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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: 2017
Dec 18, 2017

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

Dec 11, 2017

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

Dec 4, 2017

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

Nov 27, 2017

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

Nov 20, 2017

Lars Nilsson is the VP of Global Inside Sales for Cloudera and with over twenty-five years of sales and operations experience, Lars Nilsson is a global leader in enterprise software and selling solutions. One of Lars many incredible achievements was he and his team at Cloudera built the sales methodology Account-Based Sales Development (ABSD), which has transformed how businesses approach high-value targets. Prior to Cloudera, Lars founded SalesSource, a business services consulting firm specializing in CRM customization and sales process development. Lars has also served in sales executive roles at ArcSight/Hewlett Packard, Riverbed Technology and Portal Software – all three of which achieved IPOs, in addition to Cloudera (2017). As Special Advisor at True Ventures, Lars helps True portfolio companies develop sales compensation plans from the ground up, implement best-of-breed sales technologies, and rapidly scale sales teams to meet demand.

In Today’s Episode You Will Learn:

  • How did Lars make his way into the world of enterprise sales back in 1995? How has Lars seen the industry change so significantly over the last 22 years?  
  • Why does Lars believe that SDRs are the most important role in sales? How does their role of ensuring a full pipe compare to the role of demand gen and marketing?
  • How does Lars think about setting a quota that ensures a desired behaviour beyond pure revenue chasing? What is his framework for setting and optimising the right quota? Why does Lars believe that ales is all about activities? What activities is Lars most eager to measure and test?
  • What is Lars’ biggest advice to someone looking to build out their SDR team from the ground up? What core characteristics should one look for in those initial SDR hires? What is and has been Lars’ biggest challenge in building out his SDR team? Why is building SDR teams in the bay so hard?
  • How does Lars think about setting ideal customer profiles? How big a TAM is large enough to be excited, yet narrow enough  to be achievable and solve a true and inherent customer need?

60 Second SaaStr

  1. What does Lars know now that he wishes he had known at the beginning?
  2. What is Lars favourite piece of SaaS reading material?
  3. Sales rep productivity, what does Lars believe is the scale from exceptional to poor?

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

Lars Nilsson

Nov 13, 2017

Jyoti Bansal is the former Founder & CEO @ AppDynamics, backed by the likes of Lightspeed, Greylock and Kleiner Perkins just to name a few before it’s ultimate acquisition by Cisco for $3.7Bn. Today, Jyoti is the Founder and CEO @ BIG Labs essentially a laboratory for creating, developing and launching innovative ideas. The first of these ideas being turned into companies being, Harness.io the industry’s first continuous delivery as a service platform, where Jyoti is the Founder & CEO. As a result of his tremendous success, Jyoti has been a recipient of many leadership awards including, "Best Cloud Computing CEO to Work For", "Best CEO" by San Francisco Business Times.

In Today’s Episode You Will Learn:

  • How Jyoti made his way from selling agricultural machinery with his father in India to creating one of the fastest growing enterprise companies with AppDynamics?  
  • $0-3m ARR: What is the key goal and objective for startups scaling through this phase? How can startups look to accurately determine what their North Star in this stage? To what extent should the founder involve the customer in product roadmap and development?
  • $10-15m ARR: What are the core objectives for the business in this stage of the cycle? How should founders view competition through this phase? What does Jyoti mean when he says about “go-to-market strategy fit”? How can this be determined most accurately?
  • $60-80m: What should be front and centre of the mind of the entrepreneur at this stage? Why does Jyoti believe it is here that it is crucial to get sales execution right? WHere are the breaking points that occur in the team scaling at this phase? How does the role CEO change here?
  • Pre-IPO: Why is operational efficiency so crucial in this stage of the business? What did AppDynamics do best at this stage of the business? Where would Jyoti say AppDynamics could have done better in the progression through this stage?

60 Second SaaStr

  1. What does Jyoti know now that he wishes he had known at the beginning of Appdynamics?
  2. What is Jyoti’s must read SaaS material?
  3. Payback period is the most important metric?

