The Official SaaStr Podcast: SaaS | Founders | Investors

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, CMO at Okta and co-founder of Sproost, dives into the nuances of marketing in the SaaS world. He shares insights from his challenging journey to Okta, emphasizing the balance between product and company narratives. Carlson explains why hiring dual marketing roles can optimize team dynamics and stresses the importance of creating a culture that fosters collaboration. He also tackles common misconceptions about category creation, ensuring that marketing strategies evolve as a company grows.

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/

Paul Rosania is the Founder & CEO @ Balsa, the company that recognises that builders move the world forward and so they are building the best second screen for builders, integrating tools you already use like Jira, GitHub, and Figma. Coming out of stealth today with their seed round being led by Andrew Chen @ a16z and joined by former CPO @ Slack, April Underwood, Chapter One's Jeff Morris Jr and then of course, 20VC Fund. Prior to founding Balsa, Paul was Senior Director of Product @ Slack and before Slack was a Group Product Manager @ Twitter where he was responsible for the home timeline, including timeline ranking. In Today's Episode We Discuss: How Paul made his way into the world of startups with Twitter and Slack and how that led to his founding SaaS company, Balsa? Paul was central in the decision-making around changing the Twitter timeline from chronological to ranked, how did he think about that decision? How does Paul approach such large product decisions today? What were his biggest operating takeaways from seeing the internal mechanics of Twitter & Slack? What does really effective product marketing mean to Paul? How does Paul think about driving really effective change management? When engaging with bottoms up sales models, where does Paul identify the tipping points of going from bottoms up to top down? Why does Paul believe that the builders are the new pro athletes? How will the structure of orgs change around them? How will the support they receive change? How will their training change? How will their comp change? How does on do this and not discourage other functions in the org? Paul's 60 Second SaaStr: What does Paul believe is the hardest role to hire for today? What would Paul most like to change about the world of SaaS today? What do the next 5 years hold for Paul and for Balsa? Read the full transcript on our blog: https://www.saastr.com/saastr-podcast-385-with-balsa-founder-ceo-paul-rosania/ 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 Paul Rosania

We caught up with one of the SaaStr community's favorite speakers, Dharmesh Shah CTO and co-founder of Hubspot on lessons learnings launching a second product. Hubspot recently expanded its Sales products and the learnings were top of mind. Video and blog post: https://www.saastr.com/how-when-and-why-to-launch-a-second-product-a-deep-dive-with-dharmesh-shah-cto-hubspot/