Venture Capitalist at Theory

About / Categories / Subscribe / Twitter



Signs We've Touched the Bottom

July 26

How Markets Value Software Companies in 2023

July 5

Picking Teams in AI

June 26

Marketing Teams as Hedge Funds

June 21

Does an AI Premium Exist in the Fundraising Market?

June 15

What if Every SaaS App Spoke English?

June 11

Web3 in SaaS Clothing

June 8

Microsoft's Billion Dollar AI Business

April 26

When Will SaaS Budgets Increase Again?

March 17

A Flare Across the Clouds : Cloudflare's Earnings Report

February 14

Sizing the Web3 B2B Software Market

January 1


A Funny Thing Happened on the Way to Sand Hill Road

December 14

What the $6B Coupa Acquisition Means for Software Startups

December 12

Cutting R&D to Grow GTM Spend : Is it Happening Across Software Companies?

November 2

Sales Efficiency through Covid : Reading the Tea Leaves for Startups

October 30

Would You Leave the Cloud to Improve Sales Efficiency by 11%?

October 23

The Math Behind Starting a Successful Software Startup

August 2

Deliberately Underselling as Sales Strategy

July 11

The New Key Competitive Advantage for Web3 Startups

June 13

Guess the Startup Answers

March 14

The New Discipline Web3 Software Companies Must Develop

February 9


What is the Product the Customer Buys Before They Buy Yours?

September 14

The Great Game of Risk Played in Category Creation, and Why the Winning Strategy is Aggression

June 16

The Identity Crisis Facing Open Source Companies in the Cloud

April 2

How Much is 20% More NDR Worth to Your SaaS Startup?

March 5

The Feedback Loops in Data that Will Change SaaS Architecture

March 2

The Missing Insight Around Software Multiples for Valuing Companies

January 11


How Many Technologies Can a Company Adopt at Once?

October 29

How to Predict the Forward Multiple of a Software Company

September 22

How to Maximize the Impact of Your Website When Targeting Two Personas

September 14

Can You Still Make Money Starting a SaaS Company?

September 13

A Quick Diagnostic to Determine if Your Sales & Marketing Teams are Aligned

August 31

Asana S-1 Analysis - Comparing One Productivity Powerhouse to Another

August 27

How to Recruit a Marketing Team with Great Product Marketing and Demand Generation Abilities

July 26

The Unforeseen Benefits of Online Events

July 19

Top 10 Learnings from the Redpoint 2020 GTM Survey

June 25

What is the Structure of the Typical SaaS Company as it Scales?

June 21

How Predictive is SDR/BDR Quota Attainment of AE Quota Attainment?

June 17

Notes from Office Hours with Hollie Wegman

June 12

Why Margin Matters Now in Startupland

April 12

Notes from Office Hours with Lisa Lawson

March 9

The Strategic Importance of Competition

February 23

One of the Most Frequent Errors in Sales Planning and Forecasting

February 17

Simpson's Paradox in Measuring Net Dollar Retention Rate

February 3

Cloud Prem Architecture - The New Way of Serving the Enterprise with a Hub and Spoke Data Model

January 29

B2B vs B2C: How Should Your Sales Team Be Allocated to Maximize Success?

January 5


The Most Frequent Mishire in Startups

November 10

100k+ ACV SaaS Companies: Do Their Metrics Differ from Other SaaS Companies?

June 24

Why Product Innovation Slows After the Series A

June 10

As Your Sales Team Scales, Focus on Your Middle

May 30

How to Develop Best in Class Sales Efficiency

May 10

What a Valuation Implies About a Business

May 6

The Four Strategic Questions Facing AI Agencies

April 14

Hustle As Strategy

April 8

Five Reasons to Sell End-to-End Products in Early Markets

March 26

The AI Agency - A Novel GTM for Machine Learning SaaS Startups

January 17


Just Where Are SaaS Companies Priced After the 2018 Correction?

December 26

Which is More Important: New Account Growth or Account Expansion?

December 11

Selling Your Product While You Build It

December 3

A New Way to Calculate a SaaS Company's Efficiency

December 1

The Four Stages of Sales Compensation Structures in Early Stage Startups

November 25

SAP Buys Qualtrics; 2018 Catapulted to $65B in $1B+ M&A Volume

November 11

In Early Markets, Services Can Be a Competitive Advantage

October 1

Three Observations About the Adobe/Marketo Acquisition

September 24

How the Economics of Professional Services Have Changed in Software

September 16

1% of Salesforce's Revenue Makes a Unicorn

August 26

Timing Cashflows of Your Sales Commissions and Your Customers

July 15

Lessons Learned from 20 Years at the Leading Edge of SaaS

July 10

Does Winner Take Most in SaaS?

