The Official SaaStr Podcast: SaaS | Founders | Investors

Today's show is centred around The Top 10 VP of Sales Lessons Learned In Scaling To $100M ARR. Leading this conversation is Aaron Ross, author of best selling book, Predictable Revenue, providing the framework for the outbound process & sales team Aaron created for Salesforce.com. During his time at Salesforce as Director of Corporate Development and Acquisitions, Aaron added an extra $100 million in revenue in just a few years. Joining Aaron from the sales perspective we have Andrew Bothwell, VP of Sales @ TalkDesk and Aaron Schilke, VP Enterprise Sales @ Talkdesk, one of the fastest growing SaaS startups today. Providing insight from the other side of the table we have Josh Stein, Partner @ DFJ where his current board responsibilities include Box (NYSE: BOX), Chartbeat, LaunchDarkly, LendKey, SugarCRM, and previous guest with me on SaaStr in Talkdesk. But enough from me so without further ado I am going to hand over the reigns to Aaron Ross. In Today's Episode You Will Learn: What does Josh Stein believe is the toughest growth stage in SaaS? Which stage separates the men from the boys? Why is growing to 100 a case of simple maths? How does this maths affect how you should think about your sales hiring pipeline? How does this maths affect your view of forecasting? How do TalkDesk look to build a repeatable and scalable sales process? What have been their major learnings? Where do most startups make mistakes and falter? How should VPs of sales approach feedback with their reps? Why has a VP failed if a rep is blindsided by a particular piece of feedback? 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

Edith Harbaugh is the Founder & CEO @ LaunchDarkly, the startup that allows you to fearlessly and swiftly release software by separating feature rollout from code deployment. They have raised over $10m in funding from many previous guests of The Twenty Minute VC including Andy McLoughlin @ SoftTech, Josh Stein @ DFJ and the wonderful team at Bloomberg Beta. As for Edith, prior to LaunchDarkly, she was a Director of Product @ Tripit and Concur. Edith also holds two patents in deployment from her time in engineering at Vignette. In Today's Episode You Will Learn: How Edith made her way into the world of SaaS and came to found LaunchDarkly? Does Edith agree with Jason Lemkin that the hardest element is the 1-10 customer phase? How has Edith navigated this process with her differing companies? How does Edith look to structure her sales team to successfully close Fortune 500 deals? What is the fundamental difference in selling to enterprise rather than SMB? What can founders do to make NPS a more intelligent metric? How can NPS be analysed effectively to tell you more about the state of your business? What are the signs of a truly great sales person? How do they aid not only their company but the customer they are serving? What is their required knowledge base? 60 Second SaaStr What is Edith's fave SaaS resource? What does Edith know now that she wishes she had known before? Oakland Office: Why not SF? What are the benefits? 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 Edith Harbaugh

Lauren Vacarrello is VP of Marketing @ Box, one of the leading enterprise B2B brands today. At Box, Lauren leads a 50 person team that involves demand generation, global campaigns, events and more. Prior to Box, Lauren was VP of Marketing @ Adroll, where she built and scaled a 25 person global marketing team from the ground up. If that was not enough, Lauren is also the Co-Author of "The Retargeting Playbook" and "Complete B2B Online Marketing". In Today's Episode You Will Learn: How does Lauren view the relationship between sales and marketing? Why does Lauren believe the ARR pipeline is not just the responsibility of the sales team? Why is lead nurturing not just about email? What are the other core components to ensure successful progression of leads through the funnel? How does Lauren view successful lead segmentation? Why does Lauren like to segment leads into 3 distinct buckets? How does this strategy play out at different ends of the market? What is the role of marketing post-purchase? How has Lauren seen this change since the early days of her career? How does this differ when comparing SMB to enterprise? 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 Lauren Vaccarello

Aaref Hilaly is a Partner @ Sequoia Capital, one of the world's most successful VC funds with investments in the likes of Apple, Google, Paypal, Whatsapp and LinkedIn just to name a few. As for Aaref he came to the valley with 2 suitcases and the ambition to start a company. That he did and had 2 companies that were Sequoia backed, first CenterRun and then ClearWell Systems where Aaref was instrumental in the company's growth from 0 to a $100m revenue run rate in just 4 years, prior to their $410m acquisition by Symantec. Today Aaref draws on this incredible operational success to illustrate how to manage up and have a very happy board. In Today's Episode You Will Learn: Why does Aaref advocate for founders not to manage the board but to engage them? How can this be done effectively? What does Aaref state are the dangers of focussing on metrics with your board? Why should you focus on product instead? How does this shift change the dialogue with the board? When things do go wrong and the company misses a quarter, how should the founder react? Why does Aaref suggest that founders need to own the miss? How should they structure these conversations? What should they not do when they miss a quarter? How can founders most effectively put their board to work? How should this be communicated and then followed up on by the founder? Where has Aaref found the board can provide the most value? 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 Aaref Hilaly

Mark Roberge, former CRO of Hubspot, and Michele Law, former COO of OpenDNS, discuss the dangers of premature growth for startups. They share insights on the right time to focus on growth, assessing core components, and the profile of the first sales hire. The podcast also explores topics such as scaling sales teams, sales compensation plans, and aligning marketing, sales, and customer success.

