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 center 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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SaaStr 397: Going Upmarket and How Things Have Changed in a Decade, @ Trello, with Co-Founder Michael Pryor and Jason Lemkin, CEO @ SaaStr
In today's SaaStr insider episode SaaStr CEO and Founder Jason Lemkin catches up with Michael Pryor, the Co-Founder of Trello to talk about going upmarket, and how things have changed in the last decade as Trello crosses 50M+ users. Video and blog post: https://www.saastr.com/going-upmarket-and-how-things-have-changed-in-a-decade-at-trello-with-founder-michael-pryor/
SaaStr 396: Buying patterns in the Enterprise: CEOs and More- Who's Really Buying & Why with Godard Abel, Co-founder & CEO @ G2, Mike Weir, Chief Revenue Officer @ G2 and Samantha DeStefano, Vice President, Enterprise Sales @ UpWork
As digital business and collaboration models have been permanently accelerated by the events of 2020, our panel of SaaS experts discuss who's buying in the Enterprise, and how to drive conversions across multiple business functions. Video and blog post: https://www.saastr.com/buying-patterns-in-the-enterprise/
SaaStr 395: Why Seat Based pricing Will Die and Volume Based Pricing Is Optimal, How To Structure Pipeline Meetings Most Effectively & How To Think Through Demand Gen Strategically with UserTesting CEO Andy MacMillan
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
SaaStr 394: How to Hack Venture Capital with Sunil Dhaliwal, GP @ Amplify Partners and and Jason Lemkin, CEO @ SaaStr
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/
SaaStr 393: 3 Secrets to Selling Up-Market with the Leaders of Fivetran, Stripe, and Docusign
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/
SaaStr 392: 10 Simple Steps To Help Any Sales Exec Close More with SaaStr CEO and Founder Jason Lemkin
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/
SaaStr 391: The Secrets to Bootstrapping to $5M ARR in Less than a Year with Martha Bitar, CEO @ Flodesk
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/
SaaStr 390: How To Crush It With Interactive Content, What Type, Where and When To Use It Most Efficiently and Where Many People Make Mistakes with Randy Rayess, Founder @ Outgrow
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
SaaStr 389: How To Really Disrupt the Big Guys With Free with Mikael Cho, CEO @ Unsplash and Kinsey Grant, Business Editor and Podcast Host @ Morning Brew
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/
SaaStr 388: Okta CMO, Ryan Carlson on How To Measure Marketing Attribution Effectively, Why People Think About Category Creation Incorrectly Today & How You Have To Think Through The Product vs The Company Story
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
SaaStr 387: Where Product Development is Going in 2021 with Nick Mehta, CEO @ Gainsight and Jason Lemkin, CEO @ SaaStr
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/
SaaStr 386: How to Win When There are 1000 Players in Your Market with Adam Blitzer, EVP & GM @ Salesforce Digital Marketing Cloud
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/
SaaStr 385: How To Approach Core Product Decisions in SaaS, Why Storytelling is a Lost Art in SaaS & How Product and Marketing Can Work Together Most Efficiently with Paul Rosania, Founder & CEO @ Balsa
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
SaaStr 384: When to Launch a Second Product with Dharmesh Shah CTO and Co-Founder @ Hubspot and Jason Lemkin, CEO @ SaaStr
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/
SaaStr 383: Growing Product and Engineering Orgs from Zero to IPO with Nick Caldwell, VP of Engineering @ Twitter, and Tomasz Tunguz, Managing Director @ Redpoint Ventures
Nick Caldwell has built and grown product and engineering organizations at PowerBI (0 to 300 engineers), Reddit (500M MAU) and Looker ($2.7B sale to Google). Nick will share 5 big lessons he's learned along the way that you can use as you build your company's product and engineering functions from its earliest days to its largest successes. Video and blog post: https://www.saastr.com/growing-product-and-engineering-orgs-from-zero-to-ipo-with-twitter-and-redpoint-ventures/
SaaStr 382: What's Next For B2B and Cloud Events in 2021 with Amelia Ibarra, SVP & GM @ SaaStr, and Alon Alroy, Co-Founder & CMO @ Bizzabo
In today's SaaStr Insider, SaaStr SVP & GM, Amelia Ibarra, sits down with Alon Alroy, Co-Founder & CMO at Bizzabo on What's Next For the Future of B2B Events. Video and blog post: https://www.saastr.com/whats-next-for-b2b-saas-events-2021/
SaaStr 381: Churn is dead. Long Live Net Dollar Retention Rate with Dave Kellogg, Principal @ Kellogg Consulting
There are a lot of problems with calculating churn rates. Moreover, public companies don't generally release churn rates. Learn what they are and how to calculate them correctly. Video and blog post: https://www.saastr.com/churn-is-dead/
SaaStr 380: How To Effectively Sell Into Mid-Market, Why SEO Is The Best Kept Secret In SaaS & How To Show Credibility To Enterprise Customers as a Startup
Ryan Sandler is the Co-Founder and CEO @ Truework, the company that gives employees control over employment, income and other identity data. To date, Ryan has raised over $44M with Truework from the likes of Sequoia, Khosla, Menlo and from the founders of companies such as Plaid, Seatgeek, Mino Games and Checkr. Prior to founding Truework, Ryan spent 3 years as a Senior Product Manager @ LinkedIn. In Today’s Episode We Discuss: How Ryan made his way from LinkedIn Product Manager to founding Sequoia backed Truework and changing the world of identity data? Why does Ryan believe it is such an advantage to sell into mid-market? Where do most people go wrong here? How can startups show credibility to mid-market when they are so small? How can founders use case studies and references to build social credibility early on? What have Ryan’s lessons been when it comes to pricing? How does Ryan think about and approach discounting? How does Ryan feel about pilot plans? What elements can founders negotiate on to get the best pricing? Why does Ryan believe SEO is the best-kept secret in SaaS? How has Ryan structured his content and marketing team as a result? How can one automate as much of the content creation process as possible? How long should one expect in terms of lead times to see returns on the SEO strategy? Ryan’s 60 Second SaaStr: Hardest element of Ryan’s role with Truework? What would Ryan most like to change about the world of SaaS? What does Ryan know now that he wishes he had known at the beginning? Read the full transcript on our blog: https://www.saastr.com/saastr-podcast-380-with-truework-co-founder-and-ceo-ryan-sandler/ 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 Sandler
SaaStr 379: The Top 10 Mistakes Founders Make When Hiring Their First Sales Team with SaaStr CEO and Founder Jason Lemkin
From how many reps to hire, to compensation models, here are the top 10 mistakes founders make when hiring their first sales teams and how to avoid them. Full video: https://youtu.be/SrHKclELBEg Podcast transcript: https://www.saastr.com/saastr-podcast-379-with-saastr-ceo-and-founder-jason-lemkin-the-top-10-mistakes-founders-make-when-hiring-their-first-sales-team/ Sponsor message: Are you looking to better educate your audience on the value you deliver? Build products or service recommendation tools, create assessments to identify areas they can improve, and build savings calculators? Find out how you can build these same tools for your business at outgrow.co/saas.
SaaStr 378: The 5 Things That Kill Startups After Their Seed Rounds and How to Avoid them with Michael Seibel, CEO @ Y Combinator
Investment can create more problems than it solves and founders may trick themselves into thinking they have product-market fit when they don't. Michael Seibel, CEO @ Y Combinator explores the top risks founders should be aware of after funding and his best tips to avoid them. Video and blog post: https://www.saastr.com/5-things-that-kill-startups-with-y-combinator/
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