SaaStr’s Podcast “Best Of Guide” Our Top 10 Podcasts of All Time

Here is our countdown to our top ten most downloaded podcasts of all time. Sometimes oldies are goodies, especially when it comes to some of our most downloaded podcasts. Not only were they popular at launch but we continue to see our subscribers go back and listen to them time and time again…

Here is our countdown to our top ten most downloaded podcasts of all time. Sometimes oldies are goodies, especially when it comes to some of our most downloaded podcasts. Not only were they popular at launch but we continue to see our subscribers go back and listen to them time and time again. If you haven’t started tuning in, we’re now up to two episodes a week and growing our content by the day. If you’d like to join us on our podcast, submit yourself > HERE <

#1: David Skok, Matrix Partners General Partner

Episode No. 156

About the episode: 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.

  • 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?
  • Why are metrics so important? What role do they play in an organization? How do good founders respond to questions on not achieving sales targets?

#2: Tien Tzuo, Founder & CEO @ Zuora Shares the $100m Question All SaaS Founders Must Ask

Episode No. 94

About the episode: Tien Tzuo is the Founder and CEO of Zuora, one of the fastest-growing SaaS companies that has been at the forefront of the rise of subscription business models. They have funding from some of the best in the business including the likes of Benchmark, Sequoia, Redpoint and Marc Benioff, just to name a few. As for Tien, before Zuora, he was one of the ‘original forces’ at salesforce.com, joining as employee number 11. In his 9 years at salesforce.com, Tien served in numerous different roles including as Chief Marketing Officer for two years, and most recently as Chief Strategy Officer.

  • How did Tien make his way from being an early employee at Salesforce to founding Zuora?
  • What were the big takeaways for Tien from seeing the meteoric rise of Salesforce and working with Mark Benioff? How has that experience molded his running and strategy with Zuora today?

#3: Godfather of Sales John Barrow on How To React When a Lead Goes Dark

Episode No. 88

About the episode: John Barrows is essentially the Godfather of Sales. We often have VPs of Sales from tech titans on the show but who trains those VPs and sales reps to be the best in the world at sales? That is where John Barrows comes in. With clients including Dropbox, Box, Marketo, Twilio, and many more, John has amassed a wealth of knowledge and experience allowing him to provide the most proactive sales tips and strategies to optimize the sales process.

  • How did John make his way into the world of SaaS and more specifically sales optimization?
  • What are the key points all reps must cover in their first calls with new leads? Why is setting expectations so crucial?

#4: Upfront Ventures Partner Mark Suster on The One Thing That Kills Sales

Episode No. 124

About the episode: 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.

  • 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 responsibly and right spend?
  • 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?

#5: Scalyr Founder and CEO Steve Newman on How Small Numbers in SaaS Can Deceive You

Episode No. 194

About the episode: 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 (acquired 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.

  • 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 prioritizing?

#6: Benchmark/NEA General Partner Chetan Puttagunta on Why Open Source Is The Only Way To Get In Front of Today’s Developers

Episode No. 171

About the episode: Chetan Puttagunta is a General Partner @ Benchmark, and previously at NEA.  He 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.

  • How Chetan made his way 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 produce multi-billion dollar companies” have been proven?

#7: Fmr. Host Analytics CEO Dave Kellogg on Why CAC/LTV Is The Most Important Metric In SAAS

Episode No. 142

About the episode: 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 (acquired by DuPont for $300M)  and big data leader Aster Data (acquired by Teradata for $325M).

  • 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 are retention and renewal not always an accurate sign of customer satisfaction?
  • How does David think about taking an 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?

#8: Matrix Partners General Partner David Skok on The Right Way to Analyze Sales Rep Productivity

Episode No. 180

About the episode: 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.

  • How should founders assess sales rep productivity? What can they do to actively shorten the ramp time? How will early-stage investors analyze the ramp time? What suggests repeatability of process?
  • What is the most common reason that people miss plan? How must the mindset of the founder switch from extreme frugality to hyper-growth scaling? When is the right time for this transition to take place? What are the inherent challenges to this switch?

#9: Clarizen Board Member Paul Albright on Why It Is Harder To Go Enterprise Down, Than SMB Up

Episode No. 150

About the episode: Paul Albright is one of the valley’s most experienced SaaS execs with extensive operational and capital management experience, including 3 IPOs. Most recently Paul was the Founder & CEO @ Captora, the marketing acceleration software solution that raised over $25m in VC funding from the likes of NEA and Bain Capital Ventures. Prior to Captora, Paul was Chief Revenue Officer at Marketo, where he drove the overall revenue strategy across sales and marketing that delivered global revenue growth over 100% year-over-year, from $14m to $58m. In a similar position at SuccessFactors, he grew revenues to more than $200m and over 80% year-over-year growth. Previously, Paul led worldwide marketing at NetApp and at Informatica, which he joined pre-revenue through their successful IPO. If that was not enough he has also served as an entrepreneur-in-residence at Greylock.

  • Does Paul agree with Dave Kellogg in stating, “CAC/LTV is the single most important metric for SaaS startups?” What other metrics must all VPs of Demand Gen and Sales be watching constantly?
  • Why does Paul believe that it is much harder to go SMB up than enterprise down? What are the changes that are required on both ends? For this in “no man’s land of pricing” what does an efficient sales process timeline look like from lead to conversion?

#10: Brex Chief Sales Officer Sam Blond on a Step-by-Step Guide to Scaling Your Sales Team

Episode No. 184

About the episode: Sam Blond is Chief Sales Officer @ Brex, the startup that provides corporate cards for startups. To date they have raised over $380m 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.

  • 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?
  • Why does Sam believe the key to success in SaaS sales teams is “urgency?” Literally, how can reps instill a sense of urgency in their current pipeline? Why does Sam disagree with 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?
Published on November 1, 2019

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