The Official SaaStr Podcast: SaaS | Founders | Investors

Andy MacMillan is the CEO @ UserTesting, the company that provides real-time feedback, from real customers, wherever you work. To date, they have raised over $200M in funding from the likes of Accel, Greenspring, Openview and Insight to name a few. As for Andy, prior to UserTesting, he was the Chairman and CEO @ Act On Software and before that held several positions at Salesforce, including COO - Products Group. Before Salesforce Andy spent close to 5 years at Oracle as VP Product Management.   In Today’s Episode We Discuss: How did Andy make his way into the world of SaaS? How did he come to be CEO at the market leader, UserTesting? Why does Andy think the seat-based pricing model in SaaS will die? What are the downsides of it? Why is volume-based pricing optimal? How does one instil volume based pricing without disincentivizing usage? How does Andy think about discounting? How does Andy view the importance of offering trials?        What does it take to scale a sales team successfully? How can one determine a closer in the interview process? Should one hire sales reps 2x2? How does Andy think about hiring sales reps from adjacent companies and industries? How does Andy think about minimizing and optimising sales ramp times? How does Andy think about payback period?       How does Andy structure the pipeline meetings? Who is invited? How are the meetings structured? How does Andy advise on the right segmentation of pipe? How does Andy evaluate the closability of the pipe? Where do many people go wrong in pipeline meetings? What have been his biggest lessons on running them successfully? Andy’s 60 Second SaaStr: The hardest element of Andy’s role with UserTesting? What Andy would most like to change about the world of SaaS? The hardest role to hire for today and why?  Read the full transcript on our blog: https://www.saastr.com/saastr-podcast-395-with-usertesting-ceo-andy-macmillan/ 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 Andy MacMillan

Where is Venture Capital today? And how do you hack it? SaaStr CEO and Founder, Jason Lemkin, sits down with Sunil Dhaliwal, General Partner at Amplify Partners to discuss. Full video: https://youtu.be/8w6K7slhLX4 Podcast transcript: https://www.saastr.com/saastr-podcast-394-with-sunil-dhaliwal-and-jason-lemkin/

The journey for a company to move upmarket can be daunting and varies widely depending on the internal and external factors that inspire a shift in go-to-market strategy. Join these incredible sales leaders are they share their experiences in the evolution from SMB to Enterprise. Kelly Del Curto, Senior Director of Sales at Lever Tammy Aguillon, Area Vice President, Commercial Sales at DocuSign Kate Jensen, Head of Platform Sales at Stripe Lauren Schwartz, Vice President of Enterprise Sales at Fivetran Video and blog post: https://www.saastr.com/how-to-sell-upmarket-in-saas/

In today's SaaStr insider episode SaaStr CEO Jason Lemkin shares 10 Simple Steps To Help Any Sales Exec Close More. Video and blog post: https://www.saastr.com/10-simple-tips-to-help-any-account-executive-close-more/

Learn how Flodesk bootstrapped to $5M in ARR by focusing on customer-driven growth: from kickstarting growth by empowering new customers to share, to creating product viral loops that amplify and optimize these customer-led funnels. Video and blog post: https://www.saastr.com/how-to-bootstrap-to-5m-arr-in-less-than-a-year/

Randy Rayess is the Co-Founder @ Outgrow, a growth marketing platform that enables marketers to build interactive content/tools to increase customer engagement and boost demand generation. Prior to founding Outgrow, Randy co-founded VenturePact, an invite-only marketplace that connects companies with trusted software development firms. Before VenturePact Randy held roles at Ampush and then on the investor side at SilverLake. If that was not enough, Randy is also an investor having invested in the likes of SmartyPal, Nooch, Alie and AirCare Labs to name a few.   In Today’s Episode We Discuss: How Randy made his way from the world of PE with SilverLake to changing the game of digital marketing with Outgrow? What does interactive content mean? What are the most common forms? When should one start to use interactive content What resources and team does one need to engage with an interactive content strategy? Where do many people make mistakes with using interactive content?      How should one think about idea generation for interactive content? How does one know what interactive content works best? How should we test it’s effectiveness? How should interactive content be promoted? Where should it be placed? How many text inputs is it optimal to request for?      How does it convert more leads? How does Randy think about using interactive content to maximise sales rep efficiency? How should customer success engage with interactive content? What can be done to make the sales and customer success teamwork so well together?     Randy’s 60 Second SaaStr: The hardest element of Randy’s role with Outgrow today? Hardest role to hire for today? Why? What would Randy most like to change about the world of SaaS?   Read the full transcript on our blog: https://www.saastr.com/saastr-podcast-390-with-outgrow-co-founder-randy-rayess/ 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 Randy Rayess  

Mikael Cho, CEO of Unsplash shares his lessons learned from starting Unsplash as a side project and growing it to a market leader, and disrupting an industry of giants like Shutterstock, Getty, and Adobe Stock with a free business model. Full video: https://youtu.be/t3nmvxlybJM Podcast transcript: https://www.saastr.com/saastr-podcast-389-with-unsplash-ceo-mikael-cho-and-morning-brew-business-editor-kinsey-grant-how-to-really-disrupt-the-big-guys-with-free/

Ryan Carlson is the CMO @ Okta, the leading independent provider of identity for the enterprise. Prior to their incredibly successful IPO in April of 2017, they raised funding from some of the best in the business including Sequoia, a16z, Greylock, Khosla and Floodgate to name a few. As for Ryan, he has spent an incredible 9 years at Okta in numerous different roles starting with running the product marketing team before moving to run the marketing team, leading to his promotion to CMO close to 5 years ago now. Before Okta, Ryan was the Co-Founder and CEO @ Sproost, a bootstrapped online expert recommendation system.    In Today’s Episode We Discuss: How Ryan made his way into the world of enterprise SaaS? Why was joining Okta the most challenging interview process he has experienced? How did it impact how he assesses candidates today? How does Ryan distinguish between the company story vs the product story? When do they align and when do they separate? How should your strategy change as they move apart? How does the structure of your marketing team need to change with the evolution?      What should the first marketing hire look like? What experience should they have? Why does Ryan believe you should hire two in marketing to start? How do you want them to work together? How does Ryan ensure cross-function working seamlessly from the very beginning with marketing?      How does Ryan think about measuring success when it comes to product marketing? How does Ryan think about marketing attribution today? How should we think through SAL vs closed revenue as indicator of marketing success? Where does Ryan believe many go wrong with regards to marketing funnels?     Ryan’s 60 Second SaaStr: What does Ryan know now that he wishes he had known at the beginning? What makes Frederic Kerrest the special leader he is? What is the most challenging element of Ryan’s role with Okta?   Read the full transcript on our blog: https://www.saastr.com/saastr-podcast-388-with-okta-cmo-ryan-carlson/ 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 Carlson

In this CEO to CEO catch up, Nick Mehta and Jason Lemkin discuss how to do product extensions, how to sell a second product, and where product development overall is heading.  Video and blog post: https://www.saastr.com/saas-customers-have-never-been-happier-a-discussion-with-nick-mehta-ceo-of-gainsight/

How do you compete in a tough marketplace with thousands of other competitors? Join Adam Blitzer as he shares insights from launching a company in an already crowded marketing automation space and zig-zagged the way to market leadership. Video and blog post: https://www.saastr.com/how-to-win-with-1000-players-in-your-market/