

The Official SaaStr Podcast: SaaS | Founders | Investors
SaaStr
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 center 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.
Episodes
Mentioned books

Sep 5, 2019 • 25min
SaaStr 263: Eventbrite SVP of Platform Pat Poels on Engineering Your Own Luck - The 3 Key Rules of Building Globally Distributed Teams
Building a company made up of distributed teams presents a plethora of complex challenges that can derail productivity and impact employee retention. But with it comes immense benefits and competitive advantages such as the diversification of ideas, speedier product development, and representation in important regions and time zones. Come and hear about the typical pitfalls (and how to avoid them) from Eventbrite SVP of Platform Pat Poels, an executive with over seven years under his belt leading Eventbrite's now 300+ strong engineering team that sits across North America, South America, and Europe. Missed the session? Here's what Pat talks about: Engineering your own luck How to build an engineering team If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin SaaStr

Sep 2, 2019 • 37min
SaaStr 262: Box's Jon Herstein on How Customer Success Teams Should Structure, Schedule and Execute on Customer Check Ins, Why Delight is Important But Insufficient & Why Customer Success Is Not Responsible For Upsell
Jon Herstein is the Chief Customer Officer at Box, the company that provides one platform for secure content management, workflow and collaboration. Prior to their IPO, Box had raised funding from some of the best in the business including Andreesen Horowitz, Bessemer, DST, Emergence and Meritech, just to name a few. As for Jon, prior to being Chief Customer Officer at Box, he was Senior VP of Customer Success, responsible for all post-sales services Box provides from implementation to user adoption and more. Before Box, Jon spent 4 years as VP of Professional Services at NetSuite and prior to that, close to 8 years as Senior Director of professional services at Informatica. In Today's Episode We Discuss: How did Jon make his way into the world of SaaS and come to be one of the leading figures in the rising tide of the customer success movement? What does Jon mean when he says, "you have to constantly bring your customers to the forefront of your employees minds"? For non-customer facing roles, what can one do to give them that perspective? Does it work to ensure every function spends time in customer support? What is challenging about that? What can be done in the onboarding phase to ensure the individual has the most empathy for the customer, regardless of function? For those in CS, what is the right communication cadence to check in with their accounts? What should the agenda look like? What outcomes should they drive towards? Should they be involved in the upsell process? How does Jon think about post-mortems on churned clients? How do they structure them? What lost client stands out to Jon and what would he have done differently to retain them? From Jon's experience seeing Box in hyperscaling, at what stages do SaaS orgs start to break down? Why does Jon think that is? What can be done to proactively try and mitigate this? How does Jon think about the structuring of roles and responsibilities with scale? What does this done well look like? Where do many people go wrong here? Jon's 60 Second SaaStr: What does Jon know now that he wishes he had known at the beginning of his time with Box? What motto or quote does Jon frequently revert back to? What is the most challenging element of Jon's role with Box 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 Jon Herstein

Aug 29, 2019 • 22min
SaaStr 261: Workday EVP of the Planning Business Unit Tom Bogan on The Top Lessons Learned in Getting to $100M ARR
Tom Bogan, CEO of Adaptive Insights, a Workday company, will review the key principles to building a successful SaaS company. From team to vision to metrics to funding and more, these principles provide the framework for high-growth, high performing SaaS companies. How can you develop a winning culture? How can you set aggressive but realistic goals? What's needed to build the right team in SaaS today? Missed the session? Here's what Tom talks about: The important maxims about team building Insights on fundraising and why you might not want to always raise at the highest valuation Personal stories from his time building Adaptive Insights If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin SaaStr

