The Top 100+ SaaStr Posts of All Time

We recently gave the SaaStr.com website a rethink, and as part of it, I took a stab at cataloging the Top 100+ of the 3,000+ pieces of content on the site.

Much you may have read before, but as a group, these are some of our most popular and beloved pieces.

Let us know your favorites, too, in comments on otherwise!!

On Building A World-Class Sales Team:

  1. How Cheap a Product Can You Have And Still Have Salespeople?
  2. How My VP, Sales Doubled Our Sales in 90 Days. And No, It Wasn’t Magic.
  3. 10 Great Questions to Ask a VP Sales During an Interview
  4. What a Great VP Sales Actually Does. Where The Magic Is. And When to Hire One.
  5. The 48 Types of VP Sales. Make Deadly Sure You Hire the Right One.
  6. An Initial Sales Rep Comp Plan to Lower Your Stress Level, Increase Cash, and Make Everyone a Lot of Money
  7. A Basic Structure for a VP, Sales Comp Plan: 50/50/25+
  8. Your #1 Sales Rep Should Be Driving an M6 Convertible By Month 12. (And Not Buying a Panerai Watch.)
  9. If Your VP Sales Isn’t Going to Work Out — You’ll Know in 30 Days
  10. When You Hire Your First Sales Rep — Just Make Sure You Hire Two
  11. Inbound or Outbound Sales? The Answer is Yes
  12. Why The Greatest Sales Teams Just Kill It On Dec 31. When Everyone Else Has Gone Home.
  13. Why It May Take You 12–18 Months to Hire a Great VP, Sales — Period. And What to Do About It.
  14. Should Your VP Sales Start Off as a Player-Coach?
  15. How to Hire A Great VP Sales: The Full Video (and Transcript)
  16. Curse of the ‘Middlers’: Why Happiness Officers Can’t Stand In for True Sales Professionals
  17. Beware of the Confidence of High Win Rates
  18. Why SMB and Enterprise Sales Have Nothing in Common
  19. Can You Scale Sales in the Bay Area? $30k ACV is Probably The Cut-Off
  20. 15+ of the Top Sales & Marketing Mistakes SaaS Startups Make
  21. 10 Rules to Being a VP of Sales in a Startup
  22. Yes, Your VP of Sales Also Has to Be a Great Salesperson Herself
  23. The Two Most Important Things to Look For When You Hire Your First VP of Sales
  24. Field Sales: When Domain Expertise Does Matter. Just Don’t Over-Index.
  25. The Benefits of Hiring a Stretch VP of Sales (and The Risks)
  26. How Not to Fail as a First-Time VP of Sales

On Getting from 10 Customers to Initial Traction (~$1.5m):

  1. The Top 10 Mistakes First Time SaaS Founders Make
  2. How To Know You’ve Hit First Traction In SaaS. The Moment When You’ve Got A Real Company.
  3. If You Don’t Have a Truly Great Founding Team, Just Take a Pause. Don’t Start Your Start-Up Yet.
  4. How to Get From 1.0 Launch to Traction in SaaS
  5. If You Have 10 {Unaffiliated} Customers in SaaS — You Have Something.
  6. Want to Understand SaaS? If Nothing Else — Understand That It Compounds
  7. My Top 10 Year One SaaS Mistakes. Save Yourself Some Pain & Just Don’t Make Them Yourself.
  8. You Really Don’t Know if Your Market is Too Small For Quite a While
  9. In SaaS, You Have to Love the One You’re With
  10. Unfortunately, We (Probably) Have No Idea If Your SaaS Idea is Any Good
  11. The Top 10 Things I’d Tell My Younger CEO Self to Do Better Next Time
  12. How to Cope With Long Sales Cycles
  13. After $2m in ARR — Start Specializing Your Sales Team

