On Building A World-Class Sales Team:
- How Cheap a Product Can You Have And Still Have Salespeople?
- How My VP, Sales Doubled Our Sales in 90 Days. And No, It Wasn’t Magic.
- 10 Great Questions to Ask a VP Sales During an Interview
- What a Great VP Sales Actually Does. Where The Magic Is. And When to Hire One.
- The 48 Types of VP Sales. Make Deadly Sure You Hire the Right One.
- An Initial Sales Rep Comp Plan to Lower Your Stress Level, Increase Cash, and Make Everyone a Lot of Money
- A Basic Structure for a VP, Sales Comp Plan: 50/50/25+
- Your #1 Sales Rep Should Be Driving an M6 Convertible By Month 12. (And Not Buying a Panerai Watch.)
- If Your VP Sales Isn’t Going to Work Out — You’ll Know in 30 Days
- When You Hire Your First Sales Rep — Just Make Sure You Hire Two
- Inbound or Outbound Sales? The Answer is Yes
- Why The Greatest Sales Teams Just Kill It On Dec 31. When Everyone Else Has Gone Home.
- Why It May Take You 12-18 Months to Hire a Great VP, Sales — Period. And What to Do About It.
- Should Your VP Sales Start Off as a Player-Coach?
- How to Hire A Great VP Sales: The Full Video (and Transcript)
- Curse of the ‘Middlers’: Why Happiness Officers Can’t Stand In for True Sales Professionals
- Beware of the Confidence of High Win Rates
- Why SMB and Enterprise Sales Have Nothing in Common
- Can You Scale Sales in the Bay Area? $30k ACV is Probably The Cut-Off
- 15+ of the Top Sales & Marketing Mistakes SaaS Startups Make
- 10 Rules to Being a VP of Sales in a Startup
- Yes, Your VP of Sales Also Has to Be a Great Salesperson Herself
- The Two Most Important Things to Look For When You Hire Your First VP of Sales
- Field Sales: When Domain Expertise Does Matter. Just Don’t Over-Index.
- The Benefits of Hiring a Stretch VP of Sales (and The Risks)
- How Not to Fail as a First-Time VP of Sales
On Getting from 10 Customers to Initial Traction (~$1.5m):
- The Top 10 Mistakes First Time SaaS Founders Make
- How To Know You’ve Hit First Traction In SaaS. The Moment When You’ve Got A Real Company.
- If You Don’t Have a Truly Great Founding Team, Just Take a Pause. Don’t Start Your Start-Up Yet.
- How to Get From 1.0 Launch to Traction in SaaS
- If You Have 10 {Unaffiliated} Customers in SaaS — You Have Something.
- Want to Understand SaaS? If Nothing Else — Understand That It Compounds
- My Top 10 Year One SaaS Mistakes. Save Yourself Some Pain & Just Don’t Make Them Yourself.
- You Really Don’t Know if Your Market is Too Small For Quite a While
- In SaaS, You Have to Love the One You’re With
- Unfortunately, We (Probably) Have No Idea If Your SaaS Idea is Any Good
- The Top 10 Things I’d Tell My Younger CEO Self to Do Better Next Time
- How to Cope With Long Sales Cycles
- After $2m in ARR — Start Specializing Your Sales Team
On Getting from Initial Traction (~$1.5m) to Initial Scale ($10m) and Beyond
- If You Don’t Think You Need a VP of Product, Marketing, Etc. — Then You Haven’t Worked with a Great One
- Growth and Burn Rates at $1m ARR for 20+ Fast Growing SaaS Companies
- Post-Traction, You Need to Spend 20% of Your Time Recruiting
- Don’t Accidentally Bootstrap Yourself to Death
- From Initial Traction to Initial Scale (~$10M in ARR): The Hardest Phase. But — The Cavalry is Coming.
- In The Early Days, You Won’t Have Enough Customers. But Your Mini-Brand Will Come to Your Rescue.
- Around $4-$5m in ARR, You Probably Will Need a Chief MRR Officer
- The SaaS Year of Hell. And Then – Reignition.
- Everything is Sort of the Same at a Given ACV (Annual Contract Value)
- Workday is Growing 90% this Year. At $250m in ARR. So Wake Up: You Probably Need to Do A Lot, Lot Better.