Aug 26, 2019 • 40min
SaaStr 260: HelloSign COO, Whitney Bouck on How Startups Can Attract The Most Seasoned Execs In SaaS, How To Determine Whether A Seasoned Exec Has True Startup Fabric & What Separates Good From Great When It Comes To COOs
Whitney Bouck is the COO @ HelloSign (now a part of Dropbox). For those that do not know, HelloSign is the company reimagining how you approach your most important business agreements with their award-winning e-Sign solution. As for Whitney, she directly leads the organization's go-to-market efforts, including sales, marketing, business development and customer operations. Whitney is also an advisor to companies funded by the YC Continuity Fund, focusing on enterprise strategy, go-to-market strategy, leadership and execution. If that was not enough, Whitney is also on the board of Ekata, building the global standard in identity verification. Finally, prior to HelloSign Whitney spent close to 5 years at Box where as SVP Global Marketing & GM Enterprise she took on all of marketing globally for Box and was responsible for reshaping the company brand from SMB to enterprise. In Today's Episode We Discuss: How Whitney made her way into the world of SaaS originally with Box and how that led to her coming one of today's leading COOs with HelloSign? What were Whitney's biggest takeaways from seeing the hypergrowth of Box? How did that change her operating mentality? What does truly successful exec leadership look like in Whitney's mind? When is the right time for founders to think about building out their first exec team? What common mistakes do they make in the process? What can founders do to attract seasoned SaaS execs to their early-stage company? What are the questions that suggest an individual has a startup culture to them? What are the indications that they are a "big company" person? What does Whitney believe is the new role of the CIO? What has changed about their tole and what has driven this change? With their coming front and centre in the org, how does that change both the reporting and operating structure of the business? What are the nuances and intricacies of this role that many do not often consider? COO is thrown around as a term today, what does it really mean to Whitney? What does Whitney believe separates good from great when it comes to COOs? When is the right time for founders to start looking for their first COO? What should they look for in their first COO? What is the optimal onboarding process for any new COO? Whitney's 60 Second SaaStr: What does Whitney know now that she wishes she had known at the beginning? What makes for the optimal relationship between COO and CEO? What is the most challenging element of Whitney's role with HelloSign 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 Whitney Bouck Ever feel like you can't really connect with prospects or have an organized workflow to get deals closed? Outreach.io, the leading Sales Engagement platform, supports sales reps and their managers by making it simple to humanize and personalize communication at scale; automating the soul-sucking manual work; and dramatically increasing the productivity and efficiency of all revenue-generating teams. You can check them out at outreach.io/saastr to chat with them and receive a free copy of their new book -- Sales Engagement: How The World's Fastest-Growing Companies are Modernizing Sales Through Humanization at Scale.

Aug 22, 2019 • 23min
SaaStr 259: Pipedrive SVP of Global Sales Tara Bryant on Addressing the Ugly Side of Growth
Our guest today is Pipedrive SVP of Global Sales Tara Bryant. Globalization opens up a world of opportunities for sales growth. We often focus on the positive sides of growth—but what about taking a look at the ugly sides? Even what we could consider "good problems" need preparation, and it starts by understanding your team and your goals, including knowing when and how to recruit members of your team, and building in a way that compliments your growth. Do you need more man-power on the customer facing side, or do you need to bring in new management to keep everything in line? Growth isn't always linear, and the steps to success aren't always one after the other. How do you prioritize and organize to bring the best possible results? This side of success can be scary, but knowing how to prepare can set you up to reach your companies long term growth goals. Missed the session? Here's what Tara talks about: What does the ideal candidate look like? How to hire your core staff really well Enabling salespeople to share learnings If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin SaaStr

Aug 15, 2019 • 25min
SaaStr 258: Plaid CEO and Co-Founder Zach Perret on How to Build a Platform that Fuels an Ecosystem
Companies that have access to more accurate financial data have the ability to develop seamless exchanges of information, providing consumers with improved ways to manage their finances. But how do companies gain secure access to that data in the first place? Enter the platform company. Hear from Plaid co-founder and CEO, Zach Perret and CNBC's Ari Levy as he walks through his lessons learned building Plaid and how it found itself at the center of the fintech ecosystem. If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin SaaStr Zach Perret

15 snips
Aug 12, 2019 • 26min
SaaStr 257: How To Scale Sales Culture Successfully and Sustainably, The Leading Indicators of Burnout and What To Do & The 2 Inflection Points In SaaS Growth Where Things Start To Break with Justin Welsh, Former SVP Sales @ PatientPop
Former SVP Sales @ PatientPop, Justin Welsh, discusses scaling sales culture sustainably, signs of burnout, communicating with superiors about burnout, and the importance of culture over performance in a team setting.

