Guy Podjarny is the Founder & CEO @ Snyk, the developer-first solution that automates finding and fixing vulnerabilities in your dependencies. To date, Guy has raised over $32m in VC funding from Snyk from some of the great of venture including Accel, GV, our friends at Boldstart and Canaan Partners, just to name a few. As for Guy, prior to Snyk, he was the CTO of Akamai’s Web Performance Business following their acquisition of his startup, Blaze.io. Before founding Blaze, Guy built Web Application Security products, including the first Web App Firewall (AppShield), Dynamic Application Security Testing tool (AppScan) and Static Application Security Testing tool (AppScan Dev Edition). Fun fact on Guy, he is the holder of 18 patents related to security and performance.

In Today’s Episode We Discuss:

• How Guy made his way into the world of SaaS and came to found one of the hottest open source companies of our day in the form of Snyk?
• How does Guy navigate between the difficult balance of going wide on market and shallow on product or narrow in market and deep in product? What is the decision-making process? What does Guy advise founders on feature prioritisation in the early days? Does Guy agree if you are not embarrassed by V1, you have shipped too late? How does support provide a feedback loop on what to build next?  
• Why does Guy believe that, “successful freemium requires giving away your secret sauce”? How can one give away enough secret sauce in freemium without giving away too much people don’t buy? How does freemium fundamentally alter your relationship to revenue? Where does Guy see many going wrong when pursuing the freemium model?  
• How does Guy think about the problem of agency with developers using the product but having to sell to CIOs? What 2 things can be done to make this sell easier? What does Guy believe is the right framework to think about pricing through? Why is transparency in enterprise pricing not always optimal?
• What does Guy believe is required to have strong and seamless communication across functions and locations? How has Guy seen this change over time and with increased locations? Where does Guy see many going wrong when trying to scale team across location?   

Guy’s 60 Second SaaStr:

1. How does Guy know when is the right time to hire your first sales person?
2. How did Guy learn to let go and trust his team?
3. What does Guy know now that he wishes he had known at the beginning?

Read the full transcript on our blog.

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

Guy Podjarny

Claire Hughes Johnson, COO @ Stripe the new standard in online payments that handles billions of dollars of business every year for forward thinking businesses around the world. To date, Stripe has raised over $680m in funding from some of the very best in the business including Sequoia, Founders Fund, General Catalyst, Thrive, CapitalG, Kleiner Perkins and Tiger Global. As for Claire, prior to Stripe she spent over 10 years at Google in a range of different roles from VP of Google's self-driving car division to VP of Global Online Sales to VP of Google Offers. At Stripe, Claire has helped take Stripe global in February 2016 with the launch of Atlas, a toolkit that enables any business, anywhere in the world, to incorporate in the United States. If that was not enough, Claire is also a Board Member @ Hallmark Cards.

In Today’s Episode We Discuss:

• How Claire made her way into the world of SaaS with Stripe following her leading of Google’s self-driving car division?
• What does Claire mean when she discusses “founding documents”? What is the right way to go about creating them? What element do they need to contain? How can one optimise internal decision-making process with these documents? What question must one always try and ask when making big decisions?
• How does Claire define a truly special COO? What does that truly great look like? When is the right time for founders to hire that COO? Where do the majority of people go wrong in their assessment of when and what they need in a COO? What is the optimal relationship one can have between CEO and COO?
• How does Claire think about what Stripe have done right to hire so effectively at scale? What does it take in terms of benchmarks and standards to do so? What does Claire mean when she says you have to step function up your capabilities with scale? What are the core challenges in hiring at scale?  

Claire’s 60 Second SaaStr:

1. What would Claire say are her biggest strengths and weaknesses?
2. What does Claire know now that she wishes she had known at the beginning?
3. A moment in Claire’s life that has served as an inflection point and changed the way she thinks?

Read the full transcript on our blog.

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 

Claire Hughes Johnson

Krish Subramanian is the Founder & CEO @ Chargebee, the startup that lets you go beyond billing, payments and recurring invoices — to delivering subscription experiences that "wow". To date, Chargebee have “wowed” some of the world’s leading VCs to the tune of $24m including the likes of Insight Venture Partners, Tiger Global and Accel Partners. As for Krish, under Krish’s leadership the team has grown to over 200 people and over 5,000 clients making it one of the next generation in truly global SaaS businesses started in India.

In Today’s Episode We Discuss:

• How Krish made his way into the world of SaaS and came to found one of India fastest growing SaaS companies in Chargebee?
• Why does Krish believe that every SaaS company should bootstrap at some stage? What are the inherent benefits to these capital constraints? What are the drawbacks to not having the capital reserves? What was the inflection point for Krish in realising he wanted to go big and raise from Insight?  
• Why does Krish believe that it is wrong to think of the word “service” as being negative in SaaS? What are some of the foundational benefits to building out a strong services division? How does Krish think about what makes for good margins in services businesses? How can one prevent themselves from being reliant on service revenue?
• Why does Krish believe that transparency is not always good when it comes to SaaS pricing? What are the cons of transparent pricing? Why does Krish believe if you are going to try freemium, it has to be from the beginning? How does Krish think about reinventing the wheel vs copying when it comes to pricing? How does Krish think about installing usage based pricing without disincentivizing usage? How can one do it?

Krish’s 60 Second SaaStr:

1. What does Krish know now that he wishes he had known at the beginning?
2. What moment in Krish’s life has served as an inflection point and changed the way he thinks?
3. What does Krish believe that most around him disbelieve?

Read the full transcript on our blog.

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

Krish Subramanian

Karen Peacock is the COO @ Intercom, the company that provides a new and better way to acquire, engage and retain customers. To date, Intercom have raised over $240m in VC funding from some of the very best in VC including GV, Kleiner Perkins, Bessemer, ICONIQ and then individuals such as Mark Zuckerberg, John Collison, Biz Stone and Andy McLoughlin. As for Karen, prior to Intercom, she spent an incredible 17 years at Intuit leading all of Intuit’s small business products and services worldwide, a $2.2B business including QuickBooks, Accounting, Payments, and Payroll. As part of that, Karen managed a team of 500 and helped build one of the world’s largest SaaS businesses.

