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The Official Saastr Podcast: SaaS | Founders | Investors

Updated 4 days ago

Business
Technology
Investing
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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.

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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

96 Ratings
Average Ratings
82
6
3
2
3

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

96 Ratings
Average Ratings
82
6
3
2
3

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.

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Cover image of The Official Saastr Podcast: SaaS | Founders | Investors

The Official Saastr Podcast: SaaS | Founders | Investors

Updated 4 days ago

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.

SaaStr 037: Why The Whole SaaS Pricing Model Is Going To Change with Quang Hoang, Co-Founder @ Birdly

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Quang Hoang is the Co- Founder @ Birdly, Birdly are convinced by the power of messaging within organizations, they decided to build a broader service that connects your favorite business softwares to messaging apps. It is this vision that has led to them being named one of the hottest startups from YC Winter 2016 batch and has led to funding from some of the best in the industry including our own Jason lemkin, Slack, previous guest Nicolas Dessaigne and prestigious french investors Alven Capital and Partech Ventures.

In Today’s Episode with Quang We Discuss:

  • How did Quang come to found Birdly? What was the a-ha moment?
  • What did Quang learn from pivoting to Birdly? What is it important for founders to consider before a pivot?
  • How does Quang approach the challenging topic of a business model for bots?
  • Why does Quang believe that the whole pricing model for SaaS will change?
  • What were the main benefits of the YC experience and how did it impact his fundraising?
  • When is the right time for European startups to make the move to SF? How important is it to be close to your customers?

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

Jul 08 2016

21mins

Play

SaaStr 073: David Skok Part 2: What Is Negative Churn? How To Get Different ACV's From The Same Product? Should Customer Success Be Involved In The Up Sell Process?

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Part 2 with David Skok, now David 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! Huge thanks to Hardi Meybaum and Jason Lemkin for the intro to David today.

In Today’s Episode You Will Learn:

  • 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?
  • 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 up sell 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?
60 Second SaaStr

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

Nov 11 2016

15mins

Play

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

46mins

Play

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

32mins

Play

SaaStr 077: WTF Is Net Retention? Why The Best SaaS Companies Focus On It & Why You Do Not Have To Be In SF To Be Successful in SaaS with Michael Sharkey, Founder & CEO @ Autopilot

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Michael Sharkey is CEO & Co-Founder of Autopilot, the startup that allows you to automate customer journeys as simply as drawing on a whiteboard. Autopilot has funding from some of the best investors both in Australia and in SaaS with backing from the likes of Salesforce Ventures and Blackbird Ventures. Prior to founding Autopilot with his two brothers, Michael joined his brother Chris to grow start-up Stayz into a top Australian rental booking site which was acquired by FairFax Digital in 2006 and again by HomeAway for $225M in 2013. Michael also co-founded digital marketing agency Sharkey Media where he helped grow Australian startups. I would love to say a huge thank you to Matt Garratt @ Salesforce Ventures for the intro to Michael today.

In Today’s Episode You Will Learn:

  • How did Michael come to co-found Autopilot with his two brothers? What was the a-ha moment for him?
  • Why did Michael choose a self service model with Autopilot? How does this model affect their CAC? How does this model alter the outbound marketing strategy?
  • How does Michael approach the dilemma of variable or fixed pricing? Has Michael found that the lack of reliability around variable pricing causes customers concern?
  • With Michael interest in unit economics, why are we seeing many SaaS startups, Marketo and Eloqua, exiting with losses? What can founders do to adopt the unit economics first mindset? How does this attitude to unit economics affect attitudes to aggressive growth?
  • Michael focuses on 100% net retention, what does that process and strategy look like in practice? How does this commitment to 100% retention affect Michael’s management style and work processes?

60 Second SaaStr

  1. Biggest mentor to Michael and how it came about?
  2. What does Michael know now that he wishes he had known in the beginning?
  3. The biggest mistakes SaaS companies make with their email marketing processes?

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

Michael Sharkey

Nov 25 2016

26mins

Play

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

26mins

Play

SaaStr 161: Brad Feld on Structuring Your SaaS Startup For Scalability, How The Role Of CEO Should Adjust To The Growth Of The Organisation & What Makes The Most Effective Board Members

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Brad Feld is one of the world’s leading VCs having Co-Founded Foundry Group, Brad has made investments in the likes of Zynga, Makerbot and Fitbit, just to name a few. Brad is also Co-Founder of Techstars, one of the world’s most prominent startup accelerators, whose portfolio companies have raised over $1.3bn in funding. If that wasn’t enough Brad is also a best selling author having co-authoured Venture Deals: Be Smarter Than Your Lawyer and VC and Startup Communities: Building An Entrepreneurial Ecosystem In Your Community.

In Today’s Episode You Will Learn:

  • How Brad made his way into the world of VC and came to found Foundry Group?
  • Brad has previously stated that companies can be segmented into 3 different core components? What does he mean by this? How can startups be structured internally for scalability?
  • Why does Brad hate the word culture? How should culture be viewed and approach internally within startups?
  • How has Brad seen his personal development with regards to being a board member? What has he got better at? What does he believe makes a great board member?
  • Why is CAC the easiest metric to game in SaaS? How should the CAC/LTV ratio be approached? How can entrepreneurs use this to attract VC investment?

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

Brad Feld

If you have a digital product, whether it’s mobile or web, Amplitude’s product analytics helps you understand what your users are doing, iterate and ship product faster, and drive metrics like engagement and retention. To learn how you can use analytics to build a sticky product that grows your business, get your free copy of the Product Analytics Playbook from Amplitude. This 155-page book (with worksheets) will help you develop a comprehensive retention strategy for your product — just click here to download.

