I am delighted to welcome the new Head of Sales @ Front App, Cailen D’sa, to The Official SaaStr Podcast today. Cailen might just be the Head of Sales every SaaS startup founder is dreaming of having previously been the first sales hire @ Dropbox where he launched Dropbox’s first B2B product, prior to that he was a director at Box where he helped pioneer and operationalize the freemium land-and-expand sales model, which is now a core SaaS sales methodology. Now if you enjoy the episode with Cailen today and want to hear more from him then you must headover to Front’s blog where you can find Mathilde’s written interview with Cailen.

In This Episode With Cailen You Will Learn:

• How did Cailen come to be the first Sales hire @ Dropbox? What was it about Front that enticed him?
• What were Cailen’s biggest takeaways from his time at Dropbox and Box?
• How does the Sales process differ when selling a freemium product like Dropbox, compared to an enterprise product like Front?
• What does Cailen look for when hiring sales reps? What are Cailen’s sourcing strategies for new sales reps? How does Cailen incentivise the best talent to choose Front over other options?
• With the rise of data and it’s role in sales, to what extent does Cailen still believe sales to be an art and not a science?

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
• Cailen D’sa

Villi Iltchev is a Partner @ August Capital and prior to joining August Villi was a member of the leadership teams at Box and Lifelock. Before that Villi was a Vice President @ Salesforce where he led the strategy and acquisitions teams; being directly responsible for over 30 investments in the likes of Hubspot, Box, Mulesoft and many more amazing companies.

In Today’s Show with Villi We Discuss:

• How Villi made the transition from the world of operations to investing with August?
• What were Villi’s biggest takeaways from working with titans of SaaS; Box, Salesforce?
• What was the M&A environment like back in the 2000s? What was the driver behind mass consolidation? What did the on premise perpetual license business model enable companies? Where did customer success lie in this environment?
• Multiple Clouds: What is the challenges of this? How will this evolve over time? What are the current solutions?
• Customer success lies with the vendor: What do you think caused this pivotal transition? How central should customer success be to an early stage SaaS company’s strategy? What are the main benefits of customer success to you?
• SaaS distribution: Why do reseller arrangements not work? How would you like to see this evolve in the future?
• Sales productivity: What is the productivity effect of giving another product to sales? What happens to aggregate sales?

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
• Villi Itchev

Luke Kervin is the Co-Founder & Co-CEO @ PatientPop, where he has scaled the team from 10 to over 130 in just 12 months. As a result, PatientPop recently raised their Series A led by Toba Capital, allowing them to further ramp up their customer base and expand the employee ranks to over 200 people.

In Today’s Show with Luke We Discuss:

• How Luke came to found his first SaaS business in PatientPop?
• What is Luke’s criteria for selecting a potential business idea? What does the idea need to have? What elements of an idea will concern Luke?
• How did Luke go about validating the idea for PatientPop? What are the most common methods founders get product validation wrong?
• Why did Luke build a fake product, a fake website and fake business cards to validate the idea?
• PatientPop has grown from 10 to 130, so how did they scale so fast? What are the inherent challenges of company culture maintenance with such hyper-growth. 

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

Blake Bartlett is a Partner @ Openview Ventures where he helps identify value and lead investments in product-led businesses driving market dislocation. Prior to joining OpenView, he was a Vice President at Battery Ventures, where he focused on growth-stage software and Internet businesses. Blake joined Battery in 2009 and helped lead 10 investments including  the likes of Wayfair, Optimizely, Sprinklr, and Glassdoor.

In Today’s Show We Discuss:

• Why Blake decided to invest in SaaS over other sectors?
• Whether the rise of the bottoms up SaaS sales model means customer fickleness for SaaS products will increase?
• Does product led growth contradict tradition SaaS sales beliefs? How can they work in unison?
• Is product market fit and customer value a binary result? Are there varying degrees of customer value? How important is time to customer value?
• How can startups look to pull product-led growth off? What were Blake’s biggest takeaways from watching the likes of Optimizely and Expensify?

