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/

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/

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:

1. Hardest element of Ryan’s role with Truework?
2. What would Ryan most like to change about the world of SaaS?
3. 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

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.

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/

Dave McJannet is the CEO @ Hashicorp, one of the fastest-growing enterprise companies of our time providing consistent workflows to provision, secure, connect and run any infrastructure for any application. To date, the company has raised $349M in funding from some of the best in the business including Bessemer, Redpoint, True Ventures, IVP, Mayfield, TCV and GGV to name a few. As for David, prior to Hashicorp, he held some incredible roles including VP Marketing at Github and Hortonworks, Senior Director of Product Marketing @ VMWare and then also spent over 5 years at Microsoft. 

Read the full transcript on our blog: https://www.saastr.com/saastr-podcast-377-with-hashicorp-ceo-dave-mcjannet/

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

In part two, ZoomInfo founder and CEO Henry Schuck shares how he built a business from scratch and grew it into one of the most successful IPOs of the 21st century—and what it was really like...the good, the bad, and most of all, the ugly. He reflects on where he went wrong, what he would do differently, and how to avoid making the same mistakes he did.

This episode is an excerpt from Jason and Henry’s session at SaaStr Annual @ Home.

Full video: https://youtu.be/WKODWISCL7A

Transcript of this podcast: https://www.saastr.com/saastr-podcast-376-with-zoominfo-ceo-henry-schuck-10-mistakes-the-ceo-of-zoominfo-made-on-his-journey-to-ipo-part-2/

Part 1 of this interview can be found in episode 374.

GitHub’s COO, Erica Brescia, shares her experiences and lessons learned from her former life on the front lines of being a co-founder of her own company, and how those lessons apply to her current position overseeing operations for GitHub. 

Video and blog post: https://www.saastr.com/5-leadership-lessons-everyone-needs-right-now-from-github-coo-erica-brescia/

ZoomInfo founder and CEO Henry Schuck shares how he built a business from scratch and grew it into one of the most successful IPOs of the 21st century—and what it was really like...the good, the bad, and most of all, the ugly. He reflects on where he went wrong, what he would do differently, and how to avoid making the same mistakes he did.

This episode is an excerpt from Jason and Henry’s session at SaaStr Annual @ Home. 

Full video: https://youtu.be/WKODWISCL7A

Podcast transcript: https://www.saastr.com/saastr-podcasts-for-the-week-with-byron-deeter-elliott-robinson-henry-schuck-and-jason-lemkin/

Bessemer's 5th Annual State of the Cloud Report returns for a definitive look at the cloud industry today. Byron Deeter and Elliott Robinson, partners at Bessemer Venture Partners, offer macro trends in the public and private cloud markets, strategic advice to cloud founders, and insights into why entrepreneurs should feel auspicious about the future.

This episode is an excerpt from a session at SaaStr Annual @ Home. 

Full video: https://youtu.be/WrGhD0qaIow

Podcast transcript: https://www.saastr.com/saastr-podcasts-for-the-week-with-byron-deeter-elliott-robinson-henry-schuck-and-jason-lemkin/

Latane Conant is the Chief Marketing Officer at 6Sense, the company that allows you to achieve predictable revenue growth by identifying accounts looking for your solution, prioritise efforts and then engage the right way. To date, the company has raised $120M in financing from Battery Ventures, Insight, Venrock, Costanoa, Bain Capital and Salesforce Ventures to name a few. As for Latane, before 6Sense she was CMO and sales leader at Appirio where she drove 5X more effective field marketing programs and an increase in inbound leads by 300%. If that was not enough, Latane is also on the Advisory Boards of both Mediafly and Atrium. 

 In Today’s Episode We Discuss:

• How did Latane make her way into the world of SaaS and come to be the rockstar CMO and ABM thought leader she is today with 6Sense?
• What does the preparation process look like pre-sales kick off week? What is involved? Who is involved? What needs to be ready? How does Latane feel about putting comp plans as part of the week?     
• How important is a theme to having an engaging week of content? What can teams do to bring their themes to life? How does Latane advise others when it comes to keeping the content fresh and exciting?  
• What is the right way to end the week? What are the right follow up steps to take? Where do many people go wrong here?    

Latane’s 60 Second SaaStr:

1. Hardest element of Latane’s role today with 6Sense?
2. What would Latane most like to change about the world of SaaS?
3. What does Latane believe that most around her disbelieve? 

Read the full transcript on our blog: https://www.saastr.com/saastr-podcast-372-with-6sense-cmo-latane-conant/

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

Latane Conant

It’s no secret that businesses today are struggling with an unpredictable economy. In this session, Mailchimp Co-founder and CEO Ben Chestnut will share the story of Mailchimp’s founding amidst—and despite—the dot-com bubble burst, and how the company navigated a number of inflection points in the first 10 years of its founding. 

