The Official SaaStr Podcast: SaaS | Founders | Investors

Jason Lemkin is the Founder and VC @ SaaStr, or more accurately put Jason is a 2x founder, 1x VC, and constant SaaS enthusiast. He led or sourced the first VC investments in many leading enterprise/SaaS start-ups, Greenhouse.io, Pipedrive, Algolia, Talkdesk, RainforestQA, Automile, and more. He is also an advisor or smaller investor in Showpad, FrontApp, Influitive, BetterWorks, and other SaaS leaders. Jason has co-founded two successful start-ups selling to the enterprise.  Before SaaStr and VC investing, he was CEO and co-founder of EchoSign, the web’s most popular electronic signature service, from inception through its acquisition by Adobe Systems Inc. He then served as Vice President, Web Services at Adobe, where he oversaw the growth of EchoSign and Adobe Document Services to $50,000,000 in ARR in 2012 and $100,000,000+ ARR in 2013. Prior to EchoSign and Adobe, he co-founded one of the only successes in nanotechnology, NanoGram Devices, which was acquired for $50m just 13 months after founding. Other than SaaS he is like me, no known hobbies.

In Today’s Episode You Will Learn:

• How did Jason make his way into the world of SaaS and come to be Founder and VC @ SaaStr?
• ACV: What levels of ACV and characteristics suggest potential for a unicorn? How does Jason look to help founders attain higher ACVs? Why is stay focused horrible advice with regards to increasing your ACV with differing customer demands?
• Does Jason believe that founders always undersell? What advice would Jason give to founders that are nervous to ask for more? What customer response would excite Jason and what would make him concerned?
• Jason has previously said that ‘founders have to be 110% committed to sales’. What does this mean? How does this look when assessing a founder? Should founders be happy to pay their sales hires more than them? How quickly should the payback period be on these reps?
• Jason has also previously said that some founders financials are ‘simply ridiculous’. What makes him say this? What financials are fundamental to have very accurately pin pointed? Why is 100% gross margin impossible?

60 Second SaaStr

1. Why does Jason like it when startups have clients that are not in tech?
2. What does Jason know now that he wishes he had known at the beginning?
3. What should SaaS founders look for in their investors?
4. Why does Jason only invest out of the SaaStr community?

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

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Jason Lemkin is the Founder and VC @ SaaStr, or more accurately put Jason is a 2x founder, 1x VC, and constant SaaS enthusiast. He led or sourced the first VC investments in many leading enterprise/SaaS start-ups, Greenhouse.io, Pipedrive, Algolia, Talkdesk, RainforestQA, Automile, and more. He is also an advisor or smaller investor in Showpad, FrontApp, Influitive, BetterWorks, and other SaaS leaders. Jason has co-founded two successful start-ups selling to the enterprise.  Before SaaStr and VC investing, he was CEO and co-founder of EchoSign, the web’s most popular electronic signature service, from inception through its acquisition by Adobe Systems Inc. He then served as Vice President, Web Services at Adobe, where he oversaw the growth of EchoSign and Adobe Document Services to $50,000,000 in ARR in 2012 and $100,000,000+ ARR in 2013. Prior to EchoSign and Adobe, he co-founded one of the only successes in nanotechnology, NanoGram Devices, which was acquired for $50m just 13 months after founding. Other than SaaS he is like me, no known hobbies.

In Today’s Episode You Will Learn:

• How did Jason make his way into the world of SaaS and come to be Founder and VC @ SaaStr?
• ACV: What levels of ACV and characteristics suggest potential for a unicorn? How does Jason look to help founders attain higher ACVs? Why is stay focused horrible advice with regards to increasing your ACV with differing customer demands?
• Does Jason believe that founders always undersell? What advice would Jason give to founders that are nervous to ask for more? What customer response would excite Jason and what would make him concerned?
• Jason has previously said that ‘founders have to be 110% committed to sales’. What does this mean? How does this look when assessing a founder? Should founders be happy to pay their sales hires more than them? How quickly should the payback period be on these reps?
• Jason has also previously said that some founders financials are ‘simply ridiculous’. What makes him say this? What financials are fundamental to have very accurately pin pointed? Why is 100% gross margin impossible?

60 Second SaaStr

1. Why does Jason like it when startups have clients that are not in tech?
2. What does Jason know now that he wishes he had known at the beginning?
3. What should SaaS founders look for in their investors?
4. Why does Jason only invest out of the SaaStr community?

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

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Leo Widrich is the Founder & COO @ Buffer, the Simple and powerful social media scheduling, publishing & analytics. They have raised funding from some of the best including Scott and Cyan Banister, Hubspot’s Dharmesh Shah, Hiten Shah and Eric Ries just to name a few. Now in today’s talk with Leo he breaks down his and the Buffer teams Top 10 Learnings in Growing to 10m ARR.