In Today’s Episode We Discuss:

• How Karen made her way into the world of SaaS with Intuit and how that led to becoming COO @ Intercom today? What were Karen’s biggest takeaways from her time at Intuit?
• What does Karen mean when she says “watch what customers do, not what they say”? How does Karen think about the difference between being customer driven vs customer informed? Why is it important to fall in love with the problem and not the solution as an entrepreneur?
• Karen has grown Intercom from 350 to 600 in 18 months, what would Karen’s biggest advice and learnings be when it comes to team assembly and hiring the best? What can one do to stress test the fit of the candidate pre-hire? What does Karen always find to be the most revealing questions to ask?
• When does Karen believe is the right time to hire a COO? How does one know when they have the right COO fit? What are some best practices for onboarding a new COO? What is the optimal relationship between CEO and COO?
• Karen has seen incredible scaling first hand both with Intercom and Intuit, what would some of her biggest takeaways and advice be on scaling? Where does Karen see many make mistakes in the scaling phases? What does Karen mean when she speaks about “the most important metric that you probably aren’t tracking?”

Karen’s 60 Second SaaStr:

1. What does Karen know now that she wishes she had known at the beginning?
2. What motto or quote does Karen frequently revert back to?
3. What is the most challenging element in Karen’s role today?

Read the full transcript on our blog.

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

Karen Peacock

Hannah Willson is the VP of Sales @ Rainforest QA, the on-demand QA solution that allows companies to discover problems that affect the customer experience before the code hits production. To date, Rainforest have raised over $40m in funding from some of the very best in SaaS including the legendary Byron Deeter @ Bessemer, Jason Lemkin @ SaaStr, Marc Benioff himself, Andreesen Horowitz and YC. As for Hannah, she has over 10 years of experience leading sales and customer teams at both startups and publicly traded companies including seeing the first hand hyper-growth of Zenefits in their heyday and being VP of BD, Sales and Customer Renewals for the western half of the US at HelloWallet, prior to their acquisition by Morningstar.

In Today’s Episode We Discuss:

• How Hannah made her way into the world of SaaS and enterprise sales, came to join Zenefits in their heyday and how that led to her move to VP of Sales @ Rainforest?
• How does Hannah think about time allocation and prioritisation of time across leads and the sales pipeline? WHat can AEs do in terms of optimising their win rate of opportunities? How important a role should discounting play in winning potential leads? Does Hannah optimise for quality or quantity of logos in the early days?
• What does Hannah mean when she says the secret to success is “the calls between the calls”? How do these vary both in content and tone to traditional sales calls? Why must AEs be willing to open up and be vulnerable with leads? What can managers do to engender this? What is the optimal relationship for AEs and product team?
• What does Hannah believe is the right mechanism for feedback delivery? What has worked well for her in the past? Where does Hannah see many today going wrong? What guidelines need to be put in place to ensure this candid and transparent feedback is effective?

Hannah’s 60 Second SaaStr:

1. What does Hannah know now that she wishes she had known at the beginning?
2. What does Hannah believe embodies good sales rep productivity?
3. What is Hannah’s fave SaaS reading material?

Read the full transcript on our blog.

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 Birnbaum is the Founder & CEO @ Kustomer, the first intelligent platform for customer experience that enables you to know everything about every customer. To date Brad has raised over $38m in funding for Kustomer from some of the very best in the SaaS business including Tomasz Tunguz @ Redpoint, Ed Sim @ Boldstart, Canaan Partners, Box Group and Social Leverage just to name a few. Previously he was the Co-founder of Assistly, which was acquired by Salesforce and became Desk.com. Prior to that, he was CTO for Talisma and Co‑founder & CTO of eShare Technologies. In addition, Brad was also the CTO @ Sean parker’s Airtime and VP of Engineering with Salesforce.

In Today’s Episode We Discuss:

• How Brad made his way into the world of customer experience and SaaS over 20 years ago?
• This is Brad’s 4th time at the roadshow, what does Brad believe are the core benefits of repeat entrepreneurship? How did his prior experience change his operating mentality with Kustomer? What has he done differently this time? What worked and he has kept the same?
• Brad has made the transition from CTO to CEO, how did he find this transition? What were some of the most challenging elements? What have been some of the biggest surprises? What advice would Brad have for other CTOs who have made or are thinking about making the transition?
• Brad initially served SMBs with Kustomer but now primarily focuses on mid-level, what would Brad’s biggest advice be when it comes to finding the right go-to-market strategy for you? How did their transition alter their approach to pricing, product, messaging and distribution? Where does Brad see many people go wrong on go-to-market?

Brad’s 60 Second SaaStr:

1. What does Brad know now that he wishes he had known at the beginning?
2. When is the right time to pour fuel on the company fire?
3. What would Brad most like to change in the world of SaaS?

Read the full transcript on our blog.

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 Birnbaum

Jon Stein is the Founder & CEO @ Betterment, the online financial advisor built for people who refuse to settle for average investing. To date, Jon has raised $275m in VC funding with Betterment from the likes of Bessemer Ventures Partners, Menlo Ventures, Kinnevik and Francisco Partners, just to name a few. Prior to founding Betterment, Jon spent 4 years as a consultant at First Manhattan Consulting Group where he really honed his experience in working with banks and brokers including revitalizing a bank in Australia with the launch of a best-in-market auto-finance offering, resulting in 50% lift to revenue. As a result of his phenomenal success with Betterment Jon has won many awards including Fortune’s 40 Under 40.