User education is one of the most powerful ways to increase engagement and retention at scale, yet is often put in the too hard basket. Elevio is the platform that removes this burden, empowering your users to self-serve contextually relevant help via their support widget and embeddable elements, increasing retention and engagement, while reducing support load. Elevio even tells you what content to add or fix and why based on usage trends from your users. Preventing content rot, and increasing coverage, which we all know is an ongoing challenge. You can also integrate with your existing support stack for content, access to live-chat, support tickets and more. Use elevio for continuous user education with 20% off your first year at (elev dot I O / saastr) using coupon code GOHARRY

Feb 05 2018

32mins

Play

SaaStr 164: The Right Way To Sell To Enterprise Buyers, Why Sales Ops Will Be A C-Suite Role in the Next 10 Years and Whether Or Not To Engage With Pilots and Discounting with Mark Godley, President @ LeadGenius

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Mark Godley is the President of LeadGenius, the startup that provides the power of human intelligence with the scale of machine learning. To date they have raised $16m in funding from the likes of a16z, Initialized Capital, Scott and Cyan Banister and SV angel just to name a few. As for Mark, he most recently served as Chief Revenue Officer for HG Data and before that was VP of Market Development for ConnectandSell. If that was not enough, mark also holds advisory roles in the salestech and martech space, including Omniquo, ZenIQ.io and The Big Willow.

In Today’s Episode You Will Learn:

  • How Mark made his way into the world of SaaS over 25 years ago? How has he seen the industry change so remarkably over that time?
  • Why does Mark believe that many startups today are created with the wrong intentions? Who is ultimately to blame for this, the founders or the investors who back them? Why does Mark believe that SaaS founders should “ignore fundraising and sign customers”? What are the unidentified consequences to Mark of taking external money?
  • How does Mark view the function played by discounting in onboarding your first few key customers? What does Mark think of pilots? How willing should founders be to engage with unpaid pilots?
  • How can enterprise founders solve the 2 big problems today of. A.) Standing out in the sea of enterprise startups? Gain trust from enterprise CIOs when they are still a small team with little brand or track record?
  • What does Mark believe is the secret to selling to enterprise effectively? Why must founders be both credible and vulnerable when selling? What is the difference between helping someone buy and selling them a product?

60 Second SaaStr

  1. What does Mark know now that he wishes he had known at the beginning?
  2. Why are data vendors their own worst enemy?
  3. What would Mark like to change about the world of VC and startups?

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 Godley

If you have a digital product, whether it’s mobile or web, Amplitude’s product analytics helps you understand what your users are doing, iterate and ship product faster, and drive metrics like engagement and retention. To learn how you can use analytics to build a sticky product that grows your business, get your free copy of the Product Analytics Playbook from Amplitude. This 155-page book (with worksheets) will help you develop a comprehensive retention strategy for your product — just click here to download.

User education is one of the most powerful ways to increase engagement and retention at scale, yet is often put in the too hard basket. Elevio is the platform that removes this burden, empowering your users to self-serve contextually relevant help via their support widget and embeddable elements, increasing retention and engagement, while reducing support load. Elevio even tells you what content to add or fix and why based on usage trends from your users. Preventing content rot, and increasing coverage, which we all know is an ongoing challenge. You can also integrate with your existing support stack for content, access to live-chat, support tickets and more. Use elevio for continuous user education with 20% off your first year at (elev dot I O / saastr) using coupon code GOHARRY

Feb 26 2018

31mins

Play

SaaStr 152: Cloudera's Lars Nilsson on Why SDRs Are The Most Important Role In The Sales Function, How To Build An SDR Team From Nothing & How To Construct A Compensation Plan That Drives A Behaviour You Want Other Than Just Revenue

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Lars Nilsson is the VP of Global Inside Sales for Cloudera and with over twenty-five years of sales and operations experience, Lars Nilsson is a global leader in enterprise software and selling solutions. One of Lars many incredible achievements was he and his team at Cloudera built the sales methodology Account-Based Sales Development (ABSD), which has transformed how businesses approach high-value targets. Prior to Cloudera, Lars founded SalesSource, a business services consulting firm specializing in CRM customization and sales process development. Lars has also served in sales executive roles at ArcSight/Hewlett Packard, Riverbed Technology and Portal Software – all three of which achieved IPOs, in addition to Cloudera (2017). As Special Advisor at True Ventures, Lars helps True portfolio companies develop sales compensation plans from the ground up, implement best-of-breed sales technologies, and rapidly scale sales teams to meet demand.

In Today’s Episode You Will Learn:

  • How did Lars make his way into the world of enterprise sales back in 1995? How has Lars seen the industry change so significantly over the last 22 years?  
  • Why does Lars believe that SDRs are the most important role in sales? How does their role of ensuring a full pipe compare to the role of demand gen and marketing?
  • How does Lars think about setting a quota that ensures a desired behaviour beyond pure revenue chasing? What is his framework for setting and optimising the right quota? Why does Lars believe that ales is all about activities? What activities is Lars most eager to measure and test?
  • What is Lars’ biggest advice to someone looking to build out their SDR team from the ground up? What core characteristics should one look for in those initial SDR hires? What is and has been Lars’ biggest challenge in building out his SDR team? Why is building SDR teams in the bay so hard?
  • How does Lars think about setting ideal customer profiles? How big a TAM is large enough to be excited, yet narrow enough  to be achievable and solve a true and inherent customer need?

60 Second SaaStr

  1. What does Lars know now that he wishes he had known at the beginning?
  2. What is Lars favourite piece of SaaS reading material?
  3. Sales rep productivity, what does Lars believe is the scale from exceptional to poor?

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

Lars Nilsson

Nov 20 2017

30mins

Play

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

31mins

Play

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

32mins

Play

SaaStr 221: HBS Sr. Lecturer and Former Hubspot CRO Mark Roberge on His Step by Step Guide to Revenue Growth

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Mark Roberge is a senior lecturer with Harvard Business School, former CRO of Hubspot and author of the bestseller "The Sales Acceleration Formula". Join him as he takes you through his step by step guide to revenue growth.

