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The Official Saastr Podcast: SaaS | Founders | Investors

The Official Saastr Podcast is the latest and greatest from the world of Saastr, interviewing the most prominent operators and investors to discover their tips, tactics and strategies to attain success in the fiercely competitive world of SaaS. On the side of the operators, we centre around getting from $0 to $100m ARR faster, what it takes to scale successfully and what are the core elements of hiring. As for the investors, we learn what metrics they hone in on when examining SaaS business, what type of metrics excites them and what they look for in SaaS founders.
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Now displaying: 2018
Jun 18, 2018

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:

  • What are the leading indicators that early stage VCs dig deep on to assess the strength of product market fit? What level of traction both in enterprise and SMB would an early stage investor deem exciting enough to pursue? What levels of engagement are sufficient enough to suggest cause for a much larger and increased round?
  • How should founders assess sales rep productivity? What can they do to actively shorten the ramp time? How will early stage investors analyse the ramp time? What suggests repeatability of process?
  • Why does David believe there is no point focusing on CAC/LTV in the early days? What is the single biggest thing that founders can do to show repeatability of process and revenue as fast as possible?
  • What is the most common reason that people miss plan? How must the mindset of the founder switch from extreme frugality to hyper growth scaling? When is the right time for this transition to take place? What are the inherent challenges to this switch?

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

If you’re looking to simplify file version control, ensure data security and save time while increasing accessibility, Egnyte is the right solution for your business. Egnyte delivers secure content collaboration, compliant data protection and simple infrastructure modernization; all on a single SaaS platform. Founded in 2007, Egnyte is privately held, headquartered in Mountain View, CA and supports thousands of businesses worldwide. For more information, please visit egnyte.com/SaaStr.

MonkeyLearn allows companies to easily analyze text with Machine Learning. Customers like Clearbit and Segment are using MonkeyLearn to turn emails, support tickets, customer feedback, and documents into actionable data. Their platform makes it super easy to classify texts by topic, sentiment or intent or to extract specific data such as keywords, names, and companies. MonkeyLearn makes teams more efficient by automating business processes, getting insights and saving hours of manual text data processing. And if you would like to learn more, head to monkeylearn.com/saastr, that is www. m o n k e y l e a r n .com/saastr. Plus, listeners of the SaaStr podcast will have a very special opportunity to purchase monthly plans for half the price. So, check out MonkeyLearn and start getting more out of your text today.

Jun 11, 2018

Dave Kellogg is the CEO @ Host Analytics, the leader in cloud-based enterprise performance management (EPM). Previously, Dave was SVP/GM of Service Cloud at Salesforce and CEO at unstructured big data provider MarkLogic. Before that, Dave was CMO at Business Objects for nearly a decade as the company grew from $30M to over $1B. Dave has also worked in various capacities with the likes of Breeze, GainSight, Tableau and MongoDB and previously sat on the boards of ag tech leader, Granular (acq by DuPont for $300M)  and big data leader Aster Data (acquired by Teradata for $325M).

In Today’s Episode You Will Learn:

  • Why does Dave believe it is foundational to be an ARR first company? How does Dave think startups can show their ARR first mentality from the first investor meeting? How does this help drive operational efficiency? How does Dave segment ARR into 3 distinct camps?
  • Why does Dave argue that SaaS metrics are not nearly as simple as they seem? Which metrics does Dave believe most founders confuse? What metrics will the best VCs pick apart and dig deep on? How can founders respond with accuracy and confidence?
  • How does Dave respond to multi-year deals? Under what conditions are they acceptable and not acceptable? How must they be reported in accounting? Where do many startups go wrong when considering multi-year deals? How important is it for them to be pre-paid?
  • Why does Dave argue that renewals do not measure customer satisfaction?What is an accurate measurement to determine customer satisfaction? How often should this be conducted? What sample size of customer gives the right amount of data?  
  • How does Dave approach comp with regards to sales team cross-sell and upsell? Why is it not as black and white as boards often portray? Under which circumstances does Dave believe double comp is justified and not justified? How can you communicate this to your board successfully?

