The Official SaaStr Podcast: SaaS | Founders | Investors

Today we bring you a highlight from SaaStr Annual 2016 featuring a conversation between Hubspot's Dharmesh Shah and SaaStr's own Jason Lemkin. Prior to founding HubSpot in 2006, Dharmesh was founder and CEO of Pyramid Digital Solutions, which was acquired by SunGard Data Systems in 2005. In addition to co-authoring “Inbound Marketing: Get Found Using Google, Social Media and Blogs”,Dharmesh published HubSpot’s Culture Code, which has garnered over 2.5 million views on SlideShare. Named an Inc. Founders 40 in 2016, he is an active member of the Boston-area entrepreneurial community, an angel investor in over 60 startups, and a frequent speaker on startups and inbound marketing.

In Today's Episode wth Dharmesh You Will Learn:

• What were the biggest growth catalysts in the scaling of Hubspot from Day 1 to IPO?
• What were the biggest mistakes made and lessons learnt by Dharmesh and the team throughout the journey?
• How does Dharmesh think about churn? How does he define pre-churn?
• What is the customer happiness index and how can it be implemented?
• How can founders inform prospects their product is a must have not a nice to have?
• Why has the SMB space been so difficult for so long? Why is that changing now?
• Why Dharmesh and Hubspot focus on consumer behaviour not consumer feedback?

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
• Dharmesh Shah

Allison Pickens carries the customer success torch as the VP of Customer Success & Business Operations at the category leaders, Gainsight. Allison's organization @ Gainsight includes all post-sales functions: CSMs, Support, Onboarding, Services, and Operations. Prior to Gainsight, she started her career in management consulting for Fortune 500 companies while at Boston Consulting Group and later worked in private equity investing at Bain Capital. Allison decided that she couldn't pass up the opportunity to work at Gainsight when Bain Capital led the Series B.

In Today's Episode With Allison You Will Learn:

1.) So let's start with managing customer churn and I think the first and most important thing is assessing what is regrettable vs non-regrettable. How do you approach this?

• What is the internal post mortem?
• How do you identify why they churned?
• Is there a blame game that follows? How do you instill ramifications but not fear?
• How do you then look to fix the original problem that caused the churn?

2.) To do the above we need to have a great customer success team so iw ant to talk about the process of building this out and with CS being a new category this is an aspect a lot of founders are addressing at this time. So starting with the obvious?

• When do you need a customer success team?
• Where in the organization should the team sit?
• What's the playbook for rolling it out?
• How big does the team need to be? Does this vary on sector or funding availability?
• What are the levels of seniority within the team?
• What's your budget? How do you account for the costs of your team?
• What teams sit within the customer success umbrella?

60 Second Saastr produced by Nick Mehta:

What surprises you most about customer success now vs a year ago?

Importance of fast iterating team?

Fave SaaS material, book, blog, podcast?

What element of the journey have you found most challenging?

Carrying the CS torch? What is it like do you feel the pressure?

3.) Now I want to finish today by discussing the segmentation of your customer base, so at what point in the company's life do you begin segmenting the customers?

• Why is it important to segment customers?
• How do you decide the best way to segment them?
• Should these segments align with the sales team?

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
• Allison Pickens

Allison Pickens carries the customer success torch as the VP of Customer Success & Business Operations at the category leaders, Gainsight. Allison’s organization @ Gainsight includes all post-sales functions: CSMs, Support, Onboarding, Services, and Operations. Prior to Gainsight, she started her career in management consulting for Fortune 500 companies while at Boston Consulting Group and later worked in private equity investing at Bain Capital.  Allison decided that she couldn’t pass up the opportunity to work at Gainsight when Bain Capital led the Series B.

In Today’s Episode With Allison You Will Learn:

1.) So let’s start with managing customer churn and I think the first and most important thing is assessing what is regrettable vs non-regrettable. How do you approach this?

• What is the internal post mortem?
• How do you identify why they churned?
• Is there a blame game that follows? How do you instill ramifications but not fear?
• How do you then look to fix the original problem that caused the churn?

2.) To do the above we need to have a great customer success team so iw ant to talk about the process of building this out and with CS being a new category this is an aspect a lot of founders are addressing at this time. So starting with the obvious?

