Sales

2025

• A Founder's Guide: Essential Sales Advice for Startups Apr 02

2024

• AI Advantage for Startups : Changing the Workflow through Services Sep 23
• The New Software GTM Playbook Sep 11
• What Has Your GPU Done For You Today? Aug 23
• Things that Used to be Impossible, but are Now Really Hard Aug 15
• Agentic Systems' Sales Cycles Jul 22
• Extreme PMF : Sustaining Success with Scale Apr 12
• AI in the Hands of Software Buyers Mar 29
• Selling AI : Category Creation of a Different Flavor Mar 26
• The 10x Salesperson Jan 12

2023

• Purchasing Patterns in Software : Positivity Punctuating Q3 Nov 10
• Artisanal Emails Sep 26
• Avoiding the PLG Trap : Office Hours with Oliver Jay Sep 25
• How Should You Staff Your Startup in 2023 May 17
• Every Customer is a Design Partner - Leading Your Sales Motion with Sales Engineering May 02
• The Typical Startup Saw a 24% Increase in Sales Cycle in 2023 Mar 28
• Predicting Cloud Growth Rates for 2023 Feb 03
• When AI Favors the Incumbents Feb 02
• Microsoft as a Mirror - What We Can Expect for SaaS in 2023 Jan 24

2022

• PLG & Profitability : More Product Doesn't Necessarily Mean Greater Profits Dec 07
• Cutting R&D to Grow GTM Spend : Is it Happening Across Software Companies? Nov 02
• Sales Efficiency through Covid : Reading the Tea Leaves for Startups Oct 30
• Grey Skies in Cloud Earnings Oct 28
• Pipeline Supply Shocks in SaaS Sales Sep 23
• Systematizing Go-To-Market Hiring Sep 08
• 200% NDR: What Does it Take to Achieve this Stellar Milestone? Sep 02
• Pipeline Analysis Playbook Aug 18
• How to Structure a Startup Sales Team for Optimal Land & Expand Aug 15
• The Health of Cloud Spending in Mid-2022 Jul 26
• How to Structure Your Sales Compensation Plan to Deliberately Undersell Jul 25
• How Important is Your Software to Your Customer? It's Time to Find Out. Jul 22
• A Masterclass in Sales Development from Lars Nilsson at Snowflake Jul 14
• Deliberately Underselling as Sales Strategy Jul 11
• The Sales Sandwich Feb 18
• Why You Should Expect Your VP Product to Sign Up for a Lead Quota Jan 28

2021

• The Need for Two Types of Payback Period Calculations Nov 07
• What is the Product the Customer Buys Before They Buy Yours? Sep 14
• How Selling Has Changed Post-COVID, and How it Will Change Again Afterwards Mar 14
• The Most Effective Tools and Techniques for Selling Today - Office Hours with Jim Benton Feb 18
• A Common and Critical Mistake When Forecasting Next Year's Bookings Feb 01

2020

• Do You Lose Sales Opportunities Because of Sales Execution or Product Insufficiency? Dec 16
• The Three Questions to Ask When Hiring Your Startup's Head of Sales Dec 15
• Building a Product-Led Growth Machine: Office Hours with GC Lionetti Dec 07
• More Activity Means More Business. Don't Overthink It. Nov 16
• How Many Technologies Can a Company Adopt at Once? Oct 29
• A Quick Diagnostic to Determine if Your Sales & Marketing Teams are Aligned Aug 31
• Why Startups Should Establish Qualifying Signals for Sales Teams Early On Aug 24
• Top 10 Learnings from the Redpoint 2020 GTM Survey Jun 25
• What is the Structure of the Typical SaaS Company as it Scales? Jun 21
• How Should You Structure Sales Teams for Optimal Performance? Jun 18
• How Predictive is SDR/BDR Quota Attainment of AE Quota Attainment? Jun 17
• SaaS Office Hours Go to Market Survey Edition & Which Metric Should Your SDR/BDR Team Use? Jun 16
• Notes from Office Hours with Hollie Wegman Jun 12
• Benchmarking Sales Prospecting Volumes, Deal Terms, and Meetings in the Coronavirus Era Apr 29
• Six Startup Disciplines for Challenging Times Mar 20
• One of the Most Frequent Errors in Sales Planning and Forecasting Feb 17
• Simpson's Paradox in Measuring Net Dollar Retention Rate Feb 03
• What is a Best in Class Payback Period for a Software Company in 2020? Jan 20
• B2B vs B2C: How Should Your Sales Team Be Allocated to Maximize Success? Jan 05

