The Official SaaStr Podcast: SaaS | Founders | Investors

Brad Feld is one of the world's leading VCs having Co-Founded Foundry Group, Brad has made investments in the likes of Zynga, Makerbot and Fitbit, just to name a few. Brad is also Co-Founder of Techstars, one of the world's most prominent startup accelerators, whose portfolio companies have raised over $1.3bn in funding. If that wasn't enough Brad is also a best selling author having co-authoured Venture Deals: Be Smarter Than Your Lawyer and VC and Startup Communities: Building An Entrepreneurial Ecosystem In Your Community.

In Today's Episode You Will Learn:

• How Brad made his way into the world of VC and came to found Foundry Group?
• Brad has previously stated that companies can be segmented into 3 different core components? What does he mean by this? How can startups be structured internally for scalability?
• Why does Brad hate the word culture? How should culture be viewed and approach internally within startups?
• How has Brad seen his personal development with regards to being a board member? What has he got better at? What does he believe makes a great board member?
• Why is CAC the easiest metric to game in SaaS? How should the CAC/LTV ratio be approached? How can entrepreneurs use this to attract VC investment?

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

Brad Feld

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Mark Mader is the CEO @ Smartsheet, the company that allows firms the best way to plan, track, automate and report on work. To date, they have raised over $105m in funding from some of the best in the business including Insight Venture Partners. Prior to Smartsheet, Mark served as senior vice president of global services for Onyx Software, leading the consulting and customer operations teams in the Americas, Europe, and Asia. Due to this success, in 2015, he was recognized as Ernst & Young Entrepreneur of the Year in Technology for the Pacific Northwest.

In Today's Episode You Will Learn:

• Why Mark's being disrupted by Salesforce led to his entry into the world of SaaS and how he came to be CEO @ Smartsheet?
• How does Mark think that startups should approach hiring across market cycles? What have been some core lessons Mark has learnt in frothy markets and the war to win "hot talent"? How does Mark think about "paying up" for certain candidates? How flexible should startup founders be on moving their compensation bands?
• Why does Mark believe that too many people over index culture fit? How does Mark look to balance between raw IQ and culture fit? How does Mark look to really stress test someone's ability to perform a role, pre-hire? Where do most startups go wrong in their early hiring processes?
• How does Mark think about creating a structured framework for giving employee feedback? Why do people overestimate the importance of the feedback itself? What else should they be focusing on?
• In terms of providing that feedback, how does Mark assess the importance of output? How does Mark look to balance the complicated elements of output vs input? Is it really all about activity?

60 Second SaaStr

1. What does Mark know now that he wishes he had known at the beginning?
2. Management upscaling is the most important role of CEO?
3. When is a stretch VP a stretch too far?

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 Mader

Fred Shilmover is the CEO and co-founder of InsightSquared, one of Boston's premiere tech startups paving the way in the sales intelligence space. Throughout the InsightSquared journey, Fred has raised over $25m in VC funding from the likes of DFJ, Bessemer, Salesforce and Atlas Venture. Prior to founding InsightSquared, Fred was a corporate development associate with Salesforce Ventures and before that he held several key roles at Bessemer Venture Partners including associate and Director of IT. He is also a board member of TUGG, an organization that brings together tech entrepreneurs with social enterprises that support at-risk youth.

In Today's Episode You Will Learn:

• How Fred made his way into the world of SaaS, hustled his way to being a VC with Bessemer and then came to found InsightSquared from Boston?
• Why does Fred strongly argue that it is easier to start with SMB and move to enterprise than enterprise down? What are both the technical and personnel considerations of the decision? Why is it the product manager's job to lose complexity as slowly as possible?
• Why does Fred disagree and state that CAC/LTV is not the guiding metric for SaaS startups? What are the core problems of CAC/LTV? What alternatives should founders consider as their guiding metrics? Where does Fred believe most founders go wrong when assessing their metrics? What metric keeps Fred up at night?
• What does Fred believe are the fundamentals to successfully building an inside sales team from scratch? What is the lowest ACV that an inside sales team can justify? How does Fred look to create a culture of accountability and responsibility without the element of fear of not hitting quota?
• Why does Fred go against conventional wisdom and suggest that customer success is the responsibility of the entire organisation? Why is this advantageous compared to a dedicated CS team? How does this mean both time and teams are allocated towards customer success?