In Today’s Episode We Discuss:

• How Jon made his way into the world of startups and came to found democratize the world of investing with Betterment?
• When does Jon believe is that critical moment when the founding team must hire their first employee? What is the right strategy to build the candidate pipe for hiring those first employees? Where does Jon see many go wrong here? What 1-2 questions does Jon always find the most enlightening to ask in the interview?
• Once hired, what have been some of Jon’s biggest lessons in terms of optimising the onboarding experience and the first 60 days? How has their process changed over time? How does Jon determine when a stretch candidate is a stretch too far? If so, what does Jon believe is the right way to let go of an individual?
• What does Jon believe to be the 3 core roles of the CEO in any company today? From those, what has Jon found most challenging? What did he do to level up and overcome the challenges? How does Jon approach transparency with the team in delicate cases like fundraising and acquisition etc?
• With the team and product in place, scale can occur, what are the 2-3 things that all companies need to focus on when product market fit has been achieved? How does Jon determine when is the right time to really put the pedal to the metal and scale?

Jon’s 60 Second SaaStr:

1. Jon’s favourite book and why?
2. What does on know now that he wishes he had known at the beginning?
3. What is Jon’s biggest strength and weakness?

Read the full transcript on our blog. 

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 Stein

Maria Pergolino is the CMO @ Anaplan, the company that allows you to accelerate decision-making with effective planning. To date, Anaplan have raised over $299m in funding from the likes of Meritech, Salesforce Ventures, Shasta, DFJ Growth and more incredible names. As for Maria, prior to Anaplan, Maria was Senior Vice President of Global Marketing and Sales Development at Apttus, where she directed go-to-market strategy, sales development, customer advocacy, demand generation, strategic events and communications initiatives. She also has held leadership positions at Marketo, Shunra Software (acquired by Hewlett-Packard), and Chubb Ltd. It’s also important to note, Maria is renowned for building world-class teams that drive growth, product differentiation, and category development.

In Today’s Episode We Discuss:

• How Maria made her way into the world of B2B marketing? What were her biggest lessons from the days of Marketo?
• How does Maria balance between instinct driven decision making vs data-driven in B2B marketing? Is there anything wrong with instinct driven? How can marketers confidently back up their thesis with substantive proof? How does one successfully sell that to leadership?
• Maria is famous for rallying teams around her ideas, what has Maria found to be core to the success in gaining this collective approval and excitement? What is the right way to approach the marketing portfolio of strategies as a whole? What channel or segment is Maria currently most excited for?
• How does maria evaluate the current event landscape in terms of effectiveness? Are we in a B2B event bubble? How can companies determine whether this is the right strategy for them? Would Maria agree with Joe Chernov, “to do events, you have to have an appetite for losing money? What does Maria and her team do to get the most out of events?
• What does the term “marketing playbook” really mean to Maria? What does Maria mean when she suggests that marketers can let their own playbook get in the way? Why does maria think it is absurd for there to be misalignment from sales and marketing?

Maria’s 60 Second SaaStr:

1. What does Maria know now that he wishes he had known at the beginning?
2. Who does Maria believe is killing it in B2B marketing today?
3. Advice commonly stated in SaaS that Maria disagrees with?

Read the full transcript on our blog.

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

Maria Pergolino

Cristina Cordova leads the Payments Partnerships and Platform Partnerships teams at Stripe, the new standard in online payments that handles billions of dollars of business every year for forward thinking businesses around the world. To date, Stripe has raised over $680m in funding from some of the very best in the business including Sequoia, Founders Fund, General Catalyst, Thrive, CapitalG, Kleiner Perkins and Tiger Global. As for Cristina, at Stripe she manages partnerships with some of the biggest global players including Apple Pay, Google Pay, WeChat Pay and more and has also held roles such as Head of Diversity and Inclusion and Manager of Partner Engineering. Prior to Stripe, Cristina was Head of Business Development @ Pulse (acq by LinkedIn) and was in the marketing team at Tapulous (acq by Disney).

In Today’s Episode We Discuss:

• How Cristina made her way into the world of SaaS and came to be Head of Partnerships at one of the fastest growing startups in the world, Stripe?
• Does Cristina agree with the common notion that certain people are destined for certain stages of a company’s life? How can one determine whether some has the ability to scale or not? What are the leading indicators? What have been some of Cristina’s biggest lessons in scaling from 28 at Stripe to 1,300?
• What does Cristina believe is the key to success when it comes to adapting to new roles? What worked? What did not work? Where does Cristina see many go wrong? How should employees think about title both when joining and when at a high growth company? What is the right way for them to think about and approach equity?
• What does Cristina believe is so special about partnerships with early stage startups? How can partnerships be fundamentally dangerous for early stage companies? How can startups determine when is the right time to engage with partners? What are the key questions and terms startups should focus on when partnering with incumbents?
• What makes Cristina lean in on a partnership for Stripe? What does Cristina believe is the right way to communicate this excitement and set expectations? For the larger player, what does the optimal agreement look like? What are the commonalities in the reasons that Cristina passes on potential partnerships?

Cristina’s 60 Second SaaStr:

1. What does Cristina know now that she wishes she had known at the beginning?
2. Who is killing it in SaaS partnerships today?
3. When is the right time to hire a Head of Partnerships?

Read the full transcript on our blog.

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

Cristina Cordova

Claire Hughes Johnson is the COO @ Stripe, the new standard in online payments that handles billions of dollars of business every year for forward-thinking businesses around the world. To date, Stripe has raised over $680m in funding from some of the very best in the business including Sequoia, Founders Fund, General Catalyst, Thrive, CapitalG, Kleiner Perkins and Tiger Global. As for Claire, prior to Stripe she spent over 10 years at Google in a range of different roles from VP of Google's self-driving car division to VP of Global Online Sales to VP of Google Offers. At Stripe, Claire has helped take Stripe global in February 2016 with the launch of Atlas, a toolkit that enables any business, anywhere in the world, to incorporate in the United States. If that was not enough, Claire is also a Board Member @ Hallmark Cards.