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

Dave Kellogg

If you’re looking to simplify file version control, ensure data security and save time while increasing accessibility, Egnyte is the right solution for your business. Egnyte delivers secure content collaboration, compliant data protection and simple infrastructure modernization; all on a single SaaS platform. Founded in 2007, Egnyte is privately held, headquartered in Mountain View, CA and supports thousands of businesses worldwide. For more information, please visit egnyte.com/SaaStr.

Jun 4, 2018

Phil Fernandez is a Silicon Valley veteran, with more than 35 years of experience building and leading breakout technology companies. Phil co-founded Marketo in 2006 and led the company as Chairman and CEO for a decade, overseeing its successful IPO and acquisition by Vista Equity Partners. Prior to Marketo, Phil served as president and COO of Epiphany, an enterprise customer relationship management (CRM) software company. Today, Phil is a Venture Partner with Shasta Ventures, the fund with a portfolio including the likes of Nest, eero, Zuora, Canva and many more incredible companies.

In Today’s Episode You Will Learn:

  • When is the right time to hire your first CRO? Where did Phil make a big mistake in who owns what revenue numbers? What are the traits that make the best CROs? How should they look to work with both sales and marketing to drive efficiency internally?
  • Why does Phil believe you must hire the most senior Chief People Officer as soon as you can? What does the role of “Chief People Officer” really embody? How should they look to work with HR internally? Who should they report to? How does this role change with a scaling organisation?
  • How has Phil seen the relationship between average contract value and potential for expansion change? What is the correlation between and ongoing services component and both customer NPS and expansion? Where did Phil go wrong with this at Marketo?
  • How should emerging SaaS startups today be thinking about technical legacy debt? Why does Phil believe it is never to early to have a Head of Research function? How should this function work with the team to build the latest technology into new products?
  • Why did Steve sell Marketo to Vista Equity Partners? What was the thesis and big learnings from that experience? What does Phil mean when he says he did not “watch the clock properly’’? How can founders today be proactively thinking about ramp time for sales reps, new product engagement etc.    

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

Phil Fernandez

 

May 29, 2018

Bill Binch is a leader and expert in the SaaS sales industry, currently CRO @ Pendo.io,  the startup that helps you understand and guide your users, creating a product experience they can’t live without. They have raised over $58m in VC funding from some of the best in their space with the likes of Battery Ventures, Spark Capital and Salesforce Ventures, all backing them. As for Bill, prior to Pendo, Bill was the Senior Vice President of Global Sales at Marketo for 8 years. He joined when it was a small venture-backed startup with a mission to reinvent marketing automation. It was his sales leadership and expertise that formed a critical component in building Marketo into one of the fastest-growing enterprise software companies in the world, recognized through his being awarded worldwide VP of sales in 2011.

In Today’s Episode You Will Learn:

  • How Bill made his way into the world of SaaS and came to be employee #18 at Marketo before making the transition to today, as CRO @ Pendo?
  • Bill has said before that career paths are for B players. First, what is wrong with the current thinking around career paths? Why does that inherently mean that A players do not align with them? How can one determine when is the right time to step away from the career paths? What characteristics and attributes do those truly special opportunities have?
  • Bill has successfully made the transition from transactional business to enterprise business many times, what have been his core learnings on what it takes to make this transition successfully? What are the biggest challenges in making the transition? How does the internal structure of the team change when making this transition?
  • What does Bill mean when he says you have to “rig the recruiters”? What incentives can be placed in front of them that ensure you will be a priority for them? On the flip side, what incentives do you have to give the recently on boarded employees to encourage grassroots, word of mouth on the company brand?
  • How does the company and sales cycle fundamentally change when moving from $0-1m ARR? What does that mean for the company policy on discounting and pilots? How does the company alter when transitioning from $1-10m in ARR? How can sustainable social validity be built in this stage? How does a company successfully move from $15m-100m in ARR?     

60 Second SaaStr?

  1. What does Bill know now that he wishes he had known at the beginning?
  2. What keeps Bill up at night?
  3. What does Bill mean when he says you have to check your ego?

