Pricing and Packaging

An internal document combining strategic pricing analysis frameworks with an informal interview write-up for a Pricing & Packaging role at ConnectWise. This captures the analytical approach to SaaS pricing within the IT channel (MSPs serving end clients) and demonstrates the “Measure, Monitor, Model” methodology.

Pricing Analysis Frameworks

CMS Float Opportunity

• Punitive pricing analysis — understanding how pricing penalties drive behavior
• AWS pricing model as a reference (usage-based, tiered discounts)

Platform to Product Analysis

How much are customers shifting spend between products within the ConnectWise platform? If their behavior is already steady within a pre-existing product set, that behavior can be productized. This connects to 06-reference/2026-04-03-b2b-saas-pricing-masterclass and packaging strategy.

Share of Wallet Analysis

Key questions:

• What is the normal revenue of our customers?
• How much value do they get from our products?
• How do they price and package their own services?
• How much can they profitably afford to spend on tooling?

Data Hierarchy

Feature to SKU to Package/Plan — understanding the mapping from technical capability to commercial offering.

The Measure, Monitor, Model Framework

A reusable analytical progression:

1. Measure — Define the metric. If not defined, create a quantifiable answer, review with stakeholders, iterate.
2. Monitor — Track the metric over time. Can we consistently and reliably reach an answer?
3. Model — Uncover the levers that determine the metric. Build sensitivity and what-if analyses.

This progression maps directly to 06-reference/concepts/analytics-as-craft — moving from ad hoc answers to systematic understanding.

Analysis Roadmap

Descriptive (Where are we today?)

• Existing pricing and packaging offerings per product
• Customer counts per package
• Feature-to-P&P mapping
• Current discount structures
• 3rd party health diagnostics and share of wallet

Diagnostic (Where can we improve?)

• Product reasons for churn
• Reasons deals fail to close
• Differential retention curves by pricing tier

Prescriptive (What can we do next?)

• CMS Float opportunity quantification
• CMS discrete product sales

Third-Party Data Ideas

• Snowflake community data shares
• Dun & Bradstreet business health data
• ConnectWise Community Graph concept — mapping the network of ConnectWise customers, their customers, and vendors. A data product idea ahead of its time.

Stakeholder Mapping

The document includes an extensive internal network map — product leaders, embedded analysts, team leaders, and external resources (Reforge Monetization program). This demonstrates the 06-reference/concepts/systems-over-goals approach to stakeholder management: know who owns what knowledge and build relationships systematically.

Reusable Patterns

• Measure, Monitor, Model — Three-stage analytical maturity progression
• Descriptive/Diagnostic/Prescriptive — Analysis roadmap structure for any domain
• Share of wallet — Understanding customer capacity to spend before optimizing pricing
• Feature-SKU-Package hierarchy — Standard decomposition for SaaS pricing analysis
• Internal network mapping — Documenting who knows what, before you need to ask

Consulting Credibility

This document shows the ability to scope a pricing analytics program from zero — identifying data needs, stakeholders, external resources, and a phased analysis plan. Directly relevant to 01-projects/phdata/career-transition as evidence of strategic product analytics capability beyond pure data engineering.