in 2025. If you're still slicing geo maps in Excel, this one’s for you.

Why Territory Design Is Broken

Kevin Davis kicks things off by painting a familiar picture: reps feel like they’ve been handed a bag of mystery meat. It’s the fast-food version of sales ops - quick, dirty, and no one trusts what’s inside.

  • For reps, territories feel arbitrary and unfair
  • For RevOps, the data is incomplete or siloed
  • For sales leaders, it’s a black box that makes planning impossible

There’s little structure, no shared measurement system, and no guiding principles to define what “good” looks like. That’s what BoogieBoard is here to solve - with a system that pulls in quality data, uses balance goals to define fairness, and bakes equity and focus into every rep’s book of business.

“The traditional model feels like French fries for dinner. Everyone’s left hungry, and no one’s proud of the work.” – Kevin Davis

A Better Way: Pain-Based Segmentation

The core of the BoogieBoard approach is the “pain-based segmentation” framework, pioneered by Cannonball GTM. Doug Bell explains how he and Jordan Crawford, his co-founder, realized that the traditional ICP model was deeply flawed:

  • Most ICPs are built on firmographics or technographics - convenient, but not predictive of need
  • They assume all buyers in a segment are equally ready, which is never true
  • They ignore market signals like pain, urgency or conversion potential

So Cannonball flipped the model. Instead of starting with industry or company size, they identify:

  1. The Existential Data Point - the KPI that separates going concerns from failing ones
  2. Pain-Based Segments - cohorts of companies experiencing high, medium or low degrees of pain around that data point
  3. Permissionless Value Propositions - messaging tailored to each pain segment that delivers value without asking for a meeting

In Fundraise Up’s case, Doug and Jordan discovered that donor retention rate was the existential data point. Nonprofits with sub-42% retention were in “crisis” - a powerful segment to target.

“When you can organize your market by who’s in crisis vs. who’s thriving, your messaging gets 10x better and your conversion rates follow.” – Doug Bell

Using AI to Source Ingredients, Not Just Output

One of the most interesting parts of this session is how Doug and Kevin use generative AI - like Claude, Gemini, and custom GPTs - not just for content, but for research and segmentation.

They share a full prompt stack that helps RevOps teams do the following:

  • Analyze a market’s category maturity (based on Geoffrey Moore’s curve)
  • Identify 3–5 data sources to track the existential data point
  • Research macro trends and buying behavior within verticals
  • Generate pain-based segments with scoring attributes
  • Write permissionless value propositions for each segment

These prompts are packaged in open-source formats and tested with tools like Latitude to reduce hallucination. You can find the full library in BoogieBoard’s Resource Lounge and Tiki Bar.

“Most AI content is fluff. This workflow actually gives you structured data, smart segmentation, and messages your buyers care about.” – Kevin Davis

From Research to Territory Design: Meet Balance Goals

Once you’ve mapped the pain landscape, Kevin shows how BoogieBoard helps turn that research into real, measurable territory components called balance goals.

What are balance goals?

They’re the DNA of a good territory. Instead of just counting accounts, you assign a “balance goal” for the type and mix of accounts a rep should carry. For example:

  • 5 accounts in crisis (<30% donor retention)
  • 10 struggling accounts (30-42%)
  • 15 maintainers (42-55%)
  • Balanced mix of account sizes
  • 3 organizations using X integration
  • Only 1 time zone per rep

BoogieBoard’s GPT model even auto-generates a list of 30+ balance goals based on your market research, stage of company and product maturity. This is a game-changer for RevOps teams that need to operationalize fairness and focus.

“You don’t need perfect data to create a great design. You just need structure, repeatability and measurement.” – Kevin Davis

Reporting: Bringing Transparency and Feedback Into Design

Once territories are designed, Kevin recommends using Google Sheets or the BoogieBoard app to generate three views:

  1. Summary View: Compare current vs. future state by balance goals across reps
  2. All Accounts View: Show current owner, new owner, territory tags and balance goal scoring
  3. Rep Book View: A clean, filtered list for each rep with new additions, removals and balance breakdown

This framework makes your design process transparent and reviewable. It also provides the context reps need to adopt new territories faster and sell smarter.

“When you anchor the design in shared goals, feedback becomes a discussion - not a war.” – Jessica Watts

Bonus Tools: Micro-Industries, Account Hierarchies, and Rules of Engagement

The final section dives into advanced territory elements that most companies ignore:

Micro-Industries

Instead of using NAICS or flat industry codes, BoogieBoard uses LLMs to generate behavior-based “micro-industries.” For Fundraise Up, these include:

  • International relief orgs
  • Faith-based fundraising
  • Animal welfare
  • Environmental causes
  • Disaster response

Micro-verticals allow for better messaging, segment-level balance goals, and rep specialization over time.

Account Hierarchies

BoogieBoard also includes prompts to identify parent-child relationships across federated orgs, holding companies, or umbrella NGOs - allowing for better account coordination and fair distribution.

Rules of Engagement & SKO Enablement

The team provides templates to:

  • Write your rules of engagement with help from AI
  • Deliver territories at SKO with clarity and focus
  • Document balance goals and key changes with an internal Notion site

Why This Workflow Works

This territory design approach isn’t just clever - it’s practical, scalable and rooted in first principles.

✅ It shifts the focus from “fairness as opinion” to “fairness as math”

✅ It uses AI for research and structure - not just copy

✅ It builds repeatable components: balance goals, scoring, templates

✅ It treats territories as a GTM hypothesis you can test and evolve

✅ It empowers reps with clear intent and context - not just a list of accounts

Ready to Build Your Own?

You can explore the tools and resources mentioned in this session via the BoogieBoard Resource Library and the Cannonball GTM Substack.

Territory design doesn’t have to be fast food. This is your chance to serve something worthy of a Michelin star.

Looking for more great content? Check out our blog and join the community.

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