In Today’s Episode We Discuss:

• How Claire made her way into the world of SaaS with Stripe following her leading of Google’s self-driving car division?
• What does Claire mean when she discusses “founding documents”? What is the right way to go about creating them? What element do they need to contain? How can one optimise internal decision-making process with these documents? What question must one always try and ask when making big decisions?
• How does Claire define a truly special COO? What does that truly great look like? When is the right time for founders to hire that COO? Where do the majority of people go wrong in their assessment of when and what they need in a COO? What is the optimal relationship one can have between CEO and COO?
• How does Claire think about what Stripe have done right to hire so effectively at scale? What does it take in terms of benchmarks and standards to do so? What does Claire mean when she says you have to step function up your capabilities with scale? What are the core challenges in hiring at scale?  

Claire’s 60 Second SaaStr:

1. What would Claire say are her biggest strengths and weaknesses?
2. What does Claire know now that she wishes she had known at the beginning?
3. A moment in Claire’s life that has served as an inflection point and changed the way she thinks?

Read the full transcript on our blog.

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

Claire Hughes Johnson

Dan Reich is the Founder & CEO @ Troops.ai, the startup that is the ultimate slackbot for sales teams. To date, Dan has raised over $17m in VC funding with Troops from many friends of the show including Felicis Ventures, Founder Collective, First Round, Nextview, Susa Ventures and even Slack. As for Dan, he is also the Co-Founder and President of TULA, a private equity backed health and beauty business that has developed the world's first line of probiotic skincare products. Before that, Dan was a Co-Founder of Spinback (acquired by Buddy Media in May 2011, then acquired by Salesforce in June 2012).

In Today’s Episode We Discuss:

• How Dan made his way into the world of SaaS with the founding of Spinback? How that led to his founding of the ultimate slackbot for sales teams in Troops? How the experience with Spinback affected his operating mindset with Troops today?
• Why does Dan believe that the current modelling of org charts is fundamentally upside down? How does Dan think about when is the right time to insert the first level of managers? What should one look for in those managers? Does Dan believe you have to hire “logo players” from big firms at some point in the journey?
• Why does Dan believe that your customer success has to be obsessed with asking why? Taking a step back, how does Dan think about when the right time is to hire your first CS rep? How has Dan seen the best companies do post mortem analysis on churn? What can be done to ensure seamless communications between product and customer success teams?
• Dan has a knack for knowing where the puck is going with large enterprises before anyone else. How? What does this ideation process look like? Once the idea has been created, what does Dan believe is crucial to the success of partnering with the behemoths of Salesforce and Slack?
• How can startups navigate the internal politics of these mega enterprises? How can they use this exercise to not only understand the politics themselves but also build credibility and trust with the organisations once inside? Where does Dan see most founders going wrong both in introductions to enterprise and then building trust once inside?

Dan’s 60 Second SaaStr:

1. What does Dan know now that he wishes he had known at the beginning?
2. What is Dan’s favourite story of hustle? Why that one?
3. Who does Dan believe is killing it in the world of SaaS today?

Read the full transcript on our blog.

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

Dan Reich

Steve Newman is the Founder & CEO @ Scalyr, the startup that helps your devops team solve more problems in less time with log monitoring and analysis in seconds. Steve has raised over $27.5m in funding with Scalyr from many friends of the show including Susa Ventures, Bloomberg Beta, Shasta and GV. As for Steve, prior to Scalyr, he was the Founder of Writely which was acquired by Google to become the little known, Google Docs. Before that he founded 2 prior startups, Ann Arbour Softworks (acq by Ashton-Tate) and BitCraft (acquired by Macromedia). If that was not enough, Steve also sat on the Technical Advisory Board at Box for over 3 years.   

In Today’s Episode We Discuss:

• How Steve made his way into the world of startups and SaaS over 30 years ago? What is the founding story with Scalyr and what was that a-ha moment?
• Why does Steve believe that you should involve customers very early in the process of developing your narrative? Where does Steve see most startups go wrong when it comes to messaging? How does one structure the feedback mechanism? How does one determine between feedback you integrate and feedback you do not?
• Why does Steve believe that you should not focus too much on numbers in the early days? What makes them deceiving at this stage? If not numbers, what should early stage founders be focusing on and measuring? Why does Steve believe that ARR is not the leading metric? What metrics should early stage SaaS founders really be prioritising?
• How does Steve respond to PG’s “to scale, you have to do unscalable things”? What challenges and nuance does Steve present that founders must be wary of? How does Steve’s thinking here affect his view towards customisation? Why does manual input not put a cap on scalability? What are the parameters for manual involvement to be scalable?   

Steve’s 60 Second SaaStr:

1. What does Steve know now that he wishes he had known at the beginning?
2. Who does Steve believe is crushing it in the world of SaaS today?
3. The hardest element about the move from tech co-founder to CEO?

Read the full transcript on our blog.

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

Joe Chernov is the Chief Marketing Officer at Robin, the startup that simplifies scheduling, visibility and management of meeting rooms, desks and people in your workplace. To date, Robin have raised over £9m in funding from some of our dear friends in the form of BoldStart, Accomplice and FirstMark, just to name a few. As for Joe, prior to Robin he was the CMO @ Insight Squared where he led the transition from an email-driven leads model to an account-based marketing model that's tightly coupled with sales. Before InsightSquared, Joe was Head of Content Marketing at Hubspot where he increased blog traffic by more than 1M visits/month and increased leads by 40%. Finally, pre-Hubspot, Joe held VP of Marketing roles at Kinvey and Eloqua.

