The Official SaaStr Podcast: SaaS | Founders

Latest Episodes:

SaaStr 168: Why 70% of Startup's VPs of Sales Fail, How and When To Hire Your First VP of Sales & The One Question That You Must Always Ask VP of Sales Candidates with Ryan Williams, Founder @ SalesCollider Mar 26, 2018

Show notes

Ryan Williams is the Founder @ SalesCollider, the organisation that helps technical founders jumpstart sales. Ryan got his start as the first sales manager at Adroll where he grew the team from 3 to 32 reps in just 8 months, a team that was responsible for ARR growing from $4m to $58m in under 2 years. Ryan then became an advisor to the early team at InVision where he coached both CEO and sales reps to close the first dozen enterprise deals. Then his last stop before founding SalesCollider was as VP of Sales at LeadGenius where he grew enterprise sales by over 400% and added clients such as Ebay, IBM and Google, just to name a few. Ryan is also an Entrepreneur in Residence @ 500 Startups and a Mentor with First Round Capital.

In Today's Episode You Will Learn:

How Ryan made his way into the world of sales as first sales manager at Adroll and how that led to advising the CEO of InVision on gaining their first enterprise clients?
70% of VPs of Sales fail when they join early stage startups, why is this? How can founders know when is the right time to bring in their first VP of Sales? What can they do to maximise the chances of success when bringing them into the organisation?
What is the right profile type for the first VP of Sales? What are the core foundations to assessing the strength of the VP in the interview, especially for engineering minded founders? What is the one question that Ryan loves to ask potential sales candidates? What answer does he look for?
Does Ryan agree with a recent guest, "discounting is now table stakes"? Where do most early stage startups go wrong when thinking about discounts? What framework must startups utilise to analyse the right discount to offer? Why must they know the internal value they are providing to their customer in such a detailed way when discounting?

60 Second SaaStr

What does Ryan know now that he wishes he had known at the beginning?
SDR's are the most important function in sales, agree or disagree?
Sales rep productivity, what is good and what is bad?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

SaaStr 167: The Biggest Challenges In Scaling From $1-10m in ARR, How To Navigate Enterprise Sales Negotiations Successfully & Why You Must Reiterate Value At Every Touchpoint with PJ Bouten, Founder & CEO @ Showpad Mar 19, 2018

Show notes

Pieterjan (PJ) Bouten is the Founder & CEO @ Showpad, the world's leading sales enablement platform that allows for the creation of amazing buyer experiences. To date they have raised over $89m in VC funding from the likes of Insight Venture Partners, Dawn Capital and Hummingbird. As for PJ, Showpad is the second company he has founded. In 2010 he co-founded the mobile development agency, In The Pocket and still serves on its board. Prior to In The Pocket, Pieterjan held senior roles at Netlog and Accenture.

In Today's Episode You Will Learn:

How PJ made his way from the world of Accenture to founding the world's leading sales enablement platform in Showpad?
What was the most challenging element for PJ and Showpad in scaling from $1m-10m in ARR? How does the go-to-market change with this scaling? How does the team structure and composition alter? How does the branding and positioning change?
PJ has said before that you must "reiterate value at every touchpoint", what does he mean by this? How can one look to build a structure and framework to ensure one is effective with this? How does one scale this when serving thousands of SMBs?
What were PJs biggest lessons from their experiences of discounting? What advice would PJ give to founders on when and how much to discount? How does PJ think about the use of pilots and trials? How can one ensure optimal efficiency of conversion with both methods?

60 Second SaaStr

Does the role of CEO ever get easier?
What does PJ know now that he wishes he had known at the beginning?
What keeps PJ up at night?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

SaaStr 166: Why SaaS Startups Do Not Have To Scale To Enterprise, Why Usage Is The Key Metric When Serving SMBs & How To Optimise The Partnership Model In SaaS with Clate Mask, Founder & CEO @ InfusionSoft Mar 12, 2018

Show notes

Clate Mask is the CEO of Infusionsoft, the leading cloud-based CRM platform for growth-minded small businesses with more than 145,000 users worldwide. Under Clate's leadership, InfusionSoft has grown from a fledgling startup housed in a worn-down strip mall into a 550 person company, raising over $130m in VC funding in the process. If that was not enough, Clate is also an angel investor with the likes of CampusLogic, where he also sits on the board and is co-author of Conquer the Chaos: How to Grow a Successful Small Business Without Going Crazy.