Missed the session? Here’s what Mark talks about:

  • An in-depth guide to driving revenue growth by company stage
  • When to scale and how fast
  • Product market fit, go-to market fit during the experiment stages

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

Jason Lemkin

SaaStr

Mark Roberge

Mar 28 2019

30mins

Play

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

33mins

Play

SaaStr 168: Why 70% of Startup's VPs of Sales Fail, How and When To Hire Your First VP of Sales & The One Question That You Must Always Ask VP of Sales Candidates with Ryan Williams, Founder @ SalesCollider

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Ryan Williams is the Founder @ SalesCollider, the organisation that helps technical founders jumpstart sales. Ryan got his start as the first sales manager at Adroll where he grew the team from 3 to 32 reps in just 8 months, a team that was responsible for ARR growing from $4m to $58m in under 2 years. Ryan then became an advisor to the early team at InVision where he coached both CEO and sales reps to close the first dozen enterprise deals. Then his last stop before founding SalesCollider was as VP of Sales at LeadGenius where he grew enterprise sales by over 400% and added clients such as Ebay, IBM and Google, just to name a few. Ryan is also an Entrepreneur in Residence @ 500 Startups and a Mentor with First Round Capital.

In Today’s Episode You Will Learn:

  • How Ryan made his way into the world of sales as first sales manager at Adroll and how that led to advising the CEO of InVision on gaining their first enterprise clients?
  • 70% of VPs of Sales fail when they join early stage startups, why is this? How can founders know when is the right time to bring in their first VP of Sales? What can they do to maximise the chances of success when bringing them into the organisation?
  • What is the right profile type for the first VP of Sales? What are the core foundations to assessing the strength of the VP in the interview, especially for engineering minded founders? What is the one question that Ryan loves to ask potential sales candidates? What answer does he look for?
  • Does Ryan agree with a recent guest, “discounting is now table stakes”? Where do most early stage startups go wrong when thinking about discounts? What framework must startups utilise to analyse the right discount to offer? Why must they know the internal value they are providing to their customer in such a detailed way when discounting?

60 Second SaaStr

  1. What does Ryan know now that he wishes he had known at the beginning?
  2. SDR’s are the most important function in sales, agree or disagree?
  3. Sales rep productivity, what is good and what is bad?

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 Williams

Mar 26 2018

29mins

Play

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

30mins

Play

SaaStr 218: Twilio Founder, Jeff Lawson & SendGrid CEO, Sameer Dholakia on Why Developer First Is A Maturation In The Supply Chain Of Software & Why With Software Innovation Costs Being Lower Than Ever, Operators Must Maximise The Number of "At Bat" Oppor

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Jeff Lawson is the Founder & CEO @ Twilio, the company building the future of communications allowing you to engage customers like never before on voice, SMS, WhatsApp or Video. Prior to their IPO in 2016, Twilio had raised over $250m in VC funding from some of the best in venture including USV, Bessemer, Salesforce and Techstars just to name a few. As for Jeff, prior to founding Twilio, Jeff was the Founder & CTO @ Nine Star Inc and enjoyed a spell at Amazon as a Technical Product Manager.

Sameer Dholakia is the CEO @ SendGrid, the category leader in email delivery, reaching half of the world’s digital users every 3 months. Last year Twilio acquired SendGrid bringing email into one seamless customer engagement platform. As for Sameer, prior to joining SendGrid, he spent 4 years at Citrix, where he drove the company’s product strategy for cloud infrastructure and server virtualization. Sameer joined the company in 2010, when Citrix acquired VMLogix, where he served as CEO and doubled revenues during each year of his tenure. Before that, he worked for 12 years at Trilogy, where he held key leadership roles helping the company grow from a start-up to a $300 million business.

In Today’s Episode We Discuss:

  • How Jeff came to found Twilio and what was that a-ha moment for him? How did Sameer enter the world of SaaS and come to be CEO @ SendGrid?
  • How did Jeff and Sameer assess the culture fit between the 2 companies when deciding whether or not to join forces? How did they formulate and approach creating a new set of values with the 2 companies coming together? How do they distinguish between culture and values? How can leaders both be authoritative and vulnerable simultaneously?
  • What does Jeff mean when he says, “the developer first approach is a maturation of the supply chain of software”? How has Jeff seen his original thesis for “developer first” evolve and change with time? What does truly special customer experience look like in the developer first model?  
  • In terms of product strategy, how do Jeff and Sameer approach when is the right time to release a second product? What does Jeff mean when he says, “you have to maximise the number of at bat opportunities you have”? Why does Sameer think that SendGrid waited too long to release additional product lines? What were his core learnings from that?
  • How do Jeff and Sameer think about what what truly special leadership looks like today? How do they approach speaking so that people will remember? What are some of their biggest tips to aspiring entrepreneurs with regards to that and team empowerment? Why do both Jeff and Sameer believe that so much of the management wisdom today is outdated?

60 Second SaaStr:

  1. What do Jeff and Sameer know now that they wish they had known at the beginning?
  2. The book they have gifted most often and why?
  3. What does it take to truly be a great board member?
  4. What do the next 5 years look like for Twilio? How big could it get?

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

Jeff Lawson

Sameer Dholakia

Mar 18 2019

38mins

Play

SaaStr 157: MuleSoft Founder, Ross Mason on How Unbundling to A SaaS Platform Alters Revenue, Org Structure and Product Roadmap, Why Moving To Silicon Valley Was Fundamental For Mulesoft &Why Startups Can No Longer Own The Entire Customer Lifecycle

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Ross Mason is the Founder & VP of Product Strategy @ MuleSoft, one of the world’s leading software platforms making it easy to connect the world’s applications, data and devices. Following over $250m in VC funding from the likes of Lightspeed, Salesforce Ventures, Sapphire Ventures and NEA, MuleSoft then went public in March 2017, popping as much as 45% on it’s first day of trading. As for Ross, prior to MuleSoft, he was CEO of SymphonySoft, an EU-based company providing services and support for large-scale integration projects. Previously, Ross was Lead Architect for RaboBank and played a key role in developing one of the first large-scale ESB implementations in 2002.

In Today’s Episode You Will Learn:

  • How Ross made his way into the world of SaaS with the founding of MuleSoft?
  • Why did Ross decide to move full time to the West Coast having started the company in Europe? What were the biggest challenges about the move to the US? What advice would Ross give to prospective entrepreneurs, looking to make the move? Where does Europe exceed the US and vice versa?
  • What does it really mean to be a SaaS platform? What 3 elements of a company benefit when a product unbundles into a SaaS platform? How does unbundling change the process for building products and services? How does unbundling change the ability to drive new revenue streams? How does unbundling change core operational elements of the business?
  • What does Ross mean when he says we are shifting from verticals into value chains? Does Ross believe it is even possible to own the entire customer lifecycle today, from start to finish?