60 Second SaaStr

1. What does Fred know now that he wishes he had known at the beginning?
2. What is the least discussed but most worthy topic in SaaS?
3. What would Fred's biggest advice to emerging SaaS founders be?

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 Shilmover

Mike McDerment is co-founder and CEO of FreshBooks, the #1 cloud-based accounting software designed exclusively for service-based small business owners. Starting from his parent's basement, Mike has grown Freshbooks to more than 10m users worldwide and raising over $75m in VC funding from the likes of Accomplice and Georgian Partners. Mike is also the co-author of Breaking the Time Barrier, downloaded more than 250,000 downloads since its release.

In Today's Episode You Will Learn:

• How Mike came to enter the world of SaaS with the founding of Freshbooks from his parent's basement?
• Why does Mike disagree with the common notion of the "pivot"? How does Mike balance between realism when something is not working and vision?
• From Mike's conversation with USV's Fred Wilson, what does he believe are the 3 most important roles of the CEO?
• Why is the No 1 rule in SaaS, you do not replatform your software? What are the inherent dangers? How does it affect your ability to drive revenue? Where do most SaaS startups make big mistakes when replatforming?
• Where are the inflection points in SaaS team scaling? What is the biggest challenge at 20 people? How does collaboration change when your team hits 40 people? How can one maintain seamless communication when one hits 80 people?

60 Second SaaStr

1. Why is Mike so bullish on SaaS outside of Silicon Valley?
2. How does being outside the Valley affect his ability to hire?
3. What does Mike 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

Mike McDerment

Mike McDerment is co-founder and CEO of FreshBooks, the #1 cloud-based accounting software designed exclusively for service-based small business owners. Starting from his parent’s basement, Mike has grown Freshbooks to more than 10m users worldwide and raising over $75m in VC funding from the likes of Accomplice and Georgian Partners. Mike is also the co-author of Breaking the Time Barrier, downloaded more than 250,000 downloads since its release.

In Today’s Episode You Will Learn:

• How Mike came to enter the world of SaaS with the founding of Freshbooks from his parent’s basement?
• Why does Mike disagree with the common notion of the “pivot”? How does Mike balance between realism when something is not working and vision?
• From Mike’s conversation with USV’s Fred Wilson, what does he believe are the 3 most important roles of the CEO?
• Why is the No 1 rule in SaaS, you do not replatform your software? What are the inherent dangers? How does it affect your ability to drive revenue? Where do most SaaS startups make big mistakes when replatforming?
• Where are the inflection points in SaaS team scaling? What is the biggest challenge at 20 people? How does collaboration change when your team hits 40 people? How can one maintain seamless communication when one hits 80 people?

60 Second SaaStr

1. Why is Mike so bullish on SaaS outside of Silicon Valley?
2. How does being outside the Valley affect his ability to hire?
3. What does Mike 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

Mike McDerment

Ross Mason is the Founder & VP of Product Strategy @ MuleSoft, one of the world's leading software platforms making it easy to connect the world's applications, data and devices. Following over $250m in VC funding from the likes of Lightspeed, Salesforce Ventures, Sapphire Ventures and NEA, MuleSoft then went public in March 2017, popping as much as 45% on it's first day of trading. As for Ross, prior to MuleSoft, he was CEO of SymphonySoft, an EU-based company providing services and support for large-scale integration projects. Previously, Ross was Lead Architect for RaboBank and played a key role in developing one of the first large-scale ESB implementations in 2002.