In Today’s Episode We Discuss:

• How Joe made his way into the world of startups and SaaS marketing many years ago? What was Joe’s missed founding story and how does that affect his thinking today?
• Does Joe believe that ABM is a paradigm shift in the way we approach marketing or another word for high ACV target sales? How can founders determine whether they have the right business, pricing and hiring strategy that will align with an ABM strategy? Is it the right decision to focus squarely on ABM? How should it play into your overall marketing portfolio?
• Why does Joe believe we have seen a massive rise in SaaS conferences? How can a startup determine whether the conference strategy is the right strategy for them? Where does Joe see many startups going wrong when selecting this approach? Why does Joe believe you have to get comfortable with losing money in conferences? What are the determinants or leading indicators of a successful conference? What is the ideal composition in terms of attendance?
• Why does Joe believe that marketing should be held accountable to a number that is directly tied to revenue? Why does Joe believe that Head of Sales and Head of Marketing should not be separate functions? What is it that leads Joe’s thinking when saying, sales and marketing are overlapping functions?  
• What are the commonalities of the truly special CMOs? When is the right time to really consider adding the CMO to your exec team? What is the ideal relationship between the CMO and the CEO? What is the one question that will largely determine the strength of a potential CMO?

Joe’s 60 Second SaaStr:

1. What does Joe know now that he wishes he had known at the beginning?
2. Who does Joe believe is killing it in SaaS today and why?
3. Advice Joe often hears in the world of SaaS that he actively disagrees with?

Read the full transcript on our blog.

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

Joe Chernov

Michael Katz is the Founder & CEO @ mParticle, the customer data platform that integrates all of your data and orchestrates it across channels, partners and systems. To date, Michael has raised over $75m in funding with mParticle from the likes of Social Capital, Greylock Partner, GV, Battery Ventures and more great names. Prior to founding mParticle, Mike was the Founder & CEO @ Interclick, where he organically grew revenue to over $140m in 5 years. The company went public in 2009 and was acquired by Yahoo in 2012 for $270m, a 50% premium on existing share price. If that was not enough, Michael is also a board member at Adaptly and Brightline.

In Today’s Episode We Discuss:

• How did Michael make his way into the world of SaaS with the founding of Interclick? How did that translate to his founding and running of mParticle today?
• How does Michael think about building a company and a category at the same time? In terms of resource allocation, if one is required to invest heavily into brand, how can this be done with a seed round? What were the most challenging elements of category creation for Michael with mParticle?
• When it comes to selling to enterprise, how can startups look to meet and stand out in the sea of startups to the enterprise buyers of today? How can they look to build trust with those buyers? How much of a role do VCs provide in terms of providing legitimacy and validation to a startup?
• Before Michael has said ‘multi-year deals are not good’, why does he hold this belief contra to most in the ecosystem? In which cases do they work well and is there nuance? How does Michael think about the element of deferred revenue and it’s subsequent effect on potential acquirers?
• How does Michael think about pilot programs? If mainly selling to one market segment, should pilots within other segments be accepted? What conditions on signing must be set to ensure success on completion of pilot? How should pilot programs change and evolve over time with the company?

Michael’s 60 Second SaaStr:

1. What does Michael know now that he wishes he had known at the beginning?
2. Who is crushing it in SaaS right now? Why?
3. Pros and Cons of building SaaS startup in NYC?
4. Motto or quote that Michael most frequently reverts to?

Read the full transcript on our blog.

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

Michael Katz

Kyle Porter is the Founder & CEO @ Salesloft, the leading sales engagement platform delivering a better sales experience. To date, Salesloft have raised over $75m in funding from some of the best in the business including Emergence, Insight Venture Partners, Techstars and even LinkedIn. As for Kyle, he has led the team from 4 employees in 2014 to over 320 today where they have also been awarded Atlanta’s No 1 best place to work. Prior to founding Salesloft, Kyle was the Founder @ B2B camp, a conference focused on B2B revenue generating professionals. Before that he was Vice President of Marketing @ NanoLumens.

In Today’s Episode We Discuss:

• How Kyle made his way into the world of SaaS and came to found Salesloft?
• Kyle made the decision to pivot the product when it was at $7m in ARR, what was the thinking behind that? How does Kyle think about pivots more broadly? How does one know when it is truly not working? How long did it take Kyle to get the core Salesloft product to $1m in ARR?
• With the pivot, what were Kyle’s core learnings on migrating from a prior product and platform to a new one? What were his big lessons on seeing the change in buyer persona? What does Kyle mean when he says “selling is hard but buying is even harder”?
• Does Kyle agree with many CEO’s the most important role of the CEO is “management upscaling”? What elements does he find most challenging? What have been Kyle’s big lessons in the building out of his exec team? What is the fundamental element for a successful exec team to function?
• Salesloft is in an immensely competitive space, what would Kyle’s advice be in standing out in an intensely competitive space? Where do many go wrong? What are the pros and cons of being in Atlanta and not SF? What advice would Kyle give to founders operating their HQs external to the core hubs?

Kyle’s 60 Second SaaStr

Is it important to have early champions? How does one get them?

How has having kids changed your perspective on work?

Tell me a moment in your life that has served as an inflection point and changed the way you think?

When I say success in SaaS who is the embodiment of this to you?

What does Kyle know now that he wishes he had known at the beginning? 

Read the full transcript on our blog.

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
Kyle Porter

Ed Sim is the Founder & General Partner @ Boldstart Ventures, one of the leading players in early stage SaaS investing. Their MO, to be a first check VC for enterprise founders and they have backed the likes of GoToMeeting (acq by Citrix), LivePerson (IPO, NASDAQ), Divide (acq by Google), Kustomer, Snyk and BigID just to name a few. Ed is also a cofounder of MState, a growth lab for enterprise blockchain in partnership with IBM. Ed is also a board director/observer of Kustomer, Hypr Biometric, Snyk, BigID, Fortress IQ, Wallaroo Labs and Manifold. If that wasn’t enough, Ed is also the writer behind BeyondVC, a must read blog in the world of SaaS.