60 Second SaaStr

  1. What does Ross know now which he wishes he had known at the beginning?
  2. How did it feel the day MuleSoft went public?
  3. What advice does Ross commonly hear being given that he most disagrees with?

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

Ross Mason

Jan 08 2018

26mins

Play

SaaStr 188: Why The Best CEOs Are Inspirational Assholes, How To Optimise Decision-Making within Your Organisation & The Benefits of Being Old In SaaS with Fouad ElNaggar, Founder & CEO @ Sapho

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Fouad ElNaggar is the Founder & CEO @ Sapho, the only employee experience portal designed for the digital workforce. To date, Ray has raised over $27m in funding with Sapho from some real favourites of ours including Ray @ Caffeinated, Felicis, Uncork, Bloomberg Beta, Clark Landry and Howard Lindzon @ Social Leverage, just to name a few. Prior to founding Sapho, Fouad was the Chief Strategy Officer at CBS Interactive overseeing strategy, operations, partnerships, and M&A. At CBSi, Fouad structured deals with partners such as Yahoo, IAC, and Twitch and acquired premium brands such as TV Guide and Giant Bomb. Prior to CBSi, Fouad was a VC at Redpoint Ventures overseeing the firm’s LA office and helping establish a dedicated fund in Brazil. Fouad has previously founded three venture-backed companies – Marketing Technology Solutions (acquired), Liquid Light (acquired), and Hark.

In Today’s Episode You Will Learn:

  • How Fouad made his way from the world of VC to the world of CBS and media to founding SaaS companies being a serial SaaS founder with his 4th company, Sapho?
  • What does Fouad mean when he says the role of the CEO is to be an “inspirational asshole”? Why is this role so crucial and how is it embodied both in the approach to inspiring a team and driving goals and decision-making? How does Fouad think about structuring decision-making internally? Where do so many go wrong in implementing a decision-making process?
  • Why is Fouad a believer that “it is about coaching and promoting rather than signal hiring”? What does Fouad really interpret as signal hiring? When does signal hiring work well? How does Fouad determine when a stretch VP is a stretch too far? What are the leading indicators? Does Fouad agree with Mariam Naficy that rotation of function is key to internal upscaling?
  • What does Fouad believe are the 2 fundamental benefits of “being old” in SaaS? How would Fouad respond to the suggestion that the rate of decay on experience has never been greater with Moore’s law effect on technology? Applied to hiring, how does Fouad think about the decision to hire a jack of all trades vs a specialist? When is the time to make the transition?  

Fouad’s 60 Second SaaStr

  1. What does Fouad know now that he wishes he had known at the beginning?
  2. A moment in Fouad’s business life that changed the way he thinks?
  3. What would Fouad most like to change in 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

Fouad ElNaggar

Aug 13 2018

40mins

Play

SaaStr 155: Intercom Co-Founder, Des Traynor on Constructing The Right Brand Architecture, The Right Way To Integrate Customer Feedback Into Product Roadmap & Why There Is An Inverse Correlation Between Quality & Market Size

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Des Traynor is the Co-Founder, Chief Strategy Officer and VP of Marketing at Intercom, one of the world’s hottest startups that simply put, makes communicating with customers easy and efficient. They have raised over $115m in funding from some of the world’s leading investors including Social Capital, Index Ventures, Bessemer Venture Partners and then titans of industry with Mark Zuckerberg, Jack Dorsey and the Collison brothers at Stripe. Prior to Intercom, Des previously co-founded Exceptional (now a part of Rackspace), and prior was a UX designer for web applications.

In Today’s Episode You Will Learn:

  • How Des made his way from founding consultancy web design businesses in Ireland to founding SaaS superstar, Intercom, with Eoghan and moving to San Francisco?
  • Why does Des believe that “brand is the most overlooked element for new startups”? How must founders think differently when constructing their brand for a single product vs multi-product company? What is the right way to think about this brand architecture?
  • How involved should customers be in the development of product roadmap? Where are the nuances and challenges to this? When is the right time to start thinking about releasing a second product? What is the right and the wrong way for this to be marketed?
  • What does Des mean when he says, “there is an inverse correlation between quality and market size”? How should founders think about selling to both SMB and enterprise? How do their buying psychology and implementation process differ?

60 Second SaaStr

  1. When I say success, who is the first person that comes to Des’ mind?
  2. Where do most startups go wrong with their branding?
  3. What does Des 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

Des Traynor

Dec 11 2017

30mins

Play

SaaStr 213: Redpoint's Tom Tunguz on What Makes The Most Effective Free Trial, What Makes Good vs Great When It Comes To Benchmarks for Assisted vs Unassisted Conversion & Why Scoring Leads May Actually Be Dangerous

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Tom Tunguz is General Partner @ Redpoint Ventures, the venture fund with a portfolio including the likes of Stripe, Netflix, Zuora, Hashicorp and Juniper Networks just to name a few. As for Tom, he joined Redpoint in 2008 and has since led investments in Kustomer, Looker, Expensify and Gremlin all prior guests on the show I hasten to add. He is also the co-author of Winning with Data: exploring the cultural changes big data brings to business. Tom has also been named on the Forbes Midas Brink list. Before joining Redpoint, Tomasz was the product manager for Google’s AdSense social-media products and AdSense internationalization.

In Today’s Episode We Discuss:

  • How Tom made his way from creating software with his father in Brazil to being GP and forefront figure in the SaaS investment community as a GP at Redpoint today?
  • Annual contracts: To what extent do annual contracts dominate today? How does this differ when comparing enterprise to SMB? Why does Tom think in the early days one should be wary of signing too many multi-year contracts? What are the dangers there? How does Tom think about calculating churn when it comes to multi-year contracts?
  • What were the findings on what good looks like when it comes to logo retention? How does this differ when comparing SMB to enterprise? What were the commonalities of leading indicators of churn? Is it fair to always surmise that when serving SMB one will always have a higher rate of churn? What is the right way to conduct a churn analysis?
  • Assisted vs unassisted: What does Tom believe are the leading benchmarks for both? How does this differ when comparing SMB to enterprise? How does the impact of a salesperson change the conversion rate? What time frame from SAL to closed lead suggests product market fit? What one question must all founders be asking in the sales process?
  • How does Tom think about constructing comp plans the right way today? How should comp plans differ when comparing AEs to customer success? Where should the responsibility for upsell lie, customer success or sales? Should sales commission be paid on renewals?  

