The Official SaaStr Podcast: SaaS | Founders | Investors

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:

1. The hardest element of Randy's role with Outgrow today?
2. Hardest role to hire for today? Why?
3. 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:

1. What does Ryan know now that he wishes he had known at the beginning?
2. What makes Frederic Kerrest the special leader he is?
3. 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/

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:

1. What does Paul believe is the hardest role to hire for today?
2. What would Paul most like to change about the world of SaaS today?
3. 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/

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/

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/