2019

• How Much Turnover in Your Sales Team Should Your Startup Expect? Dec 12
• Benchmarking Your Sales and Customer Success Teams Nov 21
• The Siren Song of ROI Based Pricing Sep 11
• If You Have Great NDR Retention, Should You Increase Your Marketing Spend? Sep 02
• As Your Sales Team Scales, Focus on Your Middle May 30
• How to Develop Best in Class Sales Efficiency May 10
• The Four Strategic Questions Facing AI Agencies Apr 14
• Should Your Startup Employ Both Assisted and Unassisted Trials to Acquire Customers? Feb 28
• Top 10 Learnings from the Redpoint Free Trial Survey Feb 06

2018

• Which is More Important: New Account Growth or Account Expansion? Dec 11
• The Four Stages of Sales Compensation Structures in Early Stage Startups Nov 25
• In Early Markets, Services Can Be a Competitive Advantage Oct 01
• Timing Cashflows of Your Sales Commissions and Your Customers Jul 15
• An Often Forgotten Characteristic About Your Startup's Ideal Customer Profile The Ideal Customer Profile. The perfect customer. Can you describe it for your startup? The more precisely you can describe it, the better. That will simplify disqualification. But articulating the ICP well isn't enough. Mar 25
• Why Does Your Sales Team Lose Deals? Mar 04
• Reorganizing Your SaaS Startup’s Organizational Structure to Optimize the Customer Lifecycle Jan 31

2017

• The Implication of Secular Increases in SaaS CAC Nov 01
• Monte Carlo Simulations of Inside and Outside Sales Teams in a SaaS Startup Oct 09
• How Much Should A SaaS Startup Invest in Sales & Marketing? Sep 17
• The Challenges of the Platform Go To Market Sep 06
• The Theory and Data Underpinning Sales Commission Plans Sep 04
• Why Cash Conversion Cycle Matters for Your Startup Aug 15
• How to Decide When To Move Upmarket Aug 08
• The Best Book on the Fundamentals of Selling Jul 09
• The "Hiring The Buyer's Role to Sell" Fallacy Jun 01
• Hiring for Bookings Capacity in Sales May 16
• My Algorithm is Better than Yours Apr 26
• A Tale of Two Go To Market Strategies Apr 24
• Is There a No Man's Land in SaaS ACVs? Apr 21
• The Four Dimensions of a Demand Generation Portfolio Apr 17
• SMB or Enterprise - Which is the Better Go To Market in SaaS? Apr 13
• Customer Operations - An Idea for Maximizing Efficient Growth in SaaS Companies Mar 29
• The Three Types of SaaS Value Propositions Mar 17
• A Product Manager's Guide to Moving Up Market Mar 07
• Three Strategies for Engendering Negative Net Churn in Your SaaS Startup Feb 23
• The $100M ARR Customer Jan 17

2016

• When is the Right Time for Your SaaS Startup to Train its Sales People? Dec 12
• How Much to Compensate SaaS Sales Teams for New Sales, Renewals and Expansions Nov 28
• What is the Optimal Contract Length for Your SaaS Startup? Oct 20
• What's the Maximum Rate of Growth for Your SaaS Startup with Paid Customer Acquisition? Sep 19
• Designing a Sales Quota Structure at the Earliest Stages of a SaaS Startup Sep 02
• The Biggest Areas of Underinvestment in SaaS Sales Teams Aug 15
• Fighting and Leveraging Inertia in Sales Aug 04
• Which of the Three Software Budgets Does Your SaaS Startup Target? Jul 24
• The Smallest ACV to Justify an Inside Sales Team at a SaaS Startup Jul 21
• You're in the Business of Selling Promotions Jun 28
• When to Scale Sales for Your SaaS Startup Jun 07
• Comparing Two Ways to Build a SaaS Sales Team Jun 02
• What Average Contract Value is Best for a SaaS Company May 24
• The Rising Importance of Reseller Channels in SaaS May 05
• The Strategic Shift in Revenue for SaaS Startups as They Scale Mar 09
• The Other Payback Period that Matters in SaaS Feb 12
• With Smart Software, Sell Ironman Not Robocop Feb 03