Tom’s 60 Second SaaStr:

  1. What does Tom know now that he wishes he had known at the beginning?
  2. What is Tom’s favourite book and why?
  3. What is Tom’s most recent investment and why did he say yes?

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

Tom Tunguz

Feb 26 2019

35mins

Play

SaaStr 291: LucidChart CEO Karl Sun on Top Lessons Learned From Our Best and Worst Marketing Experiments

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Lucidchart has been recognized as one of the most mature Product Lead Growth business models in the market, driving over 700,000 registrations per month, combined with a hyper-efficient B2B business model. It didn’t happen by accident. It happened through experimentation: from extensive A/B testing (with over 500 marketing tests completed in 2018), to testing crazy brand videos (which have garnered over 200 million views and was named the only ad campaign that truly mattered in 2018 by Adweek), to constant iteration and expansion of the business model. Experimental marketing brings together the science and art of marketing, allowing for creativity that drives results. It’s an essential skill in the toolkit of the modern marketer, and one that’s easy to get started with, no matter your company scale. Key Takeaways: - Discover how to start or extend your marketing experimentation. - Learn how marketing experimentation can apply across funnels, brands, and business models. - Get tips on how to build a culture of experimentation that fosters creativity and drives business results.

Dec 12 2019

24mins

Play

SaaStr 290: How To Sell To CIOs Successfully; Discounting, Freemium, Trials, Multi-Year Contracts, Transparency on Product Roadmap; The Ultimate Guide with Yousuf Khan, Serial CIO, Startup & VC Advisor

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Yousuf Khan is a serial CIO, start-up and VC advisor. Most recently Yousuf was the CIO & VP of Customer Success @ Moveworks, the advanced AI built for enterprise providing automatic resolution of IT issues. During his time at the company, they raised over $108m from Lightspeed, ICONIQ, Kleiner, Sapphire and Bain Capital. Pre Moveworks, Yousuf was CIO @ Pure Storage during their period of hypergrowth both as a private and public company. Finally, before Pure, Yousuf’s first role in the valley was with Qualys again as CIO where he owned the entire global IT budget.   

In Today’s Episode We Discuss:

  • How Yousuf made his way from the UK to the valley and how that led to his becoming one of the leading CIOs today in the rising prominence of CIOs in enterprise? 
  • How open and can transparent can CEOs be with CIOs? Do CIOs know the state of early-stage companies in terms of their cash situation, fundraising etc? Does that ever put them off buying? What is the right tone and temperament to take with those CIOs in the first meetings? How does Yousuf advise founders on quality or quantity of logos in the early days? 
  • How does Yousuf advise CEOs approach CIOs when it comes to discounting? Do they make a difference to the buying decision of the CIO really? Should founders offer discounts in exchange for customer testimonials? How can CEOs provide alternative forms of social validity to other CIOs in the ecosystem, other than case studies?  
  • How does Yousuf advise founders approach CIOs when it comes to multi-year deals? Does the mindset of the CIO change when the deal is paid upfront? How should the founders position that? When it comes to implementation, how important is time to value in the mind of the CIO? What is the worst thing a founder can do when discussing implementation?    

Yousuf’s 60 Second SaaStr:

  1. What separates good from great when it comes to CIOs?
  2. What makes the best board members?
  3. What are Yousuf’s biggest strengths and weaknesses?

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

Yousuf Khan

Dec 09 2019

36mins

Play

SaaStr 289: Salesloft CEO Kyle Porter, Zoom Head of Sales Ops Hilary Headlee and FireEye VP of WW Commercial SalesChristina Foley on 7 Key Tips & Tricks to Getting More Revenue Per AE

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Salesloft CEO Kyle Porter, Zoom Head of Sales Ops Hilary Headlee and Fireeye VP of WW Sales Christina Foley share the seven tips and tricks to getting more revenue per AE.

Dec 05 2019

23mins

Play

SaaStr 288: Why Marketing Is The Gatekeeper of Customer Experience, The Relationship Between Customer Success and Marketing Today & How To Reduce Friction in The Hand-Off From Marketing to Sales with Des Cahill, CMO @ Oracle CX Cloud Suite

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Des Cahill is the Chief Marketing Officer for Oracle CX Cloud Suite, an integrated set of marketing, sales, commerce and service solutions that power customer experience for thousands of leading global brands. Prior to Oracle, Des was the CMO @ Kerio Technologies marketing to over 60,000 SMB customers and 5,000 channel partners. Before Kerio, Des was the CMO @ Ensighten, where he helped grow the customer base from 10 to 100 and revenues from $2M to $14M. Des has also spent time as CEO having founded and grown Habeas Inc from 0 to 450 customers, $9M in revenue and raising 3 rounds of venture financing. 

 In Today’s Episode We Discuss:

  • How Des made his way into the world of startups and came to be CMO of Oracle’s CX Cloud suite? 
  • Why does Des believe customers are more unpredictable now than ever before? How is their behaviour fundamentally changing? What are some great examples of how Des has seen companies amend to the changing consumer demands?
  • How does this change the role of the marketer today? How does this change the prioritisation of customer experience for marketers? What are the challenging elements of this change? How does the role of marketing also integrate with the post-sale and customer success with much of their content being used there?  
  • How does Des think about the relationship between marketing and sales teams? What are Des’ biggest tips on how to reduce friction in the handoff from marketing to sales? What works? What does not work? What is the right OKR to measure marketing teams? Does it have to be tied directly to revenue?  

Des’ 60 Second SaaStr:

  1. Biggest breakdown in the working of an efficient funnel?
  2. Who is killing it in SaaS marketing today and why?
  3. Advice in SaaS you commonly hear but disagree with?