In Today's Episode You Will Learn:

How Clate made his way into the world of SaaS and came to found the leading CRM for small businesses?
Enterprise vs SMB: Why does Clate fundamentally believe that not everyone has to move to enterprise with time? Why do so many founders believe they need to? Why is it such a preference for investors? How does the decision to remain in SMB change the future structure of the team and product roadmap? What was the hardest challenge for Clate about staying in SMB?
The Metrics Stack: What is the core metric that founders must observe to analyse the state of their business? How does this core metric affect every other metric? How does Clate view the significance of payback period, what is good to him? How does sales rep productivity change when serving SMB vs enterprise? What is good sales rep productivity? Why does Clate fundamentally believe CAC/LTV is the mothership? What is it solely driven by?
Partnerships 101: How can a founder know whether they have the right model and product for a partnerships model? How do partnership models change both the service and sales process of your company? What are the biggest risks to implementing a full-scale partnerships model? What have been the biggest challenges for Clate of scaling this partnerships model?

60 Second SaaStr

What does Clate know now that he wishes he had known at the beginning?
What is the most important element an investor can provide?
A moment in Clate's life that has changed the way he thinks and sees the world?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

SaaStr 165: Step By Step Guide To Building Truly Diverse Teams, Why Data Professionals Must Be At The Core of Your Company & How To Move Upmarket Effectively with Harry Glaser, Founder & CEO @ Periscope Data Mar 05, 2018

Show notes

Harry Glaser is the Founder & CEO @ Periscope Data, the startup that allows you to transform your business with the fastest, most powerful analytics platform. To date, Periscope have raised over $34m in funding from some of the very best in the business including Bessemer, SV Angel, DFJ, Susa Ventures and Data Collective, just to name a few. With this funding they now serve over 975 customers including Adobe, Flexport, Tinder, NewRelic and more. Prior to founding Periscope, Harry was a Product Manager @ Google. Fun fact about Periscope, it was voted the best small company to work for in 2017.

In Today's Episode You Will Learn:

How Harry made his way from being a PM at Google to convincing his co-founder Tom to leave his comfortable corporate job in Seattle to chase the startup dream in the valley?
Diverse Teams: There a a lot of all white male teams in SaaS, what should they do to create a more diverse, well-rounded team? What is the first step? What is the framework for achieving this hiring ambition? What are the biggest challenges? Where does Harry see founders most often making mistakes in building diverse teams?
Data Teams: Why does Harry believe that founding teams must have data professionals within them from Day 1? Why does Harry believe this makes those startups more successful? What are the fundamental benefits? How does this data-centricity change the decision-making of the organisation? What are the core challenges in scaling this data team?
Moving Upmarket: Why does Harry believe that it is better to do SMB to enterprise than enterprise to SMB? How does the product fundamentally change when addressing the enterprise market? How does the structure of the team change with the move? How does the messaging of the company alter with the move to a more enterprise focus?

60 Second SaaStr

What does Harry know now that he wishes he had known at the beginning?
Harry recently tweeted "you don't choose the kind of CEO you are", what kind of CEO are you then?
A moment in Harry's life that has served as an inflection point and changed the way he thinks?
What can a founder do today to instantly make a better workplace culture?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

SaaStr 164: The Right Way To Sell To Enterprise Buyers, Why Sales Ops Will Be A C-Suite Role in the Next 10 Years and Whether Or Not To Engage With Pilots and Discounting with Mark Godley, President @ LeadGenius Feb 26, 2018

Show notes

Mark Godley is the President of LeadGenius, the startup that provides the power of human intelligence with the scale of machine learning. To date they have raised $16m in funding from the likes of a16z, Initialized Capital, Scott and Cyan Banister and SV angel just to name a few. As for Mark, he most recently served as Chief Revenue Officer for HG Data and before that was VP of Market Development for ConnectandSell. If that was not enough, mark also holds advisory roles in the salestech and martech space, including Omniquo, ZenIQ.io and The Big Willow.

