GTM Strategy

How to navigate your total addressable market and competition.

How Postscript Built a High Powered Deal Desk

Mar 31, 2026

•

11 min read

How Postscript Built a High Powered Deal Desk

When to build a deal desk and how to mature it over time

CJ Gustafson

Feb 17, 2026

•

9 min read

Should You Fire Some of Your Customers?

When "bad" customers become a drag on the biz

CJ Gustafson

Can You Measure the ROI of a Superbowl Ad?

Feb 8, 2026

•

18 min read

Can You Measure the ROI of a Superbowl Ad?

Benchmarks for Operators 2/8/26

CJ Gustafson

Jan 13, 2026

•

19 min read

How AI is Changing GTM Org Structures

And WTF does 'Forward Deployed' Mean?

CJ Gustafson

Don't Trade Luka, and Don't Turn Off Your Marketing Spend

Dec 9, 2025

•

14 min read

Don't Trade Luka, and Don't Turn Off Your Marketing Spend

Program spend is easy to cut, but not the way to build a durable flywheel

CJ Gustafson

Jul 8, 2025

•

9 min read

How to Talk About Your Competition

Without sounding like a jerk

CJ Gustafson

Jun 24, 2025

•

15 min read

Preparing for Google Zero

How will we find customers when moats for distribution vanish?

CJ Gustafson

Jun 12, 2025

•

8 min read

How Upwork Optimizes LTV to CAC

A Masterclass in Marketplace Economics

CJ Gustafson

Is Product Market Fit Getting Harder to KEEP?

Apr 22, 2025

•

5 min read

Is Product Market Fit Getting Harder to KEEP?

How has AI changed our definitions of escape velocity?

CJ Gustafson

Apr 15, 2025

•

7 min read

When Churn Is the Model

"Designed to be deleted"

CJ Gustafson

A Deep Dive into TAM Calculation Strategies

Dec 12, 2024

•

6 min read

A Deep Dive into TAM Calculation Strategies

How DDOG, CRWD, and NOW calculate TAM

CJ Gustafson

You have your whole life to write your first record, and only 12 months to write your second.

Oct 29, 2024

•

8 min read

You have your whole life to write your first record, and only 12 months to write your second.

The trials and tribulations of going multi product

CJ Gustafson

Oct 6, 2024

•

10 min read

Pulling the Future Forward

10/06/24 Benchmarks for Operators

CJ Gustafson

Your Complete Guide to Customer Segmentation

Sep 26, 2024

•

15 min read

Your Complete Guide to Customer Segmentation

Identifying your best customers to maximize lifetime value

CJ Gustafson

Should You Move to a Non Standard Fiscal Year?

Aug 18, 2024

•

12 min read

Should You Move to a Non Standard Fiscal Year?

8/18/24 Benchmarks for Operators

CJ Gustafson

Burden of Proof: Guilty Until Proven Innocent

Jul 30, 2024

•

5 min read

Burden of Proof: Guilty Until Proven Innocent

And avoiding the Bandwidth Vampires

CJ Gustafson

Apr 9, 2024

•

6 min read

Going up market

Lessons from companies who have made the leap from SMB to the Enterprise

CJ Gustafson

Feb 20, 2024

•

12 min read

Your "TAM" is Why I Have Trust Issues

The pitfalls of total addressable market analyses, and how to think more critically about market sizing

CJ Gustafson

May 25, 2023

•

8 min read

Winning abroad

A framework for international expansion

CJ Gustafson

A CFOs checklist for going international

May 2, 2023

•

16 min read

A CFOs checklist for going international

What to investigate before you hit the ground running in a new country

CJ Gustafson

A Total Addressable Market (TAM) Masterclass

Mar 28, 2023

•

19 min read

A Total Addressable Market (TAM) Masterclass

Interviewing Sebastian Duesterhoeft, Partner at Lightspeed Venture Partners

CJ Gustafson

Jan 19, 2023

•

6 min read

Winner take most(ly)

Being #1 in your market is a bigger deal than you think

CJ Gustafson

Nov 1, 2022

•

8 min read

What exponential growth feels like

Boy, that escalated quickly...

CJ Gustafson

Oct 11, 2022

•

7 min read

What's the benefit?

PEOs, EORs and employee benefit uplifts

CJ Gustafson

Jul 26, 2022

•

5 min read

Not all revenue is created equal

A billings bonanza

CJ Gustafson

GTM Strategy

How Postscript Built a High Powered Deal Desk

Should You Fire Some of Your Customers?

Can You Measure the ROI of a Superbowl Ad?

How AI is Changing GTM Org Structures

Don't Trade Luka, and Don't Turn Off Your Marketing Spend

How to Talk About Your Competition

Preparing for Google Zero

How Upwork Optimizes LTV to CAC

Is Product Market Fit Getting Harder to KEEP?

When Churn Is the Model

A Deep Dive into TAM Calculation Strategies

You have your whole life to write your first record, and only 12 months to write your second.

Pulling the Future Forward

Your Complete Guide to Customer Segmentation

Should You Move to a Non Standard Fiscal Year?

Burden of Proof: Guilty Until Proven Innocent

Going up market

Your "TAM" is Why I Have Trust Issues

Winning abroad

A CFOs checklist for going international

A Total Addressable Market (TAM) Masterclass

Winner take most(ly)

What exponential growth feels like

What's the benefit?

Not all revenue is created equal

yo, btw…