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
• Blake Bartlett

I am delighted to welcome my first ever Harry to the show today in the form of Harry Glaser, Co-Founder & CEO @ Periscope Data, the worlds fast analysis suite providing data analysts with the tools they need to improve their analysis by over 150X and an astonishing fact here they have doubled their revenue every 3 months ever since launch. Periscope’s investors include Ellen Pao, Matt Ocko @ Data Collective, Chad Byers @ Susa Ventures, Wes Chan @ Felicis, Benjamin Ling at Khosla and many more. Also in the show today we mention Jason Lemkin and Aaron Ross new book From Impossible to Inevitable: How Hypergrowth Companies Create Predictable Revenue and if you have not read that, that is a must and can be found here!

In Today’s Episode with Harry We Discuss

• How Harry came to be the founder of Persicope Data and what the a-ha moment was for him?
• How did Harry look to establish a pricing model with Periscope Data as a first time SaaS founder?
• What are Harry’s learnings of hiring and building out the initial sales team?
• How did Harry build out the institutonal training program to allow non technical people to sell a very non technical product?
• What are the inherent pros of having an inbound heavy model and what are the fundamental problems?
• Why are companies suddenly seeing the need for data analysts and what are the opportunites that data analysts present?

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
• Harry Glaser

Andy Wilson is the Co-Founder and CEO @ Logikcull, where he really is the visionary behind Logikcull’s product and marketing strategy focusing on simplifying and democratizing the discovery process into three simple steps: upload > search > download. Andy leads the company it its mission to put an end to eDiscovery with the use of Discovery Automation.

In Today’s Episode with Andy We Discuss:

• The origin story of Logikcull for Andy and what a-ha moment was for him?
• How did Andy approach the transition from service based business to SaaS business?
• Does the increase of customer success not transition the customer into the client?
• What was the effect of having Jason as a investor and what are the biggest value adds that Jason provides?
• On outbound vs inbound, how did Andy increase outbound in such an established space? Where did he find the major breakthroughs?

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 Wilson

Super excited to welcome a heavy weight of the SaaS industry today as we have Mark Organ, Founder & CEO at Influitive. Influitive helps B2B companies mobilize their army of advocates for more rapid and profitable revenue growth. Prior to Influitive, Mark was the founding CEO of Eloqua, growing the business to over 150 people, hundreds of clients and a major presence around the world in 7 years. Eloqua was eventually bought by Oracle in 2012 for a reported $810m.

In Today’s Episode with Mark We Discuss:

• The founding story behind Influitive? What was the a-ha moment behind the concept?
• What were Mark’s biggest takeaways from watching Eloqua scale into the global force that it became?
• Influitive are creating a category, so how is that for Mark? What are the inherent challenges?  What are the commonalities of successful category creators?
• What is the difference between good and bad competition? Why does Mark try and encourage good competition?
• Why are brand advocates crucial to the success of a business? Is it a really scalable solution? How did you figure out the model for making customers successful?  

In a round we call the 60 Second Saastr, we also hear:

• Mark’s fave SaaS resource and reading material?
• Thought leadership: Fundamental or unnecessary?
• Target Markets; Go large or be specific and niche?

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
• Mark Organ

Laura Roeder is the Founder & CEO @ Edgar, the social media automation tool that essentially allows your social media queue to fill itself up. Now Edgar is not the usual startup story we are all familiar with as Edgar has taken some unusual steps, they have not raised VC funding, they do not have a sales team, their founder, Laura, was pregnant on launch and after all this, Edgar is a startup that actually makes money at 2.9m ARR.

In Today’s Episode with Laura We Reveal:

• How did Laura come to found Edgar? What was the a-ha moment for Laura?
• How did Laura assemble and build the team, with te restraint of being pregnant during launch? How did this hiring mindset benefit the process?
• Why does Laura deliberately not have a sales team?
• How does the SaaS math differ for bootstrapped vs venture funded SaaS startups? HOw does the exit strategy change when bootstrapped?
• Why should SMs approach social media platforms one at a time? How can startups measure their social media performance and engagement?

In a round we call the 60 Second Saastr, we also hear:

• Fave SaaS resource and reading material?
• Hardest hire in the Edgar process?
• Going up the enterprise funnel: Potential or not going to happen?

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