On Getting from Initial Traction (~$1.5m) to Initial Scale ($10m) and Beyond

  1. If You Don’t Think You Need a VP of Product, Marketing, Etc. — — Then You Haven’t Worked with a Great One
  2. Growth and Burn Rates at $1m ARR for 20+ Fast Growing SaaS Companies
  3. Post-Traction, You Need to Spend 20% of Your Time Recruiting
  4. Don’t Accidentally Bootstrap Yourself to Death
  5. From Initial Traction to Initial Scale (~$10M in ARR): The Hardest Phase. But — The Cavalry is Coming.
  6. In The Early Days, You Won’t Have Enough Customers. But Your Mini-Brand Will Come to Your Rescue.
  7. Around $4-$5m in ARR, You Probably Will Need a Chief MRR Officer
  8. The SaaS Year of Hell. And Then — Reignition.
  9. Everything is Sort of the Same at a Given ACV (Annual Contract Value)
  10. Workday is Growing 90% this Year. At $250m in ARR. So Wake Up: You Probably Need to Do A Lot, Lot Better.
  11. SaaS and The 7–10 Year Sales Cycle
  12. Silos-in-the-Enterprise: Good. But Not All They Are Cracked Up to Be.
  13. Why Most SaaS Companies Add/Have an Overseas Dev Team to Help Scale
  14. Do You Scale? It’s Harder in SaaS.
  15. SaaS Start-Ups: Buck Up — It Really Does Get Easier.
  16. Imagine a World With Unlimited Capital, and See Where It Takes You
  17. What Your First 100 Hires Will Look Like
  18. What You Want to Hit: “50+20” at $10m in ARR
  19. 7 “Easy” Ways to Increase Sales
  20. How to Gracefull Miss a Quater. And Take the Right Actions Afterwards.
  21. Your Quickest Way to Grow Faster: Move from Quarterly to Monthly Quotas. Today. Now.
  22. 10 Tips to Avoid SaaS Burnout
  23. Two Things to Do When You Don’t Know What to Do

At Scale

  1. Six Things in SaaS That Are Only Obvious at Scale
  2. Build vs. Buy is Mostly Really Now vs. Later
  3. What Lies Beyond $100m ARR? Your Company-as-a-Platform. For Others.
  4. Why You’ll Want to Raise $100,000,000 for Your SaaS Start-Up: The Incremental Customer
  5. The $64,000,000 Question: When Things Become Unstoppable

On The Journey

  1. If You Go Small, You’ll Never Have a Legacy
  2. I Don’t Know about CEO Coaches. But We All Could Use CEO Trainers.
  3. The Workday IPO and ‘F You Money
  4. I’m Tired of Running My Successful Start-up After X Years. What Should I Do?
  5. You {Probably} Aren’t Changing the World, So Let’s Make it Better
  6. To a Better Place: When is It Time as CEO/Founder to Move On?
  7. Those Brief, Rare Moments of True Wonderfulness in Start-Ups
  8. The 7 Best Pieces of Business Advice I Was Given
  9. The Hardest Part About SaaS Companies, At Each Stage
  10. The Top 10 Worst Pieces of SaaS Advice
  11. Why Some SaaS Companies Stall Out at $20m ARR or So
  12. The Friends You’ll Lose. And The Ones You’ll Gain.

On Mergers & Acquisitions (To Sell — Or Not?), IPOs and Exits:

  1. $3 Billion Is the New $1 Billion in SaaS
  2. Acquisitions — If You Do Sell, Try to Make Sure It’s At a Local Maximum
  3. If You Sell Your Company, You’ll Either Feel Like A Used Car Salesman — Or Like Hugo
  4. The Simple Reason Why There Will be 10–20 Great CRM IPOs in the Next Few Years
  5. A Real Life SaaS Case Study: Eloqua. Marketo. Pardot. There Are 3 Different Paths to Success, My Young Padwan.
  6. Why I’d Go Big. And Why You Should Ignore Me, and Most of the Others That Tell You That.
  7. BATNA, And Oracle’s $811m Purchase of Eloqua
  8. What If There Are No Natural Acquirers (For Your Company)?
  9. If You Sell Your Company, Use a Banker
  10. If You Sell Your Company — Prioritize Dollars Over Prestige
  11. “Deal or No Deal? When — and If — To Sell Your Company” on NBC’s Press:Here
  12. My Top 3 Tips On How to Help Your Team Succeed if You Are Acquired
  13. SaaStr on TechCrunch! The M&A “Nibble” And What To Do When You Get One
  14. One More Reason to Take That M&A Offer — Sponsor Turnover
  15. If You Get Acquired, You’ll Need to Learn to Move from Persuasion to Alignment
  16. Should I Sell for $50m … Or Push On And Try to Build a Unicorn?
  17. The Rise of Private Equity in SaaS: A Gift to Founders

On SaaS Start-Ups:

