Category Archives: Uncategorized

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SaaStr on NBC’s Press:Here on Box, DropBox, WhatsApp — And the Lack of Fear

NBC was kind enough to have us back on Press:Here (right after Meet-the-Press) to discuss DropBox’s almost-$1-billion in debt and equity raised this year, Box’s IPO, and beyond that, just what’s Going On in the Enterprise these days. My overall

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SaaStr on NBC’s Press:Here on Box, DropBox, WhatsApp — And the Lack of Fear

NBC was kind enough to have us back on Press:Here (right after Meet-the-Press) to discuss DropBox’s almost-$1-billion in debt and equity raised this year, Box’s IPO, and beyond that, just what’s Going On in the Enterprise these days. My overall

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Come to the SaaStr Spring Soiree April 24 on Sand Hill Road — And Also Learn How to Hire a Great VP of Marketing!

Last September, we did the first SaaStr get together, the SaaStr Summer Social.  Over 500 SaaS founders, execs, and VCs got together on Sand Hill Road for cocktails, BBQ, and a chance to discuss all things recurring revenue.  You can

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Come to the SaaStr Spring Soiree April 24 on Sand Hill Road — And Also Learn How to Hire a Great VP of Marketing!

Last September, we did the first SaaStr get together, the SaaStr Summer Social.  Over 500 SaaS founders, execs, and VCs got together on Sand Hill Road for cocktails, BBQ, and a chance to discuss all things recurring revenue.  You can

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SaaStr on RedditAMA (“Ask Me Anything”) Tomorrow, Th 3/27, at 2pm PST

If you have time, tomorrow at 2pm PST I’ll be online at Reddit answering your questions on SaaS, or I guess, about just about anything. Since it’s called Ask Me Anything. I’ve set aside at least 2 hours so if

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SaaStr on RedditAMA (“Ask Me Anything”) Tomorrow, Th 3/27, at 2pm PST

If you have time, tomorrow at 2pm PST I’ll be online at Reddit answering your questions on SaaS, or I guess, about just about anything. Since it’s called Ask Me Anything. I’ve set aside at least 2 hours so if

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The Simple Reason Why There Will be 10-20 Great CRM IPOs in the Next Few Years

I wrote a while back about Room at The Bottom, and how once a space gets big enough (~$100m) or so … the biggest guys end up abandoning many of the smallest customers and segments in their space.  And once

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The Simple Reason Why There Will be 10-20 Great CRM IPOs in the Next Few Years

I wrote a while back about Room at The Bottom, and how once a space gets big enough (~$100m) or so … the biggest guys end up abandoning many of the smallest customers and segments in their space.  And once

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SaaStr on GrowthEverywhere: “On Building a $100 Million Dollar Revenue Machine”

I had a chance to do a fun and in-depth interview (52 minutes!) with Eric Sui of Growth Everywhere on the learnings of building, scaling and growing a SaaS business. You can read it all here (EchoSign CEO Jason Lemkin

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SaaStr on GrowthEverywhere: “On Building a $100 Million Dollar Revenue Machine”

I had a chance to do a fun and in-depth interview (52 minutes!) with Eric Sui of Growth Everywhere on the learnings of building, scaling and growing a SaaS business. You can read it all here (EchoSign CEO Jason Lemkin

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5 Very Good Days, and 5 Pretty Bad Days, as a SaaS CEO

Forbes was kind enough to pick up a thread I did on Quora about my 5 favorite good days, and 5 most visceral bad days, in the early days, of getting from $0 to $10m in ARR. If you didn’t

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5 Very Good Days, and 5 Pretty Bad Days, as a SaaS CEO

Forbes was kind enough to pick up a thread I did on Quora about my 5 favorite good days, and 5 most visceral bad days, in the early days, of getting from $0 to $10m in ARR. If you didn’t

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Is 5x the New 2x in SaaS?

Back in 2012, when the SaaStr audience was about 1/30th of what it is today, I wrote a post that a lot of folks didn’t like:  “Workday is Growing 90% this Year.  At $250m in ARR.  So Wake Up:  You

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Is 5x the New 2x in SaaS?