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

Bill Binch

If you’re looking to simplify file version control, ensure data security and save time while increasing accessibility, Egnyte is the right solution for your business. Egnyte delivers secure content collaboration, compliant data protection and simple infrastructure modernization; all on a single SaaS platform. Founded in 2007, Egnyte is privately held, headquartered in Mountain View, CA and supports thousands of businesses worldwide. For more information, please visit www.egnyte.com/SaaStr

May 21, 2018

Kristina Shen is a Partner @ Bessemer Venture Partners, one of the world’s leading venture funds with a portfolio including the likes of Pinterest, Skype, Box, LinkedIn, Yelp and many more incredible companies. As for Kristina, she serves on the boards of DoubleDutch, Glint, Retail Solutions and Zoosk and is also a board observer with RainforestQA, Vidyard, Gainsight and ServiceTitan. Kristina is also one of the best data gurus as the co-author of Bessemer’s State of the Cloud 2016 and 2017 and Bessemer 10 Laws of Cloud, which captures the top trends among leading public and private cloud computing and enterprise mobile companies. Due to Kristina’s success she has been named to both Forbes and Business Insider’s 30 Under 30 in 2014 and 2016, respectively.

In Today’s Episode You Will Learn:

  • How Kristina made her way into the world of cloud investing and came to be the data guru for much of the cloud landscape?
  • What does Kristina fundamentally mean when she states the key question is, is there velocity in this SaaS business? Is velocity just about revenue or ARR growth? How can startups present real velocity with their sales funnel? How can startups present further velocity through their SQL process?
  • Why does Kristina believe that “private SaaS multiples are not expensive and we need a new framework”? What makes the existing framework inaccurate? What does this mean for the way Kristina assess ARR multiple and growth rates? How does this framework alter Kristina’s perception of the often hailed “Rule of 40”? How does it change with scaling?
  • What are the core elements Series A SaaS investors focus on today? With regards to revenue benchmarks for the A round, where do they need you to be both on the low and high end? Where do Series A investors expect startups to be for y/y ARR growth?
  • What core metrics are required to successfully raise your Series B in SaaS today? What does Kristina think is the fundamental difference between Series A and B today in SaaS? What can founders do to show repeatability and reliability of revenue streams as they move into the B round?    

60 Second SaaStr?

  1. What does Kristina know now that he wishes he had known at the beginning?
  2. Questions from Jeremy Levine: What would Kristina like her legacy to be as an investor in 20 years time?
  3. What keeps Kristina up at night?
  4. Is it worse to see an amazing deal and pass on it or to have never seen it at all?

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

Kristina Shen

May 14, 2018

Jason Lemkin is the Founder @ SaaStr, the world’s largest SaaS event with over 20,000 of the world’s best SaaS founders and investors attending every year. Jason also invests from SaaStr’s debut $70m fund and has made prior investments in the likes of Algolia, TalkDesk, MixMax, Rainforest QA and many more incredible companies.

In Today’s Episode You Will Learn:

  • How does Jason think founders should approach long sales cycles in the early days? Why does Jason believe that ultimately long sales cycles do not matter? What can the truly great VPs do to impact those long sales cycles?
  • How does Jason think founders can tackle lead optimisation with their team? How can founders determine which leads to send to which AEs? What will the effect of this tailored lead distribution be?
  • When is the right time for the founder to begin to take a step back from sales? Why does Jason believe that the founder must always be involved in the sales process? How does this look at scale when selling to thousands of customers? How does this mean the founder works with the growing scaling team over time?
  • Why does Jason believe that SaaS companies have to raise so much money today? What is the core decision that founders must make when determining how much they need to raise? How should founders approach the topic of cloning? What are the 3 core advantages they have over their clones? What must they be mindful of when being cloned by incumbents?  