  1. On “Paying” Your Mentors and Advisors: The 2.5x Rule
  2. Is 5x the New 2x in SaaS?
  3. What the Second Time SaaS CEOs are All Doing
  4. How to Figure Out Your Competitors’ Revenues in About 70 Seconds
  5. What to Do If Your Business Decelerates
  6. TAM is Great. But What Really Matters is That You Believe You Can Hit $100m ARR in 7 Years.
  7. The Pernicious Effect of Dilution in SaaS: The Cold, Hard, Bloody numbers
  8. Your (Belated) SaaS New Year’s Resolution: Add a Layer
  9. Very Good Days, and 5 Pretty Bad Days, as a SaaS CEO
  10. Day 1: Who Should Be CEO? A Checklist.
  11. The Best $500,000 I Ever Raised — And Why Party Rounds May Not Be the Way to Go in SaaS
  12. A Simple Commitment Test For You And Your Co-Founders
  13. Can an 8-Person StartUp Sell to a CIO? Yes — If You Understand The Social Contract.
  14. 4 Good Reasons Not to Start a SaaS Start-Up
  15. Why You Need 50 Million Active Users for Freemium to Actually Work
  16. In The Early Days, Don’t Forget To Pay Yourself, Too
  17. As The Year Winds Down: Get Some Rest. Or You’ll End Up Washing Out in SaaS in Year 5.
  18. It Takes at Least 7 Years in SaaS: Can You Do The Time?
  19. Start-Up Success in SaaS? You Have to Bend the Odds In Your Favor. Some Thoughts on How to Do It.
  20. Why If You Quit Every Year You Won’t Ever Make Any Money
  21. The All-In Dilution from an Outside CEO: Just Make Sure You Do the Math
  22. Hyperaggresiveness … Can You Do It?
  23. Maybe It’s More Important Your Co-Founders’ Weaknesses are Complementary To Yours

On Marketing, Leads and Partners:

  1. Why Lead Velocity Rate (LVR) Is The Most Important Metric in SaaS
  2. Hire the Right Type of VP Marketing — Or You’ll Just End Up With a Bunch of Blue Pens with Your Logo On Them
  3. How Much Can You Really Spend on Marketing? (And The “Problem” With The S+M=ACV Axiom
  4. 22 Critical Tips in Hiring a Great VP Marketing (From Marketo, EchoSign, Insightly)
  5. Yes, You Can Measure Everything. Marketing, PR, Dev, Lead Efficiency. Do It.
  6. 5 Simple Ideas to Immediately Improve Your Conversion Rates in SaaS
  7. The Law of Attach Rates, And Why Partners Can’t Really Move the Needle For You (Directly)
  8. The Shifting Sands of SaaS Relationships. Here’s How to Handle It.
  9. 50,000,000+ Views Later: What I’ve Learned About Content Marketing
  10. The Problem with Junior Marketing Hires (And What a True VP Costs)

On Pricing and Driving Up The Deal Size:

  1. The Next Wave of SMB SaaS: True Solutions. Priced as Such.
  2. A Solution Sale Can Capture 3–20x the Revenues of A Tool Sale. With Almost the Exact Same Core Product.
  3. Why Tilting Just a Smidge from Self-Service Can Grow Your Revenue 30x
  4. A Little Less About Pricing. A Little More About Deal Size. Please.
  5. 3 Tips for Building Discounts into Your SaaS Pricing Model (from OpenView Labs)
  6. Why There Is a 50/50 Chance You’ll Tilt Upmarket in SaaS
  7. The Enterprise: Go Biggish, or Go Home
  8. All Pricing is Relative. How to Make That Work in Your Favor.
  9. Don’t Forget the Services Revenue
  10. How to Best Calculate Pricing for a New Product
  11. If You Leave The Low End of the Market … Your Probably Can’t Go Back
  12. How to Sell to SMBs and Still Get to $100m in ARR

On Customer Success, Upsells and Retention:

  1. I Was Wrong. NPS is a Great Core Metric.
  2. The $2 Million Dollar Man (/Woman): How to Think About Scaling Your Customer Success Team
  3. CLTV Isn’t The Whole Story. Don’t Shortchange Second-Order Revenue.
  4. Your Customer Success Team. Hire Early. And No Squishy Goals — It’s All About the Numbers.
  5. Want Happy Customers? Implement the 5-Visits-Plus-2-Badges Rule. For Your Customer Success Team — And You.
  6. Everyone in SaaS Needs to Do Customer Support. At Least Until You Have 50 Employees. But Ideally, Forever.
  7. Got 100 Customers? Believe It Or Not, It’s Time for Your First User Conference
  8. Dreamforce, BoxWorks, Arse-Kissing, and Behavioral vs. Attitudinal Loyalty
  9. Measure Your Churn. But What’s Even More Important is to Measure Your “Almost Churn”. 5 Tricks to Help You Here.
  10. Prisoners, And Why It Doesn’t Really Matter Your App Is So Hard to Rip Out
  11. I Never Lost a Customer I Actually Visited
  12. Why It’s Year 3 When You Lose Your Customers
  13. Why I Usually (Not Always) Prefer Customer Success to Report to the CEO
  14. The 10+ Year Customer
  15. Customer Sucess is a Single Digit Hire
  16. If Nothing Else — Segment Churn