- SaaS and The 7-10 Year Sales Cycle
- Silos-in-the-Enterprise: Good. But Not All They Are Cracked Up to Be.
- Why Most SaaS Companies Add/Have an Overseas Dev Team to Help Scale
- Do You Scale? It’s Harder in SaaS.
- SaaS Start-Ups: Buck Up – It Really Does Get Easier.
- Imagine a World With Unlimited Capital, and See Where It Takes You
- What Your First 100 Hires Will Look Like
- What You Want to Hit: “50+20” at $10m in ARR
- 7 “Easy” Ways to Increase Sales
- How to Gracefull Miss a Quater. And Take the Right Actions Afterwards.
- Your Quickest Way to Grow Faster: Move from Quarterly to Monthly Quotas. Today. Now.
- 10 Tips to Avoid SaaS Burnout
- Two Things to Do When You Don’t Know What to Do
At Scale
- Six Things in SaaS That Are Only Obvious at Scale
- Build vs. Buy is Mostly Really Now vs. Later
- What Lies Beyond $100m ARR? Your Company-as-a-Platform. For Others.
- Why You’ll Want to Raise $100,000,000 for Your SaaS Start-Up: The Incremental Customer
- The $64,000,000 Question: When Things Become Unstoppable
- The 11+ Year Customer
- The 10+ Year Customer 🙂
On The Journey
- If You Go Small, You’ll Never Have a Legacy
- I Don’t Know about CEO Coaches. But We All Could Use CEO Trainers.
- The Workday IPO and ‘F You Money
- I’m Tired of Running My Successful Start-up After X Years. What Should I Do?
- You {Probably} Aren’t Changing the World, So Let’s Make it Better
- To a Better Place: When is It Time as CEO/Founder to Move On?
- Those Brief, Rare Moments of True Wonderfulness in Start-Ups
- The 7 Best Pieces of Business Advice I Was Given
- The Hardest Part About SaaS Companies, At Each Stage
- The Top 10 Worst Pieces of SaaS Advice
- Why Some SaaS Companies Stall Out at $20m ARR or So
- The Friends You’ll Lose. And The Ones You’ll Gain.
On Mergers & Acquisitions (To Sell – Or Not?), IPOs and Exits:
- $3 Billion Is the New $1 Billion in SaaS
- Acquisitions — If You Do Sell, Try to Make Sure It’s At a Local Maximum
- If You Sell Your Company, You’ll Either Feel Like A Used Car Salesman — Or Like Hugo
- The Simple Reason Why There Will be 10-20 Great CRM IPOs in the Next Few Years
- A Real Life SaaS Case Study: Eloqua. Marketo. Pardot. There Are 3 Different Paths to Success, My Young Padwan.
- Why I’d Go Big. And Why You Should Ignore Me, and Most of the Others That Tell You That.
- BATNA, And Oracle’s $811m Purchase of Eloqua
- What If There Are No Natural Acquirers (For Your Company)?
- If You Sell Your Company, Use a Banker
- If You Sell Your Company — Prioritize Dollars Over Prestige
- “Deal or No Deal? When — and If — To Sell Your Company” on NBC’s Press:Here
- My Top 3 Tips On How to Help Your Team Succeed if You Are Acquired
- SaaStr on TechCrunch! The M&A “Nibble” And What To Do When You Get One
- One More Reason to Take That M&A Offer – Sponsor Turnover
- If You Get Acquired, You’ll Need to Learn to Move from Persuasion to Alignment
- Should I Sell for $50m … Or Push On And Try to Build a Unicorn?
- The Rise of Private Equity in SaaS: A Gift to Founders
On SaaS Start-Ups:
- On “Paying” Your Mentors and Advisors: The 2.5x Rule
- Is 5x the New 2x in SaaS?
- What the Second Time SaaS CEOs are All Doing
- How to Figure Out Your Competitors’ Revenues in About 70 Seconds
- What to Do If Your Business Decelerates
- TAM is Great. But What Really Matters is That You Believe You Can Hit $100m ARR in 7 Years.
- The Pernicious Effect of Dilution in SaaS: The Cold, Hard, Bloody numbers
- Your (Belated) SaaS New Year’s Resolution: Add a Layer
- Very Good Days, and 5 Pretty Bad Days, as a SaaS CEO
- Day 1: Who Should Be CEO? A Checklist.