In Today's Episode You Will Learn:

• How Ross made his way into the world of SaaS with the founding of MuleSoft?
• Why did Ross decide to move full time to the West Coast having started the company in Europe? What were the biggest challenges about the move to the US? What advice would Ross give to prospective entrepreneurs, looking to make the move? Where does Europe exceed the US and vice versa?
• What does it really mean to be a SaaS platform? What 3 elements of a company benefit when a product unbundles into a SaaS platform? How does unbundling change the process for building products and services? How does unbundling change the ability to drive new revenue streams? How does unbundling change core operational elements of the business?
• What does Ross mean when he says we are shifting from verticals into value chains? Does Ross believe it is even possible to own the entire customer lifecycle today, from start to finish?

60 Second SaaStr

1. What does Ross know now which he wishes he had known at the beginning?
2. How did it feel the day MuleSoft went public?
3. What advice does Ross commonly hear being given that he most disagrees with?

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

Ross Mason

Ross Mason is the Founder & VP of Product Strategy @ MuleSoft, one of the world’s leading software platforms making it easy to connect the world’s applications, data and devices. Following over $250m in VC funding from the likes of Lightspeed, Salesforce Ventures, Sapphire Ventures and NEA, MuleSoft then went public in March 2017, popping as much as 45% on it’s first day of trading. As for Ross, prior to MuleSoft, he was CEO of SymphonySoft, an EU-based company providing services and support for large-scale integration projects. Previously, Ross was Lead Architect for RaboBank and played a key role in developing one of the first large-scale ESB implementations in 2002.

In Today’s Episode You Will Learn:

• How Ross made his way into the world of SaaS with the founding of MuleSoft?
• Why did Ross decide to move full time to the West Coast having started the company in Europe? What were the biggest challenges about the move to the US? What advice would Ross give to prospective entrepreneurs, looking to make the move? Where does Europe exceed the US and vice versa?
• What does it really mean to be a SaaS platform? What 3 elements of a company benefit when a product unbundles into a SaaS platform? How does unbundling change the process for building products and services? How does unbundling change the ability to drive new revenue streams? How does unbundling change core operational elements of the business?
• What does Ross mean when he says we are shifting from verticals into value chains? Does Ross believe it is even possible to own the entire customer lifecycle today, from start to finish?

60 Second SaaStr

1. What does Ross know now which he wishes he had known at the beginning?
2. How did it feel the day MuleSoft went public?
3. What advice does Ross commonly hear being given that he most disagrees with?

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

Ross Mason

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!

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?
• Metrics: 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? 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?
• Negative Churn: 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?
• Upsell: 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 upsell 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?

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

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!

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?
• Metrics: 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? 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?
• Negative Churn: 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?
• Upsell: 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 upsell 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?

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

Des Traynor is the Co-Founder, Chief Strategy Officer and VP of Marketing at Intercom, one of the world's hottest startups that simply put, makes communicating with customers easy and efficient. They have raised over $115m in funding from some of the world's leading investors including Social Capital, Index Ventures, Bessemer Venture Partners and then titans of industry with Mark Zuckerberg, Jack Dorsey and the Collison brothers at Stripe. Prior to Intercom, Des previously co-founded Exceptional (now a part of Rackspace), and prior was a UX designer for web applications.

In Today's Episode You Will Learn:

• How Des made his way from founding consultancy web design businesses in Ireland to founding SaaS superstar, Intercom, with Eoghan and moving to San Francisco?
• Why does Des believe that "brand is the most overlooked element for new startups"? How must founders think differently when constructing their brand for a single product vs multi-product company? What is the right way to think about this brand architecture?
• How involved should customers be in the development of product roadmap? Where are the nuances and challenges to this? When is the right time to start thinking about releasing a second product? What is the right and the wrong way for this to be marketed?
• What does Des mean when he says, "there is an inverse correlation between quality and market size"? How should founders think about selling to both SMB and enterprise? How do their buying psychology and implementation process differ?

60 Second SaaStr

1. When I say success, who is the first person that comes to Des' mind?
2. Where do most startups go wrong with their branding?
3. What does Des 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

Des Traynor