Back in 2012, when the SaaStr audience was about 1/30th of what it is today, I wrote a post that a lot of folks didn’t like:  “Workday is Growing 90% this Year.  At $250m in ARR.  So Wake Up:  You

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Don’t Ever Make Anyone “Head of Sales/Marketing/Engineering/Whatever” in SaaS

A few months ago, I gave a great SaaS Founder CEO a Gift. A real gift. This founder CEO was at about $1m in ARR, doing well, but with only a smidge of angel funding and limited resources. And I

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Don’t Ever Make Anyone “Head of Sales/Marketing/Engineering/Whatever” in SaaS

A few months ago, I gave a great SaaS Founder CEO a Gift. A real gift. This founder CEO was at about $1m in ARR, doing well, but with only a smidge of angel funding and limited resources. And I

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Everyone in SaaS Needs to Do Customer Support. At Least Until You Have 50 Employees. But Ideally, Forever.

I’m not sure if you saw the recent rant of David Marcus, president of PayPal.  Complaining his employees weren’t using PayPal apps. Well, dude, what do you expect? Yes, you’re right.  It’s not cool your team doesn’t use PayPal every

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Everyone in SaaS Needs to Do Customer Support. At Least Until You Have 50 Employees. But Ideally, Forever.

I’m not sure if you saw the recent rant of David Marcus, president of PayPal.  Complaining his employees weren’t using PayPal apps. Well, dude, what do you expect? Yes, you’re right.  It’s not cool your team doesn’t use PayPal every

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In SaaS, As Long As You Are Growing 60% Or More — Your Competition Can’t Really Hurt You

Recently, I met with a good friend running a SaaS company doing about $4 million in ARR.  A really good SaaS company.  And he was beside himself. First, he was just plain exhausted.  He was in that zone from $1

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In SaaS, As Long As You Are Growing 60% Or More — Your Competition Can’t Really Hurt You

Recently, I met with a good friend running a SaaS company doing about $4 million in ARR.  A really good SaaS company.  And he was beside himself. First, he was just plain exhausted.  He was in that zone from $1

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A Solution Sale Can Capture 3-20x the Revenues of A Tool Sale. With Almost the Exact Same Core Product.

Recently, I caught up with two great entrepreneurs/CEOs, both doing a few million in ARR and growing quickly.  Doing well. Both had a roughly similar make-up of customers, split between: Big Customers (Fortune 500 / Global 2000 types) — not

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A Solution Sale Can Capture 3-20x the Revenues of A Tool Sale. With Almost the Exact Same Core Product.

Recently, I caught up with two great entrepreneurs/CEOs, both doing a few million in ARR and growing quickly.  Doing well. Both had a roughly similar make-up of customers, split between: Big Customers (Fortune 500 / Global 2000 types) — not

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“Deal or No Deal? When — and If — To Sell Your Company”. On NBC’s Press:Here.

I had a great session on NBC’s Press:Here Yesterday together with The New York Times and TechCrunch on when to sell, or not.  We touched on a lot of SaaStr themes, including a personal favorite of mine — “If You

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“Deal or No Deal? When — and If — To Sell Your Company”. On NBC’s Press:Here.

I had a great session on NBC’s Press:Here Yesterday together with The New York Times and TechCrunch on when to sell, or not.  We touched on a lot of SaaStr themes, including a personal favorite of mine — “If You

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How GuideSpark Tripled ARR Two Years in a Row, Growing to Almost Eight Figures in ARR — All Using Outbound Sales

GuideSpark is one SaaS company I’ve been fortunate enough to be involved with for a while (I am a very small indirect shareholder, and have known the CEO, Keith Kitani, since ’06).  GuideSpark is a SaaS service that automates highly personalized

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How GuideSpark Tripled ARR Two Years in a Row, Growing to Almost Eight Figures in ARR — All Using Outbound Sales

GuideSpark is one SaaS company I’ve been fortunate enough to be involved with for a while (I am a very small indirect shareholder, and have known the CEO, Keith Kitani, since ’06).  GuideSpark is a SaaS service that automates highly personalized