In Today’s Episode You Will Learn:

• How Ed made his way into the world of VC from one very meaningful high school lecture that changed his life and career path?
• What does Ed mean when he says “founders should not sell their product to enterprise in the early days”. Starting from the ground up, what can founders do to begin that relationship building process with enterprise buyers and CIOs? What can a startup do to establish that trust in the mind of large buyers? How much of a role does VC backing provide in comforting enterprise buyers?
• What would Ed advise founders contemplating the debate of going SMB up to enterprise or enterprise to SMB? What role should product play in this decision-making process? What are the leading indicators in testing the product that founders should observe for and guide their direction? Where does Ed most often see founders make mistakes here?  
• How does Ed think about discounting? Would he agree with a previous guest that “discounting is now table stakes”? Rather than the financial element, what does Ed believe the founder should really be looking to get from the buyer in terms of commitment? How does Ed approach and assess pilots? To what extent should they be free or paid? What can be done to set the benchmarks for success and ensure closing?

Ed’s 60 Second SaaStr

1. What does Ed know now that he wishes he had known in the beginning?
2. Quality or quantity of logos?
3. What would Ed most like to change in the world of SaaS?

Read the full transcript on our blog.

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

Ed Sim

Craig Walker is the Founder & CEO @ Dialpad, the startup that provides a business phone system for the modern workplace. To date, Craig has raised over $120m in VC funding with Dialpad from some of the best in the business including Iconiq, Andreesen Horowitz, Google Ventures, Felicis and Bill Marris’s Section 32. Prior to Dialpad, Craig was an EiR @ Google Ventures and founded and product managed Google Voice. Before that Craig founded Grand Central Communications, a personal communications startup that was acquired by Google. Finally prior to that, Craig enjoyed roles in the world of VC as General Partner @ Sterling Payot Capital and Founder & Senior Director of Yahoo Voice.

In Today’s Episode You Will Learn:

• How Craig made his way into the world of SaaS following time as both a GP in the world of venture and then as the creator of what would become Google Voice?
• Why does Craig think go-to-market is the most challenging element of being a CEO? How does Craig think about when is the right time to go large on go-to-market? Where does Craig believe most founders make mistakes here?
• How does Craig look to balance aggressive scaling of team with the maintaining of early company culture? What are the foundations to doing this successfully? How does Craig approach the element of hiring external talent vs promotion from within? How does Craig think about managing the internal discontent if hiring an external candidate?  
• How does Craig assess the effectiveness of trials in attracting large enterprises? What are the parameters that must be set for a trial, before it is agreed? What must founders learn to say no to when it comes to trials? How does Craig approach discounting? Why does Craig argue if your client asks for aggressive discounts, you have not explained your core USPs successfully?    

Craig’s 60 Second SaaStr

1. What does Craig knows now that he wishes he had known at the beginning?
2. When I say success in SaaS, who does Craig first think to and why?
3. Quality or quantity of logos and why?

Read the full transcript on our blog.

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

Craig Walker

Fouad ElNaggar is the Founder & CEO @ Sapho, the only employee experience portal designed for the digital workforce. To date, Ray has raised over $27m in funding with Sapho from some real favourites of ours including Ray @ Caffeinated, Felicis, Uncork, Bloomberg Beta, Clark Landry and Howard Lindzon @ Social Leverage, just to name a few. Prior to founding Sapho, Fouad was the Chief Strategy Officer at CBS Interactive overseeing strategy, operations, partnerships, and M&A. At CBSi, Fouad structured deals with partners such as Yahoo, IAC, and Twitch and acquired premium brands such as TV Guide and Giant Bomb. Prior to CBSi, Fouad was a VC at Redpoint Ventures overseeing the firm’s LA office and helping establish a dedicated fund in Brazil. Fouad has previously founded three venture-backed companies – Marketing Technology Solutions (acquired), Liquid Light (acquired), and Hark.

In Today’s Episode You Will Learn:

• How Fouad made his way from the world of VC to the world of CBS and media to founding SaaS companies being a serial SaaS founder with his 4th company, Sapho?
• What does Fouad mean when he says the role of the CEO is to be an “inspirational asshole”? Why is this role so crucial and how is it embodied both in the approach to inspiring a team and driving goals and decision-making? How does Fouad think about structuring decision-making internally? Where do so many go wrong in implementing a decision-making process?
• Why is Fouad a believer that “it is about coaching and promoting rather than signal hiring”? What does Fouad really interpret as signal hiring? When does signal hiring work well? How does Fouad determine when a stretch VP is a stretch too far? What are the leading indicators? Does Fouad agree with Mariam Naficy that rotation of function is key to internal upscaling?
• What does Fouad believe are the 2 fundamental benefits of “being old” in SaaS? How would Fouad respond to the suggestion that the rate of decay on experience has never been greater with Moore’s law effect on technology? Applied to hiring, how does Fouad think about the decision to hire a jack of all trades vs a specialist? When is the time to make the transition?  

Fouad’s 60 Second SaaStr

1. What does Fouad know now that he wishes he had known at the beginning?
2. A moment in Fouad’s business life that changed the way he thinks?
3. What would Fouad most like to change in the world of SaaS today?

Read the full transcript on our blog.

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

Fouad ElNaggar

Christoph Janz is the Managing Partner @ Point Nine Capital, one of Europe’s leading early stage funds with a portfolio that includes the likes of ZenDesk, Algolia, Delivery Hero, Revolut, Contentful and many more incredible companies. Before that, he co-founded two Internet startups (DealPilot.com in 1997 and Pageflakes in 2005). In 2008 he became an angel investor and discovered Zendesk, Clio, FreeAgent – and his love for SaaS. Christoph is also the writer of the phenomenal blog, The Angel VC, a must read for me.