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

May 8, 2018

Timo Rein is the Founder & CEO @ Pipedrive, the startup that helps sales people focus on actions that close deals. To date, Timo has raised over $30m from the likes of Atomico, Bessemer Venture Partners, TransferWise Founder Taavet Hinrikus and Andy MCloughlin and has scaled the team to over 330 people across multiple continents. Prior to founding Pipedrive, Timo was a Partner @ Vain & Partners acting in a consultancy role on how to get the best ROI from your sales process and before that was himself a door-to-door salesman with SouthWestern Company selling high ACV products.

In Today’s Episode You Will Learn:

  • How Timo made his way into the world of SMB CRM with the founding of Pipedrive from the days of being a door-to-door salesman of high ACV products?
  • Why did Timo choose to go global with Pipedrive from day 1? What are the benefits of founders having this global mindset from the start? What are Timo’s biggest learnings in terms of acquiring customers globally early on? What worked? What did not work? How did Timo think about pricing on an individual country perspective? What are the challenges with this?
  • Having raised from both US and UK VCs, how does fundraising differ when comparing Europe to the US? If Timo had to say the West Coast, East Coast and European VCs each had one area they focus, what would that area be? What are the challenges with these inherent focus points? What advice would Timo have for foreign founders looking to make it big in the US?
  • How does Timo look to manage a team so spread across the globe? What are the core challenges of this? What works? What does not work? What functions can be split up by geography? What must remain in one location? Now at 300 people, how does Pipedrive ensure for the same values fit when hiring at scale?
  • Many VCs say with such low ACV and such high churn, the SMB market is too difficult. How does Timo respond to this? How does Timo think about ensuring the continuous refilling of top of funnel? How does Timo think about acquiring such small customers in a cost efficient manner?    

60 Second SaaStr?

  1. What does Pipedrive look like at $100m ARR?
  2. What keeps Timo up at night?
  3. Who is Timo’s favourite angel investor?
  4. What does Timo 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

Timo Rein

Apr 30, 2018

Jason Lemkin is the Founder @ SaaStr, the world’s largest SaaS event with over 20,000 of the world’s best SaaS founders and investors attending every year. Jason also invests from SaaStr’s debut $70m fund and has made prior investments in the likes of Algolia, TalkDesk, MixMax, Rainforest QA and many more incredible companies.

In Today’s Episode You Will Learn:

  • When is the right time to hire your first sales rep? What characteristics must those sales have? Why does Jason believe it is impossible to poach a rockstar from another fast scaling startup? Should you then hire the stretch VP or the more experienced, potentially burnt out exec?
  • How does Jason think about aligning compensation to company objectives? Within the company, which functions serve as the best test areas for variable compensation? What must you be wary of when installing a system of variable compensation?
  • When is a stretch VP a stretch too far? What must a stretch Head of Sales have done to make him ready? What must a VP of Product done before to make him ready? What resources can you build around stretch VPs to provide them with additional support?
  • How does Jason think about the first time you spend to acquire customers? Why does Jason suggest just trying to make $1 for every $1 you spend? Why is it crucial to think of your marketing spend on a blended basis? How can you create alignment between the marketing teams number and the cadence 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

 

 

Apr 23, 2018

Jon Lee is the Founder & CEO @ ProsperWorks, the #1 recommended CRM for G Suite. To date, ProsperWorks have raised over $85m in VC funding from the likes of True Ventures, Norwest, GV, Bloomberg Beta and more incredible names. As for Jon, prior to ProsperWorks, he started in investment banking at Merrill Lynch before moving to run a large operations team at Yahoo. Jon then founded Bazaar Advertising Solutions, a business self funded from a Palo Alto apartment that Jon scaled into a highly profitable $47m business in less than 2 years. Jon then sold Bazaar to Epic Media in 2006. Following the acquisition, Jon founded DNA Games, the number one casino simulation game on Facebook with more than 20 million players, ultimately acquired by Zynga in May 2011.