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SaaStr’s on TechCrunch TV on Wednesday — Please Post Your Questions You Wanted Answered On Air

I’ll be on TechCrunch TV this Wednesday … will post the video after we’re done … But please post any and all questions you might have in the comments at the end of the TechCrunch post here, in the comments

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SaaStr’s on TechCrunch TV on Wednesday — Please Post Your Questions You Wanted Answered On Air

I’ll be on TechCrunch TV this Wednesday … will post the video after we’re done … But please post any and all questions you might have in the comments at the end of the TechCrunch post here, in the comments

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Your (Belated) SaaS New Year’s Resolution: Add a Layer

I basically agree with all Start-Up Truisms.  One of the best ones is Don’t Chase the Shiny Penny.  Double Down on What Works. For sure this is true in SaaS.  If you’ve got a good thing in a certain vertical,

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Your (Belated) SaaS New Year’s Resolution: Add a Layer

I basically agree with all Start-Up Truisms.  One of the best ones is Don’t Chase the Shiny Penny.  Double Down on What Works. For sure this is true in SaaS.  If you’ve got a good thing in a certain vertical,

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Why The Greatest Sales Teams Just Kill It On Dec 31. When Everyone Else Has Gone Home.

There are some real mysteries in SaaS. Even now that I understand them, I still see them as a bit of a mystery. Let me list a few: Why do customers buy a ton of seats up front, when they

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Why The Greatest Sales Teams Just Kill It On Dec 31. When Everyone Else Has Gone Home.

There are some real mysteries in SaaS. Even now that I understand them, I still see them as a bit of a mystery. Let me list a few: Why do customers buy a ton of seats up front, when they

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SaaStr Named Top Writer of 2013 by Quora; To Top 100 Blogs for Entrepreneurs by Forbes

A big thank you to the entire SaaStr community for a terrific 2013. SaaStr started in late ’12 as an experiment in sharing back the tactical and pragmatic learnings of scaling a SaaS business from nothing to something, from initial

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SaaStr Named Top Writer of 2013 by Quora; To Top 100 Blogs for Entrepreneurs by Forbes

A big thank you to the entire SaaStr community for a terrific 2013. SaaStr started in late ’12 as an experiment in sharing back the tactical and pragmatic learnings of scaling a SaaS business from nothing to something, from initial

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As The Year Winds Down: Get Some Rest. Or You’ll End Up Washing Out in SaaS in Year 5.

If you squint, and look carefully, in a lot of the deals you see on TechCrunch, Techmeme, Pando Daily, or whatever you read, you’ll see a pattern in a good chunk of them.  You’ll see that Co. X or Y

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As The Year Winds Down: Get Some Rest. Or You’ll End Up Washing Out in SaaS in Year 5.

If you squint, and look carefully, in a lot of the deals you see on TechCrunch, Techmeme, Pando Daily, or whatever you read, you’ll see a pattern in a good chunk of them.  You’ll see that Co. X or Y

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What Lies Beyond $100m ARR? Your Company-as-a-Platform. For Others.

We’ve talked a lot about the various stages of scaling a SaaS company.  The first 10 customers, the Moment You Have Something Real.  What Initial Traction Means (say $1m ARR).  The Long, Hard Road from From Initial Traction to Initial

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What Lies Beyond $100m ARR? Your Company-as-a-Platform. For Others.

We’ve talked a lot about the various stages of scaling a SaaS company.  The first 10 customers, the Moment You Have Something Real.  What Initial Traction Means (say $1m ARR).  The Long, Hard Road from From Initial Traction to Initial

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Everything is Sort of the Same at a Given ACV (Annual Contract Value)

As you try to hire up for your SaaS company, you’re going to faced with a lot of choices and trade-offs.  No hire is the perfect package.  Do you take a risk on someone a little more junior than you’d

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Everything is Sort of the Same at a Given ACV (Annual Contract Value)

As you try to hire up for your SaaS company, you’re going to faced with a lot of choices and trade-offs.  No hire is the perfect package.  Do you take a risk on someone a little more junior than you’d