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

Jyoti Bansal

Nov 6, 2017

Paul Albright is one of the valley’s most experienced SaaS execs with extensive operational and capital management experience, including 3 IPOs. Most recently Paul was the Founder & CEO @ Captora, the marketing acceleration software solution that raised over $25m in VC funding from the likes of NEA and Bain Capital Ventures. Prior to Captora, Paul was Chief Revenue Officer at Marketo where he drove the overall revenue strategy across sales and marketing that delivered global revenue growth over 100% year-over-year, from $14m to $58m. In a similar position at SuccessFactors, he grew revenues to more than $200m and over 80% year-over-year growth. Previously, Paul led worldwide marketing at NetApp and at Informatica, which he joined pre-revenue through their successful IPO. If that was not enough he has also served as an entrepreneur-in-residence at Greylock.

In Today’s Episode You Will Learn:

  • How Paul made his way into the world with the likes of SuccessFactors and Marketo? What were his big lessons from seeing both companies scale into hyper-growth mode?  
  • Does Paul agree with Dave Kellogg in stating, “CAC/LTV is the single most important metric for SaaS startups? What other metrics must all VPs of Demand Gen and Sales be watching constantly?
  • What does an efficient sales and marketing engine look like? What are the core components to build that? What are the requirements to both run this engine and scale it quickly? How does the growth of this engine affect hiring in other parts of the business?
  • Why does Paul believe that it is much harder to go SMB up than enterprise down? What are the changes that are required on both ends? For this in “no man’s land of pricing” what does an efficient sales process timeline look like from lead to conversion?

60 Second SaaStr

  1. How does Paul think about picking the investors he works with?
  2. Is customisation always wrong?
  3. What is “good sales rep productivity” to Paul?
  4. What does Paul 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

Paul Albright

Oct 30, 2017

Jack Altman is the Founder & CEO of Lattice, the #1 performance management solution for growing companies.They have raised close to $10m in funding from some of our favourites in industry including the likes of Miles Grimshaw @ Thrive, Khosla Ventures, Elad Gil, Alexis Ohanian and YC’s Daniel Gross. Prior to founding Lattice, Jack was the Head of Business Development @ Teespring where he saw the firm move into hyper scaling. Jack has also build an incredible angel portfolio including the likes of Gusto, OpenDoor, Instacart, Zenefits and Soylent.

In Today’s Episode You Will Learn:

  • How Jack made his way from seeing the hypergrowth of Teespring to starting Lattice?
  • What does Jack identify as the 2 core challenges to rapid scaling in SaaS? Does Jack agree with Chris Caren in stating you have to hire for 3-4 years ahead of the role? How does Jack see the role and structure of communication change with the scaling of a firm?
  • How did the early days of selling look with Lattice? How did Jack incorporate the team into his learnings and development within the world of SaaS? What should founders look for in the first sales hire? How does that profile change with the scaling?
  • Why does Jack believe that each and every department should have their own North Star as well as a company North Star? Does Jack concur with Eric Ries’ believe that every department must also have their own budget?
  • In terms of metrics, how does Jack prioritise within the metric stack? What is most important for Jack to focus on? How has Jack seen this change with time? Does Jack agree with Shan Sinha @ Highfive that it is “always about payback”?

60 Second SaaStr

  1. Jack’s Favourite SaaS reading material?
  2. What does Jack know now that he wishes he had known at the beginning?
  3. How much time does Jack spend talking to customers?

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

Jason Lemkin

Harry Stebbings

SaaStr

Jack Altman

Oct 23, 2017

Rajeev Batra is a Partner at Mayfield, a firm that has championed bold entrepreneurs since 1969. Rajeev’s investments at Mayfield include the likes of Crunchbase, SmartRecruiters, Marketo (IPO then taken private by Vista Equity), ServiceMax (acquired by GE Digital) and more incredible companies. Prior to Mayfield, Rajeev was at Mobius (Softbank) Venture Capital and Austin Ventures. Before making the move into VC, Rajeev was on the operational side as an entrepreneur and executive with three of the companies he worked with going public and later being acquired, including the very notable Siebel Systems.

In Today’s Episode You Will Learn:

  • How Rajeev made the transition from successful operator with 3 IPOs under his belt to investing in the next generation of enterprise companies with Mayfield?
  • What does Rajeev mean when he says “startups do not die of starvation, they die of indigestion”? How does this realisation affect Rajeev’s approach to customer profiling and segmenting customers?
  • Why does Rajeev believe that “early product market fit can be misleading”? How does Rajeev look to provide context and action from numbers and analytics in the early days?
  • How does Rajeev feel that founders should approach gross margin from the early days? How should this relationship and thought process towards gross margin change over time?
  • Why does Rajeev believe that retention is the number 1 metric for SaaS founders to focus on? In the stack of metrics, how does this compare to gross margin, CAC/LTV and payback period?