Competition:

  1. As Long As You Are Growing 60% Or More — Your Competition Can’t Really Hurt You
  2. It Doesn’t Really Matter When Your Competitor is Acquired. (Except It Means You Weren’t.)
  3. Why Competition Is So Bitter in SaaS: Oligopolies and Dominant Strategy Equilibriums
  4. Don’t Confuse Room at the Bottom with Disruption
  5. Why You Should Kill Your Competitor in SaaS
  6. The Virtues and Opportunities in Being #2
  7. When Big Companies Can Kill You. And When They Can’t.
  8. Why Are Those Founder/CEOs So Snooty? Because They are Failing
  9. Your Start-Up’s Team Isn’t Actually Any More Agile Than the Big Guys. Why You Really Still Can Win.
  10. 5 Ways to Enter a Crowded Market. And 3+ Ways Not To.

Hiring and Retention:

  1. What Order Should You Hire Your Management Team In?
  2. 7 Simple Tips to Being a (Much) Better First Time Manager
  3. Don’t Ever Make Anyone “Head of Sales/Marketing/Engineering/Whatever” in SaaS
  4. By The Time You Give Them a Raise, They’re Already Out The Door
  5. At About $2m in ARR, Every Great Hire Will Be Accretive.
  6. I Hired My VP of Marketing at $20k MRR. It Wasn’t a Week Too Early.
  7. 5 Tips to Improve the Odds When You Hire VPs Who Were Fired or Quit
  8. Money, Bonuses, “Customers That Waste My Time”, and Greed: You Get What You Pay For
  9. You Can’t Hire a VP That You Don’t Love
  10. Alignment: Your VP Sales and VP Marketing Should Be Your Mom and Dad of Revenue
  11. When Are You Ready to Hire Pure BigCo Guys Into Your Start-Up?
  12. Why Hiring From Your Direct Competitors Usually Doesn’t Work Out
  13. How to Fire A Crummy Employee
  14. The Perils and Pitfalls of the “Been There, Done That” VP: Posers and Mercenaries
  15. Don’t Hire CEOs, Architects, Game Devs, or Dualies
  16. Don’t Forget to Pay People Right — Or at Least as Much as You Can
  17. How to Know if a Key Hire is an A or a B (or even a C)
  18. Why We’re All Ready for a CRO or COO Earlier These Days
  19. Why You’ll Need Just About $3,000,000 To Build Your First Real Sales & Marketing Team
  20. How to Get Better at Recruiting (We All Need To)

Metrics and Operations:

  1. Two SaaS Metrics That Actually Don’t Matter That Much: Absolute Churn and Sales Cycles
  2. Trust is Lost in a Heartbeat.
  3. 7 Steps to Getting to Cash-Flow Positive Faster (in SaaS)
  4. The Power and Honesty in an L4M Model. Build One Now.
  5. Knowing — and Sharing — Your Zero Cash Date
  6. We’re Still Waiting for a Cloud That Just Works
  7. At $50k in MRR, Running Out of Money in No Longer an Excuse
  8. The Top 10 Finance Mistakes First Time Founders Make

Venture Capital:

  1. Why One Compay Raises $25m+ … And Another Doesn’t
  2. The 10x Rule: What Raising $1 of Venture Capital Really Means
  3. Why if You are a VC You Should be Insanely Rich
  4. 16 Rookie Errors Founders Make Pitching to VCs — And Passing the “20 Minute” Test
  5. Tier 1 VC is Great. But More Money May Be Even Better.
  6. How to Know If You Should Go for Venture Capital, In One Easy Question
  7. What Is Your Social Contract With Your VCs?
  8. On Leaving Money on the Table and the Endless IPO Window
  9. Seven Guidelines on Selling Some of Your Stock in a VC Round
  10. Why VCs Need Unicorns Just to Survive
  11. The One Best, “Secret” Hack to Getting Venture Funding
  12. Bootstrapping in SaaS? It Works. But Add ~4 Years to the IPO Timeline
  13. 22 Reasons I Won’t Fund You
  14. If You Want to Get Funded — Dude, Make It Easy On Them

Product:

  1. A Should I Do a Free Trial or Not Checklist
  2. One Simple Rule on When to Build a “Custom” Feature
  3. Real Ent Software Don’t Need No Stinkin’ UI/UX
  4. On Not Forgetting to be 10x Better
  5. Want to Go Upmarket? You’ll Need a Great Dashboard in Your Product
Published on June 22, 2018

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