The Official SaaStr Podcast: SaaS | Founders | Investors

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: What does Krish know now that he wishes he had known at the beginning? What moment in Krish's life has served as an inflection point and changed the way he thinks? 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: What does Karen know now that she wishes she had known at the beginning? What motto or quote does Karen frequently revert back to? 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: What does Hannah know now that she wishes she had known at the beginning? What does Hannah believe embodies good sales rep productivity? 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: What does Brad know now that he wishes he had known at the beginning? When is the right time to pour fuel on the company fire? 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: Jon's favourite book and why? What does on know now that he wishes he had known at the beginning? 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: What does Maria know now that he wishes he had known at the beginning? Who does Maria believe is killing it in B2B marketing today? 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, playing a pivotal role in their rapid growth. She discusses her journey from the gaming industry to SaaS, shedding light on key traits for thriving in fast-paced environments, like adaptability and humility. Cristina shares insights on determining which individuals can scale with a company and the importance of strategic partnerships in early-stage startups. She also emphasizes the need for flexibility, rapid experimentation, and user feedback when navigating partnerships.

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: What would Claire say are her biggest strengths and weaknesses? What does Claire know now that she wishes she had known at the beginning? 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: What does Dan know now that he wishes he had known at the beginning? What is Dan's favourite story of hustle? Why that one? 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: What does Steve know now that he wishes he had known at the beginning? Who does Steve believe is crushing it in the world of SaaS today? 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