The Official SaaStr Podcast: SaaS | Founders | Investors

Steve Garrity is COO and founder of Hearsay Systems the leading advisor-client engagement solution for the financial services industry. Hearsay have backing from the likes of Sequoia, NEA, Kleiner Perkins Partner, Mike Abbott and Path Founder, Dave Morin. Before founding Hearsay, Steve worked as an engineer at Microsoft Corporation in Seattle is a graduate of Stanford University with a BS and MS in Computer Science. While at Stanford, he was selected as a Mayfield Fellow in the Stanford Technology Ventures Program. During which, he joined Fortify Software as a product manager. Steve is also an investor in, and advisor to a number of Silicon Valley start-ups.

In Today’s Episode You Will Learn:

• How did Steve made his way into the world of SaaS from the world of Microsoft?
• How does Steve approach the management around his engineering team? How does Steve balance management of engineers while still allowing creativity? Are there dangers of giving engineers freedom?
• Is it possible to have both a happy engineering and sales? How does Steve look to harmonise the team? Is it not contra popular theory to have different cultures for different segments of the team?
• Why does Steve believe that executive coaching is an almost universal requirement? How does Steve justify that to the board?

60 Second SaaStr

1. Steve’s Biggest Productivity tools?
2. What does Steve now know that he wishes he had known at the start?
3. The biggest mistake SaaS companies are enacting with their social media strategies?

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

Steve Garrity

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

Peter Reinhardt is the Founder and CEO @ Segment, the startup that allows you to collect all of your customer data and send it anywhere and they count some of the biggest and best companies in the world as customers including the likes of Reuters, HotelTonight, New Relic and Atlassian. They do not only have some of the world’s leading customers but some of the world’s best investors with the likes of Accel, Thrive and Kleiner Perkins participating in their latest $27m Series B. I would like to say a huge thanks to Grant Miller @ Replicated for the intro to Peter today.

In Today’s Episode You Will Learn:

• How did Peter make his way into the world of SaaS and come to found Segment?
• How does Peter define product market fit? Does he agree with Justin Kan in stating that it is when you get the first 10 customers that are unaffiliated?
• Why does Peter believe product market fit suffers when related to Job’s idea of the reality distortion field? What is so damaging and what should founders look to avoid?
• How do technical and non-technical co-founders differ in their approach to product market fit? How do their expectations, desires and reactions alter to differing levels of uptake?
• How did Peter navigate the process of scaling prices with time? Was he nervous when doing so? What does Peter advise founders when attempting significant price increases?

60 Second SaaStr

1. What were the biggest takeaways from YC?
2. What does Peter know now that he wishes he had known at the beginning?
3. The biggest challenge in building out the team?
4. Favourite SaaS resource or 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

Peter Reinhardt

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

Seth Besmertnik is the Co-Founder & CEO @ Conductor, the company that boasts the biggest customer list in their category including more than 500 Fortune and Internet Retailer 500 brands like Under Armour, Citi and FedEx with their web presence management and SEO. With this incredible success, the company has been ranked 13th fastest growing software company in the US and the 3rd Best Place To Work in NYC. They have also raised funding over $60m from some of the best investors on the east coast in the form of Matrix Partners and FirstMark Capital just to name a few. I would like to say a huge thanks to Fayez @ Bluecore for the intro to Seth today.  

In Today’s Episode You Will Learn:

• How did Seth make his way into the world of SaaS? What was the a-ha moment for Conductor?
• What does Seth mean when he says, ‘B2B companies need to build a weapon in their marketing’? How does this look in his approach? How does this differ according to differing startup budgets?
• Previously, Meaghan Eisenberg @ MongoDB has said ‘the largest lift you are going to see is from your site’. Does Seth agree with this? How should we prioritise the site? What are the fundamentals to consider in terms of optimising conversion?
• With the proliferation of content today, to what extent should B2B companies look to alternative platforms such as  Snapchat, Youtube and Instagram for content differentiation? What are the fundamentals to consider with platform diversification?
• How does Seth suggest creating a culture of content creation in previously segmented cultures? How can this be done with actionable strategies to encourage non-marketing professionals to produce content?

60 Second SaaStr

1. What does Seth know now that he wishes he had known before?
2. Biggest advice on content creation for B2B SaaS companies?
3. Fave SaaS reading material?
4. Being a CEO vs Being a Founder

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

Seth Besmertnik

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

Kathryn Minshew is the Founder & CEO @ The Muse, named to Forbes’ 30 Under 30 in Media and Inc.’s 15 Women to Watch in Tech. Before founding The Muse, Kathryn worked on vaccines in Rwanda and Malawi with the Clinton Health Access Initiative and was previously at McKinsey. Kathryn has spoken at MIT and Harvard, appeared on The TODAY Show and CNN, and contributes on career and entrepreneurship to the Wall Street Journal and Harvard Business Review.