60 Second SaaStr

  1. Enterprise investing is spreadsheet investing: True or false?
  2. How does Mayfield use an internal budget to align themselves to entrepreneurs?
  3. What does Rajeev mean when he says “I look for 2 act opportunities”?

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

Rajeev Batra

Oct 16, 2017

Shan Sinha is the Founder & CEO @ Highfive, the startup that quite simply makes insanely simple video conferencing. They have raised over $45m in funding from some of the best in the business including a16z, Lightspeed General Catalyst and Founder Collective and then individuals including Aaron Levie, Drew Houston and Marc Benioff. Prior to Highfive, Shan was the Group Product Manager for Google Apps for Enterprise, which he joined following Google’s 2010 acquisition of his prior company, DocVerse, which later became part of Google Drive.

In Today’s Episode You Will Learn:

  • How Shan made his way from being one of the foundations of Google Drive to changing the world of video conferencing with Highfive?
  • As a successful second time founder, how has Shan’s thesis around customer success changed? When is the right time to hire your first CS personnel? What profile should those first CS hires have? How does this vary to differing profiles in the scaling journey?
  • Logos or expansion? What does Shan believe is crucial in the early days of SaaS scaling? What metric is the true determinant of whether a customer is attaining consistent value from your product?
  • Why does Shan believe that not everything has to scale from Day 1? What are the benefits of implementing a model that is unable to scale? What does this show and teach the startup? How does Shan think about capturing the perfect customer experience?
  • Why does Shan believe that payback period is the single most important metric for SaaS startups? How does Shan think about payback and margins when selling to the traditionally smaller ACV marker of SMB? What are the challenges in doing so?

60 Second SaaStr

  1. When is a stretch VP a stretch too far?
  2. What does Shan know now that he wishes had known when he started Highfive?
  3. Challenges of doing both hardware and software simultaneously?

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

Shan Sinha

Oct 9, 2017

Chris Caren is the CEO @ Turnitin, the company revolutionising the experience of writing to learn with backing from the likes of IVP, Norwest Venture Partners and GIC. Chris has scaled the company to serve over 25m students and 2m teachers across 15,000 institutions. Prior to joining Turnitin in 2009, Chris spent 4 years with Microsoft as a General Manager and before that 3 years at Business Objects as a VP of Product Marketing.

In Today’s Episode You Will Learn:

  • How Chris made his way into the world of SaaS and came to be CEO @ Turnitin?
  • What were Chris’ biggest takeaways from watching both Business Objects and Microsoft as they scaled into hyper growth mode? What were his big lessons in management from Bernard Liautaud? What marketing takeaways did he have from working with Dave Kellogg?
  • Why does Chris believe management team upgrade is the most important role a CEO can perform? What are the core characteristics that upgrade candidates must have for them to be an attractive hire? What culture must be built into the fibre of the leadership team?
  • How does Chris look to manage internal discontent when bringing in external managers? How does Chris look to involve internal candidates for the role in the search for their next boss? What are the benefits of this?   
  • When is a stretch VP a stretch too far? What are the signs of potential strain? How does the team convey this? Once identified, what is the right post-mortem chain to take place?

60 Second SaaStr

  1. What should founders consider before selling their company?
  2. What does Chris know now that he wishes he had known at the beginning?
  3. What is Chris’ favourite SaaS reading material and why?

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

Oct 2, 2017

Greg Schott is the Chairman and CEO @ Mulesoft, provider of the leading platform for building application networks. They have raised over $250m in funding from some of the best investors in the world including NEA and Lightspeed and then some of the largest companies of the day in Cisco, Salesforce and SAP. Greg joined Mulesoft in 2009 when the company only had 20 employees, over the last 8 years Greg has scaled the team to over 1,000 today in 18 countries. A real software industry veteran with over 20 years of experience building and leading high growth technology companies from early stage through IPO.

