In today's SaaStr insider episode SaaStr CEO and Founder Jason Lemkin catches up with Todd McKinnon, CEO and co-founder of Okta. Together they discuss what it takes to build, maintain and grow a high-performance organization.

Video and blog post: https://www.saastr.com/10-learnings-from-talking-with-todd-mckinnon-ceo-of-okta/

As one of the early champions of "low-code”, Howie Liu shares the lessons he's learned building and scaling a company in an entirely new category. He'll discuss how Airtable focuses on solving customers' increasingly complex needs, all with products that are easily adoptable.

Video and blog post: https://www.saastr.com/lessons-in-scaling-a-low-code-platform-with-airtable/

SaaStr CEO and Founder Jason Lemkin catches up with Therese Tucker, Founder, and CEO at BlackLine about her SaaS journey, going long and surviving black swan events.

Video and blog post: https://www.saastr.com/going-long-the-20-year-journey-of-being-a-ceo-founder-with-blackline/

Trends are fleeting and hard to pin down. Or are they? Learn how you can leverage the science of trends and better understand market behavior. 

This episode is an excerpt of Allen’s session at SaaStr @ Home 2020. You can view the full video here: https://youtu.be/v1c08Ztdrss

Podcast transcript: https://www.saastr.com/saastr-podcast-407-with-the-creative-curve-author-allen-gannett-the-secrets-of-market-timing-and-how-to-develop-the-right-idea-at-the-right-time/

Visit dell.com/saastr for exclusive savings on Dell products and more information about the Dell for entrepreneurs program. Everything from Dell financial services to Dell rewards, Dell for Entrepreneurs wants to help your business run smarter through technology.

Bandwidth makes it easy to add enterprise-grade voice calling, text messaging and emergency calling to your platform, all backed by the power of a fully owned and operated, tier-one carrier network that gives you direct to carrier pricing with better quality, control, and insights that other API providers can't. See why the biggest brands in the world rely on Bandwidth and sign up for a free trial at bandwidth.com/saastr.

Kate Taylor is Head of Customer Experience at Notion, one of the fastest-growing startups of the last 5 years with over $68M in funding from some of the best in the business including Index, Daniel Gross, Elad Gil, Lachy Groom, Josh Kopelman and Aydin Senkut to name a few. As for Kate, prior to making the move to Notion just last month, she spent an incredible 8 years at Dropbox including holding roles such as Head of Sales Development, North America and Director of Global SMB Revenue and Operations. Before Notion, Kate spent 2 years at Salesforce in the corporate sales and enterprise business units. 

 In Today’s Episode We Discuss:

• How Kate made her way into the world of SaaS with Salesforce, how that led to her 8 year tenure at Dropbox before joining the breakout, Notion?
• Why does Kate not believe that in startups you can “do it all”? How to discover the problems people care about? How to think through prioritisation of problems at the early stage? Where do many people make mistakes here?
• How does Kate approach delegation at scale? When is the right time to start? How can founders let go and entrust others to do the role they have been doing? How can leaders build trust with the people they work with? How can leaders empower employees with act with conviction and invest in them?        
• What is the role of sales in a product-led growth organisation? How can sales and product work effectively well together? Where do many mistakes happen in sales and product? How can product and marketing also collaborate productively? What can one do to shorten the feedback cycles as much as possible?

Kate’s 60 Second SaaStr:

1. Most challenging element of Kate’s role with Notion?
2. What would Kate like to change about the world of SaaS?
3. What does Kate know now that she wishes she had known from the beginning? 

Read the full transcript on our blog: https://www.saastr.com/saastr-podcast-406-with-notion-head-of-customer-experience-kate-taylor/

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 today's SaaStr insider episode SaaStr CEO and Founder Jason Lemkin catches up with Bernadette Nixon CEO at Algolia and together they share 6 learnings on scaling to $100M ARR and what it really takes selling to customers small, medium and large.

Video and blog post: https://www.saastr.com/6-learnings-from-algolia-on-the-way-to-100000000-arr/

The benefits of managing upwards and downwards are frequent management topics. However, managing sideways and inward are also important skills for a successful leader. Learn new ways to build strong teams by managing in all directions from Arquay Harris at Slack.

This episode is an excerpt of Arquay’s session at SaaStr @ Home 2020. You can view the full video here: https://youtu.be/q40RWMgZgIo

Podcast transcript: https://www.saastr.com/saastr-podcast-404-with-slack-sr-director-engineering-arquay-harris-the-secrets-to-managing-in-all-directions/

Visit dell.com/saastr for exclusive savings on Dell products and more information about the Dell for Entrepreneurs program. Everything from Dell financial services to Dell rewards, Dell for Entrepreneurs wants to help your business run smarter through technology.

Bandwidth makes it easy to add enterprise-grade voice calling, text messaging and emergency calling to your platform, all backed by the power of a fully owned and operated Tier 1 carrier network that gives you direct-to-carrier pricing with better quality, control, and insights that other API providers can't. See why the biggest brands in the world rely on Bandwidth and sign up for a free trial at bandwidth.com/saastr.

Sam Taylor is the VP of Sales and Success @ Loom, the startup that helps you get your message across by making it easy to record instantly shareable videos. To date, they have raised over $73M from some of the best in the business including Sequoia, Kleiner Perkins, General Catalyst and Point Nine to name a few. As for Sam, prior to Loom, Sam spent over 4 years at Salesforce following their acquisition of Quip, a startup Salesforce acquired for $750M where Sam was also the 1st sales leader. Before Quip, Sam spent an incredible 3 years at Dropbox where he was the first enterprise sales rep in the entire company. 

