Case study

A $300M Data & Analytics Company Turned Reactive Order-Takers Into Enterprise Deal Closers

Categories

SalesEnablementRevenue Operations

Solutions provided

GTM Strategy & Org Design

Account Segmentation (ROAD)

Revenue Operations

The key insight

The client's sales problem was structural. A complete commercial foundation build provided reliable standards, while a rich enablement program sequenced through manager coaching to a live-deal SKO produced sellers capable of closing deals they had never won before.

Results at a glance

$1.6M+

Revenue won

50%

Of coached deals advanced

9.2/10

Sales coaching rating

+12%

Seller confidence lift

See where yours breaks

Situation

The client is a ~$300M B2B data and analytics company grown through acquisition, with a fragmented sales force spanning multiple legacy product lines. By early 2025, only ~30% of sellers were hitting quota, a figure that had persisted long enough to become an organizational expectation. Sellers in the field operated reactively, with no account prioritization, no territory structure, and no incentives aligned to growth.

The challenge

The organization lacked the commercial infrastructure and seller confidence needed to win and grow enterprise accounts.

Sellers operated as reactive order-takers with no account ownership model, territory structure, or comp designed to reward growth over maintenance.

Buyer personas, differentiated roles, quota frameworks, and aligned incentive plans for enterprise selling had never been built.

Sellers could describe the sales methodology but lacked the proof points and confidence to deploy it in competitive, high-stakes conversations.

The Cortado Group solution

Redesigned the org and incentives

Defined six GTM roles with full job descriptions, territory logic combining sector and geography, a quota calculator linking rep activity to revenue targets, and comp plans structured to over-reward quota overachievement.

Built the commercial selling system

Built sector-specific buyer personas across three verticals, a buyer-aligned GTM process for every sales stage, and a Sales Playbook for high-stakes enterprise conversations.

Prioritized 6,300+ accounts

Ranked 6,300+ accounts using the ROAD framework -- four growth tiers with differentiated sales motions -- giving the organization a defensible map of where to invest resources.

Sequenced the enablement program

Designed a gradually-intensifying enablement program ending with an SKO capstone so sellers built and proved capability before being tested under live-deal conditions.

Added a manager coaching track

Built a parallel manager-only track with DEEPER and Value Bridge frameworks and reinforcement cadences to sustain behavioral adoption.

How could the client move from 30% quota attainment to a field organization capable of winning and growing enterprise accounts at scale?

Results

$1.6M+

Revenue won

50%

Of coached deals advanced

9.2/10

Sales coaching rating

+12%

Seller confidence lift

A junior seller closed a $1.6M+ deal: Applying the full methodology, a junior seller closed a $1.6M+ three-year contract, converting a non-recurring engagement to ARR and closing four months ahead of schedule.

Big Deal Coaching moved in-flight deals: 50% of coached deals advanced, 20% grew in scope, and the program earned a 9.2/10 average rating.

Growth-aligned comp institutionalized: A hockey-stick comp structure was formalized in the client's FY26 sales plans, with uncapped accelerators and multi-year deal multipliers for the full sales organization.