• When do you need a customer success team?
• Where in the organization should the team sit?
• What's the playbook for rolling it out?
• How big does the team need to be? Does this vary on sector or funding availability?
• What are the levels of seniority within the team?
• What's your budget? How do you account for the costs of your team?
• What teams sit within the customer success umbrella?

60 Second Saastr produced by Nick Mehta:

What surprises you most about customer success now vs a year ago?

Importance of fast iterating team?

Fave SaaS material, book, blog, podcast?

What element of the journey have you found most challenging?

Carrying the CS torch? What is it like do you feel the pressure?

3.) Now I want to finish today by discussing the segmentation of your customer base, so at what point in the company's life do you begin segmenting the customers?

• Why is it important to segment customers?
• How do you decide the best way to segment them?
• Should these segments align with the sales team?

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
• Allison Pickens

Cindy Padnos is the Founder and Managing Partner at Illuminate Ventures where she focuses on all things Enterprise/B2B cloud and mobile computing sectors. Prior to founding Illuminate in 2009, she was one of three investment professionals at Outlook Ventures responsible for committing the firm's $140 million fund. Cindy also has extensive experience in the world of operations, where she founded and sold one of SaaS' first on demand startups in the form of Vivant.

In Today's Episode with Cindy We Discuss:

• How Cindy made her way into the world of SaaS and later SaaS investing?
• Why does Cindy think SaaS is a democratiser for entrepreneurship?
• Is the proliferation of Sales and Marketing tools not a challenge for startups in terms of competing for the same VC dollars?
• Is it easier or more challenging for startups to raise VC funding today than in previous years? If so, why?
• How does Cindy assess product market fit with her portfolio companies? When is the right time to put pedal to the metal?
• What does Cindy make of the Micro VC market at the moment? How prominent are party rounds? Will we see 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
• Cindy Padnos

Cindy Padnos is the Founder and Managing Partner at Illuminate Ventures where she focuses on all things Enterprise/B2B cloud and mobile computing sectors. Prior to founding Illuminate in 2009, she was one of three investment professionals at Outlook Ventures responsible for committing the firm’s $140 million fund. Cindy also has extensive experience in the world of operations, where she founded and sold one of SaaS’ first on demand startups in the form of Vivant.

In Today’s Episode with Cindy We Discuss:

• How Cindy made her way into the world of SaaS and later SaaS investing?
• Why does Cindy think SaaS is a democratiser for entrepreneurship?
• Is the proliferation of Sales and Marketing tools not a challenge for startups in terms of competing for the same VC dollars?
• Is it easier or more challenging for startups to raise VC funding today than in previous years? If so, why?
• How does Cindy assess product market fit with her portfolio companies? When is the right time to put pedal to the metal?
• What does Cindy make of the Micro VC market at the moment? How prominent are party rounds? Will we see 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
• Cindy Padnos

Fred Stevens-Smith is the Co-Founder & CEO @ Rainforest QA, which if you listened to 20VC with Byron Deeter, you will remember he discussed them and their amazing trajectory. So for QA first, it is essentially QA as a service making it fast and easy to test your webapp in multiple browsers and they are backed by some of the best as we said there Byron Deeter @ Bessemer, our own Jason Lemkin, Y Combinator, previous guest Kris Duggan @ Betterworks and Marc Benioff just to name a few. As for Fred he is the man at the helm as Co-Founder & CEO and absolutely smashing it I might add. In the show Fred mentions his favourite reading material to be Jason Lemkin and Aaron Ross's 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 Our Discussion with Fred You Will Learn:

• How did Fred come to found Rainforest QA? What was his origin story to YC?
• How did Fred look to establish the pricing model with Rainforest? Why does Fred believe most software companies undervalue their software?
• What are the challenges of going upstream? How does it affect product? Sales cycle?
• Does Fred agree with Mark Organ that in a new category, the company CEO must be the category CMO? How much of a role does content play in Rainforest QA's education funnel for customers?
• Why does Fred believe you should spend the most time with your best people? Similarly, the least amount of time with your worst people?
• How has Fred gone about building out the sales team? What did Fred look for in sales reps and Heads of 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
• Fred Stevens-Smith