Todd Olson is the Founder & CEO @ Pendo, the startup that allows you to capture all user behaviour, gather feedback and then provide contextual support. They have raised over $30m in VC funding from some of the very best in the business including Neeraj @ Battery Ventures, Megan @ Spark and Matt @ Salesforce Ventures just to name a few. As for Todd, prior to Pendo he held various different roles in product as well as co-founding 2 prior startups. In Today's Episode You Will Learn: How did Todd make his way into the world of SaaS and come to found Pendo? Why does Todd believe that there is inherent tension between customer success and product teams? How has this changed from sales and marketing team tension? What does Todd suggest to mitigate this tension? How does Todd evaluate his hiring process? At what stage does one become a specialist vs a jack of all trades? Why does Todd always believe that you should hire ahead of where you are? Todd has previously said that 'money is not all the same'. How does Todd look to select his investors? What value adds are most desired for Todd? What do the best investors do that make them so? 60 Second SaaStr What does Todd know now that he wishes he had known in the beginning? What is Todd's favourite SaaS reading material: Mattermark Daily, Tom Tunguz Creating a startup culture for adults? 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 Todd Olson

Amit Agarwal is the Chief Product Officer @ Datadog, the startup that provides cloud scale monitoring that tracks your dynamic infrastructure and applications. They have raised over $140m in VC funding from some of the best in the business including Index Ventures, IA Ventures, OpenView and RRE just to name a few. As for Amit, before Datadog, Amit was the Director of Product Management at Quest Software (now Dell), where he led the team responsible for application performance monitoring. Previously, Amit held product management roles at Datamirror (now IBM) and Embarcadero Technologies. In Today's Episode You Will Learn: How did Amit make his way into the world of SaaS and come to be Chief Product Officer @ Datadog? Why did Datadog not have a marketing strategy for the early days? What would Amit advise early stage founders with regards to optimising their marketing in the early days? Obviously a multi-product line is crucial for a SaaS startup to be successful, what is Amit's take on how, when and why to launch a second product? What have been his big learnings on this from Datadog? Amit has said before that it is tough to sell to large enterprises in the early days, does that mean startups should always start with SME's? At what price point does it become a challenge? Does Amit agree that if you are between 25K-100K you are in the valley of death price wise? 60 Second SaaStr What does Amit know now that he wishes he had known in the beginning? What is Amit's favourite SaaS reading material? When is the right time to hire a CPO and why? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Amit Agarwal

Tim Eades is the CEO @ at vArmour, the industry's first distributed security system that provides application-aware micro-segmentation. Tim joined vArmour as CEO in October, 2013. Prior to that, he was the CEO at Silver Tail Systems until the company was acquired by RSA, the security division of EMC in late 2012. Prior to leading Silver Tail Systems, Tim was CEO of Everyone.net, an SMB focused SaaS company that was acquired by Proofpoint. Tim has also held sales and marketing executive leadership positions at BEA Systems, Sana Security, Phoenix Technologies and IBM. In Today's Episode You Will Learn: How did Tim make his way from punk rock fan in the UK to leading Silicon Valley CEO? Why does Tim believe Incremental Account Opportunity (IAO) is one of the most important metrics for a growing startup? Why does Tim believe that most founders are far too late to ship their second product? How can they identify adjacent markets? When exactly is the right time to know when to ship your second product? What does it take in terms of sales team structure to successfully orchestrate the 7 figure deals that Tim does? What does that look like in terms of sales team compensation? 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 Tim Eades

David Rodnitzky is founder and CEO of 3Q Digital, a leading digital agency that was acquired by Harte Hanks in 2015. Prior to 3Q Digital, he held senior marketing roles at several Internet companies, including Rentals.com (2000-2001), FindLaw (2001-2004), Adteractive (2004-2006), and Mercantila (2007-2008). David currently serves on advisory boards for several companies, including Marin Software, MediaBoost, Mediacause, and a stealth travel start-up. Loretta Jones is the vice president of marketing at Delighted, the fastest way to gather customer feedback and put it into the hands of those who can act on it. Prior to Delighted, Loretta's marketing programs grew Insightly, a CRM for small business, from 100,000 users to over 1.2 million users. Prior to Insightly, Loretta worked at Adobe Sign (formerly Adobe EchoSign) and grew the EchoSign brand to $25 million. In Today's Episode You Will Learn: Should all companies invest in SEM? How does SEM differ for SaaS SMB businesses vs enterprise SaaS businesses? How much of a role should iterating and testing play with regards to SEM? What are the strategies that can be used to ensure for maximal dollar efficiency? David has said before that 'no demand channel is an island'. How does SEM work together with the other channels (SEO, display ads etc) to form a cohesive marketing strategy? As LTV takes a considerable time to figure out and can be inaccurate, should startups focus on their CPA (cost per acquisition) more than any other metric? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr David Rodnitzsky

Tom Tunguz is a Partner at Redpoint Ventures and one of the pre-eminent thought leaders in the rise of SaaS. Tom has made investments in the likes of Demio, Axial, Chorus.ai and more incredible companies. Tomasz is also the co-author of Winning with Data: which explores the cultural changes big data brings to business, and shows you how to adapt your organization to leverage data to maximum effect. Before joining Redpoint, Tomasz was the product manager for Google's AdSense social-media products and AdSense internationalization. If you have not checked out Tom's blog that is a must and can be found here. In Today's Episode You Will Learn: What are the 4 dominant ways startups are incorporating machine learning into their feature set? Why does Tom not believe in AI and discuss prefers to discuss machine learning? What 3 things have caused the rise of machine learning? Why now will machine learning happen in core categories in SaaS? What role does deep learning play in this rise? What are the 5 precepts of the type of companies that Tom wants to invest in using ML in SaaS? Why should startups discuss their value proposition over their technology? How does Tom advise startups can gain access to proprietary datasets? How would Tom like to see data access change in the coming years? How does Tom approach the aspect of building out a team of experts in machine learning for your startup? What should founders look for? 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 Tomasz Tunguz