This episode is an excerpt from Jason and Ben’s session at SaaStr Annual @ Home.

Full video: https://youtu.be/LfLZzakn2r0

Podcast transcript: https://www.saastr.com/saastr-podcasts-for-the-week-with-jennifer-tejada-ben-chestnut-and-jason-lemkin/

As organizations race to achieve relevance and a competitive edge in the digital era, automation is fueling the fight. Join PagerDuty’s CEO, Jennifer Tejada, as she discusses the need for agility and innovation and how automation is aiding adaptability and allowing enterprises to surge ahead.

This episode is an excerpt from a session at SaaStr Summit: Enterprise. 

Full video: https://youtu.be/7mHQotsErWc

Podcast transcript: https://www.saastr.com/saastr-podcasts-for-the-week-with-jennifer-tejada-ben-chestnut-and-jason-lemkin/

In today’s SaaStr Insider episode, SaaStr CEO and Founder Jason Lemkin and the Co-founder and CEO of HireSweet, Robin Choy, share their experiences building and scaling their companies.

Today's SaaStr insider originally aired on A-Players, a new podcast that teaches you how to hire, retain, and train top performers for your team! You can listen to A-Players on Anchor.fm, Spotify, or wherever you listen to podcasts.

Read the full transcript on our blog: https://www.saastr.com/saastr-podcasts-for-the-week-with-scott-belsky-robin-choy-and-jason-lemkin/

Success in the Enterprise means ensuring consumerization is a part of your strategy. Scott Belsky, CPO, EVP of Creative Cloud at Adobe will explore key tactics to focus on the user experience.

This episode is an excerpt from a session at SaaStr Summit: Enterprise.

Full video: https://youtu.be/FPMKXanghWM

Podcast transcript: https://www.saastr.com/saastr-podcasts-for-the-week-with-scott-belsky-robin-choy-and-jason-lemkin/

Hilary Headlee is Head of Global Sales Operations and Enablement @ Zoom. Prior to joining Zoom, Hilary was VP of Global Sales Operations and Productivity @ MindBody and before that enjoyed similar roles with Alteryx, Invoca and Lynda.com. At Lynda.com, Hilary grew the support teams from 6 to 60 people and supported more than 60 net new reps in just 3 years. If that was not enough, Hilary is also a Limited Partner in Stage 2 Capital, the venture firm focused purely on go-to-market. 

 In Today’s Episode We Discuss:

• How did Hilary make her way into the world of SaaS and come to be the sales leader she is today with the global communications leader, Zoom?
• When thinking about sales ops vs revenue ops, what are the 4 key points to consider for founders? How does lead management and onboarding alter the question of sales ops vs revenue ops? Where does Hilary see operational debt the most? How does she advise founders on removing it?    
• Given the broad scope of sales ops and engagement, is it not just rebalancing culture, comms and change? As a business scales does there not come a time where it unbundles and scales out of sales vs revenue ops? How do the roles change with time and scale? Where do the breakpoints occur? 
• Why does Hilary believe documentation is so important today? What is the toolset Hilary uses for documentation? How does Hilary train her team around the right strategy to document their processes? Where do many go wrong here? Where can you pick up small wins?   

Hilary’s 60 Second SaaStr:

1. What is the hardest element of Hilary’s role today with Zoom?
2. What would Hilary most like to change in the world of SaaS today? 
3. What does Hilary believe that most around him disbelieve? 

Read the full transcript on our blog: https://www.saastr.com/saastr-podcast-367-with-zoom-head-of-global-sales-operations-and-enablement-hilary-headlee/

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

The buzz that accompanies digital transformation trends is infinite. Cut through the noise with Aaron Levie, CEO of Box and Jason Lemkin, CEO & Co-founder of SaaStr as they share insights on what will make a lasting impact and what may fail to materialize in the future of work.

This episode is an excerpt from Jason and Aaron’s session at SaaStr Summit: Enterprise.

Full video: https://youtu.be/vBQR7G6YHFQ

Podcast transcript: https://www.saastr.com/saastr-podcasts-for-the-week-with-justin-bedecarre-jen-nguyen-jason-lemkin-and-aaron-levie/

Centralized HQs with all the perks and amenities “under one roof” have traditionally been used as recruiting tools to attract and retain top talent. In this episode, Justin and Jen discuss what the Office of the Future will be like. 

This episode is an excerpt from a session at SaaStr Summit: Enterprise. 

Full video: https://youtu.be/dT04zc22ZH4

Podcast transcript: https://www.saastr.com/saastr-podcasts-for-the-week-with-justin-bedecarre-jen-nguyen-jason-lemkin-and-aaron-levie/