Positioning

Product and market positioning and messaging in SaaS.

Positioning

Apr 10, 2026

•

4 min read

Slack is a CRM now

Plus: Updates from Canva, Monte Carlo, Framer, Pinecone, and Mem0

Rob Litterst

Outcome-Based Pricing

Feb 20, 2026

•

3 min read

Outcome-Based Positioning

Plus: Updates from Stripe, Vanta, Auth0, Vercel, and Supermetrics.

Rob Litterst

Positioning

5 ways to reframe your pricing and packaging

Jan 30, 2026

•

3 min read

5 ways to reframe your pricing and packaging

Plus: Updates from Klaviyo, Lindy, Eden AI, DeepBrain, and Hugging Face.

Rob Litterst

Positioning

Jan 22, 2026

•

2 min read

5 ways to be customer-friendly

Plus: Updates from Pylon, Gusto, Freshbooks, Ahrefs, and Zuplo.

Rob Litterst

Positioning

The Guide to Pricing Page Storytelling (5 common mistakes and how to fix them)

Oct 17, 2025

•

3 min read

The Guide to Pricing Page Storytelling (5 common mistakes and how to fix them)

Plus: Pricing updates from Salesforce, SurveyMonkey, and Sprout Social.

Rob Litterst

Positioning

The most overlooked skill in pricing and packaging

Jun 27, 2025

•

3 min read

The most overlooked skill in pricing and packaging

Plus: PricingSaaS just got an upgrade.

Enterprise

Jun 13, 2025

•

5 min read

The Playbook Behind Fullstory’s Enterprise Transformation

Plus: 3 tips to successfully move upmarket.

Positioning

How Docusign Evolved from Point Solution to Platform

May 16, 2025

•

5 min read

How Docusign Evolved from Point Solution to Platform

Plus: Updates from Asana and SurveyMonkey.

Positioning

How Superhuman Rebuilt Its Pricing Model for GTM Teams

Jan 10, 2025

•

7 min read

How Superhuman Rebuilt Its Pricing Model for GTM Teams

Plus: Updates from Calendly, HubSpot, and Zapier.

Rob Litterst

Positioning

Sep 28, 2024

•

2 min read

How Prezi and Notion Are Positioning AI Without Rebranding

Plus: Updates from Coda, Apollo, and Otter.

Rob Litterst

Positioning

Superhuman’s New Strategy: Luxury Email for Sales Teams

Aug 9, 2024

•

3 min read

Superhuman’s New Strategy: Luxury Email for Sales Teams

Plus: Crunchbase, ThoughtSpot, Chili Piper, and Dashlane

Rob Litterst

Product Updates

Notion Calendar Launch: Pricing Strategy, Positioning & Product Review

Jan 26, 2024

•

5 min read

Notion Calendar Launch: Pricing Strategy, Positioning & Product Review

Plus: Big moves from key SaaS players.

Rob Litterst

Positioning

What Opinionated Software Gets Right (and Wrong)

Mar 15, 2023

•

2 min read

What Opinionated Software Gets Right (and Wrong)

Plus: A brewing freemium battle, and how to price a social media subscription.

Rob Litterst

Positioning

How to Compete With Free Products and Win

Mar 1, 2023

•

2 min read

How to Compete With Free Products and Win

Plus: Uber's underrated pricing power and Apple's services behemoth.

Rob Litterst

Coda

Jan 8, 2023

•

2 min read

What Is Pricing Page Empathy? Lessons from Coda & Notion

Coda, Notion, and a tale of two pricing pages.

Rob Litterst

Positioning

How Vendr’s Pricing Strategy Disrupted SaaS Buying

Jul 21, 2021

•

9 min read

How Vendr’s Pricing Strategy Disrupted SaaS Buying

How a former sales rep is transforming the way we buy SaaS.

Rob Litterst

Usage-Based Pricing

How Twilio and Segment Could Redefine CRM Pricing

Nov 1, 2020

•

6 min read

How Twilio and Segment Could Redefine CRM Pricing

Bringing balance to customer relationship management.

Rob Litterst

Subscription Pricing

Oct 25, 2020

•

5 min read

How AMC Wins Streaming by Going Niche

How they're escaping the streaming wars by prioritizing depth over breadth.

Rob Litterst

Peloton

Oct 11, 2020

•

6 min read

Peloton's Talent Flywheel & Amazon's Styling Playbook

Peloton's Talent Flywheel, Amazon Personal Shopper, and Moving Down the Value Ladder

Rob Litterst

Positioning

How Nike Uses Digital Fitness to Power Personalized Commerce

Sep 20, 2020

•

9 min read

How Nike Uses Digital Fitness to Power Personalized Commerce

How digital workout data can power personalized commerce at scale.

Rob Litterst

Positioning

The BigCommerce Wedge: Competing with Shopify and Magento

Sep 6, 2020

•

6 min read

The BigCommerce Wedge: Competing with Shopify and Magento

How BigCommerce uses Shopify comparisons to their advantage.

Rob Litterst

Positioning

Jul 26, 2020

•

5 min read

Why Mailchimp Is Losing the Newsletter War

How Mailchimp is losing their lead in newsletters.

Rob Litterst

Positioning

Amazon Music’s Smart Strategy to Overtake Apple

Jul 5, 2020

•

5 min read

Amazon Music’s Smart Strategy to Overtake Apple

Why Amazon Music is poised to take over the #2 spot in music streaming.

Rob Litterst

Peloton

Jun 28, 2020

•

6 min read

The Peloton Pivot: From Hardware to Fitness Content

A new direction for the Apple of Fitness.

Rob Litterst

Positioning

Roam Research and the Art of Cult Packaging

Jun 21, 2020

•

5 min read

Roam Research and the Art of Cult Packaging

How to use packaging to promote a cultish user-base.

Rob Litterst

Positioning

Slack is a CRM now

Outcome-Based Positioning

5 ways to reframe your pricing and packaging

5 ways to be customer-friendly

The Guide to Pricing Page Storytelling (5 common mistakes and how to fix them)

The most overlooked skill in pricing and packaging

The Playbook Behind Fullstory’s Enterprise Transformation

How Docusign Evolved from Point Solution to Platform

How Superhuman Rebuilt Its Pricing Model for GTM Teams

How Prezi and Notion Are Positioning AI Without Rebranding

Superhuman’s New Strategy: Luxury Email for Sales Teams

Notion Calendar Launch: Pricing Strategy, Positioning & Product Review

What Opinionated Software Gets Right (and Wrong)

How to Compete With Free Products and Win

What Is Pricing Page Empathy? Lessons from Coda & Notion

How Vendr’s Pricing Strategy Disrupted SaaS Buying

How Twilio and Segment Could Redefine CRM Pricing

How AMC Wins Streaming by Going Niche

Peloton's Talent Flywheel & Amazon's Styling Playbook

How Nike Uses Digital Fitness to Power Personalized Commerce

The BigCommerce Wedge: Competing with Shopify and Magento

Why Mailchimp Is Losing the Newsletter War

Amazon Music’s Smart Strategy to Overtake Apple

The Peloton Pivot: From Hardware to Fitness Content

Roam Research and the Art of Cult Packaging

GoodBetterBest