Aug 8, 2019 • 20min
SaaStr 256: Google Cloud VP of Engineering Eyal Manor and Zenoss CMO Megan Lueders
As a global technology provider powering thousands of SaaS companies, Google is at the forefront of driving exciting and innovative technologies to market. Eyal Manor and Megan Lueders host a fireside chat between Google Cloud and Zenoss, a leader in software-defined IT operations. They discuss the most common and emerging challenges facing SaaS companies today. You'll also learn how leading SaaS companies are able to scale and thrive in this complex, dynamic environment. Join us for this lively discussion between two innovators. Missed the session? Here's what Eyal and Megan talks about: How to develop software faster The emergence of new A.I. services Why the "strongest" conversations need to happen between engineering and marketing If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin SaaStr

Aug 5, 2019 • 36min
SaaStr 255: Why Enablement Must Be An Early Investment and How To Structure It, Why The SaaS Incumbents of Today Are Not As Strong As We Think & How To Build A Sales Culture of Confidence Without Arrogance with Vikas Bhambri, SVP Sales and Customer Experi
Vikas Bhambri is SVP Sales and Customer Experience @ Kustomer, the startup providing Real-time, actionable views of customers with continuous omnichannel conversations and intelligence that automates repetitive, manual tasks. To date they have raised over $113m in financing from some of the best in the business including Tiger Global, Battery Ventures, Boldstart, Canaan, Cisco and Redpoint just to name a few. Prior to Kustomer, Vikas spent over 20 years implementing, consulting, marketing, and selling CRM and ContactCenter solutions with companies like LivePerson and Oracle. In Today's Episode We Discuss: How Vikas made his way into the world of SaaS and came to be at the rocketship that is Kustomer? Why does Vikas believe that a wave of SaaS incumbents are about to be displaced or disrupted? What about the changing tech stacks and infrastructures makes them vulnerable to up and comers? Does this not lead to a consolidatory environment? How does Vikas see the space play out in the coming years when it comes to acquisitions? What have been the dramatic changes that have happened in sales over the last few years? What is the right way for startup founders to address sales rep onboarding? Why is it so crucial to invest in enablement in the early days? How should this enablement be structured? How does this change sales rep payback periods? What is a good payback period? How does Vikas feel about discounting? If accepted, what must the startup ask for in return? How does Vikas think about multi-year deals? When are they good? What sort of terms make them less beneficial for the vendor? How does Vikas think about professional services? What is a good margin for professional services? What ratio of revenue is healthy for professional services to account for? When should one look to hire their first customer success reps? What should they look for in those reps? Vikas' 60 Second SaaStr: What does Vikas know now that he wishes he had known at the beginning? What is his secret to building diverse teams? The sales leader Vikas most respects and admirers 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

Aug 1, 2019 • 22min
SaaStr 254: HubSpot CEO Brian Halligan on The Funnel is Dead, Long Live the Flywheel.
The age-old sales funnel has worked fine for decades…until now. Flaws are being exposed, and a new model is imminent. Why is the sales funnel alone no longer an appropriate way thinking about customers? What will emerge to supplement or replace it? HubSpot CEO Brian Halligan and NEA's Hilarie Koplow-McAdams explore the evolution of the marketing and sales funnel you've been using for decades to generate traffic and convert and leads into customers. Missed the session? Here's what Brian talks about: Why a flywheel instead of a funnel? What does the Grateful Dead have to do with Marketing…? What role do T shaped people play? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin SaaStr Brian Halligan