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

Des Cahill

Dec 02 2019

36mins

Play

SaaStr 287: Slack's Head of NA Sales Kevin Egan and Head of Mid-Market Sales Dannie Herzberg on going From Freemium to Enterprise

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Kevin Egan, Slack's VP of North American Sales and Dannie Herzberg, Slack's Director of Sales as discuss their strategies for going from Freemium to Enterprise at Slack.

Nov 28 2019

22mins

Play

SaaStr 286: The Biggest Sales Hiring Mistakes and Lessons From Them, How To Win At Hosting B2B Events & How To Apply True Customer Segmentation and Focus To Your Customer Base with Allie Janoch, Founder & CEO @ Mapistry

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Allie Janoch is the Founder & CEO @ Mapistry, the startup that makes environmental compliance simple. As for Allie, prior to founding Mapistry she started her career in MIT’s Lincoln Lab before joining IQ Engines (acquired by Yahoo). Post acquisition, Allie integrated the technology built at IQ Engines into Flickr search. 

 In Today’s Episode We Discuss:

  • How Allie made her way from the world of Yahoo to founding the game changer of environmental compliance in Mapistry? Having had both big company, small startup and founding experience, what would Allie advise new graduates entering the workforce today? 
  • What were the biggest mistakes that Allie made when it comes to sales hiring? What were the learnings from those mistakes? How does Allie advise other founders on scaling sales teams? How does Allie think about sales rep payback period? How can one determine the effectiveness of a sales rep when they are engaging in 9-12 month sales cycles?
  • How does Allie think about the importance of focus applied to customer segmentation today? How does Allie measure true customer success? NPS? Churn? Product analytics? How does Allie explain the macro market size to VCs when they initially see the small customer segment?  
  • Why did Allie start doing their own events with Mapistry? How should startups think about whether events are the right strategy for them or not? How should founders think about resource allocation and budget when it comes to events? How does Allie measure the ROI of events? 

Allie’s 60 Second SaaStr:

  1. What does Allie know now that she wishes she had known at the beginning? 
  2. What would Allie most like to change about the world of tech and Silicon Valley?
  3. What is the biggest challenge for Allie today with Mapistry?

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

Allie Janoch

Nov 25 2019

32mins

Play

SaaStr 285: Adyen CCO Roelant Prins and Felicis Ventures Partner Aydin Senkut on How to Build a $18B+ Success Story Far Far Away from Silicon Valley

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Hear about Adyen’s journey from a Dutch payments startup to a global public company with more than 15 offices around the world working with large global companies like Facebook, Spotify, Uber and Microsoft. Roelant shares lessons from the company’s own global growth path and will be giving practical tips for companies who are thinking about expanding their business globally. Roelant is joined by Felicis Ventures Founder, Aydin Senkut, who shares the commonalities he sees in successful companies...starting with culture.

Nov 21 2019

21mins

Play

SaaStr 284: Why We Need To Remove The Title of CRO, What Happens If You Apply Customer Success To A Venture Portfolio & Why Net Retention Is The Most Important North Star Metric In SaaS with Travis Bryant, Partner for Founder Experience @ Redpoint Venture

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Travis Bryant is Partner for Founder Experience @ Redpoint Ventures, the venture fund with a portfolio including the likes of Stripe, Netflix, Zuora, Hashicorp and Juniper Networks just to name a few. As for Travis, prior to joining Redpoint, Travis was head of Customer Growth at Front, after spending 5 years building the global Sales organization at Optimizely, the world’s most popular experimentation platform. During his time at Optimizely, the company grew from from $7 to >$90M in ARR and from 40 to 400 people. Before Optimizely, Travis spent 6 years at Salesforce in a number of sales roles including building the first Platform Sales team.

In Today’s Episode We Discuss:

  • How Travis made his way into the world of venture as the first ever Partner for founder experience at Redpoint? What were the 2 biggest lessons Travis took from Salesforce? How transformational is the 12 quarter year for Salesforce?
  • Why does Travis believe we need to abolish the title of CRO? Why does it suggest misalignment between customer and vendor from Day 1? What aspects of CRO’s roles is Travis in favour of? What elements is he not in favour of? What does Travis advise founders when it comes to uniting customer facing teams?   
  • Why does Travis believe that SaaS has upended the economic model but not the engagement model? How does the engagement model with customer need to shift? What does this do to the structure of the conventional funnel? 
  • Why does Travis believe net retention must always be the guiding North Star? How does Travis think about the different steps to customer qualification today and what makes the best SDR’s? What does Travis advise founders when it comes to churn analysis? What questions must you ask? What metrics must you look for? 

Travis’ 60 Second SaaStr:

  1. What motto or quote do Travis frequently revert back to?
  2. What is the most challenging element of Travis’ role with Redpoint?
  3. How should startup operators coming out of larger organisations determine which startup to join? 

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

Travis Bryant

Nov 18 2019

37mins

Play

SaaStr 283: SocialChorus Co-Founder Nicole Alvino on What I Learned About Corporate Ethics From Enron

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Nicole Alvino, founder of SocialChorus, shares some ‘truth is crazier than fiction stories’ about her time in structured finance at Enron and how she applied what she learned to build a company that has 10 of the Fortune 50 as customers. In your constant effort to grow and win, you’ll get the 5 most important lessons on how to push the envelope just far enough - while keeping your ethics in check.

Nov 14 2019

18mins

Play

SaaStr 282: The Ultimate Guide To Remote Work; All vs Part Remote Teams, How To Maintain Culture Across Teams, Should Compensation Be Location Adjusted, How To Structure Internal Processes with Remote Teams, How Remote Teams Impact Hiring, Sales and Fundr

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Michael Pryor, Co-Founder & CEO @ Trello, now Head of Trello Product with Atlassian following their recent acquisition.

Kolton Andrus is the Founder & CEO @ Gremlin, the failure as a service startup finds weaknesses in your system before they cause problems.

Dylan Serota, Co-Founder and Chief Strategy Officer @ Terminal, the startup that helps you create world-class technical teams through remote operations as a service.