In Today’s Episode You Will Learn:

• How Christoph made his way from serial founder to angel in ZenDesk to today, founding one of Europe’s most successful early stage funds in the form of Point Nine Capital?
• Product market fit is one of the most used words in the industry, so wtf really is product market fit? What does product market fit look like in terms of metrics across the core disciplines: MRR, churn and conversion from free to paid?  
• What is the hailed question that all Series A and B investors want to know? What does it take to make the graduation from Seed to Series A today? In terms of scaling, why does pouring fuel on the marketing fire not always equal more leads? How does Christoph view the role of outbound? Why is it such high hanging fruit? What is core to executing outbound successfully?
• Point Nine did a comprehensive assessment of how founders view the fundraising process, what were the biggest elements founders dislike about the process? From now on, what is the thinking behind the strategy that Point Nine will always do their pro-rata in the Series A? How does this affect reserve allocation?  

Christoph’s 60 Second SaaStr

1. What does Christoph know now that he wishes he had known in the beginning?
2. What does it take for European founders to make it big in the US?
3. Most common mistakes CEOs make in the scaling process?

Read the full transcript on our blog.

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

Christoph Janz

Tom Bogan is the CEO of Adaptive Insights, the company that proves a new generation of business planning software for finance and beyond. Prior to their reported $1.55Bn acquisition to WorkDay, Adaptive Insights raised over $175m in VC funding from the likes of Bessemer, Salesforce Ventures, Norwest Venture Partners and many more incredible investors. Prior to Adaptive Insights, Tom was a partner at Greylock Partners where he focused on enterprise software investments. He was also president and COO at Rational Software until its acquisition by IBM. Before Rational, Tom served as CEO at Avatar Technologies and Pacific Data. He began his career as a financial officer in both public and private companies, serving as CFO at SQA and Orange Nassau, Inc., as well as vice president of finance at SCA Services.

In Today’s Episode You Will Learn:

• How Tom made his way into the world of SaaS, came to be a Partner with Greylock and then made the move back into operations with Adaptive Insights?
• Elad Gil has previously said the role of CEO is to “find product market fit, ensure the company does not run out of money and ensure the team does not implode”, how does Tom define his role as CEO of a $100m+ SaaS company? How does the role of CEo fundamentally change over time? What aspect of the role does Tom find most challenging?  
• What core role of CEO is constant throughout the lifecycle of the company? From seeing many of the world’s best SaaS CEOs, what are the commonalities in how the very best CEOs hire the very best execs? How does Tom think about the debate of hiring externally or promoting from within? How does Tom look to reduce internal discontent when hiring externally rather than promoting?
• At $100m Jyoti Bansal said on the show, this stage is about “creating and sustaining operational efficiency”. What have been Tom’s biggest learnings on the creation and maintenance of operational efficiency? What has worked? What has not worked? How does Tom think about internal asset allocation?
• Why does Tom believe that ultimately, ARR growth is the metric to rule them all? How does Tom think about and prioritise the metric stack in SaaS? How does he approach payback period vs CAC/LTV? In terms of services components of businesses, does Tom believe these should be baked into the CAC? What should the financial targets be for these services businesses?  

Tom’s 60 Second SaaStr

1. What does Tom know now that he wishes he had known at the beginning?
2. Tom’s favourite business reading material and why?
3. What would Tom most like to change in the world of SaaS today?

Read the full transcript on our blog.

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

Jonah Goodhart is the CEO @ Moat, the SaaS analytics and intelligence company focused on transforming brand advertising online. Prior to their acquisition by Oracle for a reported $850m Moat raised over $67m in VC funding from the likes of Insight Venture Partners, Founders Fund, Mayfield, Founder Collective, SV Angel and more incredible names. Prior to founding Moat, Jonah was the founding investor and board member at Right Media, acquired by Yahoo for a reported $680m. Jonah was also the founding partner of WGI Group and co-founder of Billions.org. If all of that was not enough, Jonah is also an angel investor including the likes of adroll, Namely and fitmob all in his personal portfolio.

In Today’s Episode You Will Learn:

• How Jonah made his way into SaaS with is founding investor role in Right Media? How did experiencing both bubbles change the way Jonah thinks about operations today?
• How does Jonah fundamentally define “North Star”? How plastic and flexible does Jonah believe a North Star should be? What was a time where Jonah’s decision was guided in a certain direction by his strong North Star?  
• Why does Jonah believe that in B2B your roadmap is given to you by your customers? What can founders do to clearly and quickly determine what their customers want from their conversations with them? What questions are crucial to ask? What response suggests real intent to buy from them? How does one prevent this from falling into heavy customisation?
• How does Jonah approach the element of “brand” in the world of B2B today? What does Jonah believe is the secret to brand? How does this affect how Jonah both onboards, trains and engages with new and existing employees? Was brand core to Moat being able to sell to enterprise so successfully in the early days?  

Jonah’s 60 Second SaaStr

1. What does Jonah know now that he wishes he had known at the beginning?
2. Quality or quantity of logos in the early days?
3. How important is it for SaaS founders to be involved in the process?

Read the full transcript on our blog.

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

Jonah Goodhart

Sam Blond is Chief Sales Officer @ Brex, the startup that provides corporate cards for startups. To date they have raised over $57m in funding from the likes of Y Combinator, Peter Thiel, Max Levchin, Yuri Milner, Elad Gil and many more incredible names. Prior to Brex, Sam Was Chief Revenue Officer at Rainforest QA. Before Rainforest, Sam saw firsthand the hypergrowth scaling of Zenefits as VP of Sales where he saw the company grow from 18 employees and $1m in ARR to over 1,800 employees and over $70m in ARR. Sam got his start in the SaaS industry with Jason Lemkin @ Echosign as Director of Sales.

In Today’s Episode You Will Learn:

• How Sam made his way into the world of sales and came to join Jason Lemkin with his first role in sales at Echosign?
• Why does Sam believe that more sales reps does not always equal more revenue? What are the benchmarks that suggest founders really need to add to their sales team? Does Sam agree Founders should be selling up to $1m in ARR?
• How does Sam assess who is the best person to hire for the role? What have been Sam’s lessons on what it fundamentally takes to attract the best talent? In the early days how does Sam think about both role allocation and whether to hire the young jack of all trades vs the more senior executive?
• Why does Sam believe that founders need to spend more time on top of funnel? Why does Sam believe that not all opportunities are created equal? How does Sam think about the right structure and time it should take to pass from lead to MQL to SAL to opportunity to deal? Where does this most commonly breakdown?
• Why does Sam believe the key to success in SaaS sales teams is “urgency”? Literally, how can reps instil a sense of urgency in their current pipeline? Why does Sam disagree with the conventional wisdom and say discounting is a great tool? How does Sam determine the right level of discount to give? How does Sam assess pilots as an alternative approach to getting leads over the line?  