In Today’s Episode You Will Learn:

• How Kathryn came to found The Muse? What was the a-ha moment for her?
• Why did Kathryn introduce a SaaS business model into the traditionally, transactional model of recruiting? What were the benefits and how did it alter her go to market?
• With no prior sales experience, how did Kathryn find the experience of running the sales team? What were the core takeaways? At what stage should the founder stop selling the product and hire a sales team?
• Why does Kathryn believe you have to make the customer feel slightly uncomfortable to be successful? What did Kathryn look for in her initial sales hires? Why did Kathryn hire 3 reps to start with and not 2, as usually suggested?
• How does Kathryn approach the customer success field at The Muse? When did Kathryn hire her first CS rep? What is Kathryn’s take on CS being involved in the sales process?

60 Second SaaStr

1. What does Kathryn know now that she wishes she had known when she started?
2. Biggest mistake SaaS companies are enacting with their recruiting process?
3. Productivity tips and hacks?

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

Kathryn Minshew

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 Sharkey is CEO & Co-Founder of Autopilot, the startup that allows you to automate customer journeys as simply as drawing on a whiteboard. Autopilot has funding from some of the best investors both in Australia and in SaaS with backing from the likes of Salesforce Ventures and Blackbird Ventures. Prior to founding Autopilot with his two brothers, Michael joined his brother Chris to grow start-up Stayz into a top Australian rental booking site which was acquired by FairFax Digital in 2006 and again by HomeAway for $225M in 2013. Michael also co-founded digital marketing agency Sharkey Media where he helped grow Australian startups. I would love to say a huge thank you to Matt Garratt @ Salesforce Ventures for the intro to Michael today.

In Today’s Episode You Will Learn:

• How did Michael come to co-found Autopilot with his two brothers? What was the a-ha moment for him?
• Why did Michael choose a self service model with Autopilot? How does this model affect their CAC? How does this model alter the outbound marketing strategy?
• How does Michael approach the dilemma of variable or fixed pricing? Has Michael found that the lack of reliability around variable pricing causes customers concern?
• With Michael interest in unit economics, why are we seeing many SaaS startups, Marketo and Eloqua, exiting with losses? What can founders do to adopt the unit economics first mindset? How does this attitude to unit economics affect attitudes to aggressive growth?
• Michael focuses on 100% net retention, what does that process and strategy look like in practice? How does this commitment to 100% retention affect Michael’s management style and work processes?

60 Second SaaStr

1. Biggest mentor to Michael and how it came about?
2. What does Michael know now that he wishes he had known in the beginning?
3. The biggest mistakes SaaS companies make with their email marketing processes?

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 Sharkey

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

Robert Siegel is a Partner at XSeed Capital, one of the leading seed funds in the valley. At XSeed, Rob specialises on, you guessed it, all things from the wonderful world of SaaS and he sits on the Board of Directors of Cape Productions and Caller Zen. Robert is currently on the faculty at the Stanford Graduate School of Business where he teaches an array of topics that he led to His role as the Co-President Emeritus of Stanford Angels & Entrepreneurs. Prior to joining XSeed, Robert was General Manager of the Video and Software Solutions division for GE Security, with annual revenues of $350 million. Before that, Robert was Co-Founder & Chief Executive Officer of Weave Innovations Inc. (acquired by Kodak). If that was not enough Robert also served in various management roles at Intel Corporation, including an executive position in their Corporate Business Development division, in which he invested capital in startups that were strategically aligned with Intel’s vision. I would also like to say a huge thanks to Tien @ Zuora for the intro to Robert today.

In Today’s Episode You Will Learn:

• How did Robert make his way into the world of SaaS? What was it about XSeed that made him want to make the transition from operations to VC?
• We have seen many big SaaS exits in the last year with Marketo and Nutanix, does Robert think the time for big SaaS exits has come and gone? Have we moved to a world of consolidation?
• How do companies both large and small need to react to this shift on a strategic level? How does this affect the internal infrastructure of larger companies?
• For smaller startups, how should their attitude to competition change? How does this change Robert’s search process as an investor? How can smaller startups make themselves attractive acquisition targets?
• How does Rob’s view of consolidation affect his excitement for mega returns in SaaS? How does it impact how Rob approaches valuation? How does this change Rob’s expectations of unit economics?

60 Second SaaStr

1. Strategic investors: Good or Bad?
2. What does Rob know now that he wishes he had known when he started?
3. Fave SaaS resource or reading material?
4. Greenfield opportunity in SaaS?

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

Robert Siegel

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 Thompson is CMO at Domo, the company that allows customers to turn data into opportunities. David is a highly accomplished branding expert and recognized leader in demand generation, having served as longtime CMO of WebEx, where he named the company, helped create the cloud-based conferencing category and positioned the company for its IPO and subsequent buyout by Cisco. He also co-founded and served as chief executive officer of Genius.com, a leading SaaS marketing automation company, and he launched the Sales 2.0 Conference.