Rachel Carlson, Co-Founder and CEO @ Guild Education, the leader in education benefits offering the single most scalable solution for preparing the workforce of today for the jobs of tomorrow. 

Sid Sijbrandi, Founder & CEO @ Gitlab, a single application for the entire software development lifecycle.

Jeppe Rindom is the Founder & CEO @ Pleo, the simple spending solution for your company automating expense reports and simplifying company expenses.

In Today’s Episode We Discuss:

  • How should founders think about the debate between all remote vs part remote teams? How does life and operations change with each? What are the pros and cons? Is it possible to move between the two overtime?
  • What can one do to maintain culture with remote teams? What processes need to be in place to ensure a cohesive and streamlined communication process? What technical architecture needs to be in place? Where are the breakpoints when it comes to communication? How often does one need to do in person off-sites?
  • How does being remote or part remote impact fundraising? How do VCs think about this new structure of operations? What is the right way to present it? How does being outside a core tech hub impact one’s ability to raise? How should one run a fundraising process if outside a core hub?  
  • How important is it for your team to be near your customers? How does this change according to sector and customer base? How important is it for your team to be near your investors? Does having an exec and sales team in one place and the rest of the team elsewhere work?  

Jason Lemkin

Harry Stebbings

SaaStr

Nov 11 2019

26mins

Play

SaaStr 281: Vista Equity Principal Rene Yang Stewart and Zapproved CEO Monica Enand on From Product Market Fit to Scale

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Rene Yang Stewart, Co-Head and Principal, Vista Equity Partners, and Monica Enand, Founder and CEO, Zapproved discuss growing a company from product market fit to scale. Vista Equity Partners invested in Zapproved in 2017. Hear perspectives from both the investor and founder on growth to scale.

Nov 07 2019

21mins

Play

SaaStr 280: SaaStr CEO Jason Lemkin and Mixmax Head of Revenue Don Erwin on The Secrets to Managing a Successful Sales Team

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How do you manage a sales team when you're at a company with both Free and Freemium Sales-Driven Segments? What about SMB vs. Enterprise Sales? SaaStr CEO Jason Lemkin sits down with Mixmax's Head of Revenue Don Erwin to discuss it all.

Nov 04 2019

22mins

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SaaStr 279: Glassdoor CEO Robert Hohman on Building a $1B Marketplace

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Glassdoor CEO Robert Hohman and Battery Ventures' Neeraj Agrawal  walkthrough Glassdoor's $1.2 Billion story from its launch in 2008 to its 2018 acquisition by Recruit Holdings. Hear about the early days of Glassdoor; tactical lessons on scaling—from building a business model and recruiting an all-star management team to advice on building a compelling, innovative company culture; and learn whyGlassdoor’s $1.2 Billion acquisition is just one milestone in the early innings of the company’s story.

Oct 31 2019

20mins

Play

SaaStr 278: Do You Have To Scale From SMB To Enterprise Customers, How To Make The Transition Successfully, What Changes About Customer Acquisition and Support & Why Continuous Customer Development Is The Most Important Thing You Can Do With Krish Subrama

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Krish Subramanian is the Founder & CEO @ Chargebee, the startup that lets you go beyond billing, payments and recurring invoices — to delivering subscription experiences that "wow". To date, Chargebee have “wowed” some of the world’s leading VCs to the tune of $38m including the likes of Insight Venture Partners, Tiger Global, Steadview and Accel Partners. As for Krish, under Krish’s leadership the team has grown to over 300 people and over 5,000 clients making it one of the next generation in truly global SaaS businesses started in India. 

In Today’s Episode We Discuss:

  • How Krish made his way into the world of SaaS and came to found one of India’s fastest growing SaaS companies in Chargebee?
  • What does Krish mean when he says, “in SaaS, you either sell to one of 2 customer profiles”? How does Krish think about purely serving the SMB market? Does one have to move to enterprise? Does one have to expand the product line to retain customers? How does he think about the mortality rate of SMBs?  
  • First, what is continuous customer development? Second, why does Krish believe it is one of the most important things any company must do? What is the process to do it efficiently? Does it have to be in person? What questions reveal the most? How should this data feedback into your product roadmap and pipeline? 
  • How does Krish think your customer acquisition and GTM strategy has to change with the movement from SMB to enterprise? What are the biggest challenges in making this transition? How does your customer success and customer support functions change with the move to enterprise? 

Krish’s 60 Second SaaStr:

  1. Biggest lessons from working with Lee Fixel?
  2. How does one know when is the right time to introduce a new product?
  3. What does Krish 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

Krish Subramanian

Oct 28 2019

30mins

Play

SaaStr 277: SaaStr CEO Jason Lemkin and Shopify Plus GM Loren Padleford on Revenue, Ecosystems and The Right Time to Go Upmarket

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When is the right time to go upmarket and how do you serve small, medium and large customers in the same company. SaaStr CEO Jason Lemkin sits down with Shopify Plus GM Loren Padelford to discuss.

Oct 25 2019

44mins

Play

SaaStr 276: Airtable's VP of Customer Engagement Liat Bycel on Why "Hands Off Leadership" Does Not Work, How To Align The Ambitions Of An Individual With The Objectives of The Company & Unpacking The Dilemma of Whether To Go Horizontal Or Vertical When It

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Liat Bycel is VP of Customer Engagement @ Airtable, the startup that works like a spreadsheet but gives you the power to organise anything. To date, Airtable has raised over $170m in funding from some of the best in the business including Thrive, Coatue, Founder Collective, CRV and individuals like Patrick Collison, Ashton Kutcher and Raymond Tonsing to name a few. As for Liat, prior to Airtable, she was the Chief Revenue Officer @ Assist. Before Assist, Liat spent 6 years at Twitter where she first hand saw their hyper-growth, managing a team of 40 across New York and SF and also Liat achieved 102% to quota on average every year. Finally before Twitter, Liat was VP of Sales @ Revolution Prep where she led and managed 7 offices. 