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Around $4-$5m in ARR, You Probably Will Need a Chief MRR Officer

At Dreamforce, Gainsight, a leading SaaS company/service for managing customer success, was kind enough to invite me to speak at their session on Customer Success together with Dan Steinman, their COO.  Prior to Gainsight, Dan was VP of Customer Success

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Around $4-$5m in ARR, You Probably Will Need a Chief MRR Officer

At Dreamforce, Gainsight, a leading SaaS company/service for managing customer success, was kind enough to invite me to speak at their session on Customer Success together with Dan Steinman, their COO.  Prior to Gainsight, Dan was VP of Customer Success

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Want Happy Customers? Implement the 5-Visits-Plus-2-Badges Rule. For Your Customer Success Team — And You.

If you are a SaaStr reader, you’ll know how passionate I am about Customer Success. For one simple reason: Second Order Revenue. Upsells. Renewals. Word-of-Mouth. Champion Change. What it all means is that if you do it right, you’ll make

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Want Happy Customers? Implement the 5-Visits-Plus-2-Badges Rule. For Your Customer Success Team — And You.

If you are a SaaStr reader, you’ll know how passionate I am about Customer Success. For one simple reason: Second Order Revenue. Upsells. Renewals. Word-of-Mouth. Champion Change. What it all means is that if you do it right, you’ll make

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If Your VP Sales Isn’t Going to Work Out — You’ll Know in 30 Days

We’ve talked a lot on SaaStr about how to make that critical hire: the VP Sales.  I’ve done it right, and I’ve done it wrong.  When it’s good … it’s just so good.  It all clicks.  But when you make

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If Your VP Sales Isn’t Going to Work Out — You’ll Know in 30 Days

We’ve talked a lot on SaaStr about how to make that critical hire: the VP Sales.  I’ve done it right, and I’ve done it wrong.  When it’s good … it’s just so good.  It all clicks.  But when you make

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I’m Presenting at Dreamforce. Right Before Marissa Mayer. Come See the Hottest Two Speakers at Dreamforce ’13.

OK maybe SaaStr doesn’t quite have the following of Marissa Mayer.  Yet.  Although we are up to 400,000+ views a month.  But it’s a solid pairing, don’t you think?  In any event … If you are in SaaS and haven’t

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I’m Presenting at Dreamforce. Right Before Marissa Mayer. Come See the Hottest Two Speakers at Dreamforce ’13.

OK maybe SaaStr doesn’t quite have the following of Marissa Mayer.  Yet.  Although we are up to 400,000+ views a month.  But it’s a solid pairing, don’t you think?  In any event … If you are in SaaS and haven’t

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Can an 8-Person StartUp Sell to a CIO? Yes — If You Understand The Social Contract.

Recently Erick Schonfeld was kind enough to invite me to the DEMO conference to both serve as an Enterprise panel judge, and also to join a panel with 3 esteemed CIOs on how to Sell to Enterprise CIOs.  I was

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Can an 8-Person StartUp Sell to a CIO? Yes — If You Understand The Social Contract.

Recently Erick Schonfeld was kind enough to invite me to the DEMO conference to both serve as an Enterprise panel judge, and also to join a panel with 3 esteemed CIOs on how to Sell to Enterprise CIOs.  I was

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How My VP, Sales Doubled Our Sales in 90 Days. And No, It Wasn’t Magic.

Recently I was fortunate enough to give the final talk at the inaugural Sales Hacker Conference, entitled How to Hire a Great VP Sales (And Not Screw It Up). The Sales Hacker Conference was terrific, with several hundred sales process

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How My VP, Sales Doubled Our Sales in 90 Days. And No, It Wasn’t Magic.

Recently I was fortunate enough to give the final talk at the inaugural Sales Hacker Conference, entitled How to Hire a Great VP Sales (And Not Screw It Up). The Sales Hacker Conference was terrific, with several hundred sales process

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In The Early Days, You Won’t Have Enough Customers. But Your Mini-Brand Will Come to Your Rescue.