In Today’s Episode You Will Learn:

  • How Greg made his way into the world of SaaS and came to be CEO @ Mulesoft?
  • Greg has seen Mulesoft scale from 20 to 1,000 employees today, what have been the biggest challenges in scaling the team? Where are the breaking points? What are the signs of those impending breaking points? How does that show through the team behaviour?
  • Where do most companies go wrong in the hiring process? What is the right and wrong way to respond when a bad hire has been made? How long is long enough to determine whether a bad hire is a bad hire? Does Greg agree with the hire fast, fire fast thesis?
  • If Greg could go back to 2009 when he joined the firm with 20 employees, what would Greg change about the way he approached hiring? What hiring advice would Greg give to an early stage SaaS company?   
  • How does Greg think about scaling sales teams? How does Greg view specialisation in the scaling of sales? When is the right time? What should CEO’s look for in their sales leaders? How does that alter at different points in the journey?

60 Second SaaStr

  1. How have things changed since IPO?
  2. When is the right time to expand product line and enter new segments?
  3. Biggest challenge with Mulesoft today?
  4. Which SaaS CEO does Greg most admire and why?

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 Schott

Sep 25, 2017

Andy Byrne is the Co-Founder & CEO @ Clari, the startup that helps sales teams drive more revenue and increase forecast accuracy through improved deal execution and predictive analysis. They have raised over $30m in venture funding from some of the best in the business including Sequoia and Bain Capital Ventures. Prior to Clari, Andy was part of the founding executive team at Clearwell Systems—Gartner's highest ranking e-discovery company—which he helped grow from pre-product & pre-revenue in 2005 to $100 million run rate until its acquisition by Symantec (SYMC) in Q2 2011. Prior to joining Clearwell, Andy co-founded Timestock, Inc., acquired by Computer Associates (CA) via the acquisition of Wily Technology.

In Today’s Episode You Will Learn:

  • How Andy made his way into the world of SaaS and came to found Clari? What were the key takeaways from his two prior successful founding experiences?
  • Why is it important for startups to look larger than life to potential “whale” customer? What is the methodology that startups can use to gain this appearance? What role does the website play in this?
  • Why is it important for startups to understand the risk the buyer is undertaking at large corporates when becoming a customer? How does this mean that startups should convey the product roadmap? How can startups sell the product vision and the instant value add simultaneously?
  • How can startups look to “create theatre” with their product? What does this really mean? How can startups do this when the product is in MVP stage?
  • Why is it so important for the startup to make the switch from vendor to partner? How can startups use execution time as the key way to achieve this?

60 Second SaaStr

  1. What hires does Andy wish he had made earlier with Clari?
  2. Recruiting in the valley, how hard and top tips?
  3. What is the most challenging element in the day to day running of Clari?

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

Andy Byrne

Sep 18, 2017

Ben Uretsky is the Co-Founder & CEO @ Digital Ocean. Under Ben’s leadership, DigitalOcean has risen from a cloud startup for developers to the second largest and fastest growing cloud computing platform. To date, more than 1m developers have deployed more than 50 million cloud servers, and the company has expanded its worldwide infrastructure footprint with multiple datacenter locations around the globe. The company has raised $123 million in funding from Andreessen Horowitz, Access Industries, IA Ventures, CrunchFund, and Techstars. Prior to DigitalOcean, he co-founded and built a managed hosting provider that supported some of the top websites online and generated million-dollar annual revenues.

In Today’s Episode You Will Learn:

  • How Ben made the move from co-founding a bootstrapped startup competing with Rackspace to co-founding DigitalOcean and competing with Amazon?
  • What have been Ben’s big learnings in raising $123m for DigitalOcean? How does Ben suggest building a trusted relationship with VCs?
  • How have DigitalOcean scaled to over 1m customers without a sales team? What are the core tenets that have made this possible? How does the team prioritise customer acquisition channels at DigitalOcean? How does Ben say is the right way to build a community?
  • Sean Rad has said before the hardest part is scaling with the firm. How has been seen his scaling as CEO with the firm? How has his personal relationship to the company changed with the scaling? Hear an inflection point in the scaling of DigitalOcean and how Ben’s leadership changed as a result?

60 Second SaaStr

  1. What hire des Ben wish he had made earlier?
  2. What does Ben know now that he wishes he had known earlier?
  3. What are the key inflection points in SaaS businesses?