In Today’s Episode You Will Learn:

  • How Jon made his way into the world of CRM having successfully founded and sold 2 prior business in the lead gen and gaming space? Why does Jon believe building a SaaS business is very much like building a gaming business?
  • How does on think about the scaling of company culture with the scaling of headcount? Where does Jon see the inflection points where this culture starts to break down? What does Jon mean when he suggests “the importance of a culture of innovation”?
  • Why does Jon believe it is so important to insert a culture of risk into the organisation? How does this risk mindset differ and look across different segments of the business? How does Jon aim to create a culture of risk and ambition without a fear of failure and not hitting targets?
  • Why does Jon think it is always better to start in SMB and move to enterprise? How does this decision change how one thinks about product roadmap? How does this change how one approaches traction building ahead of fundraising? What should one look to learn from rapid iteration and testing before moving to the enterprise market?   

60 Second SaaStr?

  1. What does Jon know now that he wishes he had known at the beginning?
  2. What keeps Jon up at night?
  3. What is Jon’s favourite SaaS 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

Jon Lee

Apr 16, 2018

Chetan Puttagunta is a General Partner @ NEA, one of the world’s largest venture capital firms in the world with over $3Bn in their latest fund and a portfolio including the likes of Mulesoft, Jet.com, Uber, Houzz and many more incredible companies. As for Chetan, Chetan focuses on enterprise software and has made investments in MuleSoft, MongoDB, Elastic, Heap, just to name a few. Due to his phenomenal track record, Chetan has been named to GrowthCap’s Top 40 under 40 Growth Investors, Forbes 30 under 30 All-Star Alumni List, and Forbes’ 30 under 30 in Venture Capital. 

In Today’s Episode You Will Learn:

  • How Chetan made his from the world of leveraged buyouts to the world of enterprise VC investing with NEA?
  • Why does Chetan have such conviction with regards to open source companies today? Why does he feel the big question of “Can open source product multi-billion dollar companies” has been proven”?
  • How does Chetan think about the underlying business models of open source when comparing the likes of Red Hat with 85% gross margin to Hortonworks at negative gross margins? What does Chetan believe is a healthy ratio between professional services vs closed premium features? Does Chetan believe this is the end for per seat pricing in SaaS?
  • How does Chetan approach market sizing today when evaluating potential enterprise opportunities? Why does Chetan believe there is a mental trap in the VC requirement for large markets? How can founders present the niche market they are attacking, in an exciting enough way to satiate the investor appetite for large market?
  • Chatan has said before, “if you have conviction and vision, you should not be afraid to raise capital and go big”. Does every founder not have conviction and vision in the early days? How does Chetan determine when truly is the right time to pour fuel on the fire and raise that mega war chest?   

60 Second SaaStr?

  1. A moment in Chetan’s life that has changed the way he thinks about the world?
  2. Fave SaaS reading material?
  3. What does Chetan 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

Chetan Puttagunta

Apr 9, 2018

Rob Reid is the Executive Vice President & Managing Director @ Sage Intacct, the undisputed global leader serving finance teams of any size. With over 10,000 employees and and over 3m customers, their financial solutions generate over $2Bn in revenue. As for Rob, prior to Sage Intacct, Rob led Intacct over an incredible 8 year journey culminating in their, reported $850m exit to Sage in 2017. Before that he was CEO and President of LucidEra, a market leader for on-demand business intelligence. Prior to LucidEra Rob was group Vice President of industry leading Siebel CRM for Oracle, managing the SMB sector. Fun fact, over his phenomenal 30 year career, Rob has been involved with 8 startups, 7 of which have had successful exits.  

In Today’s Episode You Will Learn:

  • How Rob made his way into the world of SaaS over 30 years ago from wanting to be in advertising and hating computer science?
  • As a multi-time CEO, how has Rob seen his role and understanding of what it takes to be a great CEO changed over the last 30 years? Does Rob agree that “management upscaling is the most important role a CEO can do”? What does Rob mean when he says, “the old school CEO approach is upside down and backward”? How should it be in that case?
  • Why does Rob believe that an executive team is like a boat of oarsman? What are the fundamentals to ensuring your executive team are aligned and working in tandem? Why is transparency across the organisation fundamental to both efficiency and culture? How does Rob think about internal promotion vs external hire when it comes to the exec team?
  • Why is Rob adamant that “cloud companies like never before have to be customer-centric”? What does this mean for thinking about optimising the structure of your organisation? How does one think about such high levels of customer success and touch points when serving the immense SMB landscape? How is this feasible? What have been Rob’s key learnings?  