- The Best $500,000 I Ever Raised — And Why Party Rounds May Not Be the Way to Go in SaaS
- A Simple Commitment Test For You And Your Co-Founders
- Can an 8-Person StartUp Sell to a CIO? Yes — If You Understand The Social Contract.
- 4 Good Reasons Not to Start a SaaS Start-Up
- Why You Need 50 Million Active Users for Freemium to Actually Work
- In The Early Days, Don’t Forget To Pay Yourself, Too
- As The Year Winds Down: Get Some Rest. Or You’ll End Up Washing Out in SaaS in Year 5.
- It Takes at Least 7 Years in SaaS: Can You Do The Time?
- Start-Up Success in SaaS? You Have to Bend the Odds In Your Favor. Some Thoughts on How to Do It.
- Why If You Quit Every Year You Won’t Ever Make Any Money
- The All-In Dilution from an Outside CEO: Just Make Sure You Do the Math
- Hyperaggresiveness … Can You Do It?
- Maybe It’s More Important Your Co-Founders’ Weaknesses are Complementary To Yours
On Marketing, Leads and Partners:
- Why Lead Velocity Rate (LVR) Is The Most Important Metric in SaaS
- Hire the Right Type of VP Marketing — Or You’ll Just End Up With a Bunch of Blue Pens with Your Logo On Them
- How Much Can You Really Spend on Marketing? (And The “Problem” With The S+M=ACV Axiom
- The Lead Plateau You May Hit Just as it Gets Good. How to Plan Around It.
- 22 Critical Tips in Hiring a Great VP Marketing (From Marketo, EchoSign, Insightly)
- Yes, You Can Measure Everything. Marketing, PR, Dev, Lead Efficiency. Do It.
- 5 Simple Ideas to Immediately Improve Your Conversion Rates in SaaS
- The Law of Attach Rates, And Why Partners Can’t Really Move the Needle For You (Directly)
- The Shifting Sands of SaaS Relationships. Here’s How to Handle It.
- 50,000,000+ Views Later: What I’ve Learned About Content Marketing
- The Problem with Junior Marketing Hires (And What a True VP Costs)
On Pricing and Driving Up The Deal Size:
- The Next Wave of SMB SaaS: True Solutions. Priced as Such.
- A Solution Sale Can Capture 3-20x the Revenues of A Tool Sale. With Almost the Exact Same Core Product.
- Why Tilting Just a Smidge from Self-Service Can Grow Your Revenue 30x
- A Little Less About Pricing. A Little More About Deal Size. Please.
- 3 Tips for Building Discounts into Your SaaS Pricing Model (from OpenView Labs)
- Why There Is a 50/50 Chance You’ll Tilt Upmarket in SaaS
- The Enterprise: Go Biggish, or Go Home
- All Pricing is Relative. How to Make That Work in Your Favor.
- Don’t Forget the Services Revenue
- How to Best Calculate Pricing for a New Product
- If You Leave The Low End of the Market … Your Probably Can’t Go Back
- How to Sell to SMBs and Still Get to $100m in ARR
On Customer Success, Upsells and Retention:
- I Was Wrong. NPS is a Great Core Metric.
- The $2 Million Dollar Man (/Woman): How to Think About Scaling Your Customer Success Team
- CLTV Isn’t The Whole Story. Don’t Shortchange Second-Order Revenue.
- Your Customer Success Team. Hire Early. And No Squishy Goals — It’s All About the Numbers.
- Want Happy Customers? Implement the 5-Visits-Plus-2-Badges Rule. For Your Customer Success Team — And You.
- Everyone in SaaS Needs to Do Customer Support. At Least Until You Have 50 Employees. But Ideally, Forever.
- Got 100 Customers? Believe It Or Not, It’s Time for Your First User Conference
- Dreamforce, BoxWorks, Arse-Kissing, and Behavioral vs. Attitudinal Loyalty
- Measure Your Churn. But What’s Even More Important is to Measure Your “Almost Churn”. 5 Tricks to Help You Here.
- Prisoners, And Why It Doesn’t Really Matter Your App Is So Hard to Rip Out
- I Never Lost a Customer I Actually Visited
- Why It’s Year 3 When You Lose Your Customers
- Why I Usually (Not Always) Prefer Customer Success to Report to the CEO
- The 10+ Year Customer
- Customer Sucess is a Single Digit Hire
- If Nothing Else — Segment Churn
Competition:
- As Long As You Are Growing 60% Or More — Your Competition Can’t Really Hurt You
- It Doesn’t Really Matter When Your Competitor is Acquired. (Except It Means You Weren’t.)