Sam’s 60 Second SaaStr

1. What does Sam know now that he wishes he had known at the beginning?
2. Quality or quantity of logos in the early days?
3. Sales rep productivity, what does Sam believe is good?

Read the full transcript on our blog.

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

Sam Blond

Eoghan McCabe is the Co-Founder & CEO @ Intercom, one of the fastest growing saas companies of the day providing a new and better way to acquire, engage and retain customers. Due to their phenomenal growth they have raised over $240m in funding from some of the best in the world including Kleiner Perkins, Social Capital, Bessemer and Index, just to name a few. As for Eoghan, prior to co-founding Intercom, he founded an award-winning software design consultancy called Contrast, and co-founded Exceptional, a developer tool startup acquired in 2011 and now a part of Rackspace.

In Today’s Episode You Will Learn:

• How did Eoghan come to be founder of one of the hottest growing startups in SaaS from founding a software design firm in Ireland?
• What does Eoghan believe are the core pillars for success in making the move from SME to enterprise? How does one reinvent oneself to make this transition? How has Eoghan seen te org structure and internal decision-making change with the adoption of many more enterprise clients?
• How does Eoghan determine between the decision to hire the young jack of all trades vs the much more experienced senior exec? Why does Eoghan believe you can never be too early to bring someone more senior than you onto the team? What makes Eoghan say, “we are all learning on the fly”?  
• How does Eoghan look to create a culture of experimentation and accountability without the fear of failure? What must the leader do to imbue this culture? Where does Eoghan see many going wrong in trying to make this happen?
• How does Eoghan think about “transparency” with SaaS companies today? Why does he think that not only is it not healthy but also largely not possible? Instead, what is a better, more sustainable solution to transparency?   

Read the full transcript on our blog.

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

Eoghan McCabe

Steve Lucas is the CEO @ Marketo, the world leader in marketing automation for companies of any size. Prior to their IPO and eventual sale to Vista Equity partners for $1.79Bn they raised over $100m in VC funding from the likes of Battery Ventures, IVP, Mayfield and Lead Edge Capital. As for Steve, prior to joining Marketo, he served in many leadership positions at SAP, Salesforce, Microsoft, BusinessObjects, and Crystal Decisions. If that wasn’t enough Steve also sits on the board of Tivo, SendGrid and The American Diabetes Society.

In Today’s Episode You Will Learn:

• How did Steve make his way into the world of SaaS and come to be CEO @ Marketo?
• Why does Steve describe his experience at Salesforce to be life-changing? What were the core takeaways for Steve? How has that impacted how he operates today with Marketo? What does Steve mean when he says Marc Benioff is a “master of relevance”?
• Why does Steve believe the key to success as a CEO is accessibility? How can CEOs be both vulnerable and strong in today’s SaaS world? What are the 2 different types of CEOs and how they engage with their CMOs? What do the best do? What do the worst do?
• Why does Steve believe that the “CRM” term is incomplete? How does Steve fundamentally believe the way that customers want to be engaged with has changed? How can marketers enact this level of personalisation and engagement with such large customer bases? How does the role of artificial intelligence fit into this mass scale personalisation?
• How does Steve view the broader martech landscape? Why does Steve strongly believe that we will be entering a period of consolidation in martech? How does Steve view the emergence of new categories such as ABM? How does this impact his overarching view on the next wave for martech?  

Steve’s 60 Second SaaStr

1. What does Steve know now that he wishes he had known when he started?
2. Management upgrade is the most important role of CEO, agree?
3. What keeps Steve up at night? How does that influence his running and operations of Marketo?

Read the full transcript on our blog.

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

Steve Lucas

Jerry Jao is the Founder & CEO @ Retention Science, the startup that brings intelligence to your marketing automation through artificial intelligence that delivers a personalized customer experience, at scale. To date, Jerry has raised over $10m in VC funding with Retention Science from great friends of the show in Forerunner Ventures, Upfront Ventures, Clark Landry, Andy Rankin and more fantastic names. Prior to founding Retention Science, Jerry founded two other e-Commerce marketing technologies and served as Strategic Innovation Officer to Clear Channel Radio. Jerry is also a Guest Lecturer at The Kellogg School of Management and sits on the board of Penango.

In Today’s Episode You Will Learn:

• How did Jerry make his way into the world of SaaS with the founding of his first company? What have been the top 3 mistakes that Jerry has made since founding Retention Science?
• With P&G, Unilever and Olay all as enterprise clients, how did Jerry first sell into them as a small startup? What is required to give these large enterprises confidence in buying from startups? What does the perfect case study look like to convert these mega accounts? In the early days is it a quality or quantity of logos game?  
• How important is it for the founder to be really actively involved in the sales process to these mega corporations? How does Jerry divide his time now between new and existing customers, as well as team and investor management How does Jerry approach multi-year and prepaid deals with these incumbents? What is the line of reasoning for suggesting prepaid is fair?
• Retention Science have been profitable since 2018, how does Jerry look to balance the mindset of fast growth and profitability? How does Jerry think about payback period for enterprise sales reps with this profitability mindset? How does this affect his thoughts and views on internal asset allocation?

Jerry’s 60 Second SaaStr

1. A moment in Jerry’s life that has changed the way he thinks?
2. When I say success in SaaS who embodies this to Jerry?
3. What does Jerry know now that he wishes he had known at the beginning?

Read the full transcript on our blog.

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

Jerry Jao