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

Ben Uretsky

Sep 11, 2017

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:

  • How Dave made his way into the world of SaaS with Salesforce, came to be CMO at Business Objects and now running his own SaaS company as CEO at Host Analytics?
  • What does David believe is the single most important metric in SaaS? How should SaaS companies structure the first four lines of their financial statements? Why is retention and renewal not always an accurate sign of customer satisfaction?
  • How does Dave look to analyse churn? What is the post-mortem? What is more important, logos or expansion? If a startup’s churn is too high, what is the top 3 things they should do? Why must you have a “standard taxonomy” for churn? How can you construct this?
  • How does David think about taking existing customer and up-selling them? How does he view this in contrast to cross-sell? Does Dave agree with David Skok on the need for more than 1 variable pricing mechanism? Why does Dave not encourage usage based pricing?
  • How does Dave analyse the benefits of multi-year contracts paid upfront? How does this distort TCV and inflate the figures? Does upfront payment misalign the provider and the consumer, in terms of care and support? With that in mind, how does David view billing frequency? Contract durations?

60 Second SaaStr

  1. What does Dave know now which he wishes he had known at the beginning?
  2. What is the 90 day rule? Why is it important?
  3. How much ARR should a good sales rep add in relation to comp?

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

Sep 5, 2017

Scot Chisholm is the Founder & CEO @ Classy, the world's leading  fundraising platform for nonprofit organizations As a result they have raised close to $50m in VC funding from the likes of Salesforce Ventures, our friends at BullPen Capital, Mithril Capital and many more great investors. With support and funding like this, since 2011, Classy has helped more than 3,000 nonprofits and social enterprises raise hundreds of millions of dollars and be named to "The World's Most Innovative Companies in Social Good" and to the "100 Brilliant Companies" by Entrepreneur Magazine. As for Scot, he is also a prolific angel investor, investing out of a fund called Mixture that includes investments in Change.org, inDinero, Iodine, Casetext and more.

In Today’s Episode You Will Learn:

  • How Scot made his way into the world of SaaS and how a “pub crawl” came to be the founding story for Classy?
  • What have been the key learnings for Scot in raising $50m for Classy, in an industry that is maybe not so sexy for investors? Why did Scot choose to raise both the seed and A round from angels? What advice would Scot give to aspiring founders, looking to raise?
  • How has Scot seen the evolution of his sales team? What are the key inflection points in the scaling when elements tend to break? How important is it to segment the sales team? When should this be done? At what speed is optimal?
  • How does Scot evaluate startups looking to move upmarket? How does the decision to move upmarket change the internal decision-making with regards to product roadmap and strategy? How does it change the role of CEO in the organisation?   
  • How does Scot look to balance the attainment of short term objectives with holding the vision for the future? How far is too far to plan ahead? How should founders think about investing in areas of the business ahead of time?

60 Second SaaStr

  1. What does Scot know now that he wishes he had known when he started?
  2. Challenges as a first time CEO/entrepreneur?
  3. The key challenges of building a SaaS company in San Diego?

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

Scot Chisholm

Aug 28, 2017

Mark Organ, Founder & CEO at Influitive. Influitive helps B2B companies mobilize their army of advocates for more rapid and profitable revenue growth. They have raised close to $50m in VC funding from some of the best in the business including the likes of Lightspeed, First Round Capital, prior guest Cindy Padnos @ Illuminate and Nick Mehta @ Gainsight, just to name a few. Prior to Influitive, Mark was the founding CEO of Eloqua, growing the business to over 150 people, hundreds of clients and a major presence around the world in 7 years. Eloqua was eventually bought by Oracle in 2012 for a reported $810m.

In Today’s Episode You Will Learn:

  • How Mark made his way into the world of SaaS, came to found Eloqua and then what the catalyst was for the founding of Influitive?
  • How did Mark make the decision to make profitability a goal? How did Mark communicate his desire to focus on profitability and unit economics over aggressive growth to his investors? What type of SaaS startups should consider this route more?
  • To what extent is “landing whales” crucial to getting to cash flow positive? What are some of Mark’s big learnings in how to attain those “whales”, having done it so successfully before with Eloqua? Where do most founders go wrong and how should they approach pricing whales?
  • Why does Mark believe paying sales reps on signing misaligns incentives? Why does he believe it is optimal to pay half on signing and half on cash being received? How do you communicate that to your sales team?   
  • To what extent should SaaS startups consider debt financing as a respectable and appropriate form of company financing? What type and stage of SaaS company does debt make perfect sense for? When is it wrong in the lifecycle to take debt?