July 8

An Often Forgotten Characteristic About Your Startup's Ideal Customer Profile

March 25

The Salesforce/Mulesoft Acquisition is a Bellwether for the 2018 M&A Market

March 20

The Clearest Articulation of a Marketing Roadmap

March 2

Private Equity as an Exit Option for SaaS Startups

February 27

Reorganizing Your SaaS Startup’s Organizational Structure to Optimize the Customer Lifecycle

January 31

How to Identify a SaaS Market that Machine Learning Will Disrupt

January 26

Jettisoning the Assumptions of Last Year

January 1


The Implication of Secular Increases in SaaS CAC

November 1

The Rising Stakes in SaaS

October 22

How Much Should A SaaS Startup Invest in Sales & Marketing?

September 17

The Challenges of the Platform Go To Market

September 6

The Theory and Data Underpinning Sales Commission Plans

September 4

Maximizing Productivity on My Commute

August 27

Has SaaS Become Commodified?

August 23

The Volatility of Multiples in the Public SaaS Market

August 21

Why Cash Conversion Cycle Matters for Your Startup

August 15

How to Decide When To Move Upmarket

August 8

A Tale of Two Go To Market Strategies

April 24

Is There a No Man's Land in SaaS ACVs?

April 21

The Four Dimensions of a Demand Generation Portfolio

April 17

SMB or Enterprise - Which is the Better Go To Market in SaaS?

April 13

Customer Operations - An Idea for Maximizing Efficient Growth in SaaS Companies

March 29

Creating Tension in Your Startup's Marketing Positioning

March 27

A Product Manager's Guide to Moving Up Market

March 7

One of the Hardest Things to Do in Sales

February 10

The $100M ARR Customer

January 17


When to Increase Your SaaS Startup's Burn

December 16

The Important SaaS Accounting Changes Coming in 2017

November 30

Are We Seeing the Beginning of SaaS Consolidation?

October 31

Why Demand Generation Can Be So Challenging For Startups

October 26

What is the Optimal Contract Length for Your SaaS Startup?

October 20

How Big is a Typical Software Company Acquisition?

October 17

The Characteristics of the Most Attractive SMB SaaS Companies

October 10

Are SMB SaaS Companies Valued Differently than Mid-Market SaaS Businesses?

September 21

What's the Maximum Rate of Growth for Your SaaS Startup with Paid Customer Acquisition?

September 19

How Should I Think About My SaaS Startup's Burn Rate

September 9

Designing a Sales Quota Structure at the Earliest Stages of a SaaS Startup

September 2

How Much is Your SaaS Startup Worth?

August 31

3 Marketing Insights from a World Class SaaS Marketer

August 29

How Fast Does a SaaS Startup Have to Grow to Survive?

July 27

Which of the Three Software Budgets Does Your SaaS Startup Target?

July 24

The Decline of New SaaS Company Formation

June 21

What Average Contract Value is Best for a SaaS Company

May 24

Just How Far Along Are We In SaaS?

April 21

In Every Great Product There's a Bit of Magic

March 15

The Strategic Shift in Revenue for SaaS Startups as They Scale

March 9

Benchmarking Exceptional Series A SaaS Companies

February 25


Pricing for SaaS Enabled Marketplaces - When to Go Free

December 7

How Much Cash Should Your SaaS Startup Burn?

November 12

What is the Optimal Quick Ratio for Your SaaS Startup?

November 3

What Quota Attainment Reveals About Your SaaS Startup's Go to Market

October 28

Five Words of Wisdom from SaaS Office Hours with Bill Macaitis

October 22

5 Mistakes SaaS Startups Often Make with Pricing

October 15

The Essential Go To Market Math for Beating Your SaaS Startup's Growth Targets

October 5

Data Network Effects in SaaS Enabled Marketplaces

September 24

The Importance of Payback Period for SaaS Startups

September 21

Do Vertical SaaS Companies Benefit from Higher Sales Efficiency?