Fred Stevens-Smith is the Co-Founder & CEO @ Rainforest QA, which if you listened to 20VC with Byron Deeter, you will remember he discussed them and their amazing trajectory. So for QA first, it is essentially QA as a service making it fast and easy to test your webapp in multiple browsers and they are backed by some of the best as we said there Byron Deeter @ Bessemer, our own Jason Lemkin, Y Combinator, previous guest Kris Duggan @ Betterworks and Marc Benioff just to name a few. As for Fred he is the man at the helm as Co-Founder & CEO and absolutely smashing it I might add. In the show Fred mentions his favourite reading material to be Jason Lemkin and Aaron Ross’s 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 Our Discussion with Fred You Will Learn:

• How did Fred come to found Rainforest QA? What was his origin story to YC?
• How did Fred look to establish the pricing model with Rainforest? Why does Fred believe most software companies undervalue their software?
• What are the challenges of going upstream? How does it affect product? Sales cycle?
• Does Fred agree with Mark Organ that in a new category, the company CEO must be the category CMO? How much of a role does content play in Rainforest QA’s education funnel for customers?
• Why does Fred believe you should spend the most time with your best people? Similarly, the least amount of time with your worst people?
• How has Fred gone about building out the sales team? What did Fred look for in sales reps and Heads of 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
• Fred Stevens-Smith

Quang Hoang is the Co- Founder @ Birdly, Birdly are convinced by the power of messaging within organizations, they decided to build a broader service that connects your favorite business softwares to messaging apps. It is this vision that has led to them being named one of the hottest startups from YC Winter 2016 batch and has led to funding from some of the best in the industry including our own Jason lemkin, Slack, previous guest Nicolas Dessaigne and prestigious french investors Alven Capital and Partech Ventures.

In Today's Episode with Quang We Discuss:

• How did Quang come to found Birdly? What was the a-ha moment?
• What did Quang learn from pivoting to Birdly? What is it important for founders to consider before a pivot?
• How does Quang approach the challenging topic of a business model for bots?
• Why does Quang believe that the whole pricing model for SaaS will change?
• What were the main benefits of the YC experience and how did it impact his fundraising?
• When is the right time for European startups to make the move to SF? How important is it to be close to your customers?

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
• Quang Hoang

Quang Hoang is the Co- Founder @ Birdly, Birdly are convinced by the power of messaging within organizations, they decided to build a broader service that connects your favorite business softwares to messaging apps. It is this vision that has led to them being named one of the hottest startups from YC Winter 2016 batch and has led to funding from some of the best in the industry including our own Jason lemkin, Slack, previous guest Nicolas Dessaigne and prestigious french investors Alven Capital and Partech Ventures.

In Today’s Episode with Quang We Discuss:

• How did Quang come to found Birdly? What was the a-ha moment?
• What did Quang learn from pivoting to Birdly? What is it important for founders to consider before a pivot?
• How does Quang approach the challenging topic of a business model for bots?
• Why does Quang believe that the whole pricing model for SaaS will change?
• What were the main benefits of the YC experience and how did it impact his fundraising?
• When is the right time for European startups to make the move to SF? How important is it to be close to your customers?

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
• Quang Hoang

Christoph Janz is the Co-Founder and the Managing Partner @ Point Nine Capital, one of Europe's best early stage venture funds and Christoph himself specializes in all things SaaS at Point Nine and has made more than 20 SaaS startup investments. Prior to Point Nine, Christoph co-founded two Internet startups and in 2008, became an angel investor and discovered Zendesk, which was his first angel investment. Also if you would like to congratulate Jason for the raising of the incredible new SaaStr Fund then you can click here to send him a congratulations tweet.

In Today's Episode with Christoph We Discuss:

• How did Christoph make his way into the world of early stage SaaS investing?
• When should startups consider making the move to the US? Is it always necessary?
• How important is it for SaaS startups to have a local US investor? What are the benefits?
• Where are there talent gaps in European SaaS? What can European founders do to find those experienced VPs of Sales and Marketing?
• Question from Jason: What made Zendesk seem like such a winner and what did that teach you?
• Where does Christoph see the next wave of the consumerisation of SaaS?
• Is it harder to get funded as a SaaS startup in today's environment than in previous years?

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
• Christoph Janz