60 Second SaaStr?

  1. Following many successful outcomes, what is Rob’s biggest splurge to date?
  2. Why does Greg Sands call Rob “The Big Fundamental”?
  3. What does Rob know now that he wishes he had known at the beginning of his career?

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

Rob Reid

Apr 2, 2018

Kolton Andrus is the Founder & CEO @ Gremlin, the failure as a service startup finds weaknesses in your system before they cause problems. To date, they have raised over $8m in VC funding from some of the best in the business including the likes of Mike Volpi @ Index Ventures and Mike Dauber @ Amplify Partners. Prior to Gremlin, Kolton was a Chaos Engineer at Netflix improving streaming reliability and operating the Edge services. Fun fact, Kolton also designed and built Netflix’s failure injection service. Before that he improved the performance and reliability of the Amazon Retail website. At both companies he has served as a ‘Call Leader’, managing the resolution of company-wide incidents.

In Today’s Episode You Will Learn:

  • How a conversation in the hallway of a conference with a VC gave Kolton the confidence that he could leave the corporate world of Netflix and Amazon and start a startup?
  • What were Kolton’s biggest takeaways from seeing the first hand scaling of behemoths like Amazon and Netflix? How did they fundamentally alter how he views goal setting today? How does Kolton look to achieve the balance of ambitious goal setting without the team losing motivation if they do not hit the goals?
  • Why does Kolton believe that a decentralised workforce is merely an evolution in how we do business? What are the core fundamentals to achieving success in creating and scaling a remote workforce? What have been some of the biggest challenges in structuring the team this way?
  • What is the single biggest tip Kolton has for other founders in ensuring high conversion rates from trials? Where do most founders go wrong with this? Today, is engineering buy in the only necessity to succeed in a bottoms up sales world?  

60 Second SaaStr?

  1. What does Kolton know now that he wishes he had known at the beginning?
  2. If an investor can provide one thing, what is most important for Kolton?
  3. What are Kolton’s favourite SaaS reading materials?
  4. When is a stretch a stretch too far for a team member?

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

Kolton Andrus

Mar 26, 2018

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

  1. What does Ryan know now that he wishes he had known at the beginning?
  2. SDR’s are the most important function in sales, agree or disagree?
  3. 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:

Jason Lemkin

Harry Stebbings

SaaStr

Ryan Williams

Mar 19, 2018

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

  1. Does the role of CEO ever get easier?
  2. What does PJ know now that he wishes he had known at the beginning?
  3. 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:

Jason Lemkin

Harry Stebbings

SaaStr

Pieterjan Bouten

Mar 12, 2018

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

  1. What does Clate know now that he wishes he had known at the beginning?
  2. What is the most important element an investor can provide?
  3. 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:

Jason Lemkin

Harry Stebbings

SaaStr

Clate Mask

 

 

Mar 5, 2018

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

  1. What does Harry know now that he wishes he had known at the beginning?
  2. Harry recently tweeted “you don’t choose the kind of CEO you are”, what kind of CEO are you then?
  3. A moment in Harry’s life that has served as an inflection point and changed the way he thinks?
  4. 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:

Jason Lemkin

Harry Stebbings

SaaStr

Harry Glaser

Feb 26, 2018

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

  1. What does Mark know now that he wishes he had known at the beginning?
  2. Why are data vendors their own worst enemy?
  3. 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:

Jason Lemkin

Harry Stebbings

SaaStr

Mark Godley

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

Feb 19, 2018

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

  1. What does Wade know now that he wishes he had known at the beginning?
  2. Why should everyone on the team do support?
  3. 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:

Jason Lemkin

Harry Stebbings

SaaStr

Wade Foster

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

Feb 12, 2018

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

 

Feb 5, 2018

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

Jan 29, 2018

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

Jan 22, 2018

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

 

 

Jan 15, 2018

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

Jan 8, 2018

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

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