60 Second SaaStr

  1. What hire does Mark wish he had made earlier?
  2. What does Mark know now that he wishes he had known at the beginning?
  3. Pros and cons of running a SaaS startup not in Silicon Valley?

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 Organ

Aug 21, 2017

Mike Dauber is a General Partner @ Amplify Partners, the fund that backs technical founders, building technical products for technical buyers. Their portfolio consists of the likes of DataDog, Fastly, Engagio and many more incredible companies. As for Mike, prior to joining Amplify he spent more than six years at Battery Ventures, where he lead early-stage enterprise investments on the West Coast. While at Battery, he was on the Boards of Cask, Duetto, Interana, and Platfora (acquired WDAY). Mike also lead Battery’s investment in Vera, which is also in Amplify’s portfolio. He also previously invested in Splunk (SPLK) and RelateIQ (acquired CRM). As a result of this success, Mike was named to Forbes’ Midas Brink List in 2014.

In Today’s Episode You Will Learn:

  • How Mike made his way into the world of early stage enterprise investing with Battery and came to be a GP with Amplify?
  • What does Mike mean when he says he looks for “practitioner founders”? What are the benefits of these types of founders? Why do they find product market fit faster? Does this tunnel vision not sometimes mean a lack of naivete, which can be good?
  • Why does Mike believe that hiring sales people is like being thirsty? How can founders discover the optimal cadence for expanding the sales team? Why must founders differentiate between customers and money?
  • Why does Mike believe that everyone needs to find their Hobbesian advisor? What characteristics should this person have? How can you find this advisor? What should their incentives be?  
  • Why does Mike believe that founders need to set the hook for VCs in the first meeting? How does this compare to how founders traditionally pitch? What should they look for in those early VC meetings?

60 Second SaaStr

  1. Why does Mike disagree with deal attribution in VC?
  2. Cyber investing: Should you invest if not a domain expert?
  3. Is enterprise investing spreadsheet investing?

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 Dauber

Aug 14, 2017

Vineet Jain is the Founder & CEO @ Egnyte, the startup that delivers smart content collaboration in the cloud or on-premises. They have raised over $60m in VC funding from the likes of Kleiner Perkins, Google Ventures and one of our favourites here, Mike Maples @ Floodgate. Prior to Egnyte, Vineet founded and successfully built Valdero, a supply chain software solution provider, funded by KPCB, MDV and Trinity Ventures. Before that, Vineet held a variety of senior operational positions at KPMG and Bechtel.

In Today’s Episode You Will Learn:

  • How Vineet made his way into the world of SaaS and came to found his second startup in Egnyte?
  • Vineet states that it is not all about top line growth, how does he look to satiate VC appetitie for growth with this mentality? Why does he think that we should discuss EBITDA margins more often within business models in Silicon Valley?
  • Considering this conservative approach, how does Vineet determine when is the right time to put the “pedal to the metal” and raise a large round of funding and really look to gain the market? What metrics suggest product market fit to this extent?
  • Why does Vineet argue that land and expand is all wrong? What alternative does Vineet offer for those looking to sell to enterprise?
  • How does Vineet evaluate “The Rule of 40% For A Healthy SaaS Company”? What are the inherent flaws in this model? How can this model be gamed by posting enormous growth figures? What figures should startups input into this ratio?

60 Second SaaStr

  1. What does Vineet know now that he wishes he had known earlier?
  2. How long is long enough to give someone who is not performing?
  3. What hire does Vineet wish he had made earlier?

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

Vineet Jain

Aug 7, 2017

Max Yoder is the Founder & CEO @ Lessonly, the modern learning software used by teams to translate important work knowledge into Lessons that accelerate productivity. They have raised funding from the likes of former ExactTarget CMO Tim Kopp, OpenView Ventures and New York Times Bestseller Jay Baer just to name a few of the impressive figures involved. Fun tact; they are based in Indianapolis and so Max brings a fantastic perspective on scaling and operating a growing SaaS business outside Silicon Valley.