In Today’s Episode You Will Learn:

• What are the 3 questions Leo asks his customers to understand them best? When is the right time to ask them? How should you follow up from this?
• How to experiment with weekly masterminds? How do masterminds work? When is the right time to do them? What is important to remember in entering a mastermind?
• How does Leo assess pricing structure? Why does he think it is important to experiment with different pricing? How do you do so without losing customers or trust?
• Why does Leo advise startup founders to get advice from mentors with conflicting opinions? Why is this important and how should a decision be reached?

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

Leo Widrich

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

John Barrows is essentially the Godfather of Sales. We often have VPs of Sales from tech titans on the show but who trains those VPs and sales reps to be the best in the world at sales? That is where John Barrows comes in, with clients including Dropbox, Box, Marketo, Twilio and many more, John has amassed a wealth of knowledge and experience allowing him to provide the most proactive sales tips and strategies to optimise the sales process. If you have not checked out his blog, that really is a must and can be found here.

In Today’s Episode You Will Learn:

• How did John make his way into the world of SaaS and more specifically sales optimisation?
• What are the key points all reps must cover in their first calls with new leads? Why is expectation setting so crucial?
• Why does John believe the best client to rep relationships are those that are equal? How can reps continue to provide value with every interaction?
• In the case of leads going dark, how can sales reps engage with the lead to ensure conversion? What words must be avoided and how should this conversation be structured?
• How can sales reps perfect the balance of being direct and being rude? How important is a summary email? What is the optimal structure and how should sales reps follow up on summary emails?

60 Second SaaStr

1. The most common question asked to John by VPs of Sales?
2. What are the benefits of Top Down prospecting?
3. Do execs need structure?

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

John Barrows

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Michael Driscoll is the Co-Founder and CEO @ Metamarkets, the startup that provide interactive analytics for programmatic marketing. They have raised over $38m in VC funding from our good friends at Data Collective, Founder Collective, IA Ventures and more incredible investors. As for Michael, prior to Metamarkets, he started two other companies: Dataspora, a life science analytics company (acquired by Via Science in 2011), and CustomInk.com, an early pioneer in e-commerce. Fun fact: Michael is also a founding Partner of the previously mentioned VC fund, Data Collective.

In Today’s Episode You Will Learn:

• How did Michael make his way from data lover to Silicon Valley SaaS Founder?
• Why does Mike believe in the inherent value of customer focus and product focus? What are the measurable benefits of being so specialised?
• Why does Mike believe it is so hard to be a cost leader in software? What are the fundamental challenges? What role does open source play in this?
• How does Mike view the alignment of the sales and the engineering team? Is it possible to have a harmonious relationship between the two?
• What should SaaS startup founders look for in potential seed investors? How can they determine whether they have these qualities? What should they look at in particular?

60 Second SaaStr

• Mike’s fave productivity tools?
• What most companies are doing wrong in their approach to data science?
• What does Mike know now that he wishes he had known at the start?

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

Michael Driscoll

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Auren Hoffman is best known for being the former CEO and Founder @ LiveRamp, the leading data onboarder that was acquired by Acxiom for $310m. Today’s talk focuses on the 5 core lessons Auren took from that incredible journey with LiveRamp. Auren was also an angel investor and board member at BrightRoll, prior to it’s $610m acquisition by Yahoo. Today, he is the CEO at SafeGraph, the startup that is unlocking the world’s most powerful data so that machines and humans can answer some of society’s toughest questions.

In Today’s Episode You Will Learn:

• What is Auren’s thesis towards hiring all round athletes as opposed to position players? When do it make sense to do either? What stage of the company is right for which persona?
• What are the two different types of sales personas? At what type of company should you hire a relationship driven sales team and then what type of company for a product driven sales team?
• Why does Auren believe you should target a very small niche of the market? What are the benefits of such focus? How can you sell such a small market to VCs?
• How does Auren perceive the future of enterprise software? How has the rise of bottoms up sales affected the SaaS environment? How many more SaaS companies and buyers of SaaS are there today, compared to 10 years ago?

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

Auren Hoffman

Algolia the robust search API that allows developers to integrate lightning fast, typo-tolerant search into their SaaS product. Out of the box, Algolia offers developers a powerful platform for building great search experiences. By owning the entire stack from engine to server, Algolia free up development teams to focus on adding intuitive search that delights users. This is perfect for existing search teams looking to spend less time on maintenance and infrastructure management and more time on user experience. For small SaaS teams, Algolia is a great investment on top of your existing stack that requires no specialist engineers. And you can learn more about how Algolia helps SaaS Scale Search and get started on their 14-day Free Trial at Algolia.com/SaaStrPodcast

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

David Hassell is the founder and CEO of 15Five, the leading web-based employee feedback and alignment solution that is transforming the way employees and managers communicate. They have backing from the likes of Matrix Partners, Point Nine Capital and many more leading investors. As for David, he was named "The Most Connected Man You Don't Know in Silicon Valley" by Forbes Magazine, David has also been featured in The New York Times, The Wall Street Journal, Inc., Entrepreneur, Wired, Fast Company, and the Financial Post.