In Today’s Episode You Will Learn:

• How did David make his way into the world of tech and SaaS pre-bubble? How did the bubble affect how David approached company building going forward?
• What should all SaaS startups consider pre spending big on marketing? What should their core gating factors be? Is it always right to have an internal marketing team?
• What are the must haves and the nice to haves in B2B marketing? Why is Facebook a must have or business branding today?
• How can businesses accurately measure the success of their marketing and branding efforts? Is it all about revenue or is there external reputation metrics to consider?
• On the whole, would David consider successful B2B branding closer to consumer or closer to enterprise marketing? What do the best in the enterprise class do?

60 Second SaaStr

1. What are David’s favourite marketing tools?
2. If David could recommend one book to SaaS founders what would it be?
3. With the martech explosion: are we entering a world of consolidation?

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 Thompson

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

Daniel Saks is the Co-CEO of AppDirect, which he founded in 2009. AppDirect is the leading commerce platform for selling cloud services and at the firm, Daniel plays a key role in the growth and development of AppDirect, from attracting a leading team, to nurturing relationships with customers and partners. AppDirect has backing from some of the leading investors in the world including the likes of Foundry Group and J.P. Morgan. Prior to AppDirect, Daniel worked at Viant Capital, a boutique tech investment bank.

In Today’s Episode You Will Learn:

• How did Daniel make the move from family business to SaaS founder? How did he get the business off the ground in the early days?
• From working in his family business, what did Daniel observe about the buying patterns of businesses? What makes Daniel believe humans like to buy from humans?
• Is it a problem that many of today’s software vendors lean on direct sales? What are the first steps to create a multi-channel approach? What does it take to support indirect sales channels such as affiliates and resellers?
• What is Daniel’s 4 Step Playbook for optimising the distribution of software? What does it take to move past the early adopter audience into the hands of the wider market?
• Why does Daniel believe that the promise of SaaS is yet to be fully realised? What excites Daniel with the rise of the cloud and the movement away from on-premise?

60 Second SaaStr

1. When is the right time to hire your first customer success rep?
2. What does Daniel know now that he wishes he had known at the beginning?
3. Biggest challenge in the AppDirect journey and how Daniel overcame it?

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

Daniel Saks

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

Part 2 with David Skok, now David is a serial entrepreneur turned VC at Matrix Partners. He founded four companies: Skok Systems, Corporate Software Europe, Watermark Software, and SilverStream Software and did one turnaround with Xionics. Three of the companies he founded went public and one was acquired. In 2001 David joined Matrix Partners, who had backed his last two startups, as a General Partner. David’s successful exits as an investor at Matrix include: HubSpot, JBoss, AppIQ, Tabblo, Netezza, Diligent Technologies, CloudSwitch, TribeHR, GrabCAD, OpenSpan and Enservio. David currently serves on the boards of Atomist, CloudBees, Digium, Meteor, Namely HR, Salsify, and Zaius. You can also find David’s amazing blog here! Huge thanks to Hardi Meybaum and Jason Lemkin for the intro to David today.

In Today’s Episode You Will Learn:

• What is negative churn? Why is it fundamental for SaaS startups to have a strong grasp of their negative churn?
• How does negative churn affect the pricing axis? What can startups do if they have no alternative product to upsell to?
• To what extent should founders be willing to engage in customisation in order to upsell a product? What are the dangers? What should founders be mindful of?
• To what extent is up sell the responsibility of customer success? Should they have a hand in the sales process? What are the dangers and concerns?
• How important is it for a startup to track their champion with the customer company? Does it matter if your champion leaves? What should you do if so?

60 Second SaaStr

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 Skok

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 Skok is a serial entrepreneur turned VC at Matrix Partners. He founded four companies: Skok Systems, Corporate Software Europe, Watermark Software, and SilverStream Software and did one turnaround with Xionics. Three of the companies he founded went public and one was acquired. In 2001 David joined Matrix Partners, who had backed his last two startups, as a General Partner. David’s successful exits as an investor at Matrix include: HubSpot, JBoss, AppIQ, Tabblo, Netezza, Diligent Technologies, CloudSwitch, TribeHR, GrabCAD, OpenSpan and Enservio. David currently serves on the boards of Atomist, CloudBees, Digium, Meteor, Namely HR, Salsify, and Zaius. You can also find David’s amazing blog here! Huge thanks to Hardi Meybaum and Jason Lemkin for the intro to David today.

In Today’s Episode You Will Learn:

• How did David make his way into the world of SaaS? What was it about Matrix that made him want to make the transition from operations to VC?
• Why are metrics so important? What role do they play in an organisation? How do good founders respond to questions on not achieving sales targets?
• Why are SaaS businesses immune from being measured on standard financials like GAP financials? What metrics in SaaS really determine the trajectory of the business?
• How can founders examine unit economics to determine whether they have a sustainable SaaS business?
• How does David address sales rep productivity? How much in ARR should they be booking in relation to their annual comp package?

60 Second SaaStr

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 Skok

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