If you’re selling to the enterprise, or even just anywhere in B2B, most start-ups in the first 12-18 months end up in a Conundrum. The good news is if you get anywhere at all in SaaS in the early days,

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In The Early Days, You Won’t Have Enough Customers. But Your Mini-Brand Will Come to Your Rescue.

If you’re selling to the enterprise, or even just anywhere in B2B, most start-ups in the first 12-18 months end up in a Conundrum. The good news is if you get anywhere at all in SaaS in the early days,

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SaaStr at Sales Hacker Conference, and on Amazing Start-up-to-CIO Panel @ DEMO, Next Week!

There are two SaaS-related events I’m speaking at next week that I’m very excited about. The first up is DEMO.  I’m first an Enterprise Judge on the start-up demos — and then doing an amazing panel with the CIOs of

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SaaStr at Sales Hacker Conference, and on Amazing Start-up-to-CIO Panel @ DEMO, Next Week!

There are two SaaS-related events I’m speaking at next week that I’m very excited about. The first up is DEMO.  I’m first an Enterprise Judge on the start-up demos — and then doing an amazing panel with the CIOs of

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Curse of the ‘Middlers’: Why Happiness Officers Can’t Stand In for True Sales Professionals

We’ve spent a ton of time on SaaStr talking about how to think about sales and sales teams; revenue/demand-focused marketing; and keeping those customers over their lifetime. A more fundamental question we’ve touched on but mostly bypassed is this:  Do

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Curse of the ‘Middlers’: Why Happiness Officers Can’t Stand In for True Sales Professionals

We’ve spent a ton of time on SaaStr talking about how to think about sales and sales teams; revenue/demand-focused marketing; and keeping those customers over their lifetime. A more fundamental question we’ve touched on but mostly bypassed is this:  Do

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The $2 Million Dollar Man (/Woman): How to Think About Scaling Your Customer Success Team

In SaaS, there are a lot of great “rules” that do make sense overall but can be confusing or borderline misleading at times.  E.g., Sales +Marketing Expenses < First Year ACV = Success?  Great rule — at Scale.  But maybe

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The $2 Million Dollar Man (/Woman): How to Think About Scaling Your Customer Success Team

In SaaS, there are a lot of great “rules” that do make sense overall but can be confusing or borderline misleading at times.  E.g., Sales +Marketing Expenses < First Year ACV = Success?  Great rule — at Scale.  But maybe

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A Basic Structure for a VP, Sales Comp Plan: 50/50/25+

One key post I missed on the VP Sales journey was how to pay this critical role.  I don’t think it’s necessarily as nuanced and interesting a topic as how to pay and scale the sales team itself, or how

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A Basic Structure for a VP, Sales Comp Plan: 50/50/25+

One key post I missed on the VP Sales journey was how to pay this critical role.  I don’t think it’s necessarily as nuanced and interesting a topic as how to pay and scale the sales team itself, or how

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Why It May Take You 12-18 Months to Hire a Great VP, Sales — Period. And What to Do About It.

We’ve talked a lot about hiring a VP, Sales.  It’s just such a critical accelerate-or-decelerate decision for a post-Initial Traction SaaS company.   We’ve talked about the 48 Different Types of VP Sales, What a VP Sales Really Does, and a Script to Use

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Why It May Take You 12-18 Months to Hire a Great VP, Sales — Period. And What to Do About It.

We’ve talked a lot about hiring a VP, Sales.  It’s just such a critical accelerate-or-decelerate decision for a post-Initial Traction SaaS company.   We’ve talked about the 48 Different Types of VP Sales, What a VP Sales Really Does, and a Script to Use

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SaaStr in Wall Street Journal, And Why Most SaaS Companies Add/Have an Overseas Dev Team to Help Scale

The Wall Street Journal asked me to write about a topic which I think is critical to all scaling SaaS companies:  talent, and talent outside the U.S. The reality is almost every SaaS company I’ve worked with, including my own,

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SaaStr in Wall Street Journal, And Why Most SaaS Companies Add/Have an Overseas Dev Team to Help Scale

The Wall Street Journal asked me to write about a topic which I think is critical to all scaling SaaS companies:  talent, and talent outside the U.S. The reality is almost every SaaS company I’ve worked with, including my own,

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Silos-in-the-Enterprise: Good. But Not All They Are Cracked Up to Be.