In Today’s Episode You Will Learn:

  • How Max made his way into the world of startups and came to found Lessonly, one of the hottest SaaS startups outside of Silicon Valley?
  • Max has previously stated that ‘SaaS scaling happens in 3 stages’. What are those stages? What is the most challenging stage? How does the CEO need to transition with each stage?
  • How does Max view the scaling of the team? Why does Max think it is bad to give large and often inflated titles in the early days? How can CEOs most effectively look to place people in the right place to ensure the most productive of scaling?
  • What does Max most look for in potential Lessonly employees? Why is it so fundamental that candidates have experienced some form of professional hardship before?
  • How does Max view the role of the board in the scaling of a SaaS organisation? What are the components that make the best boards? What are the components that make the best board members?

60 Second SaaStr

  1. What one hire does Max wish he had made sooner?
  2. What SaaS reading material can Max not live without?
  3. Pros and Cons of running a SaaS startup outside the valley?

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

Max Yoder

Jul 31, 2017

Stacey Epstein is the CEO @ Zinc, the secure communications platform for workers in front of customers, not computers. They have backing from some of the best in SaaS investing including the likes of Jason Green @ Emergence, CRV with George Zachary and GE Ventures. Prior to Zinc, Stacey was CMO at Banjo. Before Banjo, Stacey was CMO at ServiceMax where she helped fuel 5 consecutive years of triple-digit growth. Finally, before ServiceMax, Stacey was the Vice President of Global Marketing Communications at SuccessFactors. During her tenure with SuccessFactors, Stacey pioneered the marketing function in 2005, and was instrumental in the company’s successful IPO in 2007, which led to a $3.4B acquisition by SAP in 2010.

In Today’s Episode You Will Learn:

  • How Stacey made her way from Executive Assistant working for another Executive Assistant before moving to CMO and today as CEO?
  • What were the fundamental lessons Stacey took from her career as CMO to now being CEO/ What were some of the hardest elements of the transition?
  • What role should the CEO play in the marketing strategy and execution? What do CEO’s most often get wrong about CMO’s?What is the optimal and most efficient working relationship between CEO and CMO?
  • How does Stacey create alignment and strong and successful communication between the traditionally conflicting sales and marketing? How does transparency help drive better business results?
  • How can one look to instill these values and communication standards on inherited organisations they they did not found? Are there any drawbacks to transparency and communication?

60 Second SaaStr

  1. What hires does Stacey wish she had made earlier?
  2. What can females do to master the art of negotiating?
  3. Recruiting in the valley today, how tough and top tips?
  4. When is the right time to hire your CMO?

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

Stacey Epstein

Jul 24, 2017

Auren Hoffman is the Founder & CEO @ Safegraph, the startup that is unlocking the world’s most powerful data so that machines and humans can answer society's toughest questions. They have backing from likes of Naval Ravikant and prior guests of the show including SignalFire, IDG Ventures and David Rodnitzky just to name a few. Prior to Safegraph, Auren has an astonishing 5 successful exits under his belt with one being, LiveRamp (sold to Acxiom for $310m in 2014). If that was not enough, Auren is also a prolific angel investor with a portfolio including the likes of ThumbTack, Rainforest QA, Brightroll and Groupon.

In Today’s Episode You Will Learn:

  • How Auren made his way into the world of SaaS and came to found his 6th SaaS startup in Safegraph?
  • Auren has said before there are two types of successful sales people, what are these two types and what are their character profiles? What type of company should have each different profile? How does each profile interact differently with the rest of the company?
  • Why does Auren take the contrarian view and saying that highering your price is not always the right answer? In what markets is it right to higher or lower your price? When is it the wrong time? What percentage of revenue should sales and marketing be at a healthy SaaS startup?
  • Why does Auren believe that you can actually grow faster by having fewer employees? In what situation and start does this work and when does it not? ?
  • Why does Auren believe that the CEO should never delegate HR? What does Auren mean when he says the best HR professionals are real capital allocators?

60 Second SaaStr

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

Auren Hoffman

Jul 17, 2017

Promise Phelon is the CEO @ TapInfluence, bringing the first ever influencer marketing platform to the Fortune 1000. Under Promise’s leadership the company has enjoyed a 300% increase in revenue in 2015 alone, they made the successful transition from a services to a SaaS model and were successful in raising a fantastic $14m Series B. Prior to TapInfluence, Promise was the Founder and CEO at 2 startups, one of which, The Phelon Group, grew to 8 figure revenues and was successfully acquired in 2009. Before that, Promise got her start at BEA systems.