September 17

Vertical SaaS Startups Require Different Go To Market than Horizontal SaaS Companies

September 14

Why Bottoms Up Selling is a Fundamental Shift in SaaS

August 28

Four Important Data Points about Purchasing Behavior in SaaS

August 26

The Impact of the Stock Market on SaaS Valuations in 2015

August 24

The Number One Objection in the Sales Funnel

August 18

When Do SaaS Startups Hire Their First VP of Sales

August 5

Take Your Startup to the Limit

July 20

The Increasing Fragmentation of SaaS

July 7

The Beauty of Bottoms Up SaaS Businesses

June 23

Which Open Source License Should Your Project Use if You Want to Raise Venture Capital?

June 19

The Disruptive Effect of Open Source Startups

June 16

Startup Best Practices 13 - Patience with Unit Economics

June 14

How an $11B SaaS Company Measures Churn

June 10

The Expanding Role of Marketing in SaaS Companies

June 8

Why We're Only Just at the Beginning of SaaS

June 5

Unpacking the Deep Diagnostic Value of LTV/CAC for SaaS Startups

June 3

When Should Your SaaS Startup Offer Professional Services

May 31

The Health of the SaaS IPO Market

May 28

The Risk Sales Discounts Impose to Startup Burn Rates

May 26

Free SaaS Enabled Marketplaces - A Novel Go-To-Market for Software Startups

May 21

The First Generation of the Talent Software Wars

May 19

From $800k to $274M in 4 Years - The Story of Ariba

May 14

How Great Unit Economics Enables Startups to Weather the Storm - The Story of WebEx

May 7

Which is a More Efficient Way to Build a SaaS Startup - Bottoms Up or Top Down?

May 3

A SaaS History Lesson – The First SaaS Company's Exceptional Journey

April 28

The Innovator's Solution for SaaS Startups - The Flywheel SaaS Company

April 19

The Innovator's Dilemma for SaaS Startups

April 9

Are SaaS Startups Today Worth More than Ten Years Ago?

April 5

The 5 Key People in a SaaS Sales Process

March 26

The Best Book on Building a SaaS Sales Team

March 24

The SaaS Company that Grew from 0 to 4M Subscribers in 2.5 Years

March 22

The Forces in Tension in the SaaS Fundraising Market

March 18

The 5 Marketing Channels of Great SaaS Companies

March 18

Why Your Startup's Churn Rate Affects Your Company's Ability to Plan Its Future

March 16

The State of the SaaS Fundraising Market

March 13

Sales Funnel Optimization for SaaS Startups

March 10

Modeling Your SaaS Startup's Revenue Growth Effectively

February 25

Challenging Your Customers During Your SaaS Startup's Sales Process

February 13

A Single Report to Measure the Health of Your Startup's Sales Team

February 9

The Employee Productivity Patterns of Billion Dollar SaaS Companies

February 5

Benchmarks for Employee Stock Based Compensation in SaaS Startups

February 2

The Compression in SaaS Valuations

January 23

The Fundraising Patterns of Unicorn SaaS Companies

January 22

The Increasing Growth Rates of SaaS Companies

January 19

Are SaaS Startups Less Profitable than they Used to Be?

January 16

The Rising Table Stakes in SaaS

January 14

The Sales Motions of B2C2B Companies

January 12

B2C2B Startups - Why Selling with Internal Influencers is so Powerful

January 7

3 Questions about Founders as CEOs in SaaS Companies

January 6

The Sudden Shift in SaaS Product Pricing

January 5


The Concur Acquisition in Context: A SaaS MegaExit

December 14

Benchmarking Box's Updated S-1 - How 7 Key SaaS Metrics Stack Up

December 11

The 2014 Class of SaaS IPOs

December 4

How Much Should Your Startup Spend on Customer Account Expansion?

November 24

How Important are Professional Services to Your Startup?