Just a few years ago, as the next generation of SaaS companies were beginning to scale, the idea of building a Big or Biggish SaaS Company using Silos-in-the-Enterprise was all the rage.   For many it still is.   But

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Silos-in-the-Enterprise: Good. But Not All They Are Cracked Up to Be.

Just a few years ago, as the next generation of SaaS companies were beginning to scale, the idea of building a Big or Biggish SaaS Company using Silos-in-the-Enterprise was all the rage.   For many it still is.   But

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Why Tilting Just a Smidge from Self-Service Can Grow Your Revenue 30x

Recently I’ve been fortunate enough to meet with a number of outstanding entrepreneurs building self-service SaaS business at the bottom of the market.  A customer base made up of Very Small Businesses and individual business purchasers in slightly larger companies.

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Why Tilting Just a Smidge from Self-Service Can Grow Your Revenue 30x

Recently I’ve been fortunate enough to meet with a number of outstanding entrepreneurs building self-service SaaS business at the bottom of the market.  A customer base made up of Very Small Businesses and individual business purchasers in slightly larger companies.

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Everybody Lies, 2013 Edition: SaaS Revenues in the Inc. 5000 (And SaaStr at Its One-Year Anniversary).

Today marks the One Year Anniversary of SaaStr.  Our first post, on August 23, 2012 was Everybody Lies — Real SaaS Revenues in the Inc. 5000, where we looked at what some of the real revenues were for various SaaS

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Everybody Lies, 2013 Edition: SaaS Revenues in the Inc. 5000 (And SaaStr at Its One-Year Anniversary).

Today marks the One Year Anniversary of SaaStr.  Our first post, on August 23, 2012 was Everybody Lies — Real SaaS Revenues in the Inc. 5000, where we looked at what some of the real revenues were for various SaaS

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The Best $500,000 I Ever Raised — And Why Party Rounds May Not Be the Way to Go in SaaS

I’ve never gone Truly Big in any of my start-ups, not in the Yammer or Box way let alone the HootSuite or DropBox way.  But, over the years as both a founder and a start-up exec, I have raised over $40m

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The Best $500,000 I Ever Raised — And Why Party Rounds May Not Be the Way to Go in SaaS

I’ve never gone Truly Big in any of my start-ups, not in the Yammer or Box way let alone the HootSuite or DropBox way.  But, over the years as both a founder and a start-up exec, I have raised over $40m

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How Cheap a Product Can You Have And Still Have Salespeople?

One question I struggled with a lot in the early days was what price points supported inside sales reps.  It was clear to me that our freemium offering, priced at from $0 to $19/month, couldn’t really support a traditional inside

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How Cheap a Product Can You Have And Still Have Salespeople?

One question I struggled with a lot in the early days was what price points supported inside sales reps.  It was clear to me that our freemium offering, priced at from $0 to $19/month, couldn’t really support a traditional inside

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Should Your VP Sales Start Off as a Player-Coach?

The moment comes when it’s time to hire your first VP Sales. We’ve talked in the past about the 48 Different Types of VP Sales, What a VP Sales Really Does, and even given you a Script to Use When

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Should Your VP Sales Start Off as a Player-Coach?

The moment comes when it’s time to hire your first VP Sales. We’ve talked in the past about the 48 Different Types of VP Sales, What a VP Sales Really Does, and even given you a Script to Use When

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My Top 3 Tips On How to Help Your Team Succeed if You Are Acquired

We recently passed the 2 year anniversary of our acquisition by Adobe.  I’ve learned a lot that I want to cover later, but one question I was recently asked was what can do in an acquisition as a founder to

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My Top 3 Tips On How to Help Your Team Succeed if You Are Acquired

We recently passed the 2 year anniversary of our acquisition by Adobe.  I’ve learned a lot that I want to cover later, but one question I was recently asked was what can do in an acquisition as a founder to