The Official SaaStr Podcast: SaaS | Founders | Investors

Olof Mathé is the Founder & CEO @ Mixmax, the startup that allows you to be a sales pro, providing powerful analytics, automation and enhancements for your outbound communication and a product that has achieved almost the impossible in SaaS, true viral growth and a $0 CAC. As for Olof, prior to Mixmax he led the team that built Inkling Habitat, now adopted by the world’s largest publishers and before that he was an entrepreneur and worked at Skype and McKinsey.

In Today’s Episode You Will Learn:

• How Olof made his way to the bay and how he made his way into the world of SaaS with the founding of Mixmax?
• Why does Olof believe that customer success is the new marketing? What does this mean for the right time to hire your first customer success rep? What are the other subsequent advantages of instilling an early customer success team?
• Why does Olof believe that every company must have some haters? What does this suggest about your product? How should startup founders react to this? Is there a method of damage limitation with these segments Why does Olof think it is ok if they come from your core user base?
• With regards to growth, how important does Olof view the differing forms of metrics? How many should founders be focussed on? How does this approach affect your internal decision-making? How does it affect product roadmap?
• How does Olof break down the structure of Mixmax into 3 subsequent parts? Why does Olof not like employees in SF working from home? What are the drawbacks to this? What is the right way to recruit remote employees? Why is not all inbound poor quality?

60 Second SaaStr

1. What does Olof know now that he wishes he had known at the beginning?
2. How to cost effectively deal with inbound hiring applications?
3. What is the least discussed but most worthy topic 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

Olof Mathé

If you have a digital product, whether it’s mobile or web, Amplitude’s product analytics helps you understand what your users are doing, iterate and ship product faster, and drive metrics like engagement and retention. To learn how you can use analytics to build a sticky product that grows your business, get your free copy of the Product Analytics Playbook from Amplitude. This 155-page book (with worksheets) will help you develop a comprehensive retention strategy for your product — just click here to download.

User education is one of the most powerful ways to increase engagement and retention at scale, yet is often put in the too hard basket. Elevio is the platform that removes this burden, empowering your users to self-serve contextually relevant help via their support widget and embeddable elements, increasing retention and engagement, while reducing support load. Elevio even tells you what content to add or fix and why based on usage trends from your users. Preventing content rot, and increasing coverage, which we all know is an ongoing challenge. You can also integrate with your existing support stack for content, access to live-chat, support tickets and more. Use elevio for continuous user education with 20% off your first year at (elev dot I O / saastr) using coupon code GOHARRY

 

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

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

If you have a digital product, whether it’s mobile or web, Amplitude’s product analytics helps you understand what your users are doing, iterate and ship product faster, and drive metrics like engagement and retention. To learn how you can use analytics to build a sticky product that grows your business, get your free copy of the Product Analytics Playbook from Amplitude. This 155-page book (with worksheets) will help you develop a comprehensive retention strategy for your product — just click here to download.

 

User education is one of the most powerful ways to increase engagement and retention at scale, yet is often put in the too hard basket. Elevio is the platform that removes this burden, empowering your users to self-serve contextually relevant help via their support widget and embeddable elements, increasing retention and engagement, while reducing support load. Elevio even tells you what content to add or fix and why based on usage trends from your users. Preventing content rot, and increasing coverage, which we all know is an ongoing challenge. You can also integrate with your existing support stack for content, access to live-chat, support tickets and more. Use elevio for continuous user education with 20% off your first year at (elev dot I O / saastr) using coupon code GOHARRY

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

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

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

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

 

 

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

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

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

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

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!

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

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

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

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

Greg Sands is the Founder & Managing Partner @ Costanoa Ventures, one of the leading early stage enterprise funds on the West Coast with their latest $175m fund, raised earlier this year. At Costanoa, Greg has made investments in the likes of Intacct (acquired by Sage for $800m), Quizlet, DemandBase and previous guest, Grovo, just to name a few. Prior to founding Costanoa, Greg was a Managing Director at Sutter Hill, where he was an early investor in the likes of Feedburner, AllBusiness, and Return Path. Before Sutter Hill, Greg was on the other side of the table as the first hire at Netscape after its founding engineering team. As Netscape’s 1st Product Manager, Greg wrote the initial business plan, coined the name Netscape, and created the SuiteSpot Business Unit, which he grew from zero to $150m in revenue. He also served as Manager of Business Development at Cisco where he architected a global channel management plan.

In Today’s Episode You Will Learn:

• How did Greg make his way into the world of SaaS as the first non-engineering hire at Netscape and then make his way into the world of SaaS investing, subsequently?  
• Why does Greg completely disagree with the hailed notion of, “The Rule of 40”? Why does Greg believe it has achieved such status and recognition in market today? Where are the large nuances? If not the rule of 40, what metrics and benchmarks should early stage SaaS founders be focussing on?
• If we disregard “The Rule of 40”, how does that impact the emphasis that should be placed on profitability? Tom Tunguz stated on the show, ““growth is the largest determinant of value at IPO, not profitability”. What are Greg’s thoughts on this?
• In that scaling process, Greg has said to me before, “the first hire in every function should be a Swiss army knife hire and most people go wrong”. What does Greg mean when he says a Swiss Army Knife, how does that change in marketing vs sales? Where do most people go wrong within this?
• How does Greg define the different phases of product market fit? Why does Greg advocate that all founders approach product market fit with a “crawl, walk, run” approach? What examples does Greg have where this has worked and what specifically about this allowed it to work so well?

60 Second SaaStr

1. Logos or expansion?
2. Pros and cons of usage based pricing?
3. What does Greg know now that he wishes he had known in 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

Greg Sands

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

Spenser Skates is the Founder & CEO @ Amplitude, the only analytics solution built for modern product teams that helps you understand user behaviour and ship the right solutions fast. They have raised over 55m in VC funding from many friends of SaaStr and 20VC including Eric Vishria @ Benchmark, Neeraj Agrawal @ Battery Ventures, the teams at IVP, Data Collective, Box Group and SV angel, just to name a few of their incredible investors. Prior to Amplitude, Spenser founded Sonalight, an app that allowed users to text while they drive, backed by the likes of Y Combinator.

In Today’s Episode You Will Learn:

• How did Spenser make his way into the world of SaaS and come to found Amplitude?  
• How did Spenser look to build and scale his sales team, as an engineering focussed founder? Where does Spenser see most engineering founders go wrong in their approach to sales?
• What were the stumbling blocks that Spenser found hard in this learning process? What is his biggest advice to technical founders to scale the learning curve fast?
• How does Spenser view the importance of a customer’s willingness to pay? Does that suggest a correlated amount of value? How should this propensity to pay, change with the stage of the provider? How does Spenser suggest founders mitigate discounting?
• What have been Spenser’s core learnings in creating an incentivised sales team? What are the core drivers that yield the behaviour desired? How does Spenser look to align this with engineering teams, traditionally disgruntled with sales’ compensation packages?

60 Second SaaStr

1. What does Spenser know now that he wishes he had known at the beginning of Amplitude?
2. What is Spenser’s fave SaaS reading material? How does that vary according to stage of business?
3. How does Spenser view discounting?

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

Spenser Skates

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