In Today’s Episode You Will Learn:

  • How Promise made her way into the world of SaaS and came to be at BEA systems, one of the most exciting companies in the valley at the time?
  • How does Promise view the importance of building long lasting relationships with colleagues? How does Promise suggest is the right way to leave a job and sustain the best communication and relationship with former employers and colleagues?
  • What does Promise mean when she states the importance of upward empathy? What are the benefits of installing this in your organisation? What is the right way to breed a culture of upward empathy?
  • How does Promise differentiate between ‘advocate’ and ‘mentor’? What is the right way to attain each of these? At what point in one’s career is the right time to have each of these?
  • What does Promise believe is the formula for making the successful transition from a services based business to a SaaS business? How can one make the change without significant customer churn and revenue loss?

60 Second SaaStr

  1. What does Promise know now that she wishes she had known at the beginning?
  2. How does motivating people differ when outside of the valley?
  3. Should customer success be able to upsell?

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

Promise Phelon

Jul 10, 2017

Ashu Garg is a General Partner @ Foundation Capital whose portfolio includes the likes of Uber, Lending Club, Adroll and Netflix, just to name a few. As for Ashu, at Foundation he has led investments and naming just a few of them here, in the likes of Conviva, Localytics and TubeMogul, later going public in 2014. Prior to Foundation, Ashu was the General Manager for Microsoft’s online advertising business.

In Today’s Episode You Will Learn:

  • How Ashu made his way from completing to the Rubik's cube as a kid in 25 seconds to being a leading SaaS VC?
  • How does Ashu really define scaling a SaaS company? What does product market fit really look like with regards to ARR growth?
  • What are the 3 fundamentals that SaaS founders have to nail if they are to scale to $30m+ ARR? Why does Ashu believe it is so important to have a single insertion point? What does this mean for SaaS founders?
  • What does Ashu advise first time founders making their first foray into the world of SaaS? How should they think about obtaining and building an ecosystem of mentors? How should they manage weaknesses within their own skill sets? Does Ashu believe with Aaron Levie @ Box, “anyone can learn to be a great CEO”?
  • Where do technical founders most often struggle? What can be done to help them go from 0-1 on customer acquisition? Where do business led founders most often struggle? How must they think of the engineering element as a core part of the founding team?

60 Second SaaStr

  1. What does Ashu know now that he wishes he had known at the beginning?
  2. Chats: Fad in the enterprise or here to stay?
  3. Biggest inflection points and breaking points in SaaS company growth?

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

Ashu Garg

Jul 3, 2017

Kurt Bilafer is the CRO @ WePay, the most complete payments solution for platforms. To date, they have raised close to $75m in VC funding from some of the best in the business including Max Levchin and August Capital just to name a few. As for Kurt himself, prior to WePay he has had experience both in startups and large corporations with his founding of Pilot Software, sold to SAP in 2007, where he spent a further 7 years holding titles such as a Global Vice President of Sales and Director of Strategic Accounts.

In Today’s Episode You Will Learn:

  • How did Kurt make his way into the world of SaaS? What were Kurt’s big takeaways from seeing the internal machinations of SAP?
  • What is the one metric that guides Kurt’s thinking? How can you calculate your “magic number” for your business? Why must SaaS founders switch from activity based metrics to KPI’s?
  • How does Kurt assess scalability and repeatability of revenues? What is a reasonable ratio for sales and marketing expense to revenue?
  • Why should SaaS founders focus on the LPI of “time to money”. How can they look to optimize this? How has Kurt seen the enterprise sales cycles change since his time with SAP?
  • How does Kurt assess conflict within the sales and marketing teams and customer success and product teams? How can managers look to implement an element of prioritization into what sales teams submit to product teams?

60 Second SaaStr

  1. What does Kurt know now that he wishes he had known at the beginning?
  2. What is the worst piece of SaaS advice that Kurt commonly hears being given out?
  3. What should one look for in their VP of Sales?
  4. What mistake does Kurt see most in the world of 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

Kurt Bilafer

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