2015

• What is the Optimal Quick Ratio for Your SaaS Startup? Nov 03
• What Quota Attainment Reveals About Your SaaS Startup's Go to Market Oct 28
• Startup Best Practices 19 - Recognizing the Breaking Points of Your Startup's Management Structure Oct 25
• Startup Best Practices 18 - Collaborating with Your Customer During Your Sales Process Oct 11
• The Essential Go To Market Math for Beating Your SaaS Startup's Growth Targets Oct 05
• The Importance of Payback Period for SaaS Startups Sep 21
• Do Vertical SaaS Companies Benefit from Higher Sales Efficiency? Sep 17
• Four Important Data Points about Purchasing Behavior in SaaS Aug 26
• The Number One Objection in the Sales Funnel Aug 18
• When Do SaaS Startups Hire Their First VP of Sales Aug 05
• Startup Best Practices 15 - Start With the Why Jul 12
• The Beauty of Bottoms Up SaaS Businesses Jun 23
• Startup Best Practices 13 - Patience with Unit Economics Jun 14
• The Risk Sales Discounts Impose to Startup Burn Rates May 26
• The Innovator's Solution for SaaS Startups - The Flywheel SaaS Company Apr 19
• How Faster Sales Cycles Become a Competitive Advantage Apr 16
• The 5 Key People in a SaaS Sales Process Mar 26
• The Best Book on Building a SaaS Sales Team Mar 24
• Sales Funnel Optimization for SaaS Startups Mar 10
• Challenging Your Customers During Your SaaS Startup's Sales Process Feb 13
• A Single Report to Measure the Health of Your Startup's Sales Team Feb 09
• The Employee Productivity Patterns of Billion Dollar SaaS Companies Feb 05
• The Sales Motions of B2C2B Companies Jan 12
• B2C2B Startups - Why Selling with Internal Influencers is so Powerful Jan 07
• The Sudden Shift in SaaS Product Pricing Jan 05

2014

• How Much Should Your Startup Spend on Customer Account Expansion? Nov 24
• Why Your SaaS Startup Needs a VP of Customer Success Sooner Than You Might Think Nov 12
• The Marketing Math Behind Scaling a SaaS Salesforce Jun 30
• The Impact of Varying Sales Hiring Strategies on SaaS Startups May 28
• A Surprisingly Powerful Mechanism for Growing a SaaS Startup May 21
• Quantifying the Cost of a Bad Hire Apr 28
• The Challenges SaaS Businesses Face Communicating their Financial Health Apr 17
• How Fast Must a SaaS Startup Grow to Raise a Series A? Mar 17
• Great SaaS Companies Focus on Behavior Change Mar 05
• The Optimal Average Customer Value for SaaS Startups Feb 03
• The Go-To-Market Challenges of B2D Companies Jan 27
• Why Quotas Aren't the Most Important Number for Startup Sales Teams Jan 13
• The Importance of Seasonality in SaaS Startups Jan 09

2013

• Startup Best Practices 3 - How to Structure a Sales and Marketing Team Dec 03
• The Three Churn Mitigation Strategies of SaaS Startups Oct 31
• Sales Efficiency Benchmarks for SaaS Startups Oct 10
• What Your Startup’s MRR Figure Is Hiding Sep 27
• You’re Not Finished Selling Until You Change Your Customers Habits Sep 06
• A team of founders who had just made their first their first hire asked me about culture and on boarding. How do they go about managing people? How do they maintain the values of the business? Aug 21
• Framing Your Startup’s Sales Pitch: Focus on Value, Not on Cost Jul 25
• The Three Phases of Startup Sales Jul 17
• Throwing in the Towel on Google’s Go: What Programming Taught Me About Sales Jun 28
• The Most Effective Price Discovery Question for Your Startup Jun 11
• Three Counterintuitive Points about SMB SaaS May 06
• Hiring Your Startup’s First Salesperson May 03
• The Defining Characteristics of Successful SMB SaaS Startups Apr 17
• Founders, Equip Your Champions Apr 15
• How To Price and Sell Your Startup’s Product Apr 11
• Matching Marketing Tactics to The Sales Funnel Feb 22
• Freemium Businesses Switch the Hunter and Farmer Sales Roles Feb 07
• The product qualified lead (PQL) Jan 15
• To Sell is Human Jan 04

2012

• The one ideal characteristic of your startup’s first customers Dec 07
• Education sales vs execution sales Dec 04
• Segmenting customer pipelines Nov 20
• The Secret to SMB SaaS Distribution Sep 18
• Choosing market segments on customer profitability Sep 13
• The Freemium Game Plan Aug 21
• Segmenting the SaaS Market for Sales Aug 20
• Segmenting the SaaS Market for Sales Aug 20