In Today’s Episode You Will Learn:

• How did David made his way into the world of SaaS and came to found 15Five?
• How does David view competition? How should founders view additional competition to their space? What is the right response? Why did David choose such a public and deliberate fight back against one competitive attempt?
• David has said before that is passionate about the meaning and purpose of the business vehicle. What does he mean by this? How does this affect his thinking toward management and organisational structure?
• What are the keys to creating a harmonized, incentivized and happy culture for your business? How scalable is this approach and how has David seen his approach alter and develop with the growth of the company?
• Why did David choose the more bootstrapped funding option over the traditional heavy reliance on VC funding? Which startups is this right for? How can founders know when is the right time to put the pedal to the metal?

60 Second SaaStr

1. David’s fave productivity tools?
2. David’s biggest mentor and how it came about?
3. What does David know now that he wishes he had known at the start?

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

David Hassell

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Alex MacCaw is the Founder & CEO @ Clearbit, the startup that is building a suite of business intelligence APIs to help companies find more information on their customers in order to increase sales and reduce fraud. They have backing from some of the best early stage investors including the likes of First Round Capital, SV Angel, Intercom’s Eoghan McCabe, Hubspot’s Dharmesh Shah and many more incredible investors. As for Alex, as well as being a fellow Brit who loves tea, he also worked at the likes of Twitter and Stripe prior to founding Clearbit.

In Today’s Episode You Will Learn:

• How did Alex make his way into the world of SaaS and came to found Clearbit in SF having grown up in the UK?
• Should API driven companies have sales teams? Should they do outbound? What’s the most effective way to generate leads?
• Alex has said before that the trouble is, ‘everyone is treating their customers the same”. What does he mean by this? How do the smart companies differ? How possible is it to address customer specific needs at scale?
• How does this scalability alter when elements like freemium and self service models are added to the equation? How effective have freemium tools been for Alex as a lead gen to on board new customers?
• Why did Alex choose the same pricing structure as the likes of Stripe and Twilio? What was the thought process behind this?

60 Second SaaStr

1. How important is it for SaaS startups to be in SF?
2. What does Alex know now that he wishes he had known when he started?
3. Biggest mentor to Alex and how it came about?
4. Fave SaaS reading material?

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

Alex MacCaw

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Ryan Smith is the Founder & CEO @ Qualtrics, an online survey company with 1,200 employees and a valuation of more than $1bn. They have backing from some of the world’s best investors including the likes of Sequoia, Accel and Insight Venture Partners having raised a $150m Series B in 2014. As for Ryan, there are many awesome things, first, he has built Qualtrics from Utah allowing him to gain perspective outside of the traditional tech bubbles, second, he held off on attain VC funding for many years despite the common belief that it is necessary for unicorn growth and finally he has the most incredible work life balance I have seen and if you have not already you must check out this piece on him in Forbes, it really is a must.

 

In Today’s Episode You Will Learn:

1.) How Ryan made his way into startups and came to found Qualtrics?

2.) Sequoia’s Bryan Schreier states that Ryan’s success is due to running the company on ‘first business principles’. What does he mean by this? How does this affect the way Ryan runs Qualtrics?

3.) Why did Ryan decide to bootstrap the company for such a long time with the likes of Accel and Sequoia looking to invest? What are the benefits of retaining such control? What are the financial requirements to do so?

4.) What makes the best CEO’s? How do they view the internal structure of the company? How do they perceive their role? How do they manage their day and optimise their time?

5.) How does Ryan look to instill ‘radical transparency’ in the organisation? What are the benefits of doing so? Can an organisation ever be too transparent? What are the challenges of such transparency?

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

David Rodnitzky is founder and CEO of 3Q Digital, a leading digital agency that was acquired by Harte Hanks in 2015. Prior to 3Q Digital, he held senior marketing roles at several Internet companies, including Rentals.com (2000-2001), FindLaw (2001-2004), Adteractive (2004-2006), and Mercantila (2007-2008). David currently serves on advisory boards for several companies, including Marin Software, MediaBoost, Mediacause, and a stealth travel start-up.

In Today’s Episode You Will Learn:

• How did David enter the world of B2B SaaS marketing? What was the entry point for him?
• What really is SaaS marketing? Is it more consumer or B2B like? How does this alter and develop with the growth of the company?
• Before spending heavily on marketing, what gating factors should SaaS founders think heavily about before the big spend? Should this marketing plan be undertaken by an external firm or an internal team?
• What market channels should a SaaS company consider as ‘must haves’ in today’s world, as compared to ‘nice to have’s’? How does David differentiate between the two?
• We are always told if you cannot measure it, do not do it? How can SaaS companies measure the success and effect of their marketing campaigns? What are the key metrics that define success?

60 Second SaaStr

1. Biggest mistake current SaaS companies are currently enacting with their marketing?
2. Favourite marketing resources and tools?
3. What does David know now that he wishes he had known at the beginning?

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

David Rodnitzsky

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com