- Why Competition Is So Bitter in SaaS: Oligopolies and Dominant Strategy Equilibriums
- Don’t Confuse Room at the Bottom with Disruption
- Why You Should Kill Your Competitor in SaaS
- The Virtues and Opportunities in Being #2
- When Big Companies Can Kill You. And When They Can’t.
- Why Are Those Founder/CEOs So Snooty? Because They are Failing
- Your Start-Up’s Team Isn’t Actually Any More Agile Than the Big Guys. Why You Really Still Can Win.
- 5 Ways to Enter a Crowded Market. And 3+ Ways Not To.
Hiring and Retention:
- What Order Should You Hire Your Management Team In?
- 7 Simple Tips to Being a (Much) Better First Time Manager
- Don’t Ever Make Anyone “Head of Sales/Marketing/Engineering/Whatever” in SaaS
- By The Time You Give Them a Raise, They’re Already Out The Door
- At About $2m in ARR, Every Great Hire Will Be Accretive.
- I Hired My VP of Marketing at $20k MRR. It Wasn’t a Week Too Early.
- 5 Tips to Improve the Odds When You Hire VPs Who Were Fired or Quit
- Money, Bonuses, “Customers That Waste My Time”, and Greed: You Get What You Pay For
- You Can’t Hire a VP That You Don’t Love
- Alignment: Your VP Sales and VP Marketing Should Be Your Mom and Dad of Revenue
- When Are You Ready to Hire Pure BigCo Guys Into Your Start-Up?
- Why Hiring From Your Direct Competitors Usually Doesn’t Work Out
- How to Fire A Crummy Employee
- The Perils and Pitfalls of the “Been There, Done That” VP: Posers and Mercenaries
- Don’t Hire CEOs, Architects, Game Devs, or Dualies
- Don’t Forget to Pay People Right – Or at Least as Much as You Can
- How to Know if a Key Hire is an A or a B (or even a C)
- Why We’re All Ready for a CRO or COO Earlier These Days
- Why You’ll Need Just About $3,000,000 To Build Your First Real Sales & Marketing Team
- How to Get Better at Recruiting (We All Need To)
Metrics and Operations:
- Two SaaS Metrics That Actually Don’t Matter That Much: Absolute Churn and Sales Cycles
- Trust is Lost in a Heartbeat.
- 7 Steps to Getting to Cash-Flow Positive Faster (in SaaS)
- The Power and Honesty in an L4M Model. Build One Now.
- Knowing — and Sharing — Your Zero Cash Date
- We’re Still Waiting for a Cloud That Just Works
- At $50k in MRR, Running Out of Money in No Longer an Excuse
- The Top 10 Finance Mistakes First Time Founders Make
Venture Capital:
- Why One Compay Raises $25m+ … And Another Doesn’t
- The 10x Rule: What Raising $1 of Venture Capital Really Means
- Why if You are a VC You Should be Insanely Rich
- 16 Rookie Errors Founders Make Pitching to VCs — And Passing the “20 Minute” Test
- Tier 1 VC is Great. But More Money May Be Even Better.
- How to Know If You Should Go for Venture Capital, In One Easy Question
- What Is Your Social Contract With Your VCs?
- On Leaving Money on the Table and the Endless IPO Window
- Seven Guidelines on Selling Some of Your Stock in a VC Round
- Why VCs Need Unicorns Just to Survive
- The One Best, “Secret” Hack to Getting Venture Funding
- Bootstrapping in SaaS? It Works. But Add ~4 Years to the IPO Timeline
- 22 Reasons I Won’t Fund You
- If You Want to Get Funded – Dude, Make It Easy On Them
Product:
- A Should I Do a Free Trial or Not Checklist
- One Simple Rule on When to Build a “Custom” Feature
- Real Ent Software Don’t Need No Stinkin’ UI/UX
- On Not Forgetting to be 10x Better
- Want to Go Upmarket? You’ll Need a Great Dashboard in Your Product
Some of Best of SaaStr Annual videos:
Some of the best videos on scaling with Jason: