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Technology
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The Official Saastr Podcast: SaaS | Founders | Investors

Updated 1 day ago

Rank #92 in Investing category

Business
Technology
Investing
Read more

The Official Saastr Podcast is the latest and greatest from the world of Saastr, interviewing the most prominent operators and investors to discover their tips, tactics and strategies to attain success in the fiercely competitive world of SaaS. On the side of the operators, we centre around getting from $0 to $100m ARR faster, what it takes to scale successfully and what are the core elements of hiring. As for the investors, we learn what metrics they hone in on when examining SaaS business, what type of metrics excites them and what they look for in SaaS founders.

Read more

The Official Saastr Podcast is the latest and greatest from the world of Saastr, interviewing the most prominent operators and investors to discover their tips, tactics and strategies to attain success in the fiercely competitive world of SaaS. On the side of the operators, we centre around getting from $0 to $100m ARR faster, what it takes to scale successfully and what are the core elements of hiring. As for the investors, we learn what metrics they hone in on when examining SaaS business, what type of metrics excites them and what they look for in SaaS founders.

iTunes Ratings

92 Ratings
Average Ratings
80
5
3
2
2

WhoopSaaS, Inc.

By WhoopSaaS Community - May 01 2018
Read more
I don’t podcast often, but when I do, it’s SaaStr and Harry.

Fantastic content

By Steveo939 - Dec 07 2017
Read more
I’m thru the first 100 episodes, this is a must listen for anyone running a Saas business.

iTunes Ratings

92 Ratings
Average Ratings
80
5
3
2
2

WhoopSaaS, Inc.

By WhoopSaaS Community - May 01 2018
Read more
I don’t podcast often, but when I do, it’s SaaStr and Harry.

Fantastic content

By Steveo939 - Dec 07 2017
Read more
I’m thru the first 100 episodes, this is a must listen for anyone running a Saas business.
Cover image of The Official Saastr Podcast: SaaS | Founders | Investors

The Official Saastr Podcast: SaaS | Founders | Investors

Updated 1 day ago

Rank #92 in Investing category

Read more

The Official Saastr Podcast is the latest and greatest from the world of Saastr, interviewing the most prominent operators and investors to discover their tips, tactics and strategies to attain success in the fiercely competitive world of SaaS. On the side of the operators, we centre around getting from $0 to $100m ARR faster, what it takes to scale successfully and what are the core elements of hiring. As for the investors, we learn what metrics they hone in on when examining SaaS business, what type of metrics excites them and what they look for in SaaS founders.

Rank #1: Saastr 004: Index's Shardul Shah on Why Reducing Time Distance To Value Is So Important and How To Sell To CSO's Effectively

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I am thrilled to welcome, Shardul Shah, Partner @ Index Ventures to the show today. Shardul is the sole member of the Index team to have worked in all Index's offices around the world in Geneva, London and SF. Now in SF, Shardul focuses on security, software and infrastructure with investments in the likes of Squarespace, DropBox and Adaloom, just to name a few. 

Discussed In Today's Show:

  • How Shardul made his unorthodox approach into investing?
  • What Shardul really looks for in early stage SaaS products when investing?
  • Why is reducing time distance to value so important for a SaaS product?
  • How can startups effectively sell to CSO's in this new wave of cyber security?
  • What are the risks and flaws of the open source community? 
  • How can enterprise SaaS products create true customer stickiness?

In a round we call the 60 Second Saastr, we also hear:

  1. What is Shardul most concerned about in the SaaS space?
  2. Shardul's favourite SaaS resource: 
  3. Which public markets SaaS companies is Shardul most impressed with?

If you would like to find out more about the show and the guests presented you can follow us on Twitter here:

Mar 15 2016
21 mins
Play

Rank #2: SaaStr 191: Salesloft Founder Kyle Porter on Scaling A SaaS Business to $40m ARR Outside of Silicon Valley, Pivoting a Product Generating $7m in ARR & How To Fundamentally Create Cohesion In A Leadership Team

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Kyle Porter is the Founder & CEO @ Salesloft, the leading sales engagement platform delivering a better sales experience. To date, Salesloft have raised over $75m in funding from some of the best in the business including Emergence, Insight Venture Partners, Techstars and even LinkedIn. As for Kyle, he has led the team from 4 employees in 2014 to over 320 today where they have also been awarded Atlanta’s No 1 best place to work. Prior to founding Salesloft, Kyle was the Founder @ B2B camp, a conference focused on B2B revenue generating professionals. Before that he was Vice President of Marketing @ NanoLumens.

In Today’s Episode We Discuss:

  • How Kyle made his way into the world of SaaS and came to found Salesloft?
  • Kyle made the decision to pivot the product when it was at $7m in ARR, what was the thinking behind that? How does Kyle think about pivots more broadly? How does one know when it is truly not working? How long did it take Kyle to get the core Salesloft product to $1m in ARR?
  • With the pivot, what were Kyle’s core learnings on migrating from a prior product and platform to a new one? What were his big lessons on seeing the change in buyer persona? What does Kyle mean when he says “selling is hard but buying is even harder”?
  • Does Kyle agree with many CEO’s the most important role of the CEO is “management upscaling”? What elements does he find most challenging? What have been Kyle’s big lessons in the building out of his exec team? What is the fundamental element for a successful exec team to function?
  • Salesloft is in an immensely competitive space, what would Kyle’s advice be in standing out in an intensely competitive space? Where do many go wrong? What are the pros and cons of being in Atlanta and not SF? What advice would Kyle give to founders operating their HQs external to the core hubs?

Kyle’s 60 Second SaaStr

Is it important to have early champions? How does one get them?

How has having kids changed your perspective on work?

Tell me a moment in your life that has served as an inflection point and changed the way you think?

When I say success in SaaS who is the embodiment of this to you?

What does Kyle know now that he wishes he had known at the beginning? 

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin Harry Stebbings SaaStr Kyle Porter

Sep 04 2018
32 mins
Play

Rank #3: SaaStr 106: Why Early Stage SaaS Metrics Do Not Matter, The 5 Things To Look For In Early Stage SaaS Companies & How To Negotiate A Term Sheet The Right Way with Alex Rosen, Managing Director @ IDG Ventures

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Alex Rosen is a Managing Director with IDG Ventures where he focuses on investments in cloud infrastructure, SaaS applications, ad tech, and consumer marketplaces. Alex currently serves as board director at Chubbies, Krux, MindMeld, Minted, Smartling, Tempered Networks, and Uplift. He also led IDG Ventures’ investments in multiple companies including Appboy, Datanyze, Indiegogo, Nuzzel, The League and many more incredible companies. Previously, he was a General Partner at Sprout Group, where he was head of the Internet and Software group. Huge thanks to the team @ Sapphire Ventures for the intro to Alex today.

In Today’s Episode You Will Learn:

  • How did Alex make his way into the world of SaaS investing and come to be Managing Director @ IDG?
  • SaaS businesses can be massively affected by changes in a few very small data points. So what would you say is one of the single most important metric points?
  • What is a booking?  How should we break it down into the 3 different MRRs? What element of those metrics do you want to see growing?
  • How important a role does unit economics play? What are the couple of forms: customer + sales person? How much ARR should a good sales rep add to in ARR in relation to comp?
  • What is negative churn? How can you take a customer you have already sold and make more money from them? Upsell or cross-sell? What does this to the pricing axis? Why do you want more than 1 axis?

60 Second SaaStr

  1. What does Alex know now that he wishes he had known in the beginning?
  2. What are the greenfield opportunities in SaaS for Alex?
  3. What is Alex’s fave SaaS reading material?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Alex Rosen

Mar 20 2017
32 mins
Play

Rank #4: SaaStr 222: Flexport CRO Ben Braverman on Why It Is Total Horseshit That The Best Sellers Don't Make Good Managers, Why Specialisation Does Not Lead To The Best Customer Experience & Scaling Revenue From $18k MRR in 2014 to a $472m Year In 2018

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Ben Braverman is the CRO @ Flexport, one of the world’s fastest growing startups combining technology, infrastructure and expertise, to build the operating system for global trade. To date they have $1.35Bn in funding from some of the biggest and best in the business including Softbank’s Vision Fund, Founders Fund, DST, Susa Ventures and Y Combinator, just to name a few. As for Ben, he spearheads global sales and go to market teams. Prior to Flexport, Ben helped drive two high-growth companies to successful acquisitions: URX (acquired by Pinterest) and Heyzap (acquired by Fyber).

In Today’s Episode We Discuss:

  • How Ben made his way into the world of startups and came to be CRO of one of the world’s fastest growing startups in the form of Flexport?
  • Why does Ben fundamentally disagree with the specialisation of roles within SaaS companies? What does he believes this does to the customer journey and relationship? How should one thing about role segmentation and allocation of accounts with this in mind? Where does Ben see many people going wrong here?
  • Why does Ben believe it is “total horseshit to say the best sellers don’t make the best managers”? What must founders try and figure out before hiring their sales leader? What are the leading indicators that suggest a sales rep has the ability to be a sales manager? How does Ben determine between a stretch VP and a stretch too far?   
  • What does Ben mean when he says, “there are 3 distinct buckets of sales management”? What are they and what is their relationship between one another? Why does Ben believe one does not need sales management in the early days? What is the best way to train reps and determine payback period fast? Why does Ben believe sales ops is the most underappreciated role in the valley?

60 Second SaaStr:

  1. What does Ben know now that he wishes she had known at the beginning?
  2. What is the optimal relationship between CRO and CEO?
  3. What does Ben believe in SaaS that most around his disbelieve?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Ben Braverman

Apr 03 2019
39 mins
Play

Rank #5: SaaStr 194: ARR Is A Lagging Not A Leading Indicator, The Metrics You Need to Focus On, The Secret To Success In Selling To Developers, Why You Should Delay The Buildout of Customer Success Teams & How Small Numbers In SaaS Can Deceive You with Steve Newm

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Steve Newman is the Founder & CEO @ Scalyr, the startup that helps your devops team solve more problems in less time with log monitoring and analysis in seconds. Steve has raised over $27.5m in funding with Scalyr from many friends of the show including Susa Ventures, Bloomberg Beta, Shasta and GV. As for Steve, prior to Scalyr, he was the Founder of Writely which was acquired by Google to become the little known, Google Docs. Before that he founded 2 prior startups, Ann Arbour Softworks (acq by Ashton-Tate) and BitCraft (acquired by Macromedia). If that was not enough, Steve also sat on the Technical Advisory Board at Box for over 3 years.   

In Today’s Episode We Discuss:

  • How Steve made his way into the world of startups and SaaS over 30 years ago? What is the founding story with Scalyr and what was that a-ha moment?
  • Why does Steve believe that you should involve customers very early in the process of developing your narrative? Where does Steve see most startups go wrong when it comes to messaging? How does one structure the feedback mechanism? How does one determine between feedback you integrate and feedback you do not?
  • Why does Steve believe that you should not focus too much on numbers in the early days? What makes them deceiving at this stage? If not numbers, what should early stage founders be focusing on and measuring? Why does Steve believe that ARR is not the leading metric? What metrics should early stage SaaS founders really be prioritising?
  • How does Steve respond to PG’s “to scale, you have to do unscalable things”? What challenges and nuance does Steve present that founders must be wary of? How does Steve’s thinking here affect his view towards customisation? Why does manual input not put a cap on scalability? What are the parameters for manual involvement to be scalable?   

Steve’s 60 Second SaaStr:

  1. What does Steve know now that he wishes he had known at the beginning?
  2. Who does Steve believe is crushing it in the world of SaaS today?
  3. The hardest element about the move from tech co-founder to CEO?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Sep 24 2018
32 mins
Play

Rank #6: SaaStr 171: How To Figure Out Your Pricing Strategy: The Diminishing Role of The Per Seat Model, Why Open Source Is The Only Way To Get In Front of Today's Developers & Why Capital Efficiency Is Always Key with Chetan Puttagunta, General Partner @ NEA

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Chetan Puttagunta is a General Partner @ NEA, one of the world’s largest venture capital firms in the world with over $3Bn in their latest fund and a portfolio including the likes of Mulesoft, Jet.com, Uber, Houzz and many more incredible companies. As for Chetan, Chetan focuses on enterprise software and has made investments in MuleSoft, MongoDB, Elastic, Heap, just to name a few. Due to his phenomenal track record, Chetan has been named to GrowthCap’s Top 40 under 40 Growth Investors, Forbes 30 under 30 All-Star Alumni List, and Forbes’ 30 under 30 in Venture Capital. 

In Today’s Episode You Will Learn:

  • How Chetan made his from the world of leveraged buyouts to the world of enterprise VC investing with NEA?
  • Why does Chetan have such conviction with regards to open source companies today? Why does he feel the big question of “Can open source product multi-billion dollar companies” has been proven”?
  • How does Chetan think about the underlying business models of open source when comparing the likes of Red Hat with 85% gross margin to Hortonworks at negative gross margins? What does Chetan believe is a healthy ratio between professional services vs closed premium features? Does Chetan believe this is the end for per seat pricing in SaaS?
  • How does Chetan approach market sizing today when evaluating potential enterprise opportunities? Why does Chetan believe there is a mental trap in the VC requirement for large markets? How can founders present the niche market they are attacking, in an exciting enough way to satiate the investor appetite for large market?
  • Chatan has said before, “if you have conviction and vision, you should not be afraid to raise capital and go big”. Does every founder not have conviction and vision in the early days? How does Chetan determine when truly is the right time to pour fuel on the fire and raise that mega war chest?   

60 Second SaaStr?

  1. A moment in Chetan’s life that has changed the way he thinks about the world?
  2. Fave SaaS reading material?
  3. What does Chetan know now that he wishes he had known at the beginning?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Chetan Puttagunta

Apr 16 2018
26 mins
Play

Rank #7: SaaStr 262: Box's Jon Herstein on How Customer Success Teams Should Structure, Schedule and Execute on Customer Check Ins, Why Delight is Important But Insufficient & Why Customer Success Is Not Responsible For Upsell

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Jon Herstein is the Chief Customer Officer at Box, the company that provides one platform for secure content management, workflow and collaboration. Prior to their IPO, Box had raised funding from some of the best in the business including Andreesen Horowitz, Bessemer, DST, Emergence and Meritech, just to name a few. As for Jon, prior to being Chief Customer Officer at Box, he was Senior VP of Customer Success, responsible for all post-sales services Box provides from implementation to user adoption and more. Before Box, Jon spent 4 years as VP of Professional Services at NetSuite and prior to that, close to 8 years as Senior Director of professional services at Informatica.

In Today’s Episode We Discuss:

  • How did Jon make his way into the world of SaaS and come to be one of the leading figures in the rising tide of the customer success movement?
  • What does Jon mean when he says, “you have to constantly bring your customers to the forefront of your employees minds”? For non-customer facing roles, what can one do to give them that perspective? Does it work to ensure every function spends time in customer support? What is challenging about that? What can be done in the onboarding phase to ensure the individual has the most empathy for the customer, regardless of function?  
  • For those in CS, what is the right communication cadence to check in with their accounts? What should the agenda look like? What outcomes should they drive towards? Should they be involved in the upsell process? How does Jon think about post-mortems on churned clients? How do they structure them? What lost client stands out to Jon and what would he have done differently to retain them?
  • From Jon’s experience seeing Box in hyperscaling, at what stages do SaaS orgs start to break down? Why does Jon think that is? What can be done to proactively try and mitigate this? How does Jon think about the structuring of roles and responsibilities with scale? What does this done well look like? Where do many people go wrong here?  

Jon’s 60 Second SaaStr:

  1. What does Jon know now that he wishes he had known at the beginning of his time with Box?
  2. What motto or quote does Jon frequently revert back to?
  3. What is the most challenging element of Jon’s role with Box today?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Jon Herstein

Ever feel like you can’t really connect with prospects or have an organized workflow to get deals closed? Outreach.io, the leading Sales Engagement platform, supports sales reps and their managers by making it simple to humanize and personalize communication at scale; automating the soul-sucking manual work; and dramatically increasing the productivity and efficiency of all revenue-generating teams. You can check them out at outreach.io/saastr to chat with them and receive a free copy of their new book -- Sales Engagement: How The World's Fastest-Growing Companies are Modernizing Sales Through Humanization at Scale.

Sep 02 2019
36 mins
Play

Rank #8: SaaStr 211: The Ultimate Guide To SaaS Pricing From Investors @ Benchmark, Matrix, Upfront Ventures & Operators @ Figma, Snyk and Kustomer

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In Today’s Episode We Discuss:

  • David Skok: General Partner @ Matrix Partners: Why does David believe that all good products have at least one variable pricing axis? How can founders determine which variable they should choose for their product? What are the pros and cons?
  • Chetan Puttagunta: General Partner @ Benchmark: Why does Chetan believe we have seen a strong decline in the per seat pricing model? What are the major drawbacks of it? What are we seeing replace it? What has Chetan seen work well amongst his portfolio?     
  • Mark Suster: General Partner @ Upfront Ventures: What were Mark’s two biggest lessons on pricing from seeing the hyper-growth of Salesforce first hand? WHat does Mark advise founders when it comes to price anchoring and discounting? How does Mark view the sale of professional services with this in mind?
  • Amanda Kleha: Chief Customer Officer @ Figma: What were Amanda’s biggest learnings from running the Zendesk pricing playbook? What does Amanda mean when she says that successful pricing is broke up into 3 separate product features?   
  • Brad Birnbaum: Founder & CEO @ Kustomer:Why does Brad push back on the common suggestion of a “no man’s land in SaaS pricing”? Why is innovation in pricing actually detrimental to sales in most cases?
  • Guy Podjarney, Founder & CEO @ Snyk: How does Guy think about having a large enough base to test pricing strategies? How does Guy think about the balance between freemium and paid? Does one have to come first?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Feb 11 2019
26 mins
Play

Rank #9: SaaStr 124: Upfront's Mark Suster on The One Thing That Kills Sales, Why You Have To Price High and Discount & Why Sales People Are Either Farmers or Hunters?

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Mark Suster is Managing Partner at Upfront Ventures which he joined in 2007, having previously worked with Upfront for nearly 8 years as a two-time entrepreneur. Before joining Upfront Mark was Vice President, Product Management at Salesforce.com following its acquisition of Koral, where Mark was Founder and CEO. Prior to Koral, Mark was Founder and CEO of BuildOnline, a European SaaS company that was acquired by SWORD Group. Mark is also the writer of one of my favourite VC blogs, Both Sides Of The Table which is a centre piece to the whole VC community and is a must read for all interested in entrepreneurship and VC.

In Today’s Episode You Will Learn:

  • How Mark made his way into the world of startups and came to invest in SaaS with Upfront today?
  • What are 4 reasons why startups should prioritise professional services in the early days? Why do most VCs disagree with this? How did Salesforce do this right in their period of hyper-growth?
  • How should early stage startups approach the topic of pricing? How can they evaluate whether to call high or low? What are the pros and cons of doing both?
  • Mark has previously discussed the importance of finding your champion in the buying process. How can startups determine whether your champion is a decision-maker? What questions can you ask to find this out?
  • What changes as a SaaS business scales? What are the key inflection points of company development? How does Mark view the amount B2B startups are raising today? How does Mark evaluate responsible and right spend?

60 Second SaaStr

  1. What should your first sales reps be really good at?
  2. How has Mark seen early stage SaaS startups go wrong most often?
  3. IPO markets, frothy or fantastic?
  4. What does Mark know now that he wishes he had known before?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Mark Suster

May 22 2017
29 mins
Play

Rank #10: SaaStr 231: Why SQLs and MQLs Are Redundant, Why You Have To Eliminate Hand Offs Between Go-To-Market Teams & Why One North Star For The Whole Company Can Be Damaging with Jason Reichl, Founder & CEO @ GoNimbly

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Jason Reichl is the Founder & CEO @ GoNimbly, the first SaaS consultancy to focus on revenue operations. Currently growing 100% year over year, working with companies to un-silo their operations and create one strategic revenue ops team to support their Go To Market strategy. In the past, Go Nimbly has helped companies like Zendesk, Twilio, PagerDuty and Coursera to achieve alignment and increase revenue by 26%. As for Jason, prior to co-founding GoNimbly, he was Director of Product Management @ TradeShift and before that was VP of Product Management @ Lanetix.  

In Today’s Episode We Discuss:

  • How Jason made his way from Director of Product Management at Tradeshift to changing the way we think about scaling revenue operations with GoNimbly?
  • Why does Jason believe that we have to remote handoffs between go to market teams? Why are they so damaging? How does Jason believe SaaS companies can use a “swarming” effect to create the best buyer experience for their customer? What does this involve? How does this change the type of metrics that we track?
  • Why does Jason believe that your North Star has to be revenue in the go to market teams? Why does Jason also believe that it is damaging to have the same North Star across the entire company? How should North Star’s be segregated between GTM teams and biz ops teams? What are the mistakes many companies make when setting their internal North Stars?
  • Why does Jason believe that alignment is a dirty word? Why is alignment actually a negative for the customer experience? What does Jason view as vanity metrics? If one has vanity metrics in place, what does Jason recommend as to keeping them or phasing them out?

60 Second SaaStr:

  1. What does Jason know now that he wishes he had known in the beginning?
  2. How does Jason feel about multi-year deals?
  3. How does Jason feel about channel/partner sellers?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

May 06 2019
26 mins
Play

Rank #11: SaaStr 118: Why Tension Has Shifted From Sales vs Marketing To Customer Success vs Product & Why You Have To Hire For Ahead Of Where You Are Now with Todd Olson, Founder & CEO @ Pendo.io

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Todd Olson is the Founder & CEO @ Pendo, the startup that allows you to capture all user behaviour, gather feedback and then provide contextual support.  They have raised over $30m in VC funding from some of the very best in the business including Neeraj @ Battery Ventures, Megan @ Spark and Matt @ Salesforce Ventures just to name a few. As for Todd, prior to Pendo he held various different roles in product as well as co-founding 2 prior startups.

In Today’s Episode You Will Learn:

  • How did Todd make his way into the world of SaaS and come to found Pendo?
  • Why does Todd believe that there is inherent tension between customer success and product teams? How has this changed from sales and marketing team tension? What does Todd suggest to mitigate this tension?
  • How does Todd evaluate his hiring process? At what stage does one become a specialist vs a jack of all trades? Why does Todd always believe that you should hire ahead of where you are?
  • Todd has previously said that ‘money is not all the same’. How does Todd look to select his investors? What value adds are most desired for Todd? What do the best investors do that make them so?

60 Second SaaStr

  1. What does Todd know now that he wishes he had known in the beginning?
  2. What is Todd’s favourite SaaS reading material: Mattermark Daily, Tom Tunguz
  3. Creating a startup culture for adults?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Todd Olson

May 01 2017
25 mins
Play

Rank #12: SaaStr 204: 2018's Most Downloaded Episode, Claire Hughes Johnson, COO @ Stripe

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Claire Hughes Johnson, COO @ Stripe the new standard in online payments that handles billions of dollars of business every year for forward thinking businesses around the world. To date, Stripe has raised over $680m in funding from some of the very best in the business including Sequoia, Founders Fund, General Catalyst, Thrive, CapitalG, Kleiner Perkins and Tiger Global. As for Claire, prior to Stripe she spent over 10 years at Google in a range of different roles from VP of Google's self-driving car division to VP of Global Online Sales to VP of Google Offers. At Stripe, Claire has helped take Stripe global in February 2016 with the launch of Atlas, a toolkit that enables any business, anywhere in the world, to incorporate in the United States. If that was not enough, Claire is also a Board Member @ Hallmark Cards.

In Today’s Episode We Discuss:

  • How Claire made her way into the world of SaaS with Stripe following her leading of Google’s self-driving car division?
  • What does Claire mean when she discusses “founding documents”? What is the right way to go about creating them? What element do they need to contain? How can one optimise internal decision-making process with these documents? What question must one always try and ask when making big decisions?
  • How does Claire define a truly special COO? What does that truly great look like? When is the right time for founders to hire that COO? Where do the majority of people go wrong in their assessment of when and what they need in a COO? What is the optimal relationship one can have between CEO and COO?
  • How does Claire think about what Stripe have done right to hire so effectively at scale? What does it take in terms of benchmarks and standards to do so? What does Claire mean when she says you have to step function up your capabilities with scale? What are the core challenges in hiring at scale?  

Claire’s 60 Second SaaStr:

  1. What would Claire say are her biggest strengths and weaknesses?
  2. What does Claire know now that she wishes she had known at the beginning?
  3. A moment in Claire’s life that has served as an inflection point and changed the way she thinks?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Claire Hughes Johnson

Dec 10 2018
33 mins
Play

Rank #13: SaaStr 210: Why The Best Sales Reps Are Not Outgoing and Extroverted, Why Sales Reps Are Fundamentally Not Coin Operated and The Right Way To Structure Both Comp Plans and Sales Training with Bridget Gleason, VP of Sales @ Logz.io

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Bridget Gleason is VP of Sales @ Logz.io, the startup that uses predictive analytics and machine learning to provide monitoring, troubleshooting and security. To date, Logz have raised over $45m in funding from the likes of Openview, 83North and Vintage just to name a few. As for Bridget, she has the most incredible track record. Before Logz, Bridget was VP of Corporate Sales @ Sumo Logic where she drove ARR up by a record 237%. Prior to SumoLogic, Bridget was VP of Sales @ YesWare where she increased MRR per rep by 450%. Finally before YesWare, she was VP of Sales @ Engine Yard, where she tripled monthly recurring revenue, over course of 3+ year tenure, in 3 key leadership roles.

In Today’s Episode We Discuss:

  • How Bridget made her way into the world of sales and became the sales leader she is today, having started in the world of marketing?
  • Having led and scaled numerous sales teams, does Bridget agree the best sales reps are outgoing and extroverted? How does the successful profile of a sales rep depend on (1) whether you are selling to SMB or enterprise? (2) The stage of the company? How can one stress test the character type of the candidate pre-hire in the interview stage?     
  • Does Bridget believe that sales reps really are as coin operated as many suggest? Why is that potentially an unfair position to take? How does Bridget think about structuring the right comp plans for her team? What other methods of incentivisation does Bridget believe works equally as efficiently?    
  • Does Bridget believe that you should pay sales rep commissions on services revenue? Should one pay the same or lower commissions on renewals? Should multi-year deals be paid upfront? How does one structure commissions for the sales team with that in mind?  
  • When does Bridget believe is the right time to hire (1) your first sales reps? (2) Your first VP of Sales? Why does Bridget believe that 70% of VP of Sales positions do not work out in the first 9 months? What can founders do to increase the likelihood of success within their VP of Sales role? Where do many go wrong?  

Bridget’s 60 Second SaaStr:

  1. What does Bridget know now that she wishes she had known when she started in SaaS?
  2. SDR’s are the most important function in the sales process, agree or not and why?
  3. Sales training, what works? What does not?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Bridget Gleason

Feb 04 2019
32 mins
Play

Rank #14: SaaStr 229: The 2 Most Important Numbers For Your SaaS Business, Why You Should Not Have VPs Until $5m in Revenue & How To Manage Top Of Funnel Efficiently But Aggressively with Manny Medina, Founder & CEO @ Outreach

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Manny Medina is the Founder & CEO @ Outreach, the market leading sales engagement platform that turns your team into a revenue driving machine. To date, Manny has raised over $114m in funding from some great people including friends of the show in the form of Alex Clayton @ Spark, Mayfield, Trinity Ventures and DFJ Growth, just to name a few. Prior to founding Outreach, Manny spent 7 years with Microsoft where he ran the Latin America and Canada business development group for Microsoft’s emerging mobile division, representing $50M of yearly revenue. Befofe that Manny was a Senior Product Manager @ Amazon where he engineered the compensation system for Amazon Associates and Web-Services which accounts for 15% of Amazon's traffic.

In Today’s Episode We Discuss:

  • How Manny made his way to found the leader in sales engagement from product management at Amazon and Business Development @ Microsoft?
  • How does Manny fundamentally approach managing top of funnel? What are the 2 big dangers of not managing it aggressively? What can be done to ensure not only full but high quality top of funnel?
  • Why does Manny believe it is so important to track pipeline coverage as one of your core metrics? What does good look like when it comes to pipeline coverage? How does this change if you are creating vs in an existing market? How does Manny think about specialisation within the sales function? Why are SDR’s 99% of the time not able to carry leads to completion?
  • How does Manny think about quota construction today? Does Manny err on the side of setting high to be ambitious or setting low to increase confidence? How can managers really empower their reps to be aggressive in hitting their quota and exceeding it? How does Manny think about resource allocation on the individual rep level? What is sufficient? What is excessive?
  • Does Manny believe that the founder should always be responsible for selling their product at one moment in time? How did Manny sell the first $1m in ARR simply through walking the streets of SOMA and selling door-to-door? What were his biggest lessons from doing this?  Why does Manny believe that you should not have a VP before $5m?

60 Second SaaStr:

  1. What does Manny know now that he wishes he had known in the beginning?
  2. What does the future of sales prospecting look like to Manny?
  3. What would Manny like to change about the world of SaaS today?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Manny Medina

Apr 29 2019
27 mins
Play

Rank #15: SaaStr 142: Why CAC/LTV Is The Most Important Metric In SaaS, How To Analyse Churn Correctly & Why Bookings Are Inaccurate and Easy To Manipulate with Dave Kellogg, CEO @ Host Analytics

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Dave Kellogg is the CEO @ Host Analytics, the leader in cloud-based enterprise performance management (EPM). Previously, Dave was SVP/GM of Service Cloud at Salesforce and CEO at unstructured big data provider MarkLogic. Before that, Dave was CMO at Business Objects for nearly a decade as the company grew from $30M to over $1B. Dave has also worked in various capacities with the likes of Breeze, GainSight, Tableau and MongoDB and previously sat on the boards of ag tech leader, Granular (acq by DuPont for $300M)  and big data leader Aster Data (acquired by Teradata for $325M).

In Today’s Episode You Will Learn:

  • How Dave made his way into the world of SaaS with Salesforce, came to be CMO at Business Objects and now running his own SaaS company as CEO at Host Analytics?
  • What does David believe is the single most important metric in SaaS? How should SaaS companies structure the first four lines of their financial statements? Why is retention and renewal not always an accurate sign of customer satisfaction?
  • How does Dave look to analyse churn? What is the post-mortem? What is more important, logos or expansion? If a startup’s churn is too high, what is the top 3 things they should do? Why must you have a “standard taxonomy” for churn? How can you construct this?
  • How does David think about taking existing customer and up-selling them? How does he view this in contrast to cross-sell? Does Dave agree with David Skok on the need for more than 1 variable pricing mechanism? Why does Dave not encourage usage based pricing?
  • How does Dave analyse the benefits of multi-year contracts paid upfront? How does this distort TCV and inflate the figures? Does upfront payment misalign the provider and the consumer, in terms of care and support? With that in mind, how does David view billing frequency? Contract durations?

60 Second SaaStr

  1. What does Dave know now which he wishes he had known at the beginning?
  2. What is the 90 day rule? Why is it important?
  3. How much ARR should a good sales rep add in relation to comp?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Dave Kellogg

Sep 11 2017
31 mins
Play

Rank #16: SaaStr 156: Most Downloaded SaaStr of 2017: David Skok, General Partner @ Matrix Partners

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David Skok is a serial entrepreneur turned VC at Matrix Partners. He founded four companies: Skok Systems, Corporate Software Europe, Watermark Software, and SilverStream Software and did one turnaround with Xionics. Three of the companies he founded went public and one was acquired. In 2001 David joined Matrix Partners, who had backed his last two startups, as a General Partner. David’s successful exits as an investor at Matrix include: HubSpot, JBoss, AppIQ, Tabblo, Netezza, Diligent Technologies, CloudSwitch, TribeHR, GrabCAD, OpenSpan and Enservio. David currently serves on the boards of Atomist, CloudBees, Digium, Meteor, Namely HR, Salsify, and Zaius. You can also find David’s amazing blog here!

In Today’s Episode You Will Learn:

  • How did David make his way into the world of SaaS? What was it about Matrix that made him want to make the transition from operations to VC?
  • Metrics: Why are metrics so important? What role do they play in an organisation? How do good founders respond to questions on not achieving sales targets? What metrics in SaaS really determine the trajectory of the business?
  • How can founders examine unit economics to determine whether they have a sustainable SaaS business?
  • How does David address sales rep productivity? How much in ARR should they be booking in relation to their annual comp package?
  • Negative Churn: What is negative churn? Why is it fundamental for SaaS startups to have a strong grasp of their negative churn? How does negative churn affect the pricing axis? What can startups do if they have no alternative product to upsell to?
  • Upsell: To what extent should founders be willing to engage in customisation in order to upsell a product? What are the dangers? What should founders be mindful of? To what extent is upsell the responsibility of customer success? Should they have a hand in the sales process? What are the dangers and concerns?
  • How important is it for a startup to track their champion with the customer company? Does it matter if your champion leaves? What should you do if so?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

David Skok

Dec 18 2017
46 mins
Play

Rank #17: SaaStr 184: Step by Step Guide To Scaling Your Sales Team, Why Founders Need To Spend More Time On Top of Funnel & Why Discounting Is A Great Tool with Sam Blond, Chief Sales Officer @ Brex

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Sam Blond is Chief Sales Officer @ Brex, the startup that provides corporate cards for startups. To date they have raised over $57m in funding from the likes of Y Combinator, Peter Thiel, Max Levchin, Yuri Milner, Elad Gil and many more incredible names. Prior to Brex, Sam Was Chief Revenue Officer at Rainforest QA. Before Rainforest, Sam saw firsthand the hypergrowth scaling of Zenefits as VP of Sales where he saw the company grow from 18 employees and $1m in ARR to over 1,800 employees and over $70m in ARR. Sam got his start in the SaaS industry with Jason Lemkin @ Echosign as Director of Sales.

In Today’s Episode You Will Learn:

  • How Sam made his way into the world of sales and came to join Jason Lemkin with his first role in sales at Echosign?
  • Why does Sam believe that more sales reps does not always equal more revenue? What are the benchmarks that suggest founders really need to add to their sales team? Does Sam agree Founders should be selling up to $1m in ARR?
  • How does Sam assess who is the best person to hire for the role? What have been Sam’s lessons on what it fundamentally takes to attract the best talent? In the early days how does Sam think about both role allocation and whether to hire the young jack of all trades vs the more senior executive?
  • Why does Sam believe that founders need to spend more time on top of funnel? Why does Sam believe that not all opportunities are created equal? How does Sam think about the right structure and time it should take to pass from lead to MQL to SAL to opportunity to deal? Where does this most commonly breakdown?
  • Why does Sam believe the key to success in SaaS sales teams is “urgency”? Literally, how can reps instil a sense of urgency in their current pipeline? Why does Sam disagree with the conventional wisdom and say discounting is a great tool? How does Sam determine the right level of discount to give? How does Sam assess pilots as an alternative approach to getting leads over the line?  

Sam’s 60 Second SaaStr

  1. What does Sam know now that he wishes he had known at the beginning?
  2. Quality or quantity of logos in the early days?
  3. Sales rep productivity, what does Sam believe is good?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Sam Blond

Jul 16 2018
30 mins
Play

Rank #18: SaaStr 190: Why SaaS Founders Should Not Sell Their Products in The Early Days, How Founders Can Build Relationships with Enterprise CIOs and The Right Way To Think About Discounting and Pilots with Ed Sim, Founding Partner @ Boldstart Ventures

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Ed Sim is the Founder & General Partner @ Boldstart Ventures, one of the leading players in early stage SaaS investing. Their MO, to be a first check VC for enterprise founders and they have backed the likes of GoToMeeting (acq by Citrix), LivePerson (IPO, NASDAQ), Divide (acq by Google), Kustomer, Snyk and BigID just to name a few. Ed is also a cofounder of MState, a growth lab for enterprise blockchain in partnership with IBM. Ed is also a board director/observer of Kustomer, Hypr Biometric, Snyk, BigID, Fortress IQ, Wallaroo Labs and Manifold. If that wasn’t enough, Ed is also the writer behind BeyondVC, a must read blog in the world of SaaS.

In Today’s Episode You Will Learn:

  • How Ed made his way into the world of VC from one very meaningful high school lecture that changed his life and career path?
  • What does Ed mean when he says “founders should not sell their product to enterprise in the early days”. Starting from the ground up, what can founders do to begin that relationship building process with enterprise buyers and CIOs? What can a startup do to establish that trust in the mind of large buyers? How much of a role does VC backing provide in comforting enterprise buyers?
  • What would Ed advise founders contemplating the debate of going SMB up to enterprise or enterprise to SMB? What role should product play in this decision-making process? What are the leading indicators in testing the product that founders should observe for and guide their direction? Where does Ed most often see founders make mistakes here?  
  • How does Ed think about discounting? Would he agree with a previous guest that “discounting is now table stakes”? Rather than the financial element, what does Ed believe the founder should really be looking to get from the buyer in terms of commitment? How does Ed approach and assess pilots? To what extent should they be free or paid? What can be done to set the benchmarks for success and ensure closing?

Ed’s 60 Second SaaStr

  1. What does Ed know now that he wishes he had known in the beginning?
  2. Quality or quantity of logos?
  3. What would Ed most like to change in the world of SaaS?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Ed Sim

Aug 27 2018
31 mins
Play

Rank #19: SaaStr 201: How To Prioritise Your Sales Pipeline, Why You Should Spend Your Time on the 10% Least Likely Leads & Why The Secret To Success In Sales Is "Calls Between The Calls" with Hannah Willson, VP Sales @ Rainforest QA

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Hannah Willson is the VP of Sales @ Rainforest QA, the on-demand QA solution that allows companies to discover problems that affect the customer experience before the code hits production. To date, Rainforest have raised over $40m in funding from some of the very best in SaaS including the legendary Byron Deeter @ Bessemer, Jason Lemkin @ SaaStr, Marc Benioff himself, Andreesen Horowitz and YC. As for Hannah, she has over 10 years of experience leading sales and customer teams at both startups and publicly traded companies including seeing the first hand hyper-growth of Zenefits in their heyday and being VP of BD, Sales and Customer Renewals for the western half of the US at HelloWallet, prior to their acquisition by Morningstar.

In Today’s Episode We Discuss:

  • How Hannah made her way into the world of SaaS and enterprise sales, came to join Zenefits in their heyday and how that led to her move to VP of Sales @ Rainforest?
  • How does Hannah think about time allocation and prioritisation of time across leads and the sales pipeline? WHat can AEs do in terms of optimising their win rate of opportunities? How important a role should discounting play in winning potential leads? Does Hannah optimise for quality or quantity of logos in the early days?
  • What does Hannah mean when she says the secret to success is “the calls between the calls”? How do these vary both in content and tone to traditional sales calls? Why must AEs be willing to open up and be vulnerable with leads? What can managers do to engender this? What is the optimal relationship for AEs and product team?
  • What does Hannah believe is the right mechanism for feedback delivery? What has worked well for her in the past? Where does Hannah see many today going wrong? What guidelines need to be put in place to ensure this candid and transparent feedback is effective?

Hannah’s 60 Second SaaStr:

  1. What does Hannah know now that she wishes she had known at the beginning?
  2. What does Hannah believe embodies good sales rep productivity?
  3. What is Hannah’s fave SaaS reading material?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Nov 19 2018
28 mins
Play

Rank #20: SaaStr 206: 4 Core Considerations Startup Founders Must Recognise When Pricing Their Product, Why Being Good At Sales Won't Make You A Great Sales Leader and Why Boring Is Better Than Sexy When It Comes To Winning Your Market with Ryan Barretto, SVP of Gl

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Ryan Barretto is the SVP of Global Sales at Sprout Social, a leading provider of social media engagement, advocacy and analytics solutions for business. To date they have raised over $111m in funding from the likes of NEA, Goldman Sachs and their very recently announced $40m Series D led by Future Fund.  At Sprout Social Ryan oversees both the Sales and Customer Success organizations. Prior to Sprout, he was the VP of Global Sales at Pardot–a Salesforce company. At Pardot, Ryan's team tripled revenue growth in two years, making Pardot one of Salesforce's fastest growing businesses and during his 10 year tenure at Salesforce he saw the company grow from $180m to $7.5Bn.

In Today’s Episode We Discuss:

  • How Ryan made his way into the world of SaaS with Salesforce over 13 years ago? What were some of Ryan’s biggest takeaways from seeing Salesforce scale from $180m to $7.5Bn?
  • Why does Ryan think that it is lazy to believe that you have to pick a market and you can’t have them all? How can one approach the element of very different messaging being required for SMB vs enterprise? How can one do both? How does that change the structure of the team? How can one build a product with the simplicity of SMB and functionality of enterprise?  
  • When it comes to winning the market, what does Ryan mean when he says, “boring is better than sexy”? What are the 4 elements all founders must consider when pricing their SaaS product? Where does Ryan see many go wrong with pricing? When serving SMB, how can one provide enterprise quality customer support? How does Ryan feel about customisation? What number justifies it?  
  • Why does Ryan believe that being good at sales won’t make you a great sales leader? What is needed to make the transition? What can sales reps do to learn and bridge that gap? What has worked for Ryan in the past? Where has Ryan seen many go wrong here? What 3 elements does Ryan look for in al additions to the team?
  • What is the number 1 issue that is preventing people building truly diverse teams? How can we change our job descriptions to make the more inclusive? How can we expand our candidate pool to include more diverse people than usual? What can leaders do to build environments of inclusion where people can really bring their full selves to work?

Ryan’s 60 Second SaaStr:

  1. What does Ryan know now that he wishes he had known at the beginning?
  2. Sales rep productivity, what is good to Ryan?
  3. What motto or quote does Ryan frequently revert back to? Why?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Ryan Barretto

Jan 07 2019
27 mins
Play

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