November 20

Why Negative Churn is Such a Powerful Growth Mechanism

November 18

Benchmarking New Relic's S-1 - How 7 Key SaaS Metrics Stack Up

November 17

A Unique Chronicle Of A Billion Dollar Company

November 14

Why Your SaaS Startup Needs a VP of Customer Success Sooner Than You Might Think

November 12

The 7 Factors to Consider When Pricing Your Startup's Product

November 5

Using Statements of Work to Accelerate Sales Cycle and Align Sales, Customer Success and Marketing

October 24

The Obscure Economic Idea Behind SaaS Pricing Challenges

October 23

The 9 Marketing Disciplines of Great SaaS Companies

October 22

Why Revenue Isn't the Most Important Financial Metric for Startups

October 20

What You’re Making Is In A Perpetual State Of Almost Right Up Until The End

September 18

The Optimal Price to Maximize Sales Efficiency for a SaaS Startup

September 9

Benchmarking Zendesk's S-1 - How 7 Key SaaS Metrics Stack Up

September 3

The Best Way to Benchmark a SaaS Startup

August 28

Benchmarking Hubspot's S-1 - How 7 Key SaaS Metrics Stack Up

August 27

Benchmarking Consumer and SaaS Companies' Path to IPO

August 19

Why Customer Success? Why Now?

August 12

The Challenge Facing Mobile-First SaaS Companies

August 5

Building a Performant Customer Success Organization

July 31

The Next Era in SaaS

July 14

The Marketing Math Behind Scaling a SaaS Salesforce

June 30

How Much Should Your Startup Spend to Grow?

June 13

Salesforce's Marketing Secret - The Fourth Marketing P

June 2

The Common Characteristics of Successful Freemium Companies

May 30

The Impact of Varying Sales Hiring Strategies on SaaS Startups

May 28

Confessions of a Perpetual Freeloader: When to Jettison the Freemium Tier

May 22

A Surprisingly Powerful Mechanism for Growing a SaaS Startup

May 21

The 4 Challenges Facing Customer Success Teams in SaaS Startups

May 15

What's Happening to the SaaS Market?

May 1

Quantifying a SaaS Startup's Revenue at Risk

April 23

The Challenges SaaS Businesses Face Communicating their Financial Health

April 17

The Investment Patterns of SaaS Companies in Sales and Engineering Over Time

April 15

The Correction in SaaS Company Valuations

April 9

Do Startups Require Less Capital to Succeed than 10 Years Ago?

April 4

Benchmarking Box's S-1 - How 7 Key SaaS Metrics Stack Up

March 24

How Fast Must a SaaS Startup Grow to Raise a Series A?

March 17

SaaS Startup Balance Sheets: How Much Cash & How Much Debt to Raise

March 14

How Quickly Does a SaaS Startup Have to Grow to Go Public?

March 13

Why There's Never Been a Better Time to Found a SaaS Startup

March 11

Great SaaS Companies Focus on Behavior Change

March 5

What to Look for When Hiring a Head of Marketing for Your Startup

February 20

The Optimal Average Customer Value for SaaS Startups

February 3

The Maximum Viable Churn Rate for a Startup

January 29

The Go-To-Market Challenges of B2D Companies

January 27

Why Everything I Thought I Knew About Churn Is Wrong

January 15

Why Quotas Aren't the Most Important Number for Startup Sales Teams

January 13

The Importance of Seasonality in SaaS Startups

January 9

The Three Doors to SaaS Success

January 7


How to Hire a Head of Customer Success for Your Startup

December 5

Startup Best Practices 3 - How to Structure a Sales and Marketing Team

December 3

The Ratio of Engineers to Sales People in Billion Dollar SaaS Startups

November 11

The Three Churn Mitigation Strategies of SaaS Startups

October 31

The SaaS Valuation Bubble

October 22

How Much Should Your Startup Spend on Managing Churn?

October 16

Why Customer Success Is An Essential Part of Every SaaS Startup

October 11

Sales Efficiency Benchmarks for SaaS Startups

October 10

The 3 Competitive Defenses of Enduring SaaS Companies

October 1

What Your Startup’s MRR Figure Is Hiding

September 27

Six Key Benchmarks for Your SaaS Startup

September 11

The Sales and Marketing Spend Strategies of Billion Dollar SaaS Companies

August 26

The Five Characteristics of An Ideal SaaS Company

July 15

Antagonism is the Heart of the Consumerization of IT Movement

May 23

Three Counterintuitive Points about SMB SaaS

May 6

The Defining Characteristics of Successful SMB SaaS Startups

April 17

Why Freemium Negates The Leaky Bucket Myth

March 25

Freemium Businesses Switch the Hunter and Farmer Sales Roles

February 7

The product qualified lead (PQL)

January 15


The Secret to SMB SaaS Distribution

September 18

The Freemium Game Plan

August 21

Segmenting the SaaS Market for Sales

August 20

Successful SMB SaaS Companies Have a 2 Step Value Proposition

April 26