In Today's Episode You Will Learn:

How Mark made his way into the world of SaaS over 25 years ago? How has he seen the industry change so remarkably over that time?
Why does Mark believe that many startups today are created with the wrong intentions? Who is ultimately to blame for this, the founders or the investors who back them? Why does Mark believe that SaaS founders should "ignore fundraising and sign customers"? What are the unidentified consequences to Mark of taking external money?
How does Mark view the function played by discounting in onboarding your first few key customers? What does Mark think of pilots? How willing should founders be to engage with unpaid pilots?
How can enterprise founders solve the 2 big problems today of. A.) Standing out in the sea of enterprise startups? Gain trust from enterprise CIOs when they are still a small team with little brand or track record?
What does Mark believe is the secret to selling to enterprise effectively? Why must founders be both credible and vulnerable when selling? What is the difference between helping someone buy and selling them a product?

60 Second SaaStr

What does Mark know now that he wishes he had known at the beginning?
Why are data vendors their own worst enemy?
What would Mark like to change about the world of VC and startups?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

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SaaStr 163: Scaling Zapier to $35m in ARR with Just $1.3m in Funding &Why Most Founders Should Ignore Fundraising & How To Harness The Power of Completely Remote Teams with Wade Foster, Founder & CEO @ Zapier Feb 19, 2018

Show notes

Wade Foster is the Founder & CEO @ Zapier, the startup that moves information between your web apps automatically, so you can focus on your most important work. A couple of incredible achievements from Zapier, they have scaled to a phenomenal $35m in ARR, they have built a time of over 130 people, all without a central office and they have done this with just $1.2m in early stage funding from the likes of Bessemer, Y Combinator and DFJ.

In Today's Episode You Will Learn:

How Wade made his way into the world of SaaS and came to found Zapier?
Why does Wade believe that founders need to put in place traditional management sooner than they normally do? What should this structure look like? When is the optimal time to start considering it and then implementing it?
Wade has said before that most startups should "ignore fundraising", why does he believe this? How has bootstrapping Zapier influenced how he manages and scales the company? What lessons has he taken from VC backed founders that he has applied to the growth of Zapier?
Zapier is a completely remote team, what is the secret to seamless communication and company culture when building a team to 130 with no central office? What are the core benefits? What are the fundamental challenges?

60 Second SaaStr

What does Wade know now that he wishes he had known at the beginning?
Why should everyone on the team do support?
How does Wade look to scale himself as CEO?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

SaaStr 162: How To Achieve True Virality in SaaS with $0 CAC, Why Customer Success Is The New Marketing & How To Optimise Remote and Contract Workers with Olof Mathé, Founder & CEO @ Mixmax Feb 12, 2018

Show notes

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

What does Olof know now that he wishes he had known at the beginning?
How to cost effectively deal with inbound hiring applications?
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:

SaaStr 161: Brad Feld on Structuring Your SaaS Startup For Scalability, How The Role Of CEO Should Adjust To The Growth Of The Organisation & What Makes The Most Effective Board Members Feb 05, 2018

Show notes

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:

SaaStr 160: Why People Over Index Culture Fit, How To Hire Through Market Cycles & How To Balance The Assessment of Output vs Input with Mark Mader, CEO @ Smartsheet Jan 29, 2018

Show notes

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

What does Mark know now that he wishes he had known at the beginning?
Management upscaling is the most important role of CEO?
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:

SaaStr 159: Why CAC/LTV Is Not The Guiding Metric In SaaS, How To Build An Inside Sales Team From Scratch & Why SMB Up Is The Right Way with Fred Shilmover, Founder & CEO @ InsightSquared Jan 22, 2018

Show notes

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