 In Today’s Episode We Discuss:

  • How Liat made her way into the world of SaaS and came to be VP of Customer Engagement at one of Silicon Valley’s hottest startups in Airtable? 
  • What were Liat’s biggest lessons from Twitter on how to hire successfully? What were some of the key takeaways from that experience on how, why and when to fire? Is there ever a right way to do it? How does Liat think about aligning both the personal ambitions of the person with the wider objectives of the company? Why does Liat reject the notion of “hands off leadership?”  
  • Companies often worry about whether to go horizontal or vertical, how does Liat personally think about this choice? What does she advise founders as a result? What are the core questions they should ask to determine their strategy? What are the biggest challenges of having such a vertical product? How does it impact messaging and brand? Product roadmap? Pricing?
  • How does Liat think about challenging the traditional sales model? How does that challenge the structure of the conventional AE and SDR structure? How does Liat think Airtable is pushing up against the traditional customer success model? How has having children impacted how Liat thinks about operating today? What changes with children? 

Liat’s 60 Second SaaStr:

  1. What does Liat know now that she wishes she had known at the beginning of her time with Airtable?
  2. What are Liat’s biggest strengths and weaknesses?
  3. What are the challenges of prioritisation?

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

Liat Bycel

Oct 21 2019

31mins

Play

SaaStr 275: SaaStr CEO Jason Lemkin and Gainsight CEO Nick Mehta on Founder Struggles from Imposter Syndrome to Vulnerabilites

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SaaStr CEO Jason Lemkin sits down with Gainsight CEO Nick Mehta to discuss what it means to be a SaaS leader. What are the day-to-day struggles? The fears and the worries and what it means to be "crushing it" 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

SaaStr

Oct 17 2019

31mins

Play

SaaStr 274: Messagebird CEO Robert Vis on Scaling To A $60M Series A, Why You Should Not Try To "Scale" & Why You Need To Build Your Business Like A House

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Robert Vis is the Founder & CEO @ MessageBird, the company that allows you to talk to your customers via Voice, SMS and Whatsapp. The company raised a monster $60M Series A from Accel and Atomico with only one prior investor being Y Combinator. As for Robert, prior to MessageBird, he was co-founder and CEO of Zaypay.com which focused on driving mobile payments into 50+ countries, enabling 1.5bln users to pay for virtual goods through their phones (sold to Mobile Interactive Group (MIG). 

In Today’s Episode We Discuss:

  • How Robert made his way into the world of startups and SaaS and came to found Messagebird? What was the a-ha moment for him? 
  • Why does Robert believe the most important element of being a founder is “thinking big”? How as a founder do you balance between thinking big with investors and then the day to day in the weeds with the team? How does Robert as Europe’s mentality of thinking big today? Have our ambitions exceeded what they have been before? How does being in Benelux change how Robert thinks about global ambitions and growth ambitions?  
  • What does Robert mean when he tells founders, “don’t try to scale”? How does Robert think about knowing when a business is ready to scale? Where do many founders go wrong in the preparation for scale phase? What does one need to get in place before scaling?
  • Why did Robert wait 6 years before raising any VC money? Why did he decide then was the right time? Once the raise was in, did he feel the pressure of suddenly having a lot of VC funding? How did his mindset to capital allocation change post-raise? How did he see his decision-making process change post raise? How did raising from the US differ from raising in the UK? 

Robert’s 60 Second SaaStr:

  1. What does Robert know now that he wishes he had known at the beginning of his time with Messagebird?
  2. What keeps Robert up at night? 
  3. What are Robert’s strengths and weaknesses? 
  4. What advice in SaaS does Robert most often hear that he disagrees with?

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

Robert Vis 

Oct 14 2019

29mins

Play

SaaStr 273: Atlanta Tech Village Founder David Cummings on 7 Lessons Helping Start Pardot, SalesLoft, and Calendly

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David Cummings is the co-founder of the Atlanta Tech Village, Pardot which sold to ExactTarget/Salesforce.com, Hannon Hill,  Rigor, SalesLoft (raised over $75M in capital), Terminus (raised over $25M in capital), and several more. Hear his lessons learned over the years from Pardot to Calendly.

Missed the session? Here’s what David talks about:

  • How large a role does funding play?
  • Matching pricing to value
  • How to continuously level up talent

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

Jason Lemkin

SaaStr

Oct 10 2019

23mins

Play

SaaStr 272: Asana's Head of Marketing Dave King on How We Are Entering The Third Wave of SaaS Marketing, What That Means For SaaS Marketers and Companies Today & What B2B Marketing Can Learn From B2C

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Dave King is the Head of Marketing at Asana, the work management platform that teams use to stay focused on the goals that grow their business. To date, Asana has raised over $210m from some of the biggest names in tech including Mark Zuckerberg, Peter Thiel, Marc Andreesen, Ben Horowitz, Sean Parker, Ron Conway, Benchmark, Founders Fund and more incredible names. As for Dave, prior to joining Asana, he led the marketing teams at Percolate, Highfive, and Salesforce Community Cloud.

In Today’s Episode We Discuss:

  • How did Dave make his way into the world of SaaS and startups? When did he realise his love of marketing SaaS companies?
  • What does Dave mean when he says, “we are entering the 3rd wave of marketing”? What were the 1st and 2nd chapters? What does the “3rd wave” of marketing mean for marketers today? How does it change what marketing should be focusing on? How does it change how marketing works with sales and customer success? 
  • What does Dave mean when he says, “offsites serve as a crutch for 2 core elements of the marketer's role”? How does Dave advise marketers on crafting their playbook? What are the core questions to ask? Where does Dave see many going wrong here? How does one turn a playbook into a repeatable, measurable process? With channel volatility being so high, is it possible to have a repeatable and predictable process?  
  • What are Dave’s biggest observations on what B2B marketers can learn from B2C? How does that change how Dave thinks about new campaigns and community building with Asana today? Who does Dave think has done this particularly well in the world of enterprise? Are there any challenges to trying to carry over B2C into the world of B2B? 

Dave’s 60 Second SaaStr:

  1. What does Dave know now that he wishes he had known at the beginning of his career in marketing? 
  2. Biggest breakdown in the working of an efficient funnel?
  3. A moment in Dave’s life that has served as an inflection point and changed the way he 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

Dave King

Oct 07 2019

29mins

Play