 In Today’s Episode We Discuss:

• How Sam made his way into the world of SaaS with Dropbox and how that led to his leading the sales and success team today @ Loom?
• What was Sam’s biggest lesson from scaling the sales team at Dropbox? How did his 4 years at Salesforce change his operating mentality? Thinking of Dropbox, how does Sam justify the role of sales in a world of product-led growth? How do product and sales work together most efficiently? What can one do to structure that relationship?       
• Does Sam agree that the founder is the one who has to create the sales playbook? When is the right time to hire the first sales rep? Should you hire 2 at a time? What does one look for in their first sales hire? What measurements should be used to determine their success? How does this change when selling to SMBs vs enterprise?      
• How does Sam think about the relationship between sales and marketing? Are marketing becoming the new sales team with their content being used more and more in the sales funnel? How should the success of marketing be measured? Does it have to be tied to a number related to revenue?

Sam’s 60 Second SaaStr:

1. Biggest challenge of Sam’s role with Loom today?
2. What would Sam most like to change in the world of SaaS?
3. What is Sam’s biggest weakness as a sales leader? 

Read the full transcript on our blog: https://www.saastr.com/saastr-podcast-403-with-loom-vp-of-sales-sam-taylor/

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

Marten Mickos, CEO of HackerOne, explains their innovative approach of packaging customer value derived from a variety of activities into an annually recurring subscription offering that delivers outstanding value to customers while simplifying the buying process and the customer journey. 

This episode is an excerpt of Mårten’s session at SaaStr @ Home 2020. You can view the full video here: https://youtu.be/GAw4vKbMevk

Full transcript: https://www.saastr.com/saastr-podcast-402-with-hackerone-ceo-marten-mickos-customers-want-value-simplicity-the-must-haves-to-deliver/

Want to see why Adobe, Salesforce, and Marketo use Outgrow? Try building quizzes, ROI calculators, and assessments on Outgrow. Find out how you can build these tools with Outgrow's powerful builder, learn more at outgrow.co/saas.

If you don't have a SOC 2 report, you aren't going to be able to sell to major customers. Secureframe helps startups get and maintain software compliance in as little as two weeks. Join companies like Stream, Hasura, Benepass, and unlock more sales with Secureframe. SaaStr listeners get 10% off at secureframe.com/saastr.

In this session, you will learn how to make the Freemium model work while also incorporating the traditional sales-driven strategy. Olof Mathe will share how the two strategies can blend together and specific lessons he has learned from his experience.

Full video: https://youtu.be/9dIaJpuBCU4

Transcript: https://www.saastr.com/saastr-podcast-401-with-mixmax-ceo-olof-mathe-the-secrets-to-doing-freemium-and-sales-driven-sales-at-the-same-time/

Bandwidth makes it easy to add enterprise-grade voice calling, text messaging, and emergency calling to your platform, all backed by the power of a fully owned and operated tier-one carrier network that gives you direct-to-carrier pricing with better quality control and insights that other API providers can't. See why the biggest brands in the world rely on Bandwidth, and sign up for a free trial at bandwidth.com/SaaStr.

Dell for Entrepreneurs is here to help your business scale faster through technology. Reach out to startups@dell.com for a free IT consultation. From laptops, desktops to servers and cloud, Dell Technologies is there for you.

In today's SaaStr insider episode SaaStr CEO and Founder Jason Lemkin catches up with Ben Hindman, Co-Founder & CEO at Splash to talk about the future of digital events.

This interview was part of Splash’s Boom, a video series about the innovation explosion in events and the tech stack.

Podcast transcript: https://www.saastr.com/saastr-podcast-400-with-splash-ceo-ben-hindman-and-saastr-ceo-jason-lemkin-the-future-of-digital-events/

Building the world's largest and most trusted software developer and technologist community and going from 0 to 120 million users happened rapidly for Stack Overflow. Hear four steps from its CEO, Prashanth Chandrasekar, on how your product-led startup can grow its community and its revenue.

Video and blog post: https://www.saastr.com/four-steps-to-scaling-to-250m-from-stack-overflow/

Rob Gonzalez is the Co-Founder & CMO @ Salsify, empowering brand manufacturers to deliver the product experiences consumers demand at every point in their buying journey. To date, Salsify has raised over $250M in funding from the likes of Venrock, Underscore, Warburg Pincus, Matrix Partners & Greenspring to name a few. As for Rob, prior to founding Salsify, he was the first-ever product manager at Cambridge Semantics and before that was a Senior Product Manager @ Endeca helping grow the company to it’s $Bn exit. 

 In Today’s Episode We Discuss:

• How Rob made his way into the world of SaaS as a product manager and how that led to his founding Salsify over 8 years ago?
• How does Rob think about the bundled vs unbundled thesis within SaaS? When is it right for SaaS companies to turn down potential customers? How can they do that the right way? What is the right way to think about customer segmentation? How should startups decide which customer segment to focus on?      
• How should startups think about implementing partnerships? When is the right time? What is the right way to onboard them? How can they be trained in implementation efficiently? What does great change management look like to Rob? What does Rob believe are the biggest misconceptions around change management?       
• How does Rob think through pricing today in a way that encourages land and expand? What can you do to make the land as frictionless as possible? What does it take to expand effectively? How does Rob think about usage vs seat-based pricing in SaaS? How should sales and marketing work together on pricing?

Rob’s 60 Second SaaStr:

1. Most challenging element of Rob’s role with Salsify?
2. What would Rob most like to change in the world of SaaS today?
3. What does Rob know now that he wishes he had known at the beginning? 

Read the full transcript on our blog: https://www.saastr.com/saastr-podcast-398-with-salsify-co-founder-cmo-rob-gonzalez/

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

Rob Gonzalez

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/

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/

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:

1. The hardest element of Andy’s role with UserTesting?
2. What Andy would most like